nmr database of lignin and cell wall model …...i nmr database of lignin and cell wall model...
TRANSCRIPT
i
NMR Database of Lignin and Cell Wall Model Compounds
Sally Ralph US Forest Products Laboratory (FPL) USDA Forest Service One Gifford Pinchot Drive Madison, WI 53705 email: [email protected] 608-231-9449 John Ralph Department of Biochemistry and the Great Lakes Bioenergy Research Center Wisconsin Energy Institute University of Wisconsin, Madison 1552 University Ave Madison, WI 53726-4084 (608) 890-2429 E-mail: [email protected] This database was designed to provide a coherent, single source of NMR data of lignin and other plant cell wall model compounds. The database exists in several different formats: a FileMaker Pro© database for cross-platform use, an Adobe© pdf cross-platform file for viewing and printing, and a hardcopy version derived from the FileMaker Pro database. FileMaker Pro and pdf versions are available for downloading over the internet from the Dairy Forage Research Center (DFRC) web site: http://www.dfrc.ars.usda.gov (under the Software section) A hardcopy version is available by request from the authors at the Forest Products Laboratory, but users are encouraged to print their own version. The use of trade or firm names in this publication is for reader information and does not imply endorsement by the US Department of Agriculture of any product or service.
In general 13C NMR data was collected in three common deuterated solvents (acetone, chloroform and dimethyl sulfoxide) for each compound. We used the center line of the solvent peaks as our reference, 2.04 and 29.83 ppm for acetone-d6, 7.24 and 77.00 for CDCl3 and 2.49 and 39.50 ppm for DMSO-d6. The 1H NMR data early on was reported for only one solvent. A standard set of acquisition parameters was used to acquire and process the spectra to keep the data as uniform and constant as possible. The samples were run at ambient temperature, about 298° K. Those compounds with an index number less than 1000 were run on a Bruker 250 MHz spectrometer at FPL and those compounds with an index number between 1000 and 10,000 were run at the DFRC on a Bruker 360 MHz instrument. The order of the compounds in the database reflects their arrival at the spectrometer rather than a preordained plan. The inclusion of analogous series of structures with small structural differences allows calculation of substituent effects that are invaluable for chemical shift predictions of structures not included in the database. The chemical shift assignments for most of the compounds were made by comparison with other compounds, literature values, and in some cases using the standard set of 1D and 2D NMR experiments. Every effort was made to correctly assign the chemical shifts; however, limited time and resources precluded confirming the shifts for many of the compounds. The shifts are reported to the second decimal place only to distinguish very close shifts; comparisons between spectra are practical only within ± 0.1 ppm. The authors would greatly appreciate learning of any corrections on suspect assignments. [email protected]
ii
The compounds themselves came from many sources — in-house collections, syntheses and donations from other researchers for which we are grateful. The source of the compounds is often given in the “Notes” field along with other pertinent data. This database was originally intended as an aid for the assignment of chemical shifts for wood and plant lignin NMR spectra. The trivial names used throughout are well known to wood chemists as is the numbering system. We have attempted to include more formal chemical names for many of the compounds and these were obtained using Beilstein’s Autonom© program. The chemical names for the larger 3 and 4 ring models became so cumbersome that the authors employed an abbreviated system to identify both the moieties involved as well as the linkages between the moieties. Examples of the naming, numbering and linking conventions used are given below.
OH
OHOCH3
OCH3
OCH3
OHOCH3CH3O
guaiacyl veratryl
syringyl4-hydroxyphenyl (coumaryl)
Fig. 1 Trivial names for substituents at the
3,4 and 5 positions on the aromatic ring.
The naming of the larger oligomer lignin models uses a combination of upper case letters to describe the ring structure and lower
case letters and numbers to describe the type of linkage between the rings.
Table 2. Terminology of Abbreviated Structural Entities
Entity Abbreviation guaiacyl ring G syringyl ring S coumaryl ring H α–O–4 linkage a β–O–4 linkage b β–5 (phenylcoumaran) c β–1 linkage b1 β–β (resinol) r 5-5 (biphenyl) 5,5 coniferyl alcohol end unit CA sinapyl alcohol end unit SA p-coumaryl alcohol end unit HA ferulic acid end unit FA erythro e threo t
G-5,5-G
CH3OOH OH
OCH3
5-5 (biphenyl)
6
B1
23
β-O-4
123
45
OHOCH3
HO
HO
OOCH3
G-b-G
A
45
6
αβ
γ
iii
OHOCH3
HO OH
OHOCH3
CH3Oβ-1
S-r-S
O
O
HOOCH3
CH3O
OCH3
OCH3
OH
β-β (resinol)
S-b1-G
OOCH3 OH
OCH3
4-O-5
O
OCH3OH
HO OCH3
OH
β-5 (coumaran)
G-c-CA
G-4-O-5-G
Fig. 2 Examples of linkages and abbreviated names.
With this convention the name FA-5,5-FA would represent a diferulic acid biphenyl structure. The trimer CA-a-G-b-CA would be a guaiacyl unit with two coniferyl alcohol end groups etherified at the α- and β-positions. The structure index is arranged based upon the number of rings in the structure. Where possible the structures are also arranged by ring type such as guaiacyl, syringyl etc. The number under the structure refers to the index number at the top of the data sheet. An asterisk after a number indicates the acetylated analog of that compound. In some cases only the acetylated compound is included. We hope to continue adding to and improving this database. Regular updates will be made to the database to keep the online sources current. This database was written and prepared for the most part by U.S. Government employees on official time, and it is therefore in the public domain and not subject to copyright. Please feel free to contact the authors with suggestions or questions. The authors gratefully acknowledge the many generous contributions made by others at both labs towards this database; Foremost Larry Landucci for compounds, patience, assignments and encouragment. William Landucci for software development, Martin Wesolowski and Kolby Hirth, NMR spectroscopists, and the frequent donation of compounds from Mike Mozuch, Noritsugu Terashima, Stéphane Quideau, Rich Helm, Fachuang Lu, Hoon Kim, Jamie Milhaupt and Susana Luque. The authors also acknowledge partial support of the National Research Initiative Competitive Grants Program/USDA (Wood Section), award #94-03465.
iv Structure
Index
Contents
Monomers v β-O-4 dimers, 2-carbon sidechain and 3 carbon sidechain with α-C=O vii β-O-4 dimers, 3-carbon sidechain viii β-5 dimers x β-β dimers xi 5-5 dimers, β-1 dimers , 4-O-5 dimers xii Trimers xiii Trimers containing ferulic or coumaric acid xiv Tetramers xvi Misc. xvii Misc. ctd. xviii
O CH3
OH
O CH3
OCH3
CH3 OH
OCH3
O H
OCH3
O CH3
CH3O OCH3
OCH3
O CH3
CH3O OCH3
OH
O CH3
OCH3
OCH3
O CH3
OCH3
OH
O OCH3
OH
O OCH3
OCH3
O OCH3
OCH3
OH
O OCH3
OCH3
OCH3
O OCH3
CH3O OCH3
OH
O OH
CH3O OCH3
OH
O OH
OCH3
OCH3
O OH
OCH3
OH
O OH
OCH3
O OH
OH
CH3 OH
CH3O OCH3
OH
CH3 OH
OCH3
OCH3
CH3 OH
OCH3
OH
CH3 OH
OH
O H
OH
O H
OCH3
OH
O H
OCH3
OCH3
O H
CH3O OCH3
OH
OH
OH
OH
OCH3
OH
OCH3
OH
OH
OCH3
OCH3
OH
CH3O OCH3
OH
CH3O OCH3
OCH3
CH3O OCH3
OH
OCH3
OCH3
OCH3
OHOCH3OH
Monomers
v
18,17* 25
6,173* 36 7,103* 9 8,177* 156
209,210*
203
64,191*6965,180*
43,175*4442,192*2058,208*
41,206*5715,174*14,207*
12,195*13,204*11,202*10,23*
16,201*5,143*19,200*37,205*4,24*
5540,189*5639,176*5438,190*
HOOH
CH3
OCH3
OH
OHO
CH3
OCH3
OCH3
R=OCH3
R=OH
CH3O
CH3
OH
OCH3
R
R2=OH
R1=H, R2=OCH3
R2=OH
R=OCH3
R=H R=OCH3
R1
OH
HOOH
OCH3
R2
OH
OCH3
OH
OCH3
OH
H
OCH3
O
OHH O
R OCH3
OH R
OHO
OH
OCH3
OH
CH3
OCH3
OH
OHO
HO
OCH3
OCH3
CH3
O O
OH
R1
R2
O
CH3
OCH3
OH
OCH2CH3
OCH3
H O
CH3O OCH3
OH
OH
CH3O OCH3
CH3O
OH
O
OCH3
CH3O
OCH3
O
OCH3
CH3O
OH
OCH3O
OH
O CH3O
OCH3
O
CH3O OCH3
CH3O
OCH3
O
CH3O OCH3
HO
OCH3
OHO
OCH3
OHO
OH
O
OCH3
HO
OH
O
OCH3
HO
OCH3
O
CH3O OCH3
HO
OH
O
CH3O OCH3
H
OH
O
OCH3
H
OCH3
O
OCH3
H
OH
OH
OH
O
OCH3
OH
OH
OCH3
OCH3
OH
OH
OH
293
291, 295*
292, 296*
290, 294*
264, 265* R1=H, R2=OH
130 R1=OCH3, R2=OAc272*,285 R1=OCH3
160
240* R1=H
35127,128*279, 280*
219,220*
Monomers ctd
vi
215
Misc. Monomers
161,1*
9596113,115* R=H
114,116* 94112,111* 136
167
2002,211*
6260,196*7068,149*5961,148*
6346,178*4748t,124c,108t*4945,129*
153,155*150144,141*152,223*
145,159*87,2001,142*, cis 231151,2003,222*
CH3O OCH3
OCH3
OH
302
OCH3
OH
O
297
OCH3
CH3CH3O
CH3O
AcO
O
OAc
OCH3
O
OCH3
O
CH3CH3O
CH3O
HO
O
OAc
OCH3
O
CH3O OCH3
OAc
O
HO
OCH3
O
CH3
O
CH3O OCH3
OAc
O
HO
OOCH3
CH3
O
CH3O OCH3
OAc
O
HO
O
OCH3
OCH3
O
HO
OCH3
O
OCH3
OH
O
HO
OCH3
OOCH3
CH3O
CH3O
HO
O
OH
OCH3
O
CH3O
CH3O
OCH3
OCH3
OH
OO
CH3O
OCH3
OCH3
OAc
OO
OCH3
OCH3
OH
OO
CH3
O
OCH3
OCH3
OCH3
OO
CH3
OH
OCH3
OH
HOO
CH3OCH3
O
CH3O
OCH3
OCH3
OCH3
OO
CH3
O
CH3O
OCH3
OCH3
OCH3
OO
CH3
O
CH3O OCH3
OCH3
OO
CH3O
OCH3
OCH3
OH
HOO
OCH3
OCH3
OCH3
HOO
OCH3
OCH3
OH
HOO
OH
HOO
246
b-O-4 Dimers, 3-Carbon Sidechain, a-C=O
79
92,2067
80 81
110,163* 106,162*,1028(monoacetate) 21,2082(monoacetate)
vii
154,1027* 27
22,26*
146132,138*
535251
50147126125
b-O-4 Dimers, 2-Carbon Sidechain
HO
HO
OH
OCH3
O
OCH3
HO
HO
OCH3
OCH3
O
OCH3
CH3O
HO
HO
OH
OCH3
O
OCH3
R2
R1
CH3
OH
CH3O
HO
HO
OH
OCH3
O
R2
R1
CH3
OH
HO
HO
OCH3
OCH3
O
R2
R1
CH3
OH
HO
HO
OH
OCH3
O
OCH3
CH3O
OH
CH3HO
OH
OCH3
OOCH3
CH3OHO
OH
OCH3
O
OCH3
CH3O
OAc
CH3AcO
AcO
OAc
O
R1
OCH3
OH
CH3O
HO
HO
OH
OCH3
O
R2
R1
CH3HO
HO
OH
OCH3
OHO
OCH3
CH3OHO
OH
OCH3
O
OH
OCH3
OCH3
HO
HOO
H
O
OCH3
OCH3
HO
HOO
R2
R1
CH3
CH3O
HO
HO
OH
OCH3
O
CH3O OCH3
O
OCH3
CH3OHAcO
AcO
OAc
O
R2
R1
CH3HO
HO
OH
O
R2
R1 OCH3
OH
OCH3
HO
O
OH
R1 OCH3
OH
R2
OCH3
HO
HOO
b-O-4 Dimers, 3-Carbon Sidechain
101e,102t,74t*,214e*
104t,105e,3e*
90,99*
135217,218*
viii
225
(1029t,1030e a,g Ac'd)
133,137* R1=R2= H131,140* R1= OCH3, R2= H134,139* R1= OCH3, R2= OCH3
244 R1=R2= H248t,227e* R1= OCH3, R2= H242,232* R1= OCH3, R2= OCH3
179
31,32* R1=R2= H34,33* R1= OCH3, R2= H2,29* R1= OCH3, R2= OCH3
166 168
91,100* R1=R2= H88,97* R1= OCH3, R2= H89,98* R1= OCH3, R2= OCH3
245 R1= OCH3, R2= H243,230* R1= OCH3, R2= OCH3
212,213* R1= H229* R1= OCH3
3025 R1=R2= H3026 R1= H, R2= OCH3
3027 R1= OCH3, R2= H3028 R1=R2= OCH3
2013t,2014e,2012e*,2011t*,3008t* R1=R2= H3067,188* R1= H, R2= OCH3
186* R1= OCH3, R2= H185* R1=R2= OCH3
228
241,238* R1= OCH3,
249 R1= OCH3,
R2=HR2=H
268e,269t,270e*,271t* R1=R2=H
O
OCH3
HO OH
OCH3
O
O
O
H
OCH3
HO OH
OCH3
O
O
O
OCH3
HO OH
OCH3
OH
O
O
R1 OCH3
R2
OCH3O
OO
HO
O
R1
OCH3
R2
OCH3
OH
O
O O
R1
R2
OCH3
OCH3
OH
O
HO
R2
R1
O
OCH3
H
OH
OCH3
O
O
OCH3
O
CH3CH2O
OCH3
O
HO
O
O
CH3
CH3O
R
O
OCH3
O
R O
OCH3
OH
R
OH
OCH3
HO
HO
OCH3
H
O
O
HO
O
H
OCH3
CH3CH2O
OH
O
OCH3
O
O
R
OCH3
CH3CH2O
OH
O
OCH3
O
5-Hyroxyconiferyl alcohol b-O-4 Dimers, 3-Carbon Sidechain
307030693068
3050, 3051 isomers R1=H, R2=OCH3
3054, 3055 isomers R1=OCH3, R2=H
3052, R1=H, R2=OCH3
3056, R1=OCH3, R2=HR1 = OCH3, R2 = H3057,
3053, R1 = H, R2 = OCH3
3034, 3035* R1,R2 = H3036, 3037* R1 = OCH3, R2 = H3038, 3039* R1 = H, R2 = OCH3
3040, 3041* R1, R2 = OCH3
3031 R = H2040 R = OH
3010t*, 3011e* R = H3071 R = OCH3 (with only g-Ac)
ix
2043e,2044t2045e,2046t
2041 R = OCH3
2042 R = H
More b-O-4 Dimers, 3-Carbon Sidechain
A
B
A
B
A
B
H
HO OCH3
OH
OCH3
O
O
OCH3
OH
OCH3
H O
H
O
O
OH
OH
OCH3
H O
OCH3
OH
OAc
AcO
O
OAc
ORO
OH
OCH3
ORO
OH
OCH3
OAcAcO
AcO
OCH3AcO
O
OAc
OCH3
R
AcO
CH3
O
OCH3
OAc
OCH3
H O
HO
O
OH
OCH3
OCH3CH3 O
O
O O
O
OH
OCH3
CH3
OCH3HO
O
RO O
O
OH
OCH3
OH
HO
O
OCH3
R
OCH3
OCH3
OH
HO
CH3O
O
OH
OCH3
CH3
O
OCH3
CH3
OH
OCH3
CH3
O
OCH3
CH3
R
OCH3
30593061
267
3030
262
239 R= H234 R= OCH3
x
2054 R= H2019 R= Et
2006
2021
2018 R= H2052 R= Et
2004,2005* R= OH
2051,221* R= OCH3
3063,187*
6766 R= OH73 R= OCH3
b-5 Dimers
CH3O OCH3
OH
CH3O OCH3
OH
HO
H O
CH3O
HO
O
O
OCH3
OH
OH
O
OCH3
OH
HO
CH3O
OR2
CH3O
OH
OCH3
OH
O
OR1
O
OCH3
OH
H
H
O
O
CH3O
OH
OAc
OAcAcO
CH3O
OAc
OAc
OAc
OAc
OCH3CH3O
OAc
AcO
OCH3
OH
OCH3
OH
OR
O
OO
H
HOCH3
OH
O
O
O
H H
OCH3
HO
OCH3
OH
OR
HO
O
O
CH3O
OH
H
HHH
O
HO
OH
OCH3
OCH3
O
O
R
R
O
O
HO
OH
OCH3
OCH3
O
OR
R
HO
OH
OCH3
OCH3
O
O
3060
3017, 3016*
3014, 3015 isomers
2035 R1, R2 = CH3
2036 R1, R2 = H2062 R1 = CH3, R2 = H
3032
2032 R = CH32031 R = H
(epimers)
2029,2030*20282027
117,123* R = OCH3
2020,109* R = H
xi
b-b Dimers
2069,3018
2070
2033 R = H2034 R = OCH3
2026
2008 R = H3002, 3042* R = OCH3
R=OCH3
OCH3
O
R
CH3O
CH3O OCH3
OH OH
OHOH
OH
OCH3CH3O
OH
OCH3
O
OH
OH
CH3O
HO
OH
OCH3
O
CH3O
O
RO
O
OCH3
RO O
OCH3
OH
O
OHOH
OH
OCH3CH3O
OH
RR OO
OH
OCH3CH3O
OH
H
O
OCH3
OAc
OCH3
O
AcO
AcO
OAc
OCH3
CH3CH3
CH3O
OAc
OCH3
OAc
OCH3
OAc
AcO
O
CH3O
O
H O
CH3O
CH3
O
OCH3
OH
CH3O
O
H O
OH
OCH3
OH
OH
CH3O
O
OH
OCH3
OH
OCH3
OH
OCH3
OH
HO
HO
OHOH
OH
OCH3CH3O
OH
OH
OCH3
OHHO
CH3O
OHOCH3
OCH3
ORRO
CH3O
OCH3
286
283
Biphenyl methane Dimer
281, 282*
273, 274*
275, 276*
259, 260*3033 R = H2056 R = OH2057 R = OCH2CH3
3007e
g'
b'a'
3003 R = H3001 R = CH2CH3
247
233
xii
5-5 Dimers
b-1 Dimers
5-O-4 Dimers
20372038
2039
171, 3004e172*, 3005t*, 3006e*
2058
71 R = H72 R = OH28
CH3O
O
O
OH
OCH3
O
300
R
HO
OCH3
R2
OCH3
R1
HOO
HO
OCH3
OH
O
AcO
CH3O OCH3
OAc
OCH3
CH3O
AcOO
AcO
OCH3
OAc
CH3O
OAc
O
O
OH
OCH3
O
CH3O
OH
OCH3
OH
OH
R
R2
OCH3
OH
O
O
OH
OCH3
HO
OHO
CH3O
OCH3
R2
R1
AcO
OCH3
OCH3
CH3O
AcOO
AcO
OCH3
OAc
OAc
O
R
RR
CH3
CH3O
O
OAc
OCH3
OCH3
CH3
O
OAc
OCH3
OAc
O
O
OAc
OCH3
AcO
OAcO
OCH3
CH3O
CH3
CH3O
AcO
OCH3
OCH3
AcOO
AcO
OCH3
OAc
OAc
O
OAc
HO
CH3O
O
OAc
OCH3
OCH3
O
OAc
CH3O
O
OH
OH
OCH3
H O
O
H O
OCH3 R
OAc
AcO
OCH3
OAc
OCH3
AcO
AcO
O
OCH3
OAc
OAc
OCH3AcO
AcO
O
OAc
AcO
CH3O
OCH3
Trimers
2015e,2022e*
xiii
CA-a-G-b-CA
237
226 R1 = R2 = H G-b-S-b-G250 R1 = OCH3 R2 = CH3 G-b-S-b-S
263 G-b-G-r-G
261 S-b-G-S
258
2049
G-b-G-b1-G236, 3013 R = HS-b-G-b1-G235 R = OCH3
3012
193 S-b-S-b-SA
R = H G-a-G-b-GR = OCH3 S-a-S-b-S266
1
3064 R1,R2 = H, G-b-S-r-G
198,199* R1,R2 = OCH3 , S-b-S-r-S
183,184* R1 = H , G-b-S-r-S, R2= OCH3
181,182* R = H, R1 = OCH3, R2= CH2OH G-b-S-c-CA216* R = H, R1 = H, R2= CH2OH G-b-G-c-CA3065 R = H, R1 = OCH3, R2=CHO G-b-G-c-CAld3072 R = OCH3, R1 = H, R2= CH2OH S-b-G-c-CA
OCH3
OHOH
CH3O
H O
H
O
OCH3
OO
OCH3
HO
OH
OH HO
CH3O
O
OCH3
OH
OCH3
OH
HO
CH3O OCH3
HOOH
OO
CH3O
OCH3
OCH3
OH
H O
OH
O
O
H O
R
O
O
OAc
OCH3
OCH3
O
O
AcO
CH3O
CH3 O O
OAcOAc
O
OCH3
O
OCH3
OAc
CH3O
HO
O
HO
OCH3
OCH3
OH
O
O
HO
O
HO
OCH3
OCH3
OH
O
O
284, 289*
277, 278*
3062
3058
Trimers Cont'd
1011t,1012e (diacetates, phenolic)
1015t,1016e,1019t *,1020e *,82t *,83e *
(diacetates, phenolic)1013t,1014e1017t,1018e,1021t *,1022e *,76e*,75t *
xiv
Trimers Containing Ferulic or Coumaric Acid
20161010 R = OCH3
1009 R = H
O
H3CO O
OAc
AcO
AcO
OAc
OCH3
OCH3
299
R
HO
OO
O
OH
OCH3
OCH3
HO
R OCH3
O
AcO
AcO
AcO
OCH3
O
O
OCH3
O
O
AcO
OCH3
OCH3
OAc
O
OCH3
OH
CH3O
OHHO
O
O
HO
OCH3
CH3OO
R3
OCH3
O
OCH3
R1
OCH3
O
O
R2
O
OCH3
OH
O
CH3O
O
HO
OHO
OCH3 OCH3
CH3O
HOO
HO
O
CH3O
O
OH
OCH3
R1
AcO
O
O
CH3O
O
O
OAc
OCH3
OCH3
85, 86
1003t,1004e,1007t *,1008e * R = OCH3
1001t,1002e,1005t *,1006e *,78t *,77e * R = H
1025t,1026e,84e R = OCH3
1023t,1024e R = H
30663024 R1= OCH3, R2= OAc, R3= OCH3
3023 R1= OCH3, R2= OH, R3= OCH3
3022 R1=R2= OH, R3= OCH3
3021 R1= OCH3, R2= OAc, R3= H3020 R1= OCH3, R2= OH, R3= H
3019 R1=R2= OH, R3= H
2079t, 2080e (diacetate, phenolics)
2071t, 2072e, 2073t*, 2074e*
xv
More Trimers Containing Ferulic, Coumaric or p-OH-Benzoic Acid
2076t, 2078e 2075t*,2077e* 2068e, (diacetate, phenolic)
2066 R = H2081 R = OCH3
R2 R2
R1R1
OCH3OCH3
AcOOAc
O O
CH3O OCH3
OAcOAc
OH
OH
O
OH
OCH3
O
O
OH
OCH3
HO
HO
O
CH3O
OCH3
OCH3
OCH3
OH
OO
OH
O
O
OCH3
O
OCH3
OCH3
CH3O
O
OOAc
CH3O
OAc
OCH3
OCH3
OAc
OAcOAc
O
OH
OCH3
O
O
O
CH3O
O
OHOH
OH
OCH3
OCH3
OH
CH3OOH
OCH3
OCH3
OCH3
OHOH
O
O
O
CH3O
O
O
OH
CH3O
O
O
OH
OCH3
OH
OCH3CH3O
OH
CH3
O
CH3O
OH
CH3O
O
OCH3
OH
OCH3
CH3
3009 R1 = OAc, R2 = H224 R1 = H, R2 = OCH3
xvi
2060,2061*
2025e ,2059*
2023e 2017e,2024t*
164,165*
170,169*
Tetramers
194,197*
CH3O
OCH3
OH
OH
HO O
CH3O
H O
CH3
O
OO
O
CH3O
O CH3
O
O O
CH3O
CH3
CH3
OO
H O
CH3
CH3O
HO OCH3
OH
H
HH
O OO
CH3 O
OCH3R
OH
OH
O
O
O
O
OH
OCH3R
OH
OCH3
OH
O
O
OCH3
OH
HO
OCH3
HO
AcO
CH2OAc
O
OAc
OAc
O
O
R1 R2
HO
CH2OH
O
OH
OH
OH
O
OO
OCH3
OH
O
OH
OH
O
CH2OH
HO
OAc
OAc
OAc
O
AcO
O
OH
OHO
O
2063 R = H2064 R = OCH3
157 R1, R2 = H
119,121*R1, R2 = OCH3
118,120* R1 = H, R2 = OCH3
xvii
2053 2055
2047 2048
2050
2065 R = OCH3
20102009 R = H
2007
158*
Misc. Compounds
93
107
122, a &b30
OH
OCH3CH3O
S
S
OH
OCH3R1
S
S
R1 OCH3
OH
OCH3
HO OH
O
O
OCH3
OH
AcO
OAc
OCH3
O
OCH3
O
O
OCH3
OH
OO
OAc
OCH3
OH
O
OH
O
OCH3
OAc
O
O
OCH3
OAc
O
O
AcO
O
O
OCH3
OAc
O
O
OCH3
OH
O
O
OCH3
OAc
O
O
3046 R1 = OCH3
3049 R1 = H
3045 R1 = OCH3
3048 R1 = H3047
g
ba
g
bag
ba
3043, 3044*
3029
257256255
254
253
252
251
Misc. Compounds
xviii
OH
OCH3
298
O
OH
O
OH
OCH3
OH
OCH3
301
O
AcO
OCH3
OCH3
OAc
M. Mozuch #36/46/Ac21 mg
Notes:
1Compound Number
FPL/DFRC NMR Database -- April 2009
2,3-Diacetoxypropioveratrone2,3-diacetoxy-3',4'-dimethoxypropiophenone
13C
7471
9897
8498
10091
98
55
41
40
4836
48
20.6720.72
56.0556.15
63.2272.99
110.32110.64
123.33
127.41
149.31
154.16
170.21170.75
191.52
CDCl3
CS i
20.4920.58
56.1156.25
63.6474.14
111.60111.66
123.85
128.35
150.31
155.21
170.35170.88
192.03
7264
98100
9696
9192
98
38
30
30
3232
36
AcetoneCS i
20.3020.42
55.5155.77
62.6073.28
110.35111.03
123.02
126.67
148.72
153.72
169.61170.03
191.18
8887
95100
7185
7884
88
77
71
63
6756
66
CS i
DMSO
Ac MeAc Me
OMeOMe
γβ
25
6
1
3
4
Ac C=OAc C=O
α
Atom
1HJMultH Shifts
2.082.19
3.953.95
4.254.686.18
7.566.93
7.71
dddddd
ddd
dd
12.1, 7.912.1, 3.17.9, 3.1
8.42.0
8.4, 2.0
Ac MeAc Me
OMeOMe
γ1γ2β
A2A5
A6
Atom
(chloroform)
HO
OCH3
OCH3
OHO
OH
CH3
OCH3
CH3O
A
B
S. Ralph III-1260mg
Notes:
2Compound Number
FPL/DFRC NMR Database -- April 2009
1-(3,4-Dimethoxyphenyl)-2-[4-(1-hydroxyethyl)-2,6-dimethoxyphenoxy]propane-1,3-diol
13C
34
1001009999
29433937
6767
364134
3824
302929
6161
25.45
55.8755.8756.0856.08
60.4870.1173.9888.94
102.25102.25
110.28111.02119.80
132.56134.08
143.04148.73148.90
152.84152.84
CDCl3
CS i
26.23
55.9756.0356.4456.44
61.2669.9373.8989.58
103.30103.30
111.78112.18120.22
134.74135.39
144.54149.58149.86
153.52153.52
49
5851100100
38514547
8484
384742
3218
292225
4848
AcetoneCS i
25.86
55.3155.4355.8055.80
60.1368.1771.3687.10
102.50102.50
110.60111.08118.84
134.53134.53
143.01147.64148.03
152.20152.20
44
5253100100
25433231
5555
323234
6363
373134
6565
CS i
DMSO
B β
OMeOMe
B OMeB OMe
γB α
αβ
B2B6
A2A5A6
A1B1
B4A4A3
B3B5
Atom
1HJMultH Shifts
1.45
3.853.853.873.89
4.815.02
6.63
6.9
6.83
6.9
d
ssss
qd
s
m
d
m
6.4
6.48.7
8.7
B β
OMeOMeOMeOMe
B αα
B2,6
A2
A5
A6
Atom
(chloroform)
threo
M. Mozuch #36/46/Ac21 mg
Notes:
1Compound Number
FPL/DFRC NMR Database -- April 2009
2,3-Diacetoxypropioveratrone2,3-diacetoxy-3',4'-dimethoxypropiophenone
13C
7471
9897
8498
10091
98
55
41
40
4836
48
20.6720.72
56.0556.15
63.2272.99
110.32110.64
123.33
127.41
149.31
154.16
170.21170.75
191.52
CDCl3
CS i
20.4920.58
56.1156.25
63.6474.14
111.60111.66
123.85
128.35
150.31
155.21
170.35170.88
192.03
7264
98100
9696
9192
98
38
30
30
3232
36
Acetone
CS i
20.3020.42
55.5155.77
62.6073.28
110.35111.03
123.02
126.67
148.72
153.72
169.61170.03
191.18
8887
95100
7185
7884
88
77
71
63
6756
66
CS i
DMSO
Ac MeAc Me
OMeOMe
γβ
25
6
1
3
4
Ac C=OAc C=O
α
Atom
1HJMultH Shifts
2.082.19
3.953.95
4.254.686.18
7.566.93
7.71
dddddd
ddd
dd
12.1, 7.912.1, 3.17.9, 3.1
8.42.0
8.4, 2.0
Ac MeAc Me
OMeOMe
γ1γ2β
A2A5
A6
Atom
(chloroform)
S. Ralph III-1260mg
Notes:
2Compound Number
FPL/DFRC NMR Database -- April 2009
1-(3,4-Dimethoxyphenyl)-2-[4-(1-hydroxyethyl)-2,6-dimethoxyphenoxy]propane-1,3-diol
13C
34
1001009999
29433937
6767
364134
3824
302929
6161
25.45
55.8755.8756.0856.08
60.4870.1173.9888.94
102.25102.25
110.28111.02119.80
132.56134.08
143.04148.73148.90
152.84152.84
CDCl3
CS i
26.23
55.9756.0356.4456.44
61.2669.9373.8989.58
103.30103.30
111.78112.18120.22
134.74135.39
144.54149.58149.86
153.52153.52
49
5851100100
38514547
8484
384742
3218
292225
4848
Acetone
CS i
25.86
55.3155.4355.8055.80
60.1368.1771.3687.10
102.50102.50
110.60111.08118.84
134.53134.53
143.01147.64148.03
152.20152.20
44
5253100100
25433231
5555
323234
6363
373134
6565
CS i
DMSO
B β
OMeOMe
B OMeB OMe
γB α
αβ
B2B6
A2A5A6
A1B1
B4A4A3
B3B5
Atom
1HJMultH Shifts
1.45
3.853.853.873.89
4.815.02
6.63
6.9
6.83
6.9
d
ssss
qd
s
m
d
m
6.4
6.48.7
8.7
B β
OMeOMeOMeOMe
B αα
B2,6
A2
A5
A6
Atom
(chloroform)
threo
L. Landucci51mgthreo data in acetone γ 63.8 α 75.7 β 80.8
Notes:
3Compound Number
FPL/DFRC NMR Database -- April 2009
Veratrylglycerol-β-guaiacyl ether diacetate
1,3-diacetoxy-1-(3,4-dimethoxyphenyl)-2-(2-methoxyphenoxy)propane
13C
3438
55100100
384245
514544464448
463024262522
2421
20.7821.05
55.7855.8855.88
62.8274.1280.10
110.86110.89112.55119.18120.08120.93
123.41128.98147.32148.84149.09151.04
169.67170.75
CDCl3
CS i
20.6120.89
56.0256.0856.15
63.2374.7780.28
112.24112.24113.68119.51120.79121.56
123.82130.15148.36150.10150.29151.93
169.85170.71
3840
635754
444948
10010057525457
643120231920
2320
Acetone
CS i
20.4120.65
55.3855.3855.54
62.1073.3578.39
110.87111.27112.80117.70119.63120.62
122.70128.71146.74148.43148.65150.27
169.18170.00
2227
10010064
331741
203939363862
415850524756
4545
CS i
DMSO
Ac MeAc Me
OMeOMeOMe
γαβ
A2A5B2B5A6B6
B1A1B4A4A3B3
Ac C=OAc C=O
Atom
1HJMultH Shifts
2.032.07
3.793.833.86
4.234.43
6.03
4.71
ss
sss
dddd
d
m
11.0, 4.011.9, 5.9
5.3
Ac MeAc Me
OMeOMeOMe
γ1γ2
α
β
Atom
(chloroform)
erythro
J. Ralph: JR A91.1150mgNot very soluble in CDCL3
Notes:
4Compound Number
FPL/DFRC NMR Database -- April 2009
p-Hydroxybenzyl alcohol4-hydroxybenzyl alcohol
13CCDCl3
CS i
64.54
115.69115.69
129.05129.05
133.96
157.23
34
9999
100100
13
18
Acetone
CS i
62.68
114.66114.66
127.92127.92
132.61
156.03
43
100100
100100
31
35
CS i
DMSO
α
35
26
1
4
Atom
1HJMultH Shifts
4.62
6.82
7.22
s
m
m
α
3,5
2,6
Atom
(chloroform)
J. Ralph: JR A91.1450mg
Notes:
5Compound Number
FPL/DFRC NMR Database -- April 2009
3,4-Dimethoxybenzyl alcohol3,4-dimethoxybenzyl alcohol
13C
10084
79
86
96
95
38
25
27
55.7855.90
65.04
110.45
111.04
119.33
133.66
148.43
149.00
CDCl3
CS i
55.9356.11
64.58
111.69
112.54
119.62
135.95
149.32
150.19
10097
70
82
88
78
21
16
18
Acetone
CS i
55.2755.47
62.79
110.51
111.48
118.50
135.03
147.60
148.54
10094
88
74
73
81
58
36
41
CS i
DMSO
OMeOMe
α
2
5
6
1
4
3
Atom
1HJMultH Shifts
3.853.85
4.56
6.82
6.86
6.86
ss
s
m
m
m
OMeOMe
α
2
5
6
Atom
(chloroform)
J.Ralph: JR A95.1150mg
Notes:
6Compound Number
FPL/DFRC NMR Database -- April 2009
p-Hydroxyacetophenone4-hydroxyacetophenone
13C
51
100100
17
9797
19
12
26.28
115.66115.66
129.16
131.35131.35
161.90
199.32
CDCl3
CS i
26.25
115.89115.89
130.38
131.48131.48
162.54
196.40
39
9898
11
100100
20
93
Acetone
CS i
26.16
115.11115.11
128.56
130.64130.64
161.98
195.89
39
100100
23
9191
35
21
CS i
DMSO
β
35
1
26
4
α
Atom
1HJMultH Shifts
2.60
7.92
7.00
s
m
m
8.8
8.8
β
3,5
2,6
Atom
(chloroform)
J. Ralph: JR A95.1250mg
Notes:
7Compound Number
FPL/DFRC NMR Database -- April 2009
Acetovanillone4-hydroxy-3-methoxyacetophenone
13C
82
81
62
85
100
20
29
34
23
26.16
56.01
109.89
113.97
124.06
130.02
146.77
150.66
197.14
CDCl3
CS i
26.22
56.17
111.40
115.26
124.22
130.65
148.16
152.12
196.30
74
91
65
85
100
22
23
28
19
Acetone
CS i
26.14
55.52
111.04
114.85
123.34
128.84
147.45
151.65
195.98
77
92
76
100
98
59
61
82
57
CS i
DMSO
β
OMe
2
5
6
1
3
4
α
Atom
1HJMultH Shifts
2.56
3.91
7.53
6.95
7.53
s
s
m
d
m
8.7
β
OMe
2
5
6
Atom
(chloroform)
J. Ralph: JR A95.1346mg
Notes:
8Compound Number
FPL/DFRC NMR Database -- April 2009
Acetosyringone3,5-dimethoxy-4-hydroxyacetophenone
13C
44
100100
9090
22
21
4141
16
26.21
56.4556.45
105.81105.81
128.21
139.89
146.79146.79
196.64
CDCl3
CS i
26.30
56.6356.63
106.97106.97
129.13
141.75
148.29148.29
196.31
41
100100
8484
16
16
3434
14
Acetone
CS i
26.22
56.0256.02
106.13106.13
127.33
140.86
147.44147.44
196.06
45
100100
8484
29
29
6565
30
CS i
DMSO
β
OMeOMe
26
1
4
35
α
Atom
1HJMultH Shifts
2.57
3.943.94
7.24
s
ss
s
β
OMeOMe
2,6
Atom
(chloroform)
J. Ralph: JR A95.1455mg
Notes:
9Compound Number
FPL/DFRC NMR Database -- April 2009
Acetoveratrone3,4-dimethoxyacetophenone
13C
63
92100
86
70
95
30
26
27
23
26.17
55.9556.04
109.99
110.09
123.27
130.48
148.99
153.30
196.70
CDCl3
CS i
26.25
55.9656.10
111.17
111.30
123.73
131.24
150.00
154.38
196.34
72
91100
56
77
94
17
17
17
17
Acetone
CS i
26.23
55.4355.68
110.17
110.74
123.04
129.88
148.55
153.06
196.22
78
10090
91
87
98
55
41
43
33
CS i
DMSO
β
OMeOMe
2
5
6
1
3
4
α
Atom
1HJMultH Shifts
2.56
3.933.94
7.52
6.90
7.57
s
ss
d
d
dd
2.0
8.4
8.4, 2.0
β
OMeOMe
2
5
6
Atom
(chloroform)
J. Ralph: JR A97.1134mg Almost insoluble in CDCl3
Notes:
10Compound Number
FPL/DFRC NMR Database -- April 2009
1-(4-Hydroxyphenyl)ethanol1-(4-hydroxyphenyl)ethanol
13C
100100
9595
115.28115.28
126.91126.91
CDCl3
CS i
26.10
69.61
115.55115.55
127.31127.31
138.90
156.98
54
28
8989
100100
12
15
Acetone
CS i
25.83
67.70
114.54114.54
126.31126.31
137.56
155.86
91
101
180180
180180
61
75
CS i
DMSO
β
α
35
26
1
4
Atom
1HJMultH Shifts
1.48
4.85
6.81
7.25
d
q
m
m
6.5
6.5
8.6
8.6
β
α
3,5
2,6
Atom
(chloroform)
J. Ralph: JR A97.12Notes:
11Compound Number
FPL/DFRC NMR Database -- April 2009
Apocynol1-(4-hydroxy-3-methoxyphenyl)ethanol
13C
95
99
89
80
94
100
40
32
33
25.07
55.88
70.30
108.05
114.20
118.31
137.91
144.96
146.62
CDCl3
CS i
26.22
56.09
69.81
109.76
115.21
118.65
139.67
146.13
147.97
87
87
78
76
87
100
31
31
22
Acetone
CS i
25.88
55.42
67.89
109.54
114.80
117.47
138.35
144.98
147.11
78
98
100
71
82
77
64
69
52
CS i
DMSO
β
OMe
α
2
5
6
1
4
3
Atom
1HJMultH Shifts
1.46
3.87
4.81
6.81
6.91
6.84
d
s
q
m
m
m
6.5
β Me
OMe
α
5
2
6
Atom
(chloroform)
J. Ralph: JR A97.13Notes:
12Compound Number
FPL/DFRC NMR Database -- April 2009
1-(4-Hydroxy-3,5-dimethoxyphenyl)ethanol1-(4-hydroxy-3,5-dimethoxyphenyl)ethanol
13C
52
100100
51
9494
22
32
4343
25.22
56.2556.25
70.50
102.15102.15
133.90
137.22
147.01147.01
CDCl3
CS i
26.28
56.4956.49
70.07
103.61103.61
135.46
138.70
148.36148.36
45
100100
43
8787
14
20
2424
Acetone
CS i
25.94
55.7955.79
68.16
102.65102.65
133.93
137.53
147.56147.56
56
100100
62
8585
35
39
7575
CS i
DMSO
β
OMeOMe
α
26
1
4
35
Atom
1HJMultH Shifts
1.46
3.853.85
4.79
6.58
d
ss
q
6.4
6.4
β
OMeOMe
α
2,6
Atom
(chloroform)
J. Ralph: JR A97.14Notes:
13Compound Number
FPL/DFRC NMR Database -- April 2009
1-(3,4-Dimethoxyphenyl)ethanol1-(3,4-dimethoxyphenyl)ethanol
13C
99
9487
94
67
78
100
40
27
28
25.12
55.8055.91
70.08
108.68
110.98
117.50
138.65
148.26
148.99
CDCl3
CS i
26.25
55.9956.15
69.72
110.38
112.56
118.18
140.97
149.17
150.14
92
10089
86
59
62
95
19
14
11
Acetone
CS i
25.92
55.2955.48
67.82
109.24
111.43
117.10
139.99
147.40
148.43
88
9994
100
72
82
85
62
39
45
CS i
DMSO
β
OMeOMe
α
2
5
6
1
4
3
Atom
1HJMultH Shifts
1.46
3.853.87
4.81
6.82
6.85
6.92
d
ss
q
d
6.4
6.4
1.7
β
OMeOMe
α
5
6
2
Atom
(chloroform)
J. Ralph: JR A87.1152mg
Notes:
14Compound Number
FPL/DFRC NMR Database -- April 2009
p-Hydroxybenzaldehyde4-hydroxybenzaldehyde
13C
100100
14
9797
19
39
116.01116.01
129.81
132.54132.54
161.65
191.28
CDCl3
CS i
116.62116.62
130.34
132.77132.77
163.80
191.02
100100
11
8585
15
35
Acetone
CS i
115.80115.80
128.40
132.04132.04
163.28
190.80
100100
25
8383
31
42
CS i
DMSO
35
1
26
4
α
Atom
1HJMultH Shifts
7.00
7.82
9.85
7.00
7.79
9.84
9.40
m
m
s
8.6
8.6
3,5
2,6
α
acetone
3,5
2,6
α
OH
Atom
(chloroform)
J. Ralph: JR A87.1266mg
Notes:
15Compound Number
FPL/DFRC NMR Database -- April 2009
Vanillin4-hydroxy-3-methoxybenzaldehyde
13C
100
50
67
89
22
20
20
47
56.07
109.02
114.59
127.57
129.70
147.34
151.99
191.16
CDCl3
CS i
56.24
110.82
115.87
126.98
130.62
148.86
153.45
191.07
100
72
97
83
29
23
32
85
Acetone
CS i
55.52
110.63
115.36
126.04
128.70
148.12
153.00
190.89
100
69
100
81
64
53
61
82
CS i
DMSO
OMe
2
5
6
1
3
4
α
Atom
1HJMultH Shifts
3.92
7.417.047.44
9.81
3.91
7.467.007.43
9.81
8.30
s
mdm
s
s
ddm
s
bs
8.6
1.88.6
OMe
256
α
acetone
OMe
256
α
OH
Atom
(chloroform)
J. Ralph: JR A91.1320mg Almost insoluble in acetone.
Notes:
16Compound Number
FPL/DFRC NMR Database -- April 2009
Syringyl alcohol4-hydroxy-3,5-dimethoxybenzyl alcohol
13C
100100
39
8282
21
15
3535
56.2956.29
65.68
103.88103.88
132.06
134.19
147.10147.10
CDCl3
CS i
56.5456.54
64.98
105.08105.08
133.80
135.75
148.54148.54
100100
26
7575
12
9
2323
Acetone
CS i
55.7755.77
63.09
103.91103.91
132.48
134.03
147.67147.67
100100
40
7272
26
26
5252
CS i
DMSO
OMeOMe
α
26
1
4
35
Atom
1HJMultH Shifts
3.883.88
4.60
6.60
3.793.79
4.074.50
6.637.08
s
s
ss
btbd
sbs
OMeOMe
α
2,6
acetone
OMeOMe
OH-αα
2,6ph-OH
Atom
(chloroform)
L. Landucci53mg
Notes:
17Compound Number
FPL/DFRC NMR Database -- April 2009
Methyl 4-acetoxybenzoate4-acetoxybenzoic acid methyl ester
13C
29
38
9494
14
100100
14
10
11
21.12
52.16
121.60121.60
127.70
131.14131.14
154.30
166.25
168.79
CDCl3
CS i
20.97
52.37
122.82122.82
128.46
131.60131.60
155.56
166.47
169.23
37
44
100100
13
100100
14
11
11
Acetone
CS i
20.82
52.13
122.21122.21
127.08
130.70130.70
154.20
165.49
168.72
50
50
9292
21
100100
25
17
20
CS i
DMSO
Ac Me
OMe
35
1
26
4
α
Ac C=0
Atom
1HJMultH Shifts
2.30
3.90
7.16
8.06
s
s
m
m
8.9
8.9
Ac Me
OMe
3,5
2,6
Atom
(chloroform)
Aldrich62mg
Notes:
18Compound Number
FPL/DFRC NMR Database -- April 2009
Methyl 4-hydroxybenzoate4-hydroxybenzoic acid methyl ester
13C
43
9797
15
100100
23
10
52.12
115.31115.31
122.22
131.97131.97
160.36
167.53
CDCl3
CS i
51.86
116.00116.00
122.33
132.37132.37
162.58
167.07
29
100100
12
8383
25
5
Acetone
CS i
51.55
115.31115.31
120.29
131.40131.40
161.97
166.05
32
100100
15
100100
24
14
CS i
DMSO
OMe
35
1
26
4
α
Atom
1HJMultH Shifts
3.90
6.89
7.95
s
m
m
8.9
8.9
OMe
3,5
2,6
Atom
(chloroform)
Aldrich54mg
Notes:
19Compound Number
FPL/DFRC NMR Database -- April 2009
4-Hydroxy-3-methoxybenzyl alcohol4-hydroxy-3-methoxybenzyl alcohol
13C
100
79
90
92
100
31
33
23
55.90
65.44
109.94
114.27
120.22
132.93
145.26
146.65
CDCl3
CS i
56.11
64.76
111.37
115.37
120.29
134.62
146.37
148.10
100
76
78
87
95
33
31
25
Acetone
CS i
55.38
62.93
110.91
114.93
119.00
133.37
145.17
147.24
100
95
72
83
93
62
64
49
CS i
DMSO
OMe
α
2
5
6
1
4
3
Atom
1HJMultH Shifts
3.89
4.60
s
s
OMe
α
Atom
(chloroform)
Aldrich52mg
Notes:
20Compound Number
FPL/DFRC NMR Database -- April 2009
p-Anisic acid4-methoxybenzoic acid
13C
45
9797
11
100100
18
16
55.48
113.75113.75
121.67
132.35132.35
164.04
171.45
CDCl3
CS i
55.86
114.50114.50
123.67
132.48132.48
164.39
167.54
46
8888
12
100100
13
13
Acetone
CS i
55.36
113.74113.74
122.97
131.32131.32
162.80
167.00
51
9999
22
100100
26
29
CS i
DMSO
OMe
35
1
26
4
α
Atom
1HJMultH Shifts
3.89
6.96
8.07
s
m
m
9.0
9.0
OMe
3,5
2,6
Atom
(chloroform)
Has acetyl piperidine in sample.J. Ralph JRA127.P127mg γ - protons coupled to OH's, shifts not determined.
Notes:
21Compound Number
FPL/DFRC NMR Database -- April 2009
�2-(2,6-Dimethoxyphenoxy)-3-hydroxy-1-(4-hydroxy-3,5-dimethoxyphenyl)propan-1-one
13C
1001008686
39
48
8888
8282
49
30
18
29
5858
4949
28
55.9755.9756.4956.49
63.48
87.16
105.27105.27
106.35106.35
124.34
126.98
136.46
140.05
146.79146.79
152.73152.73
194.84
CDCl3
CS i
56.3556.3556.7156.71
63.66
86.21
106.32106.32
107.69107.69
124.78
127.86
137.37
141.99
148.31148.31
153.86153.86
195.15
9292100100
47
51
9191
6363
46
23
10
14
3737
3838
20
Acetone
CS i
55.7355.7355.9755.97
61.95
82.80
105.46105.46
106.56106.56
123.51
126.22
135.80
140.92
147.30147.30
152.43152.43
194.71
1001009898
34
31
8181
6363
37
35
27
37
6868
7373
35
CS i
DMSO
OMeOMeOMeOMe
γ
β
B2B6
A2A6
B1
A1
B4
A4
A3A5
B3B5
α
Atom
1HJMultH Shifts
3.743.92
5.10
7.42
6.59
7.03
ss
dd
s
d
t
6.4, 2.7
8.4
8.4
OMeOMe
β
A2,6
B2,6
B1
Atom
(chloroform)
J. Ralph JRA127.P223mg
Notes:
22Compound Number
FPL/DFRC NMR Database -- April 2009
�2-(2,6-Dimethoxyphenoxy)-1-(4-hydroxy-3,5-dimethoxyphenyl)ethanone
13C
1001009898
41
8989
8484
48
25
11
22
4848
4242
24
56.0956.0956.4856.48
75.45
105.33105.33
106.07106.07
124.20
126.68
136.48
139.89
146.74146.74
153.30153.30
193.61
CDCl3
CS i
56.4256.4256.7256.72
75.90
106.47106.47
107.45107.45
124.87
127.09
137.55
142.15
148.39148.39
154.43154.43
193.69
1001009494
47
9898
9797
53
19
11
13
2727
3232
23
Acetone
CS i
55.8255.8256.0356.03
74.39
105.52105.52
105.97105.97
123.84
124.92
135.85
141.14
147.50147.50
152.85152.85
192.75
1001009898
30
8080
6363
35
34
21
33
7171
6161
29
CS i
DMSO
B OMeB OMeA OMeA OMe
β
B2B6
A2A6
B1
A1
B4
A4
A3A5
B3B5
α
Atom
1HJMultH Shifts
3.823.94
5.11
7.43
6.59
7.03
ss
s
s
d
t
8.4
8.4
OMeOMe
β
A2,6
B2,6
B1
Atom
(chloroform)
J. Ralph JRA93.522mg
Notes:
23Compound Number
FPL/DFRC NMR Database -- April 2009
Hydroxyphenylethanol diacetate1-acetoxy-1-(4-acetoxyphenyl)ethane
13C
3328
41
42
100100
100100
18
15
14
13
21.1021.30
22.14
71.68
121.57121.57
127.31127.31
139.18
150.16
169.41
170.21
CDCl3
CS i
20.9121.08
22.48
72.03
122.53122.53
127.84127.84
140.39
151.29
169.58
170.16
3931
55
51
9999
100100
18
14
14
11
Acetone
CS i
20.7420.89
21.95
71.01
121.70121.70
126.99126.99
139.13
149.79
169.11
169.54
4540
46
53
100100
9696
31
25
16
15
CS i
DMSO
Ac MeAc Me
β
α
35
26
1
4
A4 Ac C=O
α Ac C=O
Atom
1HJMultH Shifts
2.012.24
1.48
5.84
7.09
7.40
ss
d
q
m
m
6.6
6.6
8.6
8.6
Ac MeAc Me
β
α
3,5
2,6
Atom
(acetone)
S. Ralph SRIII-2052mg
Notes:
24Compound Number
FPL/DFRC NMR Database -- April 2009
p-Hydroxybenzyl alcohol diacetate4-acetoxybenzyl acetate
13C
2431
38
100100
9797
22
16
15
11
20.9521.08
65.58
121.70121.70
129.50129.50
133.56
150.53
169.31
170.72
CDCl3
CS i
20.7620.92
65.80
122.59122.59
130.02130.02
134.84
151.60
169.53
170.77
2535
40
100100
9393
18
12
7
6
Acetone
CS i
20.6220.75
64.83
121.78121.78
129.25129.25
133.67
150.15
169.08
170.14
3240
37
9494
100100
29
21
18
12
CS i
DMSO
Ac MeAc Me
α
35
26
1
4
A4 Ac C=O
α Ac C=O
Atom
1HJMultH Shifts
2.082.29
5.08
7.08
7.37
ss
s
m
m
8.6
Ac MeAc Me
α
3,5
2,6
Atom
(chloroform)
S. Ralph SRIII-2150mg
Notes:
25Compound Number
FPL/DFRC NMR Database -- April 2009
Methyl-p-anisatemethyl 4-methoxybenzoate
13C
31
41
100100
10
8181
13
8
51.82
55.39
113.59113.59
122.60
131.57131.57
163.33
166.82
CDCl3
CS i
51.94
55.83
114.51114.51
123.36
132.12132.12
164.35
166.84
32
50
9898
9
100100
11
6
Acetone
CS i
51.73
55.45
113.95113.95
121.88
131.20131.20
163.12
165.88
48
44
100100
16
9393
18
14
CS i
DMSO
4 OMe
α OMe
35
1
26
4
α
Atom
1HJMultH Shifts
3.83
3.86
6.89
7.99
s
s
m
m
8.8
8.8
4 OMe
α OMe
3,5
2,6
Atom
(chloroform)
J. Ralph GV 49.125mg
Notes:
26Compound Number
FPL/DFRC NMR Database -- April 2009
1-(4-acetoxy-3,5-dimethoxyphenyl)-2-(2,6-dmethoxyphenoxy)ethanone
13C
37
9393100100
39
9090
9090
49
30
30
14
5252
4343
23
28
20.42
56.0856.0856.3756.37
75.54
105.35105.35
105.54105.54
124.26
133.12
133.12
136.45
152.26152.26
153.27153.27
168.11
194.03
CDCl3
CS i
20.23
56.4456.4456.7156.71
75.99
106.34106.34
106.50106.50
124.95
133.94
134.21
137.50
153.30153.30
154.36154.36
168.15
194.58
35
1001009898
39
9494
9696
50
7
19
11
3333
3131
16
24
Acetone
CS i
20.02
55.8255.8256.1856.18
74.59
104.87104.87
105.53105.53
123.88
132.10
132.64
135.81
151.80151.80
152.74152.74
167.60
193.75
40
100100100100
32
8080
9494
45
24
38
28
7272
6969
32
40
CS i
DMSO
Ac Me
B OMeB OMeA OMeA OMe
β
B2B6
A2A6
B1
A1
A4
B4
A3A5
B3B5
Ac C=0
α
Atom
1HJMultH Shifts
2.34
3.80
3.87
5.13
7.40
6.58
7.02
s
s
s
s
s
d
t
8.4
8.4
Αχ Με
Β ΟΜε
Α ΟΜε
β
Α2,6
Β2,6
Β1
Atom
(chloroform)
J. Ralph GV 35.125mg
Notes:
27Compound Number
FPL/DFRC NMR Database -- April 2009
1-(4-acetoxy-3,5-dimethoxyphenyl)-2-(2-methoxyphenoxy)ethanone
13C
41
47
100100
35
8484
48495149
12271617
4949
20
25
20.41
55.85
56.3456.34
72.53
105.25105.25
112.26114.95120.89122.64
133.41132.58147.37149.79
152.41152.41
168.06
193.77
CDCl3
CS i
20.23
56.25
56.7356.73
72.65
105.90105.90
113.68115.73121.56122.80
134.14133.81148.96150.90
153.45153.45
168.14
194.35
36
48
9292
40
100100
56485656
8201616
3636
20
20
Acetone
CS i
20.03
55.51
56.2456.24
70.85
104.78104.78
112.48113.80120.45121.37
132.32132.38147.33148.96
151.90151.90
167.59
193.70
47
60
100100
32
8484
44394843
17393429
7474
35
42
CS i
DMSO
Ac Me
B OMe
A OMeA OMe
β
A2A6
B2B5B6B1
A1A4B3B4
A3A5
Ac C=0
α
Atom
1HJMultH Shifts
2.35
3.87
3.87
5.26
7.34
s
s
s
s
s
Ac Me
B OMe
A OMe
β
A2,6
Atom
(chloroform)
J. Ralph KM 77.125mg contains impurities As this compound has a plane of symmetry the shifts forthe other half are identical.
Notes:
28Compound Number
FPL/DFRC NMR Database -- April 2009
Dehydrodivanillin6,6'-Dihydroxy-5,5'-dimethoxybiphenyl-3,3'-dicarbaldehyde
13CCDCl3
CS i
Acetone
CS i
55.94
109.08
124.54
127.61
128.05
148.12
152.93
190.97
100
53
47
75
53
59
16
72
CS i
DMSO
OMe
2
6
5
1
4
3
α
Atom
1HJMultH Shifts
3.94
7.44
7.44
9.81
3.95
7.42
7.55
9.84
s
s
s
s
s
d
d
s
J = 1.84
J = 1.84
OMe
2
6
α
Acetone
OMe
2
6
α
Atom
(DMSO)
S. Ralph III-1465mg sample has impuritiesγ1 proton hidden by OMe's
Notes:
29Compound Number
FPL/DFRC NMR Database -- April 2009
Veratrylglycerol-β-syringol ether triacetate
1,3-diacetoxy-1-(3,4-dimethoxyphenyl)-2-(4-(1-acetoxyethyl)-2,6-dimethoxyphenoxy)propane
13C
413234
34
6361100100
26294546
7777284549
40144135336060
222431
20.7521.0121.34
22.22
55.8855.9756.0856.08
63.8472.3876.0180.76
103.29103.29110.70111.02119.92
129.64136.22137.37148.89149.10152.88152.88
169.76170.15170.57
CDCl3
CS i
20.6220.9621.14
22.58
56.0256.0256.3356.33
64.4372.7076.6981.52
103.91103.91112.03112.31120.59
130.68137.06138.53150.05150.25153.68153.68
169.78170.14170.59
515241
52
7171100100
48495152
8686445148
32192529225151
251924
Acetone
CS i
20.3620.6220.96
22.03
55.4355.5055.8055.80
63.3671.7075.6580.30
102.90102.90110.80111.51119.58
129.28135.43137.28148.53148.74152.27152.27
169.11169.52169.89
403538
27
5258100100
21332226
5050293130
39223346386666
373440
CS i
DMSO
Ac MeAc MeAc Me
B β
A OMeA OMeB OMeB OMe
γB α
αβ
B2B6A2A5A6
A1B1B4A3A4B3B5
Ac C=0Ac C=OAc C=O
Atom
1HJMultH Shifts
1.922.002.07
1.513.863.863.80
-4.295.796.114.59
6.556.946.816.95
sss
dsss
-ddqdm
smdm
6.6
11.7, 3.66.67.1
8.8
Ac MeAc MeAc Me
B βOMeOMe
B OMe
γ1γ2
B ααβ
B2,6A2A5A6
Atom
(chloroform)
threo
IPC Xylan 79-760mg 147- Quantitative run 148- Run at 363Kshifts at 58.94 and 101.14 are for end groups
Notes:
30Compound Number
FPL/DFRC NMR Database -- April 2009
XylanXylan,Birch
13CCDCl3
CS i
Acetone
CS i
58.94
63.09
72.56
73.83
75.40
101.14
101.65
35
73
96
92
92
54
100
CS i
DMSOAtom
1HJMultH ShiftsAtom
(DMSO)
S. Ralph SR111-7 28mgNotes:
31Compound Number
FPL/DFRC NMR Database -- April 2009
1-(3,4-Dimethoxyphenyl)-2-[4-(1-hydroxyethyl) phenoxy] propane-1,3-diol
13C
34
8888
32342734
3434
8888
41
100100
2729
2729
29
25.03
55.8855.88
61.0669.7473.4782.92
110.00111.00
116.35116.35
119.26
126.84126.84
132.46139.26
148.81148.98
157.45
61.46
73.88
82.00
CDCl3
CS i
26.15
55.9956.04
61.6069.4873.1884.04
111.73112.18
116.61116.61
119.84
127.14127.14
135.41140.44
149.53149.91
158.87
61.94
73.81
83.67
33
4141
37334141
3733
9090
43
100100
2420
1212
20
Acetone
CS i
25.81
55.3055.40
59.9267.5770.7782.98
110.57111.17
115.34115.34
118.62
126.15126.15
134.78139.27
147.69148.13
157.62
59.92
71.37
82.98
39
4444
24444134
4134
9393
39
100100
4429
2929
49
CS i
DMSO
B β
OMeOMe
γB α
α
β
A2A5
B3B5
A6
B2B6
A1B1
A3A4
B4
erythro isomer
γ
α
β
Atom
1HJMultH Shifts
1.28
3.713.71
5.36
d
ss
d 5.1
B β
OMeOMe
α
Atom
(DMSO)
threo
S. Ralph SR III-17AC28mg
Notes:
32Compound Number
FPL/DFRC NMR Database -- April 2009
1,3-diacetoxy-1-(3,4-dimethoxyphenyl)-2-[4-(1-acetoxyethyl)phenoxy] propane
13C
354339
38
5849
42222041
3842848439100100
3227272320
261824
20.6921.0421.35
22.01
55.9155.99
62.9171.8674.3478.43
110.51111.20116.40116.40119.92127.62127.62
128.58135.13149.10149.41158.17
169.81170.27170.55
62.59
73.95
78.43
CDCl3
CS i
20.5620.8921.13
22.35
56.0656.17
63.4672.1775.3579.30
112.16112.54117.10117.10120.84128.22128.22
130.00136.10150.34150.61159.27
169.90170.11170.58
63.11
74.41
78.93
263428
38
5456
30383434
3338676749100100
2520181620
161616
Acetone
CS i
20.3820.6420.93
21.78
55.4155.51
62.3271.1474.2577.67
110.85111.52115.98115.98119.82127.29127.29
128.62134.59148.60148.87157.76
169.28169.51169.92
61.88
72.92
76.96
676469
51
8272
28494139
4138100100419595
4444464441
414638
CS i
DMSO
Ac MeAc MeAc Me
B β
OMeOMe
γB α
αβ
A2A5B3B5A6B2B6
A1B1A3A4B4
Ac C=0Ac C=OAc C=O
erythro isomer:
γ
α
β
Atom
1HJMultH Shifts
2.032.032.05
1.51
3.873.87
4.004.24
5.846.024.70
sss
d
ss
dddd
qdm
6.6
11.8, 6.211.9, 4.0
6.66.6
Ac MeAc MeAc Me
B β
OMeOMe
γ1γ2
B ααβ
Atom
(chloroform)
threo
S. Ralph SR III-15AC35mg
Notes:
33Compound Number
FPL/DFRC NMR Database -- April 2009
1,3-diacetoxy-1-(3,4-dimethoxyphenyl)-2-[4-(1-acetoxyethyl)-2-methoxyphenoxy] propane
13C
404145
44
97100100
32413340
352941404742
453118292723
262127
20.7121.0521.35
22.09
55.9155.9555.95
63.2672.0674.8780.44
110.58110.75111.12118.23118.66119.88
128.93136.59147.72149.04149.30150.65
170.54170.23169.76
62.74
74.08
79.98
CDCl3
CS i
20.5920.9521.14
22.45
56.0656.1456.32
63.8072.3975.6780.88
111.79112.17112.49118.74119.19120.73
130.22137.61148.68150.28150.51151.56
169.88170.14170.59
63.25
74.76
80.23
645248
70
1007679
61766470
706473677676
554536333930
303036
Acetone
CS i
20.3620.6420.94
21.87
55.4155.4655.66
62.6171.3674.5479.23
110.64110.84111.48117.02118.08119.74
128.75135.92147.12148.57148.83149.86
169.22169.52169.91
62.04
73.25
78.29
705577
45
1005768
29543636
343839394339
453636464338
394145
CS i
DMSO
Ac MeAc MeAc Me
B β
OMeOMeOMe
γB α
αβ
B2A2A5B5B6A6
A1B1B4A3A4B3
Ac C=OAc C=OAc C=O
erythro isomer:
γ
α
β
Atom
1HJMultH Shifts
2.002.022.06
1.52
3.853.863.87
4.273.99
4.826.074.63
sss
d
sss
dddd
qdm
6.5
11.9, 4.011.9, 5.8
6.56.7
Ac MeAc MeAc Me
B β
OMeOMeOMe
γ2γ1
B ααβ
Atom
(chloroform)
threo
S. Ralph SR III-1528mg
Notes:
34Compound Number
FPL/DFRC NMR Database -- April 2009
1-(3,4-dimethoxyphenyl)-2-[4-(1-hydroxyethyl)-2-methoxyphenoxy] propane-1,3-diol
13C
35
100100100
28383219
283238323417
26
21
21222515
25.22
55.9255.9255.92
61.0869.9873.8489.01
109.33110.03111.10118.40119.56120.22
132.23
141.94
146.76148.90149.08151.00
60.82
72.78
87.01
CDCl3
CS i
26.10
55.9356.0156.17
61.6869.6673.6288.12
110.46111.67112.14118.58119.22119.99
134.87
142.61
148.03149.54149.87151.20
61.68
73.62
86.50
95
1009088
67906752
606771645269
40
33
36333633
Acetone
CS i
25.83
55.2055.4155.52
59.9667.7970.7284.56
109.79110.65111.08115.57117.24118.59
134.50
140.50
146.78147.68148.07149.33
59.96
71.51
83.82
91
9283100
55865038
444771356256
58
61
56557964
CS i
DMSO
B β
OMeOMeOMe
γB α
αβ
B2A2A5B5B6A6
A1
B1
B4A3A4B3
erythro isomer:
γ
α
b
Atom
1HJMultH Shifts
1.46
3.863.863.86
4.834.944.01
3.463.60
d
sss
qdm
mmdd
6.4
6.47.7
B β
OMeOMeOMe
B ααβ
γ1γ2
Atom
(chloroform)
threo
J. Obst35mg
Notes:
35Compound Number
FPL/DFRC NMR Database -- April 2009
Dihydroferulic Acid3-(4-hydroxy-3-methoxyphenyl)propanoic acid
13C
96
88
96
96
100
95
44
51
37
40
30.38
36.01
55.92
111.10
114.52
120.89
132.15
144.16
146.55
178.88
CDCl3
CS i
31.24
36.38
56.22
112.81
115.64
121.47
133.23
145.76
148.17
174.26
100
95
94
91
85
93
36
36
25
18
Acetone
CS i
30.00
35.68
55.52
112.52
115.25
120.21
131.62
144.68
147.34
173.77
93
100
96
82
98
95
67
73
60
61
CS i
DMSO
α
β
OMe
2
5
6
1
4
3
γ
Atom
1HJMultH Shifts
2.64
2.88
3.84
6.71
6.82
6.69
t
t
s
m
d
m
7.4
7.4
7.6
α
β
OMe
2
5
6
Atom
(chloroform)
Aldrich57mg
Notes:
36Compound Number
FPL/DFRC NMR Database -- April 2009
4-Methoxyacetophenone4-methoxyacetophenone
13C
30
60
8686
15
100100
11
12
26.28
55.43
113.68113.68
130.35
130.55130.55
163.48
196.62
CDCl3
CS i
26.33
55.85
114.45114.45
131.28
131.18131.18
164.31
196.23
31
47
9595
12
100100
11
8
Acetone
CS i
26.29
55.44
113.75113.75
129.89
130.40130.40
163.06
196.14
34
50
100100
18
9797
20
14
CS i
DMSO
β
OMe
35
1
26
4
α
Atom
1HJMultH Shifts
2.53
3.85
6.90
7.90
s
s
m
m
8.8
8.8
β
OMe
3,5
2,6
Atom
(chloroform)
Aldrich65mg
Notes:
37Compound Number
FPL/DFRC NMR Database -- April 2009
p-Methoxybenzyl alcohol4-methoxybenzyl alcohol
13C
49
35
100100
9797
16
13
55.23
64.68
113.87113.87
128.56128.56
133.21
159.05
CDCl3
CS i
55.39
64.34
114.27114.27
128.82128.82
135.23
159.64
58
45
100100
9292
13
12
Acetone
CS i
54.94
62.59
113.40113.40
127.86127.86
134.49
158.14
56
46
100100
9999
27
19
CS i
DMSO
OMe
α
35
26
1
4
Atom
1HJMultH Shifts
3.75
4.51
6.86
7.20
s
s
m
m
8.7
8.7
OMe
α
3,5
2,6
Atom
(chloroform)
Aldrich JR 85-1154mg
Notes:
38Compound Number
FPL/DFRC NMR Database -- April 2009
Phenolphenol
13C
100100
47
8585
18
115.41115.41
120.89
129.71129.71
155.25
CDCl3
CS i
116.03116.03
120.13
130.16130.16
158.16
100100
54
9494
15
Acetone
CS i
115.18115.18
118.70
129.26129.26
157.29
100100
49
8989
23
CS i
DMSO
35
1
26
4
Atom
1HJMultH Shifts
6.84
6.93
7.22
m
m
m
3,5
1
2,6
Atom
(chloroform)
Aldrich JR A85.1254mg
Notes:
39Compound Number
FPL/DFRC NMR Database -- April 2009
Guaiacol2-methoxyphenol
13C
100
95
83
94
85
21
17
55.86
110.81
114.60
120.15
121.47
145.70
146.63
CDCl3
CS i
56.16
112.48
115.84
120.39
121.94
147.48
148.33
94
99
94
100
92
21
19
Acetone
CS i
55.47
112.30
115.51
119.09
120.83
146.52
147.59
99
97
85
91
100
49
37
CS i
DMSO
OMe
2
5
1
6
3
4
Atom
1HJMultH Shifts
3.83
5.72
s
s
OMe
OH
Atom
(chloroform)
Aldrich JR A 85.1356mg
Notes:
40Compound Number
FPL/DFRC NMR Database -- April 2009
Syringol2,6-dimethoxyphenol
13C
100100
100100
49
12
2323
56.2756.27
105.03105.03
119.06
134.97
147.31147.31
CDCl3
CS i
56.5556.55
106.57106.57
119.16
137.08
148.86148.86
100100
100100
44
8
1616
Acetone
CS i
55.8955.89
105.70105.70
118.06
135.70
148.16148.16
100100
9595
42
21
3939
CS i
DMSO
OMeOMe
26
1
4
35
Atom
1HJMultH Shifts
3.863.86
6.56
6.78
ss
d
t
8.1
8.1
OMeOMe
2,6
1
Atom
(chloroform)
J. Ralph JRA87.1362mgPoor solubility
Notes:
41Compound Number
FPL/DFRC NMR Database -- April 2009
Syringaldehyde3,5-dimethoxy-4-hydroxybenzaldehyde
13C
100100
8080
24
20
3030
52
56.4856.48
106.81106.81
128.34
141.03
147.44147.44
190.79
CDCl3
CS i
56.6456.64
107.74107.74
129.02
142.92
148.94148.94
191.05
100100
8080
19
15
2525
45
Acetone
CS i
56.0256.02
107.05107.05
127.14
142.11
148.09148.09
190.99
100100
6767
34
28
5656
38
CS i
DMSO
OMeOMe
26
1
4
35
α
Atom
1HJMultH Shifts
3.95
7.15
9.81
3.91
7.23
9.81
8.20
s
s
s
s
s
s
bs
OMe
2,6
α
acetone
OMe
2,6
α
OH
Atom
(chloroform)
J. Ralph JRA89.1255mgnot very soluble in CDCl3
Notes:
42Compound Number
FPL/DFRC NMR Database -- April 2009
Vanillic acid4-hydroxy-3-methoxy benzoic acid
13CCDCl3
CS i
56.28
113.46
115.43
122.70
124.90
147.96
152.03
167.84
95
87
87
33
100
31
28
33
Acetone
CS i
55.50
112.73
115.00
121.62
123.46
147.17
151.05
167.16
100
83
84
52
83
71
69
53
CS i
DMSO
OMe
2
5
1
6
3
4
α
Atom
1HJMultH Shifts
3.96
7.59
6.97
7.72
s
d
d
dd
1.9
8.3
8.3, 1.9
OMe
2
5
6
Atom
(chloroform)
J. Ralph JRA 89-1355mg not very soluble in CDCl3
Notes:
43Compound Number
FPL/DFRC NMR Database -- April 2009
Syringic acid3,5-dimethoxy-4-hydroxybenzoic acid
13CCDCl3
CS i
56.6656.66
108.20108.20
121.40
141.61
148.30148.30
167.68
9898
100100
19
14
2929
19
Acetone
CS i
55.9255.92
106.85106.85
120.32
140.17
147.37147.37
167.14
100100
8282
29
43
8181
38
CS i
DMSO
OMeOMe
26
1
4
35
α
Atom
1HJMultH Shifts
3.96
7.40
s
s
OMe
2,6
Atom
(chloroform)
J. Ralph JRA 89-1455mg
Notes:
44Compound Number
FPL/DFRC NMR Database -- April 2009
Veratric acid3,4-dimethoxybenzoic acid
13C
10086
87
87
46
94
56
46
50
56.0256.06
110.36
112.38
121.77
124.61
148.72
153.78
172.08
CDCl3
CS i
56.0856.12
111.64
113.34
123.64
124.42
149.89
154.37
167.53
10091
81
72
25
78
22
19
28
Acetone
CS i
55.4155.58
110.93
111.93
122.98
123.16
148.30
152.60
167.08
10093
85
73
43
85
54
42
55
CS i
DMSO
OMeOMe
2
5
1
6
3
4
α
Atom
1HJMultH Shifts
3.943.95
7.60
6.92
7.78
ss
d
d
dd
1.9
8.5
8.5, 1.9
OMeOMe
2
5
6
Atom
(chloroform)
Fluka60mg*not soluble in CDCl3
Notes:
45Compound Number
FPL/DFRC NMR Database -- April 2009
p-Coumaric acid4-hydroxycinnamic acid
13CCDCl3
CS i
115.51
116.66116.66
126.95
130.90130.90
145.95
160.49
169.03
45
100100
22
9191
45
26
19
Acetone
CS i
115.30
115.72115.72
125.24
129.98129.98
144.11
159.54
167.90
38
100100
34
9999
43
43
39
CS i
DMSO
β
35
1
26
α
4
γ
Atom
1HJMultH Shifts
7.54
6.83
7.53
6.32
d
d
d
d
16.0
8.6
8.6
16.0
α
3,5
2,6
β
Atom
(DMSO)
trans
Lancaster Synthesis60mg *not very soluble in CDCl3
Notes:
46Compound Number
FPL/DFRC NMR Database -- April 2009
Sinapinic acid3,5-dimethoxy-4-hydroxycinnamic acid
13CCDCl3
CS i
56.6856.68
106.84106.84
116.20
126.19
139.43
146.23
148.90148.90
168.26
100100
100100
50
22
22
58
4444
28
Acetone
CS i
56.0456.04
106.04106.04
116.03
124.59
138.05
144.74
148.00148.00
167.90
100100
7474
37
38
38
39
7979
45
CS i
DMSO
OMeOMe
26
β
1
4
α
35
γ
Atom
1HJMultH Shifts
3.83
7.00
7.50
6.44
s
s
d
d
15.9
15.9
OMe
2,6
α
β
Atom
(DMSO)
trans
K & K Labs60mg
Notes:
47Compound Number
FPL/DFRC NMR Database -- April 2009
3,4-Dimethoxycinnamic acid3,4-dimethoxycinnamic acid
13C
9892
94
96
94
100
72
91
53
47
77
55.9255.99
109.88
111.09
114.94
123.10
127.08
146.95
149.31
151.56
172.53
CDCl3
CS i
56.0856.13
111.20
112.40
116.60
123.43
128.31
145.64
150.61
152.48
168.11
90100
84
82
80
94
39
90
29
27
27
Acetone
CS i
55.4955.56
110.35
111.50
116.68
122.53
127.05
144.08
148.97
150.77
167.83
94100
74
71
75
76
72
71
68
55
71
CS i
DMSO
OMeOMe
2
5
β
6
1
α
3
4
γ
Atom
1HJMultH Shifts
3.923.92
7.08
6.88
7.14
7.73
6.33
ss
d
d
dd
d
d
2.0
8.3
8.3, 2.0
15.9
15.9
OMeOMe
2
5
6
α
β
Atom
(chloroform)
trans
Aldrich60mg not very soluble in CDCl3 Note: .0238 was run in d4-MeOH.
Notes:
48Compound Number
FPL/DFRC NMR Database -- April 2009
Ferulic acid4-hydroxy-3-methoxycinnamic acid
13C
56.44
111.71
115.89
116.46
123.94
127.77
146.89
149.30
150.43
170.93
CDCl3
CS i
56.28
111.30
115.77
116.00
123.80
127.38
146.16
148.64
149.97
168.88
98
95
87
90
98
51
100
46
51
60
Acetone
CS i
55.64
111.14
115.52
115.60
122.72
125.76
144.44
147.87
149.04
167.93
100
74
77
73
76
62
71
79
81
76
CS i
DMSO
OMe
2
β
5
6
1
α
3
4
γ
d4-MeOH
Atom
1HJMultH Shifts
3.84
7.29
6.83
7.10
7.53
6.39
s
d
d
dd
d
d
1.9
8.2
8.2,1.9
15.9
15.9
OMe
2
5
6
α
β
Atom
(DMSO)
trans
Aldrich66mg not CDCl3 soluble
Notes:
49Compound Number
FPL/DFRC NMR Database -- April 2009
4-Methoxycinnamic acid4-methoxycinnamic acid
13CCDCl3
CS i
55.68
115.14115.14
116.52
128.02
130.58130.58
145.19
162.41
168.11
51
100100
44
18
9898
53
16
22
Acetone
CS i
55.22
114.30114.30
116.51
126.82
129.84129.84
143.65
160.90
167.78
52
9797
41
29
100100
42
28
35
CS i
DMSO
OMe
35
β
1
26
α
4
γ
Atom
1HJMultH Shifts
3.85
6.92
7.75
7.51
6.32
s
m
d
m
d
8.8
15.9
8.8
15.9
OMe
3,5
α
2,6
β
Atom
(chloroform)
trans
S. Ralph SG 100mg33mg
Notes:
50Compound Number
FPL/DFRC NMR Database -- April 2009
Syringylglycol-β-guaiacyl ether
1-(3,5-dimethoxy-4-hydroxyphenyl)-2-(2-methoxyphenoxy)ethanol
13C
50
100100
54
48
9696
52
50
51
56
36
31
5656
27
23
55.84
56.3256.32
72.47
76.39
103.11103.11
112.06
115.96
121.12
122.50
130.84
134.46
147.12147.12
148.06
150.11
CDCl3
CS i
56.24
56.5856.58
72.85
76.15
104.79104.79
113.44
115.52
121.76
122.29
133.07
136.13
148.46148.46
149.62
150.84
49
100100
51
45
8484
45
38
55
55
27
24
5151
22
18
Acetone
CS i
55.41
55.8155.81
70.97
73.98
103.73103.73
112.25
113.40
120.66
120.79
132.54
134.51
147.57147.57
148.11
148.94
52
100100
47
38
7979
42
38
48
47
40
36
7777
33
37
CS i
DMSO
B OMe
A OMeA OMe
α
β
A2A6
B2
B5
B6
B1
A1
A4
A3A5
B3
B4
Atom
1HJMultH Shifts
3.85
3.87
5.00
3.944.14
6.66
s
s
dd
tdd
s
9.9, 3.0
9.99.9, 3.0
B OMe
A OMe
α
β1β2
A2,6
Atom
(chloroform)
L. Landucci LLL XVII 9A26mg contains trace impurity
Notes:
51Compound Number
FPL/DFRC NMR Database -- April 2009
�2-(4-Acetylphenoxy)-1-(3,4,5-trimethoxyphenyl)ethanone
13C
46
8686
35
35
8181
9494
26
100100
26
12
5757
28
3219
26.34
56.4256.42
61.00
70.62
105.84105.84
114.44114.44
129.36
130.62130.62
131.16
143.65
153.32153.32
161.77
192.49196.55
CDCl3
CS i
26.37
56.6856.68
60.72
71.10
106.60106.60
115.27115.27
130.72
131.11131.11
131.70
144.27
154.41154.41
163.09
193.05196.23
43
8888
33
37
9090
9696
20
100100
20
10
4141
22
2416
Acetone
CS i
26.34
56.1256.12
60.12
70.11
105.47105.47
114.45114.45
129.38
130.26130.26
130.11
142.41
152.88152.88
161.79
192.70196.12
60
100100
52
37
8787
9797
38
9292
37
25
7777
40
3735
CS i
DMSO
B β
A3 OMeA5 OMe
A4 OMe
β
A2A6
B3B5
A1
B2B6
B1
A4
A3A5
B4
αB α
Atom
1HJMultH Shifts
2.54
3.92
3.94
5.32
7.26
6.96
7.92
s
s
s
s
s
m
m
8.9
8.9
B β
A3,5 OMe
A4 OMe
β
A2,6
B3,5
B2,6
Atom
(chloroform)
L. Landucci LLL XVII 9c28.5mg trace impurity present
Notes:
52Compound Number
FPL/DFRC NMR Database -- April 2009
2-(4-Acetyl-2-methoxyphenoxy)-1-(3,4,5-trimethoxyphenyl)ethanone�
13C
55
53
100100
47
32
9292
434353
2833173027
5555
2525
26.23
56.01
56.3256.32
60.96
71.57
105.79105.79
110.85112.27122.87
129.33131.48143.44149.31151.49
153.23153.23
192.68196.64
CDCl3
CS i
26.30
56.28
56.6456.64
60.70
71.84
106.70106.70
112.10113.40123.39
130.74131.98144.21150.23152.98
154.34154.34
193.34196.32
53
51
100100
33
42
9393
454852
2521122118
4545
2219
Acetone
CS i
26.25
55.58
56.1256.12
60.13
70.48
105.57105.57
110.84112.24122.56
129.40130.24142.45148.52151.61
152.85152.85
192.76196.19
49
56
100100
49
28
7474
363841
3636234444
8585
3636
CS i
DMSO
B β
B OMe
A3 OMeA5 OMe
A4 OMe
β
A2A6
B2B5B6
A1B1A4B3B4
A3A5
αBα
Atom
1HJMultH Shifts
2.54
3.95
3.92
3.93
5.39
7.47
7.636.807.52
s
s
s
s
s
s
dddd
1.98.3
8.3, 1.9
B β
B OMe
A3,5 OMe
A4 OMe
β
A2,6
B2B5B6
Atom
(chloroform)
L. Landucci LLL XVII 9d37mg
Notes:
53Compound Number
FPL/DFRC NMR Database -- April 2009
2-(4-Acetyl-2,6-dimethoxyphenoxy)-1-(3,4,5-trimethoxyphenyl)ethanone��
13C
26
100100
100100
22
22
100100
100100
1515
108
3333
3333
1514
26.43
56.3356.33
56.3356.33
60.94
74.82
105.87105.87
105.87105.87
129.99132.67
140.75142.94
152.53152.53
153.12153.12
193.28196.71
CDCl3
CS i
26.55
56.6156.61
56.6656.66
60.67
75.43
106.81106.81
106.95106.95
131.21133.62
141.68143.88
153.61153.61
154.23154.23
193.81196.70
43
100100
7575
32
45
8686
9191
2019
1310
3838
3636
2219
Acetone
CS i
26.52
56.0456.04
56.0956.09
60.08
74.15
105.52105.52
105.84105.84
129.69132.05
140.24142.15
152.04152.04
152.80152.80
193.11196.61
47
100100
9595
43
28
7070
7070
3033
2720
6565
7070
3528
CS i
DMSO
B β
A3 OMeA5 OMe
B3 OMeB5 OMe
A4 OMe
β
A2A6
B2B6
A1B1
B4A4
B3B5
A3A5
αB α
Atom
1HJMultH Shifts
2.59
3.92
3.88
3.91
5.29
7.31
7.22
s
s
s
s
s
s
s
B β
A3,5 OMe
B3,5 OMe
A4 OMe
β
A2,6
B2,6
Atom
(chloroform)
Aldrich40mg
Notes:
54Compound Number
FPL/DFRC NMR Database -- April 2009
AnisoleMethoxybenzene
13C
70
100100
61
100100
12
55.08
113.92113.92
120.64
129.52129.52
159.60
CDCl3
CS i
55.28
114.62114.62
121.19
130.14130.14
160.63
73
9898
64
100100
14
Acetone
CS i
54.86
113.84113.84
120.39
129.39129.39
159.24
54
9999
43
100100
10
CS i
DMSO
OMe
35
1
26
4
Atom
1HJMultH Shifts
3.77
6.90
7.27
s
m
m
OMe
3,5,1
2,6
Atom
(chloroform)
Aldrich40mg
Notes:
55Compound Number
FPL/DFRC NMR Database -- April 2009
1,2,3-trimethoxybenzene
13C
100100
38
8888
51
8
2323
56.0956.09
60.80
105.34105.34
123.61
138.27
153.56153.56
CDCl3
CS i
56.3556.35
60.43
106.54106.54
124.30
139.52
154.67154.67
9191
38
100100
42
8
1919
Acetone
CS i
55.7755.77
59.90
105.56105.56
123.57
137.69
153.16153.16
100100
48
9595
49
10
3333
CS i
DMSO
3 OMe5 OMe
4 OMe
26
1
4
35
Atom
1HJMultH Shifts
3.85
3.85
6.57
6.98
s
s
d
t
8.3
8.3
3,5 OMe
4 OMe
2,6
1
Atom
(chloroform)
Aldrich40mg
Notes:
56Compound Number
FPL/DFRC NMR Database -- April 2009
Veratrole1,2-dimethoxybenzene
13C
100100
7676
8383
1616
55.8055.80
111.44111.44
120.85120.85
149.08149.08
CDCl3
CS i
56.0156.01
113.02113.02
121.60121.60
150.50150.50
100100
8989
8686
1717
Acetone
CS i
55.3855.38
111.98111.98
120.67120.67
148.88148.88
100100
9999
100100
2929
CS i
DMSO
OMeOMe
25
16
34
Atom
1HJMultH Shifts
3.86
6.89
6.89
s
m
m
OMe
2,5
1,6
Atom
(chloroform)
Aldrich40mg
Notes:
57Compound Number
FPL/DFRC NMR Database -- April 2009
Veratraldehyde3,4-dimethoxybenzaldehyde
13C
100
93
65
88
79
37
21
25
70
56.00
56.17
109.05
110.46
126.77
130.19
149.66
154.51
190.78
CDCl3
CS i
56.07
56.29
110.31
111.85
126.72
131.21
150.77
155.63
191.16
100
91
80
91
94
27
20
16
79
Acetone
CS i
55.47
55.82
109.46
111.22
126.00
129.65
149.17
154.18
191.21
100
85
66
83
79
49
38
37
84
CS i
DMSO
OMe
OMe
2
5
6
1
3
4
α
Atom
1HJMultH Shifts
3.94
3.97
7.41
6.98
7.46
9.85
s
s
d
d
dd
s
1.8
8.2
8.2, 1.8
OMe
OMe
2
5
6
α
Atom
(chloroform)
Aldrich40mg *CDCl3 insoluble
Notes:
58Compound Number
FPL/DFRC NMR Database -- April 2009
4-hydroxybenzoic acid
13CCDCl3
CS i
115.99115.99
122.43
132.78132.78
162.65
168.24
9494
14
100100
21
20
Acetone
CS i
115.06115.06
121.35
131.47131.47
161.55
167.11
100100
27
8787
39
33
CS i
DMSO
35
1
26
4
α
Atom
1HJMultH Shifts
6.85
7.83
m
m
8.8
8.8
3,5
2,6
Atom
(DMSO)
J. Ralph PS 137x195mg
Notes:
59Compound Number
FPL/DFRC NMR Database -- April 2009
methyl (4-methoxy)cinnamate
13C
45
43
9898
41
21
100100
49
17
18
51.50
55.32
114.34114.34
115.30
127.14
129.71129.71
144.49
161.42
167.68
CDCl3
CS i
51.58
55.70
115.14115.14
115.96
127.84
130.63130.63
145.04
162.42
167.81
43
47
9898
43
17
100100
45
14
15
Acetone
CS i
51.23
55.28
114.36114.36
115.09
126.65
130.08130.08
144.28
161.17
166.90
37
47
100100
51
36
8989
45
32
23
CS i
DMSO
γ OMe
4 OMe
35
β
1
26
α
4
γ
Atom
1HJMultH Shifts
3.79
3.82
7.46
7.65
6.89
6.31
s
s
m
d
m
d
8.8
16.0
8.8
16.0
γ OMe
4 OMe
2,6
α
3,5
β
Atom
(chloroform)
J. Ralph JRPS 135x152mg
Notes:
60Compound Number
FPL/DFRC NMR Database -- April 2009
Methyl Sinapatemethyl (3,5-dimethoxy-4-hydroxy)cinnamate
13C
45
100100
8686
47
30
28
52
5353
25
51.60
56.3456.34
105.17105.17
115.50
125.85
137.30
145.15
147.29147.29
167.58
CDCl3
CS i
51.46
56.6856.68
106.83106.83
115.73
126.08
139.46
145.99
148.88148.88
167.78
24
8888
100100
47
22
19
38
4343
11
Acetone
CS i
51.13
56.0656.06
106.26106.26
114.58
124.34
138.36
145.32
148.00148.00
166.98
51
100100
8585
42
43
37
43
8282
32
CS i
DMSO
γ OMe
3 OMe5 OMe
26
β
1
4
α
35
γ
Atom
1HJMultH Shifts
3.79
3.90
6.76
7.60
6.30
s
s
s
d
d
15.9
15.9
γ OMe
3,5 OMe
2,6
α
β
Atom
(chloroform)
trans
J. Ralph JRPS 133.2x168mg
Notes:
61Compound Number
FPL/DFRC NMR Database -- April 2009
Methyl p-Coumaratemethyl 4-hydroxycinnamate
13C
38
36
9191
21
100100
38
24
14
51.71
114.98
115.95115.95
126.98
130.00130.00
144.89
158.12
168.18
CDCl3
CS i
51.49
115.22
116.64116.64
126.90
130.82130.82
145.33
160.45
167.87
41
40
100100
20
9494
46
28
14
Acetone
CS i
51.13
113.90
115.78115.78
125.07
130.21130.21
144.69
159.87
166.99
44
44
9999
35
100100
51
46
30
CS i
DMSO
γ OMe
β
35
1
26
α
4
γ
Atom
1HJMultH Shifts
3.80
7.64
6.86
7.42
6.28
s
d
m
m
d
16.0
8.7
8.7
16.0
γ OMe
α
3,5
2,6
β
Atom
(chloroform)
trans
J. Ralph JRPS 139x192mg
Notes:
62Compound Number
FPL/DFRC NMR Database -- April 2009
methyl (3,4,5-trimethoxy)cinnamate
13C
43
100100
39
9090
46
33
16
52
5353
25
51.61
56.1556.15
60.89
105.36105.36
117.04
129.90
140.24
144.81
153.46153.46
167.29
CDCl3
CS i
51.57
56.4556.45
60.58
106.58106.58
117.70
130.70
141.27
145.45
154.51154.51
167.51
41
100100
42
8484
50
28
11
49
4242
22
Acetone
CS i
51.31
56.0256.02
60.06
105.99105.99
117.06
129.61
139.61
144.75
153.11153.11
166.78
48
100100
46
8484
46
36
19
45
4242
34
CS i
DMSO
γ OMe
3 OMe5 OMe
4 OMe
26
β
1
4
α
35
γ
Atom
1HJMultH Shifts
3.74
3.82
3.82
6.70
7.54
6.29
s
s
s
s
d
d 15.9
γ OMe
3,5 OMe
4 OMe
2,6
α
β
Atom
(chloroform)
trans
Aldrich100mg
Notes:
63Compound Number
FPL/DFRC NMR Database -- April 2009
3,4,5-trimethoxy cinnamic acid
13C
100100
35
8181
44
39
18
42
7676
32
56.1956.19
60.96
105.67105.67
116.55
129.52
140.62
147.02
153.48153.48
172.46
CDCl3
CS i
56.4956.49
60.60
106.62106.62
118.15
130.83
141.24
145.87
154.54154.54
168.33
100100
43
8787
55
30
12
46
4747
28
Acetone
CS i
55.9855.98
60.05
105.77105.77
118.51
129.87
139.38
144.14
153.10153.10
167.72
100100
69
8080
49
48
27
53
9191
52
CS i
DMSO
3 OMe5 OMe
4 OMe
26
b
1
4
α
35
γ
Atom
1HJMultH Shifts
3.89
3.89
6.78
7.70
6.36
s
s
s
d
d
15.9
15.9
3,5 OMe
4 OMe
2,6
α
β
Atom
(chloroform)
trans
J. Ralph JRPS 7x193.3mg
Notes:
64Compound Number
FPL/DFRC NMR Database -- April 2009
Syringic acid methyl estermethyl (4-hydroxy-3,5-dimethoxy)benzoate
13C
47
100100
9999
24
27
5454
18
52.07
56.4156.41
106.80106.80
120.96
139.49
146.78146.78
166.92
CDCl3
CS i
52.11
56.6756.67
107.87107.87
121.07
141.65
148.33148.33
167.16
47
9898
100100
22
25
4646
15
Acetone
CS i
51.78
56.0456.04
106.82106.82
119.28
140.72
147.58147.58
166.10
50
100100
8282
34
37
6666
29
CS i
DMSO
α OMe
3 OMe5 OMe
26
1
4
35
α
Atom
1HJMultH Shifts
3.89
3.90
7.31
s
s
s
α OMe
3,5 OMe
2,6
Atom
(chloroform)
J. Ralph JRPS 3.1101mg
Notes:
65Compound Number
FPL/DFRC NMR Database -- April 2009
Vanillic acid methyl estermethyl (3-methoxy-4-hydroxy)benzoate
13C
83
100
81
91
37
98
34
45
24
52.02
56.07
111.98
114.33
122.13
124.23
146.41
150.29
167.12
CDCl3
CS i
52.00
56.29
113.20
115.58
122.43
124.53
148.08
152.14
167.15
79
91
89
89
38
100
29
46
23
Acetone
CS i
51.64
55.60
112.54
115.19
120.52
123.44
147.36
151.53
166.06
89
100
80
96
53
88
64
78
46
CS i
DMSO
α OMe
4 OMe
2
5
1
6
3
4
α
Atom
1HJMultH Shifts
3.88
3.88
7.53
6.93
7.62
s
s
d
d
dd
1.8
8.3
8.3, 1.8
α OMe
4 OMe
2
5
6
Atom
(chloroform)
J. Ralph JRL 109x244mg
Notes:
66Compound Number
FPL/DFRC NMR Database -- April 2009
Dihydrodehydrodiisoeugenol2-Methoxy-4-(7-methoxy-3-methyl-5-propyl-2,3-dihydro benzofuran-2-
yl)phenol
13C
8072
84
7185
100100
66
7265637476
52454544244335
13.9017.44
25.07
38.0945.81
55.9955.99
93.61
109.04111.91114.11115.46119.94
132.28132.98136.29143.86145.41145.77146.71
CDCl3
CS i
14.0817.83
25.74
38.5446.43
56.2856.41
93.80
110.69113.63115.55116.39120.22
133.03134.12136.62144.78146.59147.52148.39
8888
97
7991
10097
94
8576768591
53445941324438
Acetone
CS i
13.6517.17
24.52
37.2744.71
55.5955.64
92.37
110.56112.24115.20115.35119.25
130.82132.91135.32143.30144.93146.67147.59
8581
94
7774
100100
70
6657666874
77686464457777
CS i
DMSO
B γγ
B β
B αβ
OMeOMe
α
A2B2A5B6A6
A1B5B1B4A4B3A3
Atom
1HJMultH Shifts
0.961.36
1.64
2.553.44
3.863.87
5.07
6.596.626.896.896.99
td
m
tdd
ss
d
ssmms
7.36.8
7.3
7.39.6,6.8
9.6
B γγ
B β
B αβ
OMeOMe
α
B2B6A5A6A2
Atom
(chloroform)
J. Ralph JRKM 67-1150mg
Notes:
67Compound Number
FPL/DFRC NMR Database -- April 2009
Dehydrodiisoeugenol2-Methoxy-4-(7-methoxy-3-methyl-5-propenyl-2,3-dihydro
benzofuran-2-yl) phenol
13C
4341
52
100100
47
4841464747
47
51
263432
28313032
17.6018.34
45.62
55.9755.97
93.76
108.97109.40113.36114.14119.91
123.41
130.98
132.11132.22133.30
144.15145.82146.62146.71
CDCl3
CS i
17.8618.42
46.21
56.2556.33
93.96
110.66111.06114.30115.55120.21
123.22
132.05
132.81132.83134.43
145.03147.53147.72148.36
8993
100
9381
84
8677878493
97
93
676154
26532044
Acetone
CS i
17.2518.06
44.51
55.5955.61
92.55
109.74110.58113.29115.23119.25
122.60
130.68
130.93131.39133.30
143.61146.07146.71147.59
7278
60
10095
60
5058585560
60
52
656265
60455560
CS i
DMSO
γB γ
β
OMeOMe
α
A2B2A5B6A6
B β
B α
A1B5B1
B4A4B3A3
Atom
1HJMultH Shifts
1.371.87
3.44
3.853.88
5.09
6.11
6.36
6.766.786.886.806.97
ddd
dt
ss
d
dq
dq
ssmms
6.85.3, 1.2
9.4, 6.8
9.4
15.8, 5.3
15.8, 1.2
γB γ
β
OMeOMe
α
B β
B α
B2B6A5A6A2
Atom
(chloroform)
J. Ralph JRKM 85.154mg
Notes:
68Compound Number
FPL/DFRC NMR Database -- April 2009
Methyl ferulate methyl 4-hydroxy-3-methoxycinnamate
13C
80
90
92
96
85
100
58
92
51
58
47
51.60
55.93
109.56
114.86
115.09
123.00
126.92
145.03
146.89
148.11
167.80
CDCl3
CS i
51.47
56.32
111.34
115.51
116.03
123.78
127.38
145.65
148.66
149.99
167.82
86
100
98
100
98
88
50
96
44
50
40
Acetone
CS i
51.12
55.68
111.32
114.19
115.54
122.99
125.56
145.02
147.92
149.38
167.02
90
100
71
72
81
81
66
78
65
72
62
CS i
DMSO
γ OMe
3 OMe
2
β
5
6
1
α
3
4
γ
Atom
1HJMultH Shifts
3.79
3.89
7.31
7.61
6.90
7.05
6.28
s
s
d
d
d
dd
d
1.8
15.9
8.1
8.1, 1.8
15.9
γ OMe
3 OMe
2
α
5
6
β
Atom
(chloroform)
trans
J. Ralph JRPS 5.155mg
Notes:
69Compound Number
FPL/DFRC NMR Database -- April 2009
Methylveratratemethyl 3,4-dimethoxybenzoate
13C
45
100100
45
46
16
49
17
16
14
51.93
55.9955.99
110.32
112.05
122.71
123.58
148.65
153.00
166.82
CDCl3
CS i
52.00
56.1056.10
111.65
112.99
123.37
124.08
149.90
154.38
166.92
68
100100
75
70
25
77
23
19
19
Acetone
CS i
51.79
55.5055.66
111.07
111.70
121.84
123.13
148.46
152.98
165.96
86
10094
86
82
51
93
51
43
35
CS i
DMSO
α OMe
OMe OMe
2
5
1
6
3
4
α
Atom
1HJMultH Shifts
3.89
3.933.93
7.54
6.88
7.67
s
ss
d
d
dd
1.9
8.4
8.4, 1.9
α OMe
OMe OMe
2
5
6
Atom
(chloroform)
J. Ralph JRPS 21x152mg
Notes:
70Compound Number
FPL/DFRC NMR Database -- April 2009
methyl 3,4-dimethoxycinnamate
13C
79
92
100
79
84
78
81
56
85
40
41
49
51.55
55.89
55.96
109.77
111.12
115.53
122.56
127.41
144.74
149.27
151.18
167.58
CDCl3
CS i
51.50
56.07
56.12
111.23
112.38
116.15
123.46
128.19
145.41
150.59
152.54
167.71
77
100
96
88
88
89
93
43
88
32
32
39
Acetone
CS i
51.20
55.52
55.59
110.49
111.51
115.26
122.81
126.85
144.67
149.00
151.02
166.92
96
97
100
77
83
83
89
68
80
61
58
61
CS i
DMSO
γ OMe
3 OMe
4 OMe
2
5
β
6
1
α
3
4
γ
Atom
1HJMultH Shifts
3.79
3.903.90
7.04
6.86
7.09
7.63
6.30
s
ss
d
d
dd
d
d
1.9
8.2
8.2, 1.9
15.9
15.9
γ OMe
OMe OMe
2
5
6
α
β
Atom
(chloroform)
trans
Obst38 mg contains impurityAs this compound has a plane of symmetry the shifts for the other half areidentical.
Notes:
71Compound Number
FPL/DFRC NMR Database -- April 2009
Dehydrodiveratraldehyde5,6,5',6'-Tetramethoxybiphenyl-3,3'-dicarbaldehyde
13C
100
79
86
83
48
60
35
50
100
56.05
60.95
110.43
127.51
131.76
132.06
152.36
153.37
190.87
CDCl3
CS i
56.40
60.98
111.92
127.15
133.01
133.21
153.02
154.27
191.51
90
73
90
97
33
47
23
40
100
Acetone
CS i
55.94
60.36
111.39
125.97
131.52
131.76
151.50
152.82
191.60
100
93
63
74
58
82
44
72
75
CS i
DMSO
3 OMe
4 OMe
2
6
5
1
4
3
α
Atom
1HJMultH Shifts
3.773.99
7.517.40
9.91
3.754.01
7.587.44
9.96
ss
dd
s
ss
dd
s
1.91.9
4 OMe3 OMe
26
α
acetone
4 OMe3 OMe
26
α
Atom
(chloroform)
Obst 35 mg* only soluble in DMSO * aldehyde impurityAs this compound has a plane of symmetry the shifts for the other half areidentical.
Notes:
72Compound Number
FPL/DFRC NMR Database -- April 2009
Dehydrodiveratric acid5,6,5',6'-Tetramethoxybiphenyl-3,3'-dicarboxylic acid
13CCDCl3
CS i
Acetone
CS i
55.81
60.19
112.91
124.10
125.84
131.27
150.04
152.11
166.72
98
100
48
65
73
62
67
94
60
CS i
DMSO
3 OMe
4 OMe
2
6
1
5
4
3
α
Atom
1HJMultH Shifts
3.64
3.93
7.42
7.71
s
s
d
d
1.9
1.9
3 OMe
4 OMe
2
6
Atom
(DMSO)
Obst45mg
Notes:
73Compound Number
FPL/DFRC NMR Database -- April 2009
2-(3,4-Dimethoxyphenyl)-7-methoxy-3-methyl-5-propyl-2,3-dihydrobenzofuran
13C
65
63
676360
10010062
61
5758565263
25443832253332
13.90
17.47
25.0638.0945.77
55.9255.9256.00
93.48
109.62110.88111.90115.44119.22
132.90132.95136.30143.87145.42149.10149.16
CDCl3
CS i
14.08
17.90
25.7438.5346.47
56.1256.1256.41
93.58
111.03112.57113.62116.40119.68
134.07134.25136.69144.80146.57150.40150.49
55
55
636255
10010060
62
5358535555
33333228182223
Acetone
CS i
13.66
17.18
24.5337.2844.87
55.4755.4755.66
92.11
110.01111.58112.28115.37118.85
132.49132.86135.46143.34144.92148.83148.83
88
75
816968
10010076
62
6060516064
55576154379393
CS i
DMSO
B γ
γ
B βB α
β
OMeOMeOMe
α
A2A5B2B6A6
B5A1B1B4B3A3A4
Atom
1HJMultH Shifts
0.961.37
1.642.554.45
3.863.873.88
5.09
6.596.626.836.967.00
td
ht
dq
sss
d
ssddddd
7.36.8
7.37.3
9.6, 6.8
9.6
8.28.2, 1.9
1.9
B γγ
B βB α
β
OMeOMeOMe
α
B2B6A5A6A2
Atom
(chloroform)
R. Helm RFH5C50mg
Notes:
74Compound Number
FPL/DFRC NMR Database -- April 2009
Guaiacylglycerol-β-guaiacyl ether triacetate
1-(4-acetoxy-3-methoxyphenyl)-1,3-diacetoxy-2-(2-methoxyphenoxy)propane
13C
867888
10094
758687
8690
9184907891
6849
545455
484951
20.6320.6821.02
55.8155.96
63.0974.5280.26
111.75112.58
118.79119.58121.00122.79123.31
135.35139.93
147.96150.84151.12
168.71169.65170.52
CDCl3
CS i
20.4520.5820.91
56.2156.30
63.5875.3780.68
112.66113.76
119.22120.27121.66123.52123.75
136.66140.88
149.05151.81152.18
168.83169.94170.62
898461
92100
798787
8779
9595877987
6137
373947
343942
Acetone
CS i
20.2820.3520.63
55.5455.76
62.4774.2879.05
111.62112.75
117.47119.36120.64122.57122.62
135.40139.19
147.54150.13150.67
168.31169.30169.89
9410082
10091
526767
6476
7364765858
7958
617373
586167
CS i
DMSO
Ac MeAc MeAc Me
OMeOMe
γα
β
A2B2
B5A6B6A5B1
A1A4
B4B3A3
A4 Ac C=Oα Ac C=Oγ Ac C=O
Atom
1HJMultH Shifts
1.992.052.29
3.803.81
4.064.326.124.63
sss
ss
dddddm
11.9, 5.711.9, 4.5
6.3
Ac MeAc MeAc Me
OMeOMe
γ1γ2αβ
Atom
(chloroform)
threo
R. Helm RFH101D140mg Vinyl C's at 124.08 and 145.16 in acetone. In CDCl3 123.23 and 144.62Acetone 1H data in J. Ag. Food Chem. 41(4) 570-576, 1993
Notes:
75Compound Number
FPL/DFRC NMR Database -- April 2009
3-(4-Acetoxy-3-methoxyphenyl) acrylic acid 3-acetoxy- 3- (4- acetoxy-3-methoxyphenyl)-2-(2-methoxyphenoxy) propyl ester
13C
939342
53100100
283537
373544
35
44405144354940
30332628
42
33333040
28
373333
20.6120.6121.06
55.8055.9555.95
63.3574.6480.51
111.27111.74112.54
117.58
119.01119.55120.99121.44122.85123.23123.35
133.16135.34139.93141.61
144.62
147.96150.93151.14151.42
166.24
168.67168.70169.70
CDCl3
CS i
20.4620.4620.95
56.2156.2956.41
63.9475.5480.85
112.46112.70113.74
118.62
119.32120.29121.67122.25123.57123.78124.08
134.09136.65140.91142.73
145.16
149.08151.87152.20152.64
166.62
168.75168.82169.99
10010048
545454
393941
504343
48
52435046464861
30302626
48
26262835
35
352628
Acetone
CS i
20.3020.3020.67
55.5555.7555.96
62.8774.4479.20
111.68111.86112.75
117.53
117.68119.38120.66121.62122.58122.67123.15
132.81135.41139.21141.10
144.30
147.57150.16150.68151.13
165.74
168.22168.29169.34
10010058
676271
213333
334650
54
54335846423858
46465042
42
46465054
50
545046
CS i
DMSO
Ac MeAc MeAc Me
OMeOMeOMe
γαβ
C2A2B2
C β
B5A6B6C6A5B1C5
C1A1A4C4
C α
B4B3A3C3
C γ
Ac C=OAc C=OAc C=O
Atom
1HJMultH Shifts
2.282.312.07
3.803.803.87
4.204.424.706.20
6.357.54
sss
sss
ddddmd
dd
11.9, 5.211.9, 4.2
6.5
15.915.9
Ac MeAc MeAc Me
OMeOMeOMe
γ1γ2βα
C βC α
Atom
(chloroform)
threo
R. Helm RFH101D230mg Vinyl C's at 124.09 and 145.13 in acetoneAcetone 1H data in J. Ag. Food Chem. 41(4) 570-576, 1993
Notes:
76Compound Number
FPL/DFRC NMR Database -- April 2009
3-(4-Acetoxy-3-methoxyphenyl) acrylic acid 3-acetoxy- 3-(4- acetoxy-3-methoxyphenyl)-2-(2-methoxyphenoxy) propyl ester
13C
707041
48100100
303138
383339
36
75754538384442
31343020
34
33303431
34
312823
20.6420.6421.05
55.8155.9655.96
62.8873.9680.46
111.31112.05112.63
117.70
119.74119.74121.00121.44122.60123.23123.66
133.22135.53139.80141.58
144.61
147.23151.00151.20151.42
166.40
168.68168.75169.50
CDCl3
CS i
20.4620.4620.90
56.2256.3056.41
63.3474.7280.52
112.47112.77113.80
118.62
119.97120.44121.65122.22123.37124.09124.09
134.09136.71140.79142.74
145.13
148.30152.11152.11152.65
166.64
168.75168.86169.89
10010042
485662
364244
464646
40
50444848448686
32382820
48
30363232
32
322828
Acetone
CS i
20.3220.3220.66
55.6055.7355.97
62.2673.2878.58
111.72111.86112.91
117.70
118.08119.41120.67121.60122.50122.90123.16
132.80135.37139.11141.11
144.28
146.70150.38150.58151.16
165.77
168.20168.31169.20
10010044
764262
313041
233458
41
54325431444455
56524449
48
61386139
45
344535
CS i
DMSO
Ac MeAc MeAc Me
OMeOMeOMe
γαβ
C2A2B2
C β
B5A6B6C6A5B1C5
C1A1A4C4
C α
B4B3A3C3
C γ
Ac C=OAc C=OAc C=O
Atom
1HJMultH Shifts
2.322.292.10
3.773.823.87
4.444.534.756.14
6.357.54
sss
sss
ddddmd
dd
11.9, 4.211.9, 5.3
5.5
16.016.0
Ac MeAc MeAc Me
OMeOMeOMe
γ1γ2βα
C βC α
Atom
(chloroform)
erythro
R. Helm RFH119D147mg
Notes:
77Compound Number
FPL/DFRC NMR Database -- April 2009
3-(4-Acetoxyphenyl) acrylic acid 3-acetoxy-1-(4-acetoxy- 3-methoxyphenyl)-2-(2-methoxyphenoxy)propyl ester
13C
645760
5564
344540
4551
47
494753919143
47
100100
344334
43
36363836
40
323236
20.6420.7521.09
55.8255.94
62.7374.1280.25
111.88112.68
117.66
119.58119.66121.02122.15122.15122.60
123.63
129.31129.31
131.91135.38139.78
144.58
147.18151.01151.15152.28
165.33
168.74168.99170.72
CDCl3
CS i
20.4620.6220.95
56.2456.31
63.1674.9780.43
112.82113.82
118.65
119.87120.45121.67123.20123.20123.38
124.06
130.25130.25
132.79136.60140.82
145.09
148.38152.04152.11153.54
165.76
168.85169.36170.71
674848
6054
384446
4248
40
48464810010044
46
9292
353827
46
25292929
29
293331
Acetone
CS i
20.3020.3920.79
55.6155.74
62.0673.5078.57
111.73112.91
117.55
118.04119.31120.68122.31122.31122.52
122.89
129.65129.65
131.49135.32139.12
144.32
146.76150.34150.57152.10
164.86
168.32168.82169.95
717768
7474
293935
4255
48
48394510010042
45
9797
484848
42
52393545
52
555255
CS i
DMSO
Ac MeAc MeAc Me
OMeOMe
γαβ
A2B2
C β
B5A6B6C3C5A5
B1
C2C6
C1A1A4
C α
B4B3A3C4
C γ
Ac C=OAc C=OAc C=O
Atom
1HJMultH Shifts
2.022.282.30
3.773.81
4.324.484.776.20
6.44
7.137.53
7.65
sss
ss
ddddmd
d
mm
d
11.9, 4.311.9, 5.9
5.0
16.0
8.68.6
16.0
Ac MeAc MeAc Me
OMeOMe
γ1γ2βα
C β
C2,6C3,5
C α
Atom
(chloroform)
erythro
R. Helm RFH119D244mg
Notes:
78Compound Number
FPL/DFRC NMR Database -- April 2009
3-(4-Acetoxyphenyl)�acrylic acid 3-acetoxy-1-(4-acetoxy- 3-methoxyphenyl)-2-(2-methoxyphenoxy)propyl ester
13C
565651
5959
364639
4351
49
464354909038
46
100100
393638
43
38343630
33
303330
20.6420.7221.10
55.7755.97
63.2674.9680.52
111.71112.47
117.78
118.91119.49120.96122.14122.14122.84
123.30
129.26129.26
131.96135.41139.94
144.34
148.08150.89151.14152.23
165.46
168.70169.02170.56
CDCl3
CS i
20.4420.6020.95
56.1756.31
63.6975.7880.86
112.73113.68
118.73
119.33120.27121.62123.16123.16123.56
123.75
130.15132.78
132.78136.68140.94
144.86
149.10151.87152.21153.47
165.84
168.77169.32170.62
443447
5951
304044
3438
43
42453810010038
34
6926
262923
29
26212129
14
191422
Acetone
CS i
20.2920.3820.78
55.5355.80
62.5874.6179.18
111.71112.71
117.56
117.63119.36120.62122.28122.28122.57
122.69
129.56129.56
131.50135.44139.25
144.10
147.56150.17150.69152.04
165.03
168.27168.81169.90
787463
8574
334137
4156
56
52375210010052
48
9393
564852
44
59564444
52
374448
CS i
DMSO
Ac MeAc MeAc Me
OMeOMe
γαβ
A2B2
C β
B5A6B6C3C5A5
B1
C2C6
C1A1A4
C α
B4B3A3C4
C γ
Ac C=OAc C=OAc C=O
Atom
1HJMultH Shifts
2.012.282.30
3.773.82
4.144.364.726.23
6.37
7.127.49
7.55
sss
ss
ddddmd
d
mm
d
11.9, 5.811.9, 4.4
6.4
16.0
8.68.6
16.0
Ac MeAc MeAc Me
OMeOMe
γ1γ2βα
C β
C2.6C3.5
C α
Atom
(chloroform)
threo
SR III - 3945mg
Notes:
79Compound Number
FPL/DFRC NMR Database -- April 2009
1-(4-acetoxy-3,5-dimethoxyphenyl)-2-(4-acetyl-2,6-dimethoxy phenoxy)-3-hydroxypropan-1-one
13C
49
57
1001008989
3336
94947676
274848
21
68687070
27
29
24
20.41
26.41
56.2456.2456.3956.39
63.3687.06
105.72105.72105.75105.75
133.17133.27133.27
140.52
152.33152.33152.36152.36
168.05
194.74
196.50
CDCl3
CS i
20.22
26.54
56.5656.5656.7056.70
63.6786.08
106.52106.52106.62106.62
133.66133.80134.87
141.29
153.21153.21153.21153.21
168.15
195.71
196.65
50
50
8282100100
3239
84849090
271123
16
94949494
21
23
21
Acetone
CS i
20.06
26.48
56.0156.0156.1856.18
62.3983.67
105.44105.44105.85105.85
131.79132.05133.69
140.22
151.62151.62151.71151.71
167.60
195.27
196.51
54
53
1001008989
3732
67677070
392537
28
68687979
33
35
35
CS i
DMSO
Ac Me
B β
OMeOMeOMeOMe
γβ
A2A6B2B6
A1A4B1
B4
A3A5B3B5
Ac C=O
B α
α
Atom
1HJMultH Shifts
2.35
2.58
3.813.86
5.22
7.367.21
s
s
ss
dd
ss
7.2, 3.3
Ac Me
B β
A3,5 OMeB3,5 OMe
β
A2,6B2,6
Atom
(chloroform)
SR III - 3740mgB2,6 and A1 shifts changes places in DMSO
Notes:
80Compound Number
FPL/DFRC NMR Database -- April 2009
1-(4-acetoxy-3,5-dimethoxyphenyl)-2-(4-acetylphenoxy)-3-hydroxypropan-1-one
13C
49
56
100100
3849
8989
8585
9292
333118
6060
33
24
29
31
20.40
26.33
56.3656.36
63.3281.33
105.67105.67
114.83114.83
130.78130.78
131.38132.25133.87
152.55152.55
161.00
168.06
194.60
196.64
CDCl3
CS i
20.21
26.34
56.7656.76
63.9482.26
106.40106.40
115.68115.68
131.20131.20
131.80133.97134.34
153.47153.47
162.44
168.11
195.47
196.21
46
50
100100
3740
9090
9696
8787
232912
4646
27
19
19
17
Acetone
CS i
20.05
26.28
56.3156.31
62.4180.64
105.42105.42
114.78114.78
130.36130.36
130.19132.74132.55
151.98151.98
161.22
167.62
194.76
196.08
51
53
100100
2932
6464
7373
6666
373424
6464
41
34
34
31
CS i
DMSO
Ac Me
B β
OMeOMe
γβ
A2A6
B3B5
B2B6
A1B1A4
A3A5
B4
Ac C=O
B α
α
Atom
1HJMultH Shifts
2.34
2.51
3.82
4.195.60
7.32
6.90
7.87
s
s
s
mdd
s
m
m
5.8, 4.2
8.9
8.9
Ac Me
B β
A3,5 OMe
γβ
A2,6
B3,5
B2,6
Atom
(chloroform)
SR III - 3817mgB1 and A4 switch places in DMSO A4 has very low intensity and is easy to follow
Notes:
81Compound Number
FPL/DFRC NMR Database -- April 2009
1-(4-acetoxy-3,5-dimethoxyphenyl)-2-(4-acetoxy-2-methoxyphenoxy)-3-hydroxypropan-1-one
13C
38
67
565959
2738
100100
4033
41
353716
33165757
16
1721
20.39
26.23
55.9156.3256.32
63.4783.63
105.80105.80
111.17114.89
123.01
132.23132.38133.75
149.76150.76152.47152.47
168.00
194.85196.57
CDCl3
CS i
20.21
26.30
56.2856.6956.69
63.9183.76
106.56106.56
112.34114.72
123.46
132.37134.04134.22
150.40152.27153.35153.35
168.08
195.94196.27
45
55
45100100
4250
9292
4545
53
212111
21214545
24
2421
Acetone
CS i
20.05
26.23
55.5556.2256.22
62.3281.51
105.45105.45
111.05113.02
122.65
130.46132.75132.46
148.67150.96151.87151.87
167.57
195.02196.14
38
71
41100100
3246
6666
4656
41
475121
47505454
24
5041
CS i
DMSO
Ac Me
B β
B OMeA OMeA OMe
γβ
A2A6
B2B5
B6
A1B1A4
B3B4A3A5
Ac C=O
B αα
Atom
1HJMultH Shifts
2.34
2.53
3.893.85
4.175.53
7.38
7.536.82
7.45
s
s
ss
dt
s
dd
dd
5.15.1
2.08.4
8.4, 2.0
Ac Me
B β
B3 OMeA3,5 OMe
γβ
A2,6
B2B5
B6
Atom
(chloroform)
R. Helm RFH87D136.6mg129.85 and 129.57 for Bα and C2,6 change places in DMSO see 1019
Notes:
82Compound Number
FPL/DFRC NMR Database -- April 2009
4-Acetoxycinnamic acid 3-acetoxy-3-(4-acetoxy- 3-methoxyphenyl)-2-(2-methoxyphenoxy)propyl ester
13C
385560
4944
283636
3342
39
47354310010036
41
8383
353432
44
30302827
32
253225
20.6321.0721.10
55.8155.95
63.3974.6280.50
111.78112.55
117.58
118.98119.56121.01122.13122.13122.84
123.35
129.30129.30
131.95135.36139.94
144.22
148.00150.92151.14152.23
166.28
168.70169.02169.68
CDCl3
CS i
20.4620.9520.95
56.2156.28
63.9375.5380.88
112.71113.75
118.56
119.36120.30121.68123.17123.17123.56
123.78
130.20130.20
132.78136.67140.90
144.71
149.10151.88152.20153.48
166.56
168.81169.35169.96
388989
5252
332141
3842
41
47345110010036
48
8282
293018
42
27212327
30
223622
Acetone
CS i
20.2920.6720.78
55.5555.75
62.8674.4379.25
111.70112.76
117.51
117.59119.38120.66122.29122.29122.59
129.85
129.57129.57
131.49135.43139.21
143.87
147.59150.18150.67152.04
165.66
168.28168.83169.32
455257
6752
213333
3145
40
50294810010040
17
9090
434040
40
50433640
40
334540
CS i
DMSO
Ac MeAc MeAc Me
OMeOMe
γαβ
A2B2
C β
B5A6B6C3C5A5
B1
C2C6
C1A1A4
C α
B4B3A3C4
C γ
Ac C=OAc C=OAc C=O
Atom
1HJMultH Shifts
2.072.282.30
3.793.80
4.234.42
4.726.196.34
7.127.51
7.55
sss
ss
dddd
mdd
mm
d
11.9, 5.811.9, 4.2
6.316.0
8.68.6
16.0
Ac MeAc MeAc Me
OMeOMe
γ1γ2
βα
C β
C2,6C3,5
C α
Atom
(chloroform)
threo
Rich Helm RFH87D238.6mgsee 1020
Notes:
83Compound Number
FPL/DFRC NMR Database -- April 2009
4-Acetoxycinnamic acid 3-acetoxy-3-(4-acetoxy- 3-methoxyphenyl)-2-(2-methoxyphenoxy)propyl ester
13C
505051
4954
323944
3940
46
71714410010042
469090313933
43
29353324
33
253135
20.6521.0321.10
55.8055.94
62.9374.0180.43
112.04112.64
117.67
119.73119.73121.01122.11122.11122.59
123.66129.30129.30132.00135.53139.80
144.19
147.25151.00151.19152.21
166.42
168.74169.02169.50
CDCl3
CS i
20.4720.9020.95
56.2156.28
63.3474.7380.54
112.78113.79
118.54
120.01120.44121.64123.17123.17123.35
124.09130.18130.18132.77136.71140.78
144.68
148.31152.10152.10153.48
166.57
168.84169.35169.87
404250
5048
344236
3646
44
44444810010042
449898463034
38
22464622
30
242624
Acetone
CS i
20.2920.6320.78
55.5855.70
62.2673.2878.58
111.71112.89
117.46
118.09119.39120.65122.29122.29122.48
122.89129.54129.54131.46135.36139.08
143.85
146.69150.35150.55152.02
165.67
168.32168.84169.21
655862
6958
233531
4246
46
46354610010042
469696354646
46
46425038
46
465046
CS i
DMSO
Ac MeAc MeAc Me
OMeOMe
γαβ
A2B2
C β
B5A6B6C3C5A5
B1C2C6C1A1A4
C α
B4B3A3C4
C γ
Ac C=OAc C=O Ac C=O
Atom
1HJMultH Shifts
2.102.292.30
3.763.81
4.474.75
4.75
6.14
6.35
7.56
sss
ss
dddd
m
d
d
d
11.9, 4.211.9, 5.6
5.4
16.0
16.0
Ac MeAc MeAc Me
OMeOMe
γ1γ2
β
α
C β
C α
Atom
(chloroform)
erythro
R. Helm RFH9D39.4mgsee 1026
Notes:
84Compound Number
FPL/DFRC NMR Database -- April 2009
3-(4-Acetoxy-3-methoxyphenyl)acrylic acid 4-[1,3-diacetoxy-2-(2-methoxyphenoxy)propyl]phenyl ester
13C
776870
8579100
575757
685764
57
6855646855686049454040
57
47575153
42
514038
20.6220.7621.01
55.8155.9456.00
62.5973.8480.22
111.41112.04112.68
117.16
119.55119.75121.01121.54122.67123.33123.63133.17135.48139.77141.78
145.85
147.18151.10151.14151.49
164.57
168.64169.50170.74
CDCl3
CS i
20.4720.6120.87
56.2156.2856.44
63.0074.6180.32
112.60112.79113.81
118.04
119.82120.45121.63122.47123.42124.04124.16134.02136.73140.70142.96
146.39
148.26152.04152.17152.73
164.96
168.74169.86170.70
927974
1008989
687471
746187
71
8471957966848263503934
66
39505561
50
585042
Acetone
CS i
20.3120.3720.60
55.5855.7255.98
61.8973.1778.40
111.69112.13112.90
117.09
117.96119.36120.64121.90122.54122.87123.18132.77135.40139.03141.30
145.79
146.63150.32150.63151.17
164.22
168.21169.20169.96
818881
10075100
445044
445669
50
6944755644566250505050
50
69626262
50
565669
CS i
DMSO
Ac MeAc MeAc Me
OMeOMeOMe
γαβ
C2A2B2
C β
B5A6B6C6A5B1C5C1A1A4C4
C α
B4B3A3C3
C γ
Ac C=OAc C=OAc C=O
Atom
1HJMultH Shifts
2.032.102.32
3.793.823.86
4.274.47
4.696.11
6.60
7.80
sss
sss
dddd
md
d
d
11.9, 4.011.9, 5.6
5.4
15.9
15.9
Ac MeAc MeAc Me
OMeOMeOMe
γ1γ2
βα
C β
C α
Atom
(chloroform)
erythro
R. Helm RFH111D139.0 mgIsomer of 86
Notes:
85Compound Number
FPL/DFRC NMR Database -- April 2009
3-{4-[3-Acetoxy-1-(4-acetoxy-3-methoxyphenyl)-2-(2-methoxyphenoxy)propoxy]phenyl}acrylic acid methyl ester
13C
5451
49
5652
414443
4748
48
10010044544849444795954632
44
34353434
3230
39
20.6220.72
51.54
55.7255.96
62.7978.8482.13
110.95112.61
115.75
116.22116.22119.05119.92121.05122.86123.75127.82129.63129.63136.23139.65
144.26
147.06151.23151.32159.48
167.59168.70
170.74
CDCl3
CS i
20.4520.60
51.52
56.1756.27
63.1879.6981.73
112.62113.79
116.52
117.18117.18119.93120.27121.63123.50123.99128.60130.56130.56137.03140.73
144.77
148.41152.04152.26160.44
167.59168.78
170.69
5548
52
6161
425248
4855
52
10010055455552483594944226
55
29293232
2929
32
Acetone
CS i
20.2920.39
51.19
55.5355.70
62.2077.7579.67
111.97112.85
115.50
116.08116.08117.78119.39120.62122.52122.69127.21129.96129.96135.78139.00
143.99
146.95150.26150.58158.88
166.74168.24
169.98
7771
71
8781
394548
4561
52
94945845614545581001005558
52
61655861
6542
65
CS i
DMSO
Ac MeAc Me
C γ OMe
OMeOMe
γαβ
A2B2
C β
C3C5B5A6B6A5B1C1C2C6A1A4
C α
B4B3A3C4
A γ C=OA4 C=O
C γ
Atom
1HJMultH Shifts
1.952.27
3.713.763.77
4.614.465.51
6.27
6.88
7.39
7.59
ss
sss
mmd
d
m
m
d
5.0
16.0
8.7
8.7
16.0
Ac MeAc Me
OMeOMeOMe
γβα
C β
C3,5
C2,6
C α
Atom
(chloroform)
Rich Helm RFH111D235mgIsomer of 85
Notes:
86Compound Number
FPL/DFRC NMR Database -- April 2009
3-{4-[3-Acetoxy-1-(4-acetoxy-3-methoxyphenyl)-2-(2-methoxyphenoxy)propoxy]phenyl}acrylic acid methyl ester
13C
6255
51
5559
374343
4553
51
99994650554649381001004229
50
33293339
3928
33
20.6220.72
51.53
55.6955.96
63.3279.7981.51
111.00112.43
115.68
116.25116.25119.13119.23120.95122.93123.40127.72129.58128.58135.56139.86
144.28
148.03150.94151.42159.50
167.60168.64
170.50
CDCl3
CS i
20.4520.59
51.52
56.1456.30
63.7080.5781.71
112.61113.68
116.43
117.12117.12119.33120.27121.61123.67123.67128.47130.52130.52136.80140.88
144.80
149.21151.85152.37160.59
167.60168.76
170.62
5050
55
5052
364348
4852
40
9595484845646443100434326
48
29292631
2929
24
Acetone
CS i
20.2820.36
51.17
55.4555.74
62.5578.9979.91
111.77112.70
115.36
116.02116.02117.27119.42120.58122.35122.70127.02129.90129.90135.66139.12
144.02
147.68150.07150.75159.19
166.74168.21
169.91
9284
72
9280
364444
4460
52
1001005644644444601001005652
52
56565260
6452
60
CS i
DMSO
Ac MeAc Me
C γ OMe
OMeOMe
γαβ
A2B2
C β
C3C5B5A6B6A5B1C1C2C6A1A4
C α
B4B3A3C4
C γ C=OA4 C=O
A γ
Atom
1HJMultH Shifts
1.992.28
3.75
3.773.79
4.134.42
4.685.516.27
7.37
7.59
ss
s
ss
dddd
mdd
m
d
11.8, 5.911.7, 4.3
5.316.0
8.7
16.0
Ac MeAc Me
C γ OMe
OMeOMe
γ1γ2
βα
C β
C2,6
C α
Atom
(chloroform)
Aldrich30mgProton data from 360 MHz spectrum in acetone..S.Q.
Notes:
87Compound Number
FPL/DFRC NMR Database -- April 2009
Coniferyl alcohol4-hydroxy-3-methoxy cinnamyl alcohol
13C
100
87
80
93
87
90
45
82
46
38
55.88
63.71
108.52
114.57
120.25
126.22
129.30
131.24
145.63
146.75
CDCl3
CS i
56.20
63.42
110.06
115.76
120.60
128.07
130.26
130.45
147.14
148.41
100
80
76
83
91
78
41
72
41
30
Acetone
CS i
55.47
61.63
109.66
115.36
119.30
127.38
128.41
128.87
146.06
147.60
100
86
84
86
86
91
67
81
67
63
CS i
DMSO
OMe
γ
2
5
6
β
1
α
4
3
Atom
1HJMultH Shifts
3.783.86
4.18
6.22
6.49
6.766.847.04
7.63
ts
td
dt
dt
dddd
s
5.6
5.5, 1.5
15.9, 5.5
15.9, 15
8.18.1,1.9
1.9
γ OHOMe
γ's
β
α
562
4 OH
Atom
(acetone)
trans
S Ralph SRIII-4330mg Small amount of 4 Ac present.
Notes:
88Compound Number
FPL/DFRC NMR Database -- April 2009
1-(4-Hydroxy-3,5-dimethoxyphenyl)-2-[4-(1-hydroxyethyl)-2-methoxyphenoxy]propane-1,3-diol
13C
37
47100100
2848
3330
6666
363522
282529255252
18
25.24
55.8756.3356.33
61.0469.95
74.1289.03
103.79103.79
109.30118.40120.27
130.71134.56142.02146.66147.09147.09
150.99
CDCl3
CS i
26.23
56.2756.5956.59
61.9469.73
74.0588.50
105.36105.36
110.58118.65119.45
132.80136.12142.85148.27148.38148.38
151.38
47
59100100
3454
4632
9595
394434
22206294343
21
Acetone
CS i
25.84
55.4455.7355.73
59.9967.80
70.8784.39
104.06104.06
109.65115.29117.20
131.93134.24140.36146.73147.30147.30
149.23
70
69100100
2663
2821
5353
272736
342931337373
37
CS i
DMSO
B β
B OMeA OMeA OMe
γB α
αβ
A2A6
B2B5B6
A1A4B1B4A3A5
B3
Atom
1HJMultH Shifts
1.38
3.87
3.80
4.50
6.77
d
s
s
d
s
6.4
3.9
B β
B OMe
A3,5 OMe
α OH
A2,6
Atom
(acetone)
threo
S Ralph SRIII-4430mg
Notes:
89Compound Number
FPL/DFRC NMR Database -- April 2009
1-(4-Hydroxy-3,5-dimethoxyphenyl)-2-[4-(1-hydroxyethyl)-2,6-dimethoxyphenoxy]propane-1,3-diol
13C
37
9494100100
31433737
75757070
3321
3132
56565656
25.43
56.1256.1256.3156.31
60.4870.2174.3488.97
102.27102.27104.04104.04
130.99134.10
134.46142.94
147.02147.02152.88152.88
CDCl3
CS i
26.27
56.5056.5056.5756.57
61.4169.9874.2289.69
103.41103.41105.46105.46
132.60135.54
136.11144.61
148.30148.30153.58153.58
45
1001009595
29413636
87877272
2512
2126
36364242
Acetone
CS i
25.84
55.8055.8055.8055.80
60.1568.0971.5487.11
102.49102.49104.14104.14
131.97134.22
134.50142.91
147.25147.25152.14152.14
28
100100100100
12261616
32323030
1715
1717
36363535
CS i
DMSO
B β
OMeOMeOMeOMe
γB α
αβ
B2B6A2A6
A1B1
A4B4
A3A5B3B5
Atom
1HJMultH Shifts
1.39
3.803.89
4.81
4.97
6.776.76
3.31
4.27
4.44
d
ss
m
dd
ss
m
d
d
6.4
7.3, 2.9
4.1
2.9
B β
A3,5 OMeB3,5 OMe
B α
α
B2,5A2,6
γ 2
B α OH
α OH
Atom
(acetone)
threo
S. Ralph SRIII-4530mg
Notes:
90Compound Number
FPL/DFRC NMR Database -- April 2009
Syringylglycerol-β-guaiacyl ether
�1-(4-Hydroxy-3,5-dimethoxyphenyl)-2-(2-methoxyphenoxy) propane-1,3-diol
13C
56
100100
373934
64645040
5340
2419
49491723
55.88
56.3256.32
61.0274.1689.22
103.81103.81112.16120.86
121.67124.17
130.71134.57
147.10147.10147.58151.22
CDCl3
CS i
56.24
56.5456.54
61.8973.9788.19
105.28105.28113.27119.66
121.91123.30
132.72136.07
148.34148.34149.60151.65
62
100100
404046
7474394
5256
2316
36361815
Acetone
CS i
55.45
55.7255.72
60.0170.8884.03
104.07104.07112.38115.52
120.58120.90
131.89134.26
147.31147.31148.18149.55
75
100100
183632
59595133
5137
3930
72722633
CS i
DMSO
B OMe
A OMeA OMe
γαβ
A2A6B2B5
B6B1
A1A4
A3A5B4B3
Atom
1HJMultH Shifts
3.86
3.79
4.88
4.22
4.49
6.86
s
s
dd
m
d
s
6.0, 3.7
3.7
B OMe
A3,5 OMe
α
β
α OH
A2,6
Atom
(acetone)
threo
S. Ralph SRIII-4620mg contains 4-AC impurity.
Notes:
91Compound Number
FPL/DFRC NMR Database -- April 2009
�1-(4-Hydroxy-3,5-dimethoxyphenyl)-2-[4-(1-hydroxy
ethyl)phenoxy]propane-1,3-diol
13C
39
100100
30422824
5252
6464
8484
232323
4444
19
25.07
56.3456.34
61.1469.7573.8582.97
103.70103.70
116.34116.34
126.84126.84
130.90134.56139.33
147.07147.07
157.42
CDCl3
CS i
26.17
56.5856.58
61.7369.5073.5484.14
105.27105.27
116.64116.64
127.15127.15
133.23136.00140.47
148.32148.32
158.98
58
9494
32583432
6464
100100
9090
261420
4444
18
Acetone
CS i
25.81
55.8255.82
60.0167.5771.0983.01
104.12104.12
115.34115.34
126.13126.13
132.31134.31139.21
147.36147.36
157.69
88
100100
27733333
5858
100100
8585
393039
7676
42
CS i
DMSO
B β
A OMeA OMe
γB α
αβ
A2A6
B3B5
B2B6
A1A4B1
A3A5
B4
Atom
1HJMultH Shifts
1.35
3.79
6.77
7.23
d
s
s
m
6.4
8.6
B β
A3,5 OMe
A2,6
B2,6
Atom
(acetone)
S. Ralph SRIII-4030mg *A1 + A4 switch around in CDCl3
Notes:
92Compound Number
FPL/DFRC NMR Database -- April 2009
1-(4-acetoxy-3,5-dimethoxyphenyl)-3-hydroxy-2-(2-methoxyphenoxy)propan-1-one
13C
54
54100100
4047
8787
49425042
1228
23264848
20
22
20.41
55.7356.2956.29
63.3984.41
105.84105.84
112.33117.86121.23123.61
133.42132.81
146.71150.24152.32152.32
168.06
195.72
CDCl3
CS i
20.21
56.0756.6056.60
63.8884.02
106.50106.50
113.57116.84121.57123.15
133.93134.31
148.17150.90153.19153.19
168.10
196.70
44
49100100
2136
8282
41295340
718
16163434
17
20
Acetone
CS i
20.04
55.3956.1256.12
62.3581.59
105.38105.38
112.64114.73120.49121.67
132.25132.99
146.73149.13151.75151.75
167.58
195.86
65
60100100
3832
6868
38324838
2037
35337777
32
35
CS i
DMSO
Ac Me
B OMeA OMeA OMe
γβ
A2A6
B2B5B6B1
A4A1
B4B3A3A5
Ac C=O
α
Atom
1HJMultH Shifts
2.34
3.823.83
4.095.38
7.36
s
ss
dt
s
5.25.2
Ac Me
B OMeA3,5 OMe
γβ
A2,6
Atom
(chloroform)
Aldrich60mg Al changes position in DMSO
Notes:
93Compound Number
FPL/DFRC NMR Database -- April 2009
Phenyl benzoateBenzoic acid phenyl ester
13C
9090
52
100100
100100
15
9595
48
12
9
121.70121.70
125.84
128.54128.54
129.45129.45
129.57
130.13130.13
133.53
150.96
165.11
CDCl3
CS i
122.61122.61
126.51
129.47129.47
130.15130.15
130.42
130.60130.60
134.39
151.99
165.32
8989
51
100100
9696
19
9898
54
14
9
Acetone
CS i
121.85121.85
125.92
128.88128.88
129.50129.50
128.94
129.72129.72
133.93
150.62
164.51
8585
43
100100
100100
25
9999
42
27
15
CS i
DMSO
B3B5
B1
A2A6
B2B6
A1
A3A5
A4
B4
α
Atom
1HJMultH Shifts
8.21 m 8.3A2,6
Atom
(chloroform)
Aldrich60mg
Notes:
94Compound Number
FPL/DFRC NMR Database -- April 2009
Ethyl 4-hydroxybenzoateethyl 4-hydroxybenzoate
13C
46
44
100100
21
9090
26
17
14.30
61.13
115.34115.34
122.13
131.94131.94
160.74
167.45
CDCl3
CS i
14.63
60.84
115.92115.92
122.69
132.30132.30
162.44
166.49
47
42
100100
10
9090
22
10
Acetone
CS i
14.24
60.04
115.27115.27
120.61
131.35131.35
161.93
165.56
53
44
9191
20
100100
40
21
CS i
DMSO
CH3
CH2
35
1
26
4
α
Atom
1HJMultH Shifts
1.39
4.36
6.91
7.95
t
q
m
m
7.1
7.1
8.8
8.8
CH3
CH2
A3,5
A2,6
Atom
(chloroform)
Fluka60mg
Notes:
95Compound Number
FPL/DFRC NMR Database -- April 2009
Cinnamyl alcohol(E)-3-phenyl-2-propen-1-ol(E)-cinnamyl alcohol
13C
41
7272
41
100100
100
34
13
63.39
126.40126.40
127.57
128.52128.52
128.52
130.86
136.66
CDCl3
CS i
63.12
126.98126.98
127.93
129.25129.25
129.90
130.90
138.08
52
100100
51
9595
42
49
14
Acetone
CS i
61.50
126.05126.05
127.08
128.49128.49
128.37
130.72
136.87
42
8888
48
100100
40
47
18
CS i
DMSO
γ
26
β
35
4
α
1
Atom
1HJMultH Shifts
4.25
6.30
6.54
dd
dt
dt
5.6, 1.1
15.9, 5.6
15.9, 1.1
γ
β
α
Atom
(chloroform)
trans
Fluka60mg
Notes:
96Compound Number
FPL/DFRC NMR Database -- April 2009
Cinnamaldehyde(E)-3-phenyl-2-propenal(E)-cinnamaldehyde
13C
100100
100
9292
41
12
21
25
128.45128.45
128.45
129.04129.04
131.20
133.96
152.66
193.54
CDCl3
CS i
129.30129.30
129.40
129.81129.81
131.78
135.19
153.19
193.96
9191
48
100100
55
12
32
30
Acetone
CS i
128.69128.69
128.50
129.02129.02
131.13
134.07
153.00
194.19
100100
48
9696
48
23
35
32
CS i
DMSO
26
4
35
β
1
α
γ
Atom
1HJMultH Shifts
6.69
7.50
9.68
dd
d
d
16.0, 7.7
16.0
7.7
β
α
γ
Atom
(chloroform)
trans
S. Ralph SRIII-4340mgca 90% threo
Notes:
97Compound Number
FPL/DFRC NMR Database -- April 2009
1-(4-acetoxy-3,5-dimethoxyphenyl)-1,3-diacetoxy-2-[4-(1-acetoxyethyl)-2-methoxyphenoxy]
13C
42323742
34
50100100
21262424
5555
182426
1832261632
5353
26182426
20.4220.7021.0421.35
22.08
55.8856.2156.21
62.9872.0674.6580.12
104.09104.09
110.64118.22118.65
128.83134.71136.72147.53150.58
152.17152.17
168.47169.66170.27170.55
CDCl3
CS i
20.2320.6220.9321.15
22.46
56.2956.5256.52
63.5872.4075.6480.68
104.93104.93
111.71118.71119.18
129.65136.12137.72148.51151.52
153.14153.14
168.40169.96170.17170.65
49464044
40
59100100
37484133
8181
323043
1032242225
5151
21191719
Acetone
CS i
20.0420.3720.6320.93
21.87
55.6155.9655.96
62.4271.3574.5479.08
103.91103.91
110.55117.03118.05
127.78134.92136.00146.99149.82
151.52151.52
167.88169.32169.52169.92
58675067
42
54100100
25422929
3333
213342
2138334242
7575
33333833
CS i
DMSO
Ac MeAc MeAc MeAc Me
B β
B OMeA OMeA OMe
γB α
αβ
A2A6
B2B5B6
A4A1B1B4B3
A3A5
A4 Ac C=Oα Ac C=O
B αAc C=OγAc C=O
Atom
1HJMultH Shifts
2.002.062.072.32
1.52
3.833.81
4.074.32
4.60
5.826.08
6.67
ssss
d
ss
dddd
m
qd
s
6.6
11.8, 5.711.8, 4.6
6.66.2
Ac MeAc MeAc MeAc Me
B β
B OMeA3,5 OMe
γ1γ2
β
B αα
A2,6
Atom
(chloroform)
threo
S. Ralph SRIII-44131mg
Notes:
98Compound Number
FPL/DFRC NMR Database -- April 2009
1-(4-acetoxy-3,5-dimethoxyphenyl)-1,3-diacetoxy-2-[4-(1-acetoxyethyl)-2,6-dimethoxyphenoxy]propane
13C
47423136
31
9696100100
18253135
46464646
14281132
61613838
19151925
20.4220.7221.0221.33
22.25
56.0256.0256.2156.21
63.5372.3575.6180.64
103.14103.14104.18104.18
128.64135.46135.95137.57
151.98151.98152.87152.87
168.49169.70170.16170.50
CDCl3
CS i
20.2320.6320.9221.14
22.56
56.3656.3656.4556.45
64.1872.6876.6281.44
103.92103.92104.78104.78
129.42136.61136.96138.68
152.94152.94153.69153.69
168.37169.80170.11170.56
40353141
29
9191100100
32352633
55555757
9291726
49494949
20222019
Acetone
CS i
20.0620.3720.6220.95
22.02
55.7855.7855.9855.98
63.2271.7275.7380.27
102.85102.85103.76103.76
127.75135.39135.48137.40
151.52151.52152.27152.27
167.93169.27169.56169.95
49463557
32
1001009595
22371823
38384949
11323535
65656666
29354040
CS i
DMSO
Ac MeAc MeAc MeAc Me
Bβ
OMeOMeOMeOMe
γB ຶ
ααβ
B2B6A2A6
A4A1B1B4
A3A5B3B5
A4 Ac C=Oα Ac C=O
B αAc C=Oγ Ac C=O
Atom
1HJMultH Shifts
2.012.072.082.32
1.52
3.783.80
3.944.364.545.796.12
6.556.70
ssss
d
ss
ddddmqd
ss
6.6
11.8, 7.311.8, 4.5
6.66.1
Ac MeAc MeAc MeAc Me
B β
OMeOMe
γ1γ2β
B αα
B2,6A2,6
Atom
(chloroform)
threo
S. Ralph SRIII-4555mg ca 80% threo*CS assignments for overlapping 1H patterns A2,6 and B1,B2,B5 and B6from deconvolution and simulation spectra, MacNuts, Acorn NMR Inc.
Notes:
99Compound Number
FPL/DFRC NMR Database -- April 2009
1-(4-acetoxy-3,5-dimethoxyphenyl)-1,3-diacetoxy-2-(2-methoxyphenoxy)propane
13C
483640
54100100
323536
6161344041
4210312020
5050
212019
20.4220.7121.05
55.7756.2056.20
63.0874.7780.23
104.08104.08112.48118.61120.98
123.28128.79134.80147.92150.76
152.16152.16
168.47169.68170.55
CDCl3
CS i
20.2420.6220.94
56.2056.5256.52
63.6075.6780.64
104.93104.93113.71119.04121.66
123.68129.65136.18149.06151.75
153.14153.14
168.41169.97170.66
564844
63100100
434348
8181444348
4410271721
4141
291719
Acetone
CS i
20.0520.3920.65
55.5255.9755.97
62.4874.5879.00
103.92103.92112.69117.31120.63
122.49127.81134.99147.54150.06
151.56151.56
167.89169.34169.94
685047
59100100
263535
6262414153
3521413835
7474
292629
CS i
DMSO
Ac MeAc MeAc Me
B OMeOMeOMe
γαb
A2A6B2B5B6
B1A4A1B4B3
A3A5
A4 Ac C=Oα Ac C=Oγ Ac C=O
Atom
1HJMultH Shifts
1.972.022.21
3.803.81
4.044.264.796.08
6.856.976.997.046.87
sss
ss
ddddmd
smmmm
11.9, 5.611.9, 4.2
6.5
8.2, 8.1, 1.38.2, 1.08.0, 1.3
8.0, 8.1, 1.0
Ac MeAc MeAc Me
A3,5 OMeOMe
γ1γ2βα
A2,6B1B2B5B6
Atom
(acetone)
threo
S. Ralph SRIII-4624mgCDCl3 spectrum poor
Notes:
100Compound Number
FPL/DFRC NMR Database -- April 2009
1-(4-acetoxy-3,5-dimethoxyphenyl)-1,3-diacetoxy-2-[4-(1-acetoxyethyl)phenoxy] propane
13C
33404548
36
100100
33452126
767660608888
53129
5252
19
21242124
20.4320.6821.0321.36
22.01
56.2556.25
62.6771.8574.2478.17
104.09104.09116.32116.32127.67127.67
128.95134.35135.26
152.28152.28
158.02
168.44169.69170.30170.56
CDCl3
CS i
20.2320.6020.8921.15
22.36
56.5856.58
63.3172.1975.4579.23
105.05105.05117.12117.12128.29128.29
129.80135.98136.24
153.25153.25
159.20
168.39170.02170.19170.68
49384740
36
8989
33403622
89894949100100
42724
4747
18
22201320
Acetone
CS i
20.0420.3820.6220.92
21.76
56.0156.01
62.1571.1274.3277.60
104.00104.00116.00116.00127.28127.28
127.83134.66134.81
151.57151.57
157.68
167.86169.37169.52169.94
66695972
50
100100
25222825
626284847878
55659
7272
34
28384131
CS i
DMSO
Ac MeAc MeAc MeAc Me
B β
OMeOMe
γB α
αβ
A2A6B3B5B2B6
A4B1A1
A3A5
B4
A4 Ac C=Oα Ac C=O
B α Ac C=Oγ Ac C=O
Atom
1HJMultH Shifts
1.992.052.052.32
1.51
3.80
4.064.254.695.836.03
6.636.897.28
ssss
d
s
ddddmqd
smm
6.6
11.8, 6.111.8,-
6.66.3
7.87.8
Ac MeAc MeAc MeAc Me
B β
A3,5 OMe
γ1γ2β
B αα
A2,6B3,5B2,6
Atom
(chloroform)
threo
J. Ralph JRB 178.330mgJ. Ralph Holzforschung 42(1988) p273-5
Notes:
101Compound Number
FPL/DFRC NMR Database -- April 2009
Guaiacylglycerol-β-guaiacyl ether
1-(4-hydroxy-3-methoxyphenyl)-2-(2-methoxyphenoxy)propan-1,3-diol
13C
82100
767675
717584
737590
80
51
49453539
55.8655.94
60.7572.7887.02
108.81112.19114.31
119.07120.57121.59
124.00
131.95
145.09146.64146.89151.40
CDCl3
CS i
56.2056.27
61.8173.8286.72
111.38113.50115.12
119.70120.45121.85
123.32
134.23
146.61147.93149.04151.96
97100
8181100
948190
9094100
100
55
42393535
Acetone
CS i
55.3555.52
60.0471.6083.67
111.35112.60114.48
115.86119.43120.56
120.89
133.15
145.35146.86148.00149.68
10084
597266
626966
596678
69
69
78726256
CS i
DMSO
OMeOMe
γαβ
A2B2A5
B5A6B6
B1
A1
A4A3B4B3
Atom
1HJMultH Shifts
3.833.84
4.954.16
ss
dm
4.8
OMeOMe
αβ
Atom
(chloroform)
erythro
J. Ralph JRGV 135.X121mgJ. Ralph Holzforschung 42(1988) p.273-5
Notes:
102Compound Number
FPL/DFRC NMR Database -- April 2009
Guaiacylglycerol-β-guaiacyl ether
1-(4-hydroxy-3-methoxyphenyl)-2-(2-methoxyphenoxy)propane-1,3-diol
13C
92100
728072
868888
887594
85
46
48423538
55.9155.97
61.0674.0089.45
109.46112.18114.35
120.25120.98121.69
124.21
131.51
145.59146.68147.63151.27
CDCl3
CS i
56.2156.31
61.9073.9388.58
111.41113.40115.21
120.06120.57121.95
123.44
133.81
146.82148.00149.70151.80
96100
758484
968678
908880
88
43
39293129
Acetone
CS i
55.3355.53
60.0270.9084.37
110.96112.50114.57
115.79118.92120.60
120.96
132.86
145.33146.89148.32149.62
97100
596962
666662
626276
69
76
79665959
CS i
DMSO
OMeOMe
γαβ
A2B2A5
B5A6B6
B1
A1
A4A3B4B3
Atom
1HJMultH Shifts
3.863.90
4.964.02
ss
dm
8.0
OMeOMe
αβ
Atom
(chloroform)
threo
IPC45mg
Notes:
103Compound Number
FPL/DFRC NMR Database -- April 2009
Acetylated acetovanillone4-acetoxy-3-methoxyacetophenone
13C
65
81
100
97
88
95
37
26
33
30
30
20.61
26.49
56.05
111.51
121.94
122.80
135.96
143.87
151.41
168.46
196.91
CDCl3
CS i
20.46
26.63
56.37
112.44
122.38
123.77
136.93
144.80
152.40
168.64
196.89
64
84
97
97
93
100
30
21
24
26
29
Acetone
CS i
20.29
26.62
55.88
111.62
121.56
123.02
135.62
143.21
150.92
168.12
196.88
83
88
100
77
83
84
51
35
41
44
40
CS i
DMSO
Ac Me
β
OMe
2
6
5
1
4
3
Ac C=O
α
Atom
1HJMultH Shifts
2.59
2.33
3.88
7.59
7.12
7.54
s
s
s
d
d
dd
1.9
8.1
8.1, 1.9
Ac Me
β
OMe
2
5
6
Atom
(chloroform)
LL Landucci75mg Shifts reported are for threo isomer-minor isomer of this mixture, see 105 also
Notes:
104Compound Number
FPL/DFRC NMR Database -- April 2009
Veratrylglycerol-β-guaiacyl ether
1-(3,4-Dimethoxyphenyl)-2-(2-methoxyphenoxy)propane-1,3-diol
13C
76100100
161614
154543
15151917
12
10121211
55.8455.8855.88
61.0473.7788.82
110.05111.07112.21
119.55120.52121.61123.93
132.38
147.65148.83149.04151.07
CDCl3
CS i
56.0356.1156.27
61.7073.6487.92
111.89112.29113.36
120.03119.56121.83123.30
135.01
148.92149.67149.96151.61
1009794
607428
677431
72323466
16
25153210
Acetone
CS i
55.2255.4255.52
60.0270.7784.26
110.67111.13112.52
115.84118.62120.56120.95
134.47
147.72147.98148.25149.67
7282100
481820
205323
23223223
22
27432023
CS i
DMSO
OMeOMeOMe
γα
β
A2A5B2
A6B5B6B1
A1
B4A4A3B3
Atom
1HJMultH Shifts
3.823.833.84
4.96
4.15
sss
d
m
5.0
OMeOMeOMe
α
β
Atom
(chloroform)
threo
LL Landucci30mg alpha OH proton 4.55 in acetone
Notes:
105Compound Number
FPL/DFRC NMR Database -- April 2009
Veratrylglycerol-β-guaiacyl ether
1-(3,4-Dimethoxyphenyl)-2-(2-methoxyphenoxy)-propane-1,3-diol
13C
73100100
465050
465053
50504845
37
26262726
55.8755.9155.91
60.8172.7587.10
109.41111.08112.21
118.49120.68121.58124.02
132.70
146.96148.48149.02151.47
CDCl3
CS i
56.0756.1556.30
61.7973.7586.58
111.97112.35113.55
120.06119.64121.86123.32
135.50
149.03149.63150.04151.96
878795
303674
808484
100858787
31
31313431
Acetone
CS i
55.2355.4455.54
60.0371.5483.62
111.03111.14112.61
115.95119.18120.56120.95
134.79
147.76147.99148.10149.72
9210097
616967
727575
72678172
69
56616753
CS i
DMSO
OMeOMeOMe
γα
β
A2A5B2
A6B5B6B1
A1
B4A4A3B3
Atom
1HJMultH Shifts
3.853.853.854.994.173.693.926.906.99
3.763.773.814.914.293.673.817.116.86
sssdmmmmm
dd
4.8
2.18.45
OMeOMeOMe
αβγ1
γ2A2A6
acetoneOMeOMeOMe
αβγ1
γ2A2A6
Atom
(chloroform)
erythro
S. Ralph45mg
Notes:
106Compound Number
FPL/DFRC NMR Database -- April 2009
Erone3-Hydroxy-1-(4-hydroxy-3-methoxyphenyl)-2-(2-methoxy
phenoxy)-propan-1-one
13C
10096
7288
87898779
928888
56
55594262
52
55.8256.02
63.7083.94
110.88112.35114.21117.56
121.18123.26124.16
127.68
146.91146.95150.12151.28
194.91
CDCl3
CS i
56.2056.24
64.1183.69
112.48113.65115.50116.70
121.57122.94124.66
128.72
148.29148.36150.86152.76
195.64
97100
4182
73858281
888286
42
36412741
42
Acetone
CS i
55.4655.50
62.5281.32
111.71112.67114.48114.98
120.48121.47123.51
126.79
146.94147.49149.13152.22
194.69
96100
5561
56605755
666054
52
56615468
50
CS i
DMSO
OMeOMe
γβ
A2B2A5B5
B6B1A6
A1
B4A3B3A4
α
Atom
1HJMultH Shifts
3.833.87
4.08
5.43
ss
d
t
5.1
5.1
OMeOMe
γ
β
Atom
(chloroform)
M.Mozuch 88/71/120mg not soluble in CDCl3
Notes:
107Compound Number
FPL/DFRC NMR Database -- April 2009
Vanillyl-β-D-Glucoside
2-(4-Hydroxy-3-methoxybenzyloxy)-6-hydroxymethyltetrahydropyran-3,4,5-triol
13CCDCl3
CS i
56.30
63.00
70.9871.7474.90
77.48
78.02102.70
112.81115.41121.77
130.28147.00148.21
100
76
769086
84
8879
888787
504633
Acetone
CS i
55.46
61.09
69.4070.0973.40
76.66
76.82101.52
112.29114.90120.50
128.57145.80147.25
100
57
618693
89
8682
828279
797571
CS i
DMSO
OMe
B6
B4B2B5
α
B3B1
A2A5A6
A1A3A4
Atom
1HJMultH ShiftsAtom
Not run
R. Helm RFH 83F150mg not suluble in CDCL3
Notes:
108Compound Number
FPL/DFRC NMR Database -- April 2009
Acetylated ferulic acid4-acetoxy-3-methoxycinnamic acid
13CCDCl3
CS i
20.48
56.42
112.48
119.48
122.03
124.11
134.38
142.62
144.79
152.71
167.70
168.78
86
96
80
76
91
100
39
26
89
34
41
36
Acetone
CS i
20.29
55.90
111.79
119.47
121.20
123.10
133.19
140.77
143.23
151.09
167.50
168.29
98
100
76
80
84
82
64
56
80
64
78
66
CS i
DMSO
Ac Me
OMe
2
β
6
5
1
4
α
3
Ac C=O
γ
Atom
1HJMultH Shifts
2.33
3.88
7.04
6.41
s
s
d
d
15.9
15.9
Ac Me
OMe
α
β
Atom
(chloroform)
J. PewAs this compound has a plane of symmetry the shifts for the other half areidentical.
Notes:
109Compound Number
FPL/DFRC NMR Database -- April 2009
Pinoresinol diacetateAcetic acid 4-[4-(4-acetoxy-3-methoxyphenyl) tetrahydrofuro[3,4-c]
furan-1-yl]-2-methoxyphenyl ester
13C
86
94
100
86
93
87
88
77
37
61
48
42
20.62
54.36
55.92
71.95
85.50
109.91
117.92
122.74
139.13
140.11
151.23
168.99
CDCl3
CS i
20.48
55.42
56.23
72.58
86.22
111.12
118.63
123.46
140.15
141.80
152.28
168.98
76
92
100
79
92
81
84
83
27
43
35
25
Acetone
CS i
20.28
53.75
55.67
71.24
84.64
110.33
117.78
122.50
138.42
140.41
150.70
168.44
85
85
100
78
80
78
76
83
51
71
66
58
CS i
DMSO
Ac Me
β
OMe
γ
α
2
6
5
4
1
3
Ac C=O
Atom
1HJMultH Shifts
2.30
3.83
3.08
3.92
4.27
4.78
6.88
6.99
7.00
s
s
m
dd
dd
d
dd
m
m
9.0, 3.2
9.0, 6.8
3.9
8.1, 1.4
Ac Me
OMe
β
γ1
γ2
α
6
2
5
Atom
(chloroform)
LL Landucci34mg
Notes:
110Compound Number
FPL/DFRC NMR Database -- April 2009
Veratrone1-(3,4-Dimethoxyphenyl)-3-hydroxy-2-(2-methoxyphenoxy)
propan-1-one
13C
94100100
77
89
81838974859477
42
34473840
49
55.8255.9756.10
63.73
84.31
110.17111.04112.35117.96121.17123.40123.63
128.10
146.97149.20150.30153.95
195.04
CDCl3
CS i
56.0556.0556.21
64.11
83.88
111.53112.23113.74116.95121.59123.04124.28
129.44
148.43150.07151.01154.89
195.92
5959100
52
65
56576761696556
28
20222022
26
Acetone
CS i
55.3955.4655.70
62.47
81.38
110.75110.87112.68114.58120.48121.56123.24
127.88
146.88148.50149.14153.40
195.14
8410087
68
71
68717171747465
61
52655558
55
CS i
DMSO
OMeOMeOMe
γ
β
A2A5B2B5B6B1A6
A1
B4A3B3A4
α
Atom
1HJMultH Shifts
3.843.903.93
4.08
5.42
7.617.76
sss
m
t
ddd
5.2
2.08.4, 2.0
OMeOMeOMe
γ
β
A2A6
Atom
(chloroform)
J. Ralph JRPS115.150mg
Notes:
111Compound Number
FPL/DFRC NMR Database -- April 2009
acetylated isoeugenol1-(3-methoxy-4-acetoxyphenyl)-1-propene
13C
91
73
100
77
96
85
85
87
41
25
31
32
18.37
20.62
55.77
109.69
118.36
122.65
126.01
130.48
137.06
138.65
151.02
169.04
CDCl3
CS i
18.45
20.45
56.10
110.54
118.90
123.53
126.34
131.36
137.70
139.88
152.26
168.95
81
68
100
89
97
97
94
94
35
21
24
23
Acetone
CS i
18.11
20.32
55.64
109.73
117.99
122.68
125.80
130.24
136.44
138.24
150.86
168.46
94
86
100
95
100
92
79
92
71
46
52
40
CS i
DMSO
γ
Ac Me
OMe
2
6
5
β
α
1
4
3
Ac C=O
Atom
1HJMultH Shifts
1.85
2.28
3.81
6.17
6.35
dd
s
s
dq
dd
6.35, 1.4
15.7, 6.35
15.7, 1.4
γ
Ac Me
OMe
β
α
Atom
(chloroform)
Aldrich50mg contains an impurity
Notes:
112Compound Number
FPL/DFRC NMR Database -- April 2009
Isoeugenol1-(3-methoxy-4-hydroxyphenyl)-1-propene
13C
86
100
81
95
98
86
42
96
44
26
18.30
55.82
108.01
114.43
119.30
123.34
130.66
130.78
144.79
146.61
CDCl3
CS i
18.38
56.13
109.64
115.66
119.89
122.97
130.93
131.86
146.61
148.28
88
100
83
89
100
89
30
85
37
27
Acetone
CS i
18.05
55.50
109.41
115.41
118.78
121.98
129.11
130.87
145.80
147.64
98
100
87
91
95
95
56
88
72
61
CS i
DMSO
γ
OMe
2
5
6
β
1
α
4
3
Atom
1HJMultH Shifts
1.83
3.84
6.05
6.30
dd
s
dq
dd
6..5, 1.6
15.7, 6.5
15.7, 1.6
γ
OMe
β
α
Atom
(chloroform)
Aldrich50mg
Notes:
113Compound Number
FPL/DFRC NMR Database -- April 2009
Eugenol4-Allyl-2-methoxyphenol
13C
84
100
94
98
86
96
36
72
32
27
39.88
55.86
111.17
114.31
115.46
121.19
131.90
137.83
143.93
146.47
CDCl3
CS i
40.32
56.16
112.83
115.31
115.61
121.66
132.07
139.05
145.68
148.13
90
100
81
71
93
86
27
68
32
25
Acetone
CS i
39.08
55.49
112.58
115.11
115.35
120.48
130.39
138.13
144.72
147.43
99
100
82
82
100
76
56
82
63
50
CS i
DMSO
α
OMe
2
γ
5
6
1
β
4
3
Atom
1HJMultH Shifts
3.30
3.84
5.04
5.94
6.83
d
s
m
ddt
d
6.6
6.6
8.5
α
OMe
γ
β
5
Atom
(chloroform)
Aldrich 50mg Extraneous peaksaround 106 and 119
Notes:
114Compound Number
FPL/DFRC NMR Database -- April 2009
4-Allyl-2,6-dimethoxyphenol
13C
49
9797
100100
46
23
16
43
3636
40.31
56.2656.26
105.26105.26
115.65
131.06
133.10
137.60
147.03147.03
CDCl3
CS i
40.73
56.5856.58
106.83106.83
115.42
131.13
135.19
138.95
148.60148.60
53
9999
100100
45
19
15
36
2828
Acetone
CS i
39.53
55.8955.89
105.83105.83
115.26
129.63
133.81
137.98
147.93147.93
66
100100
8383
48
30
28
47
5454
CS i
DMSO
α
OMeOMe
26
γ
1
4
β
35
Atom
1HJMultH Shifts
3.30
3.85
6.40
5.04
5.94
d
s
s
m
ddt
6.7
16.8, 10.2, 6.7
α
OMe
2,6
γ1
β
Atom
(chloroform)
J. Ralph JRC91.150mg
Notes:
115Compound Number
FPL/DFRC NMR Database -- April 2009
acetylated eugenol1-(3-methoxy-4-acetoxyphenyl)-2-propene
13C
76
100
89
89
76
100
100
78
24
43
28
32
20.64
40.08
55.81
112.76
116.12
120.66
122.51
137.03
138.05
138.98
150.89
169.12
CDCl3
CS i
20.45
40.51
56.08
113.66
116.03
121.10
123.37
138.32
139.24
139.72
152.10
168.95
73
100
100
87
79
92
92
69
21
37
25
25
Acetone
CS i
20.30
39.26
55.57
112.82
115.87
120.15
122.48
137.34
137.53
138.66
150.61
168.47
69
100
81
67
68
76
68
68
31
43
33
33
CS i
DMSO
Ac Me
α
OMe
2
γ
5
6
β
4
1
3
Ac C=O
Atom
1HJMultH Shifts
2.29
3.36
3.80
5.07
5.95
6.756.776.94
s
d
s
m
ddt
mmd
6.7
16.8, 10.2, 6.7
7.9
Ac Me
α
OMe
2
γ
β
A6A2A5
Atom
(chloroform)
J. Ralph JRPS143.150mg
Notes:
116Compound Number
FPL/DFRC NMR Database -- April 2009
1-(3,5-dimethoxy-4-acetoxyphenyl)-2-propene
13C
40
45
100100
8888
39
8
38
25
3434
13
20.43
40.64
56.0756.07
105.16105.16
116.22
126.99
136.90
138.52
151.97151.97
168.81
CDCl3
CS i
20.24
41.06
56.3256.32
105.93105.93
116.11
128.10
138.24
139.32
153.06153.06
168.56
38
47
9494
100100
44
6
37
20
2525
15
Acetone
CS i
20.09
39.89
55.8055.80
105.01105.01
115.97
126.33
137.27
138.31
151.58151.58
168.06
52
100
9797
8888
47
12
47
35
5757
27
CS i
DMSO
Ac Me
α
OMeOMe
26
γ
4
β
1
35
Ac C=O
Atom
1HJMultH Shifts
2.31
3.34
3.79
6.43
5.09
5.95
s
d
s
s
m
ddt
6.7
16.8, 10.1, 6.7
Ac Me
α
OMe
2,6
γ
β
Atom
(chloroform)
IPC - Pearl14mgAs this compound has a plane of symmetry the shifts for the other half areidentical.
Notes:
117Compound Number
FPL/DFRC NMR Database -- April 2009
Syringylresinol3,3’,5,5’-tetramethoxy-7,9’,7’,9-diepoxylignan-4,4’-diol
13C
49
100100
47
44
7979
29
25
5050
54.38
56.4156.41
71.83
86.08
102.78102.78
132.13
134.38
147.19147.19
CDCl3
CS i
55.33
56.6956.69
72.37
86.81
104.52104.52
133.24
136.23
148.69148.69
61
100100
57
54
100100
26
17
2626
Acetone
CS i
53.59
55.9555.95
70.99
85.26
103.59103.59
131.36
134.81
147.82147.82
39
100100
41
41
7878
35
33
6969
CS i
DMSO
β
OMeOMe
γ
α
26
1
4
35
Atom
1HJMultH Shifts
4.28
3.90
4.28
4.73
6.58
m
s
m
d
s
4.3
β
OMe
γ2
α
2,6
Atom
(chloroform)
IPC - Pearl53mg only soluble in DMSOTerashima, Ralph, Landucci, Holzforschung, 50(1995)p. 151-155
Notes:
118Compound Number
FPL/DFRC NMR Database -- April 2009
Coniferin4-(3-hydroxy-1-propenyl)-2-methoxyphenyl-
β-D-glucopyranoside
13CCDCl3
CS i
Acetone
CS i
55.57
60.60
61.51
69.6073.1276.7676.91100.00
109.84115.25118.89
128.31128.87
130.95145.89148.94
100
49
88
6868677065
565863
7970
706770
CS i
DMSO
OMe
B6
γ
B4B2B5B3B1
A2A5A6
αβ
A1A4A3
Atom
1HJMultH Shifts
3.78
4.106.286.47
7.067.026.894.89
3.34-3.18
3.463.67
4.54
4.83
s
dddtd
ddddd
nr
mddd
t
t
5.0315.9,5.0
15.9
1.88.4
8.4,1.87.3
5.7
5.6
OMe
γ1,γ2βα
A2A5A6B1
B2,3,4,5
B6 αB6 β
B6 OH
γ OH
Atom
(DMSO)
IPC - Pearl50mgonly soluble in DMSOTerashima, Ralph, Landucci, Holzforschung, 50(1995)p. 151-155
Notes:
119Compound Number
FPL/DFRC NMR Database -- April 2009
Syringin4-(3-hydroxy-1-propenyl)-2,6-dimethoxy- β-D-glucopyranoside
13CCDCl3
CS i
Acetone
CS i
56.2756.27
60.82
61.37
69.8674.0976.4577.08102.51
104.39104.39
128.35
130.05
132.52133.80
152.60152.60
100100
29
45
3737373735
6262
37
37
3526
7777
CS i
DMSO
OMeOMe
B6
γ
B4B2B5B3B1
A2A6
α
β
A1A4
A3A5
Atom
1HJMultH Shifts
3.77
4.116.636.47
6.73
4.91
3.18-3.04
3.43.59
4.29
4.85
s
dddtd
s
d
nr
mddd
t
t
5.015.9,4.7
15.9
4.8
5.4
5.5
OMe
γ1βα
A2,6
B1
B2,3,4,5
B6 αB6 β
B6 OH
γ OH
Atom
(DMSO)
S. Ralph III-5850mg
Notes:
120Compound Number
FPL/DFRC NMR Database -- April 2009
Coniferin acetate4-(3-hydroxy-1-propenyl)-2-methoxy pheny-l β-D-glycopyranoside
pentaacetate
13C
1001001006646
57
38
52
47474548
47444648
56
37
48
3238
3432343422
20.6020.6020.6020.6620.95
56.07
61.97
64.93
68.4671.2472.0272.61
100.67110.58119.57119.93
122.83
133.02
133.58
146.09150.69
169.26169.36170.15170.47170.71
CDCl3
CS i
20.5120.5920.5920.5920.78
56.47
62.69
65.23
69.3371.9672.5673.23
100.79111.55119.77120.26
123.86
133.63
133.82
147.19151.44
169.58169.96170.22170.58170.69
5010010010043
50
36
45
43394138
48383740
44
30
40
2626
2425282616
Acetone
CS i
20.2320.2820.3020.4120.65
55.90
61.66
64.32
68.1570.7770.8671.92
98.76110.61118.05119.34
123.02
132.14
132.67
145.66149.91
168.91169.24169.49169.90170.07
751001007792
77
33
67
46485246
46524654
58
54
60
5658
5052565844
CS i
DMSO
Ac MeAc MeAc MeAc MeAc Me
OMe
B6
γ
B4B2B5B3
B1A2A5A6
β
A1
α
A4A3
Ac C=OAc C=OAc C=OAc C=OAc C=O
Atom
1HJMultH Shifts
2.032.032.072.072.09
3.80
4.70
6.20
6.59
6.89
6.94
7.07
s
d
dt
d
bd
bs
d
6.4
15.8, 6.3
15.8
8.2
8.2
Ac MeAc MeAc MeAc MeAc Me
OMe
γ
β
α
A6
A2
A5
Atom
(chloroform)
S. Ralph III - 5850mg
Notes:
121Compound Number
FPL/DFRC NMR Database -- April 2009
Syringin acetate4-(3-hydroxy-1-propenyl)-2,6-dimethoxy phenyl-β-D-
glucopyranoside penta acetate
13C
5210010010039
8989
32
41
3642424036
7272
39
31
42
236363
2930302520
20.6020.6820.6820.6820.95
56.3256.32
62.35
64.84
68.5671.9972.0873.11101.21
104.09104.09
123.30
133.11
133.86
134.56153.07153.07
169.25169.41170.31170.51170.75
CDCl3
CS i
20.5620.5620.5620.6720.77
56.6956.69
62.91
65.14
69.4772.5172.8173.61101.69
105.10105.10
124.38
134.02
134.11
135.38154.06154.06
169.59169.94170.24170.48170.64
1001001004943
9797
40
49
4846484843
8989
46
33
41
195454
2224292417
Acetone
CS i
20.2520.3620.3620.3620.64
56.1356.13
61.82
64.19
68.2670.7371.5472.14100.48
104.09104.09
123.74
132.79
132.79
133.87152.68152.68
168.94169.24169.48169.81170.04
5175757554
100100
25
42
3131312931
5656
36
56
56
326868
3436313732
CS i
DMSO
Ac MeAc MeAc MeAc MeAc Me
OMeOMe
B6
γ
B4B2B5B3B1
A2A6
β
A1
α
A4A3A5
Ac C=OAc C=OAc C=O Ac C=OAc C=O
Atom
1HJMultH Shifts
2.032.032.032.032.09
3.84
4.716.226.57
6.61
sssss
s
ddtd
s
6.416.8, 6.4
16.8
Ac MeAc MeAc MeAc MeAc Me
OMe
γβ
α
A2,6
Atom
(chloroform)
S. Ralph III - 5850mg mixture of α + β
Notes:
122Compound Number
FPL/DFRC NMR Database -- April 2009
α + β Xylose Acetate
13C
6240838388884155
4931325310010038345431
3737183135352327
20.4220.5420.6020.6020.6620.6620.7420.79
60.6562.7668.3568.6769.3969.3969.5370.9789.2692.05
168.92168.92169.22169.65169.68169.68169.75170.02
CDCl3
CS i
20.3520.4620.5120.5520.5520.5520.6520.65
61.1263.1469.0969.2269.8770.2470.3071.5489.7692.67
169.35169.53169.66170.01170.10170.19170.22170.22
5943711001001007070
57354159636748375641
1721171723403636
Acetone
CS i
20.2120.2520.3420.3420.3420.3420.4420.52
60.0562.0167.9968.1068.8368.9369.3670.5288.6091.49
168.78169.02169.02169.36169.41169.49169.54169.58
43541001001001006249
32184128414125233824
1943432433243337
CS i
DMSO
Ac MeAc MeAc MeAc MeAc MeAc MeAc MeAc Me
5544332211
Ac C=OAc C=OAc C=OAc C=OAc C=OAc C=OAc C=OAc C=O
Atom
1HJMultH Shifts
2.022.0492.0492.0522.0522.062.112.17
ssssssss
Ac MeAc MeAc MeAc MeAc MeAc MeAc MeAc Me
Atom
(chloroform)
S. Ralph III - 5820mgAs this compound has a plane of symmetry the shifts for the other half areidentical.
Notes:
123Compound Number
FPL/DFRC NMR Database -- April 2009
Syringylresinol diacetateAcetic acid 4-[4-(4-acetoxy-3,5-dimethoxyphenyl) tetrahydrofuro[3,4-c]
furan-1-yl]-2,6-dimethoxyphenyl ester
13C
42
41
100100
47
47
8585
12
30
5050
23
20.46
54.42
56.2356.23
72.11
85.85
102.29102.29
128.06
139.63
152.30152.30
168.76
CDCl3
CS i
20.26
55.41
56.4656.46
72.71
86.51
103.30103.30
128.91
141.41
153.23153.23
168.59
52
58
9898
54
56
100100
8
31
4444
15
Acetone
CS i
20.07
53.72
55.9055.90
71.38
84.93
102.44102.44
127.04
140.03
151.60151.60
168.01
44
41
100100
36
34
6363
19
31
6868
29
CS i
DMSO
Ac Me
β
OMeOMe
γ
α
26
1
4
35
Ac C=O
Atom
1HJMultH Shifts
2.33
3.09
3.83
3.954.31
4.77
6.59
s
m
s
dddd
d
s
9.1, 3.39.1, 6.7
4.1
Ac Me
β
OMe
γ1γ2
α
A2,6
Atom
(chloroform)
J. Obst25mg Thanks to Rong Ji et.al, Chemosphere (2005) 1169-1181 for noting the missassignment of C6 and Cβ
Notes:
124Compound Number
FPL/DFRC NMR Database -- April 2009
cis - Ferulic Acid(Z)-4-hydroxy-3-methoxycinnamic acid
13C
100
8789
87
80
44
38
76
51
44
55.93
113.15113.98
115.50
126.17
126.79
145.97
146.36
147.50
171.34
CDCl3
CS i
56.16
114.99115.23
116.82
126.51
127.80
144.40
147.60
149.04
167.85
97
89100
97
100
36
89
31
39
31
Acetone
CS i
55.38
114.30114.78
116.77
124.78
126.09
141.90
146.72
147.90
167.54
100
8075
69
82
57
70
52
41
51
CS i
DMSO
OMe
25
β
6
1
α
3
4
γ
Atom
1HJMultH Shifts
3.85
5.77
6.80
6.767.097.70
s
d
d
dddd
12.9
12.9
8.08.1, 2.0
2.0
OMe
β
α
562
Atom
(methanol)
cis
JR C37.152mg
Notes:
125Compound Number
FPL/DFRC NMR Database -- April 2009
1-(4-hydroxyphenyl)-2-phenoxyethanol
13C
43
49
9393
9898
51
9898
100100
20
28
20
72.31
73.25
114.73114.73
115.51115.51
121.33
127.80127.80
129.55129.55
131.68
155.77
158.41
CDCl3
CS i
72.42
74.32
115.43115.43
115.76115.76
121.37
128.39128.39
130.12130.12
133.53
157.61
159.84
41
50
9090
8888
46
9595
100100
22
22
15
Acetone
CS i
70.55
73.07
114.49114.49
114.74114.74
120.38
127.42127.42
129.32129.32
132.63
156.54
158.52
44
39
100100
9292
42
8585
9494
25
38
29
CS i
DMSO
α
β
B3B5
A3A5
B1
A2A6
B2B6
A1
A4
B4
Atom
1HJMultH Shifts
5.05
4.05
dd
m
8.3, 3.6α
β
Atom
(chloroform)
JR 145.262mg * 76.50 shift in CDCL3falls under solvent peak.
Notes:
126Compound Number
FPL/DFRC NMR Database -- April 2009
1-(4-hydroxy-3-methoxyphenyl)-2-(2-methoxyphenoxy)ethanol
13C
8787
67
100
707777737777
7333
30272320
55.9055.97
72.20
76.50
108.87112.16114.26116.21119.37121.13
122.58131.61
145.46146.68148.10150.26
CDCl3
CS i
56.2856.35
72.71
76.32
111.01113.67115.37115.93119.89121.83
122.45134.17
146.84148.12149.74151.06
9592
70
95
9588827595100
9035
30222518
Acetone
CS i
55.5255.52
70.81
74.15
110.75112.51113.75114.92118.67120.74
120.92133.46
145.66147.21148.23149.10
100100
61
51
525249575566
6047
52444338
CS i
DMSO
OMeOMe
α
β
A2B2A5B5A6B6
B1A1
A4A3B3B4
Atom
1HJMultH Shifts
3.883.89
5.02
3.93
4.15
ss
dd
dd
dd
9.3, 3.0
10.0, 9.3
10.0, 3.0
OMeOMe
α
β1
β2
Atom
(chloroform)
IPC Pearl Coll.60mg
Notes:
127Compound Number
FPL/DFRC NMR Database -- April 2009
Dihydrocoumaric acid3-(4-hydroxyphenyl)propionic acid
13C
53
40
9292
100100
14
22
5
29.94
35.75
115.46115.46
129.36129.36
132.10
154.55
176.90
CDCl3
CS i
30.68
36.33
115.99115.99
130.00130.00
132.54
156.42
174.68
43
46
100100
7979
17
18
10
Acetone
CS i
29.58
35.70
115.04115.04
129.00129.00
130.92
155.46
173.81
43
41
9393
100100
34
34
27
CS i
DMSO
α
β
35
26
1
4
γ
Atom
1HJMultH Shifts
2.63
2.88
6.77
7.06
t
t
m
m
7.0
7.0
8.6
8.6
β
α
3,5
2,6
Atom
(chloroform)
IPC Pearl Coll.60mg Contains unacetylated cmpd also
Notes:
128Compound Number
FPL/DFRC NMR Database -- April 2009
acetylated dihydrocoumaric acid3-(4-acetoxyphenyl)propionic acid
13C
39
51
46
100100
100100
27
19
14
20
21.06
29.96
35.48
121.56121.56
129.24129.24
137.78
149.17
169.78
178.63
CDCl3
CS i
20.91
30.80
35.80
122.37122.37
129.94129.94
139.24
150.24
169.65
174.18
39
53
55
8686
100100
20
14
13
17
Acetone
CS i
20.73
29.68
35.14
121.47121.47
129.09129.09
138.29
148.70
169.14
173.60
45
46
36
100100
9494
29
25
23
24
CS i
DMSO
Ac Me
α
β
35
26
1
4
Ac C=O
γ
Atom
1HJMultH Shifts
2.27
2.67
2.92
6.99
7.19
s
t
t
m
m
7.3
7.3
8.5
8.5
Ac Me
β
α
2,6
3,5
Atom
(chloroform)
IPC Pearl coll.60mg
Notes:
129Compound Number
FPL/DFRC NMR Database -- April 2009
acetylated coumaric acid(E)-4-acetoxycinnamic acid
13C
45
47
100100
100100
26
42
24
21
13
21.12
117.38
122.22122.22
129.48129.48
131.82
145.80
152.50
168.98
171.14
CDCl3
CS i
20.96
119.32
123.19123.19
130.07130.07
133.04
144.44
153.41
167.68
169.39
43
50
100100
9595
19
43
17
21
14
Acetone
CS i
20.76
119.29
122.28122.28
129.32129.32
131.89
142.88
151.80
167.48
168.92
54
38
9898
100100
38
43
31
30
26
CS i
DMSO
Ac Me
β
35
26
1
α
4
Ac C=O
γ
Atom
1HJMultH Shifts
2.31
6.41
7.15
7.57
7.75
s
d
m
m
d
16.0
8.6
8.6
16.0
Ac Me
β
3,5
2,6
α
Atom
(chloroform)
trans
IPC Pearl coll.60mg
Notes:
130Compound Number
FPL/DFRC NMR Database -- April 2009
2-acetoxy-1-(4-hydroxy-3,5-dimethoxyphenyl)propan-1-one
13C
41
29
100100
47
8484
16
13
3030
13
16
17.44
20.78
56.5756.57
70.94
106.12106.12
125.83
140.42
147.02147.02
170.45
195.11
CDCl3
CS i
17.77
20.63
56.8556.85
71.98
107.38107.38
126.17
142.41
148.59148.59
170.42
195.30
43
38
100100
48
9898
13
7
1818
13
15
Acetone
CS i
17.43
20.40
56.2256.22
71.15
106.43106.43
124.02
141.67
147.75147.75
169.70
194.63
51
43
100100
40
7676
31
29
5757
29
29
CS i
DMSO
γ
Ac Me
OMeOMe
β
26
1
4
35
Ac C=O
α
Atom
1HJMultH Shifts
1.53
2.15
3.94
5.96
7.24
d
s
s
q
s
7.0
7.0
γ
Ac Me
OMe
β
2,6
Atom
(chloroform)
S. Ralph SRIII-62-135mg
Notes:
131Compound Number
FPL/DFRC NMR Database -- April 2009
1-(4-hydroxy-3-methoxyphenyl)-2-[4-(1-hydroxyethyl)-2-methoxyphenoxy]propane-1,3-diol
13C
68
86100
46735951
5457
59626549
3843
51543535
25.20
55.9055.98
61.0970.0173.9389.03
109.35109.54
114.42118.41120.17120.23
131.56141.90
145.57146.72146.78150.99
60.8
72.8
86.9
132.0
CDCl3
CS i
26.21
56.2456.31
61.8969.7473.9588.72
110.67111.45
115.24118.70119.68120.59
133.85142.92
146.83148.04148.31151.45
61.9
73.8
86.9
134.3
66
85100
61806351
5876
64646871
3441
41293131
Acetone
CS i
25.80
55.3555.52
60.0267.7870.9184.74
109.79110.98
114.57115.62117.24118.93
132.89140.44
145.31146.87146.87149.31
60.0
71.6
83.9
133.2
90
6787
49853836
3638
49384944
5438
5910010046
CS i
DMSO
B β
OMeOMe
γB α
α β
B2A2
A5B5B6A6
A1B1
A4A3B4B3
erythro isomer:
γ
α
β
A1
Atom
1HJMultH Shifts
1.46
3.843.86
4.824.92
7.03
d
ss
qd
d
6.4
6.47.7
8.2
B β
OMeOMe
B αα
A5
Atom
(chloroform)
threo
S. Ralph SRIII-63-150mg
Notes:
132Compound Number
FPL/DFRC NMR Database -- April 2009
1-(4-hydroxy-3-methoxyphenyl)-2-[4-(1-hydroxyethyl)-2-methoxyphenoxy]ethanol
13C
40
52
445044
44
8787
56
52
100100
2523
2525
23
25.05
55.98
69.9172.4373.58
108.82
114.64114.64
114.37
119.33
126.73126.73
131.66138.66
145.57146.70
157.81
CDCl3
CS i
26.20
56.27
69.5072.6574.65
110.89
115.07115.07
115.42
119.88
127.27127.27
134.30140.41
146.86148.16
158.80
40
50
394648
39
8484
38
41
100100
2121
2115
18
Acetone
CS i
25.83
55.50
67.5270.6873.22
110.55
113.95113.95
114.88
118.63
126.28126.28
133.30139.30
145.60147.17
157.19
54
62
624638
35
9696
46
42
100100
3737
4038
38
CS i
DMSO
B β
OMe
B ααβ
A2
B3B5
A5
A6
B2B6
A1B1
A4A3
B4
Atom
1HJMultH Shifts
1.46
3.90
3.964.06
4.845.03
d
s
dddd
qdd
6.4
9.7, 8.69.7, 3.5
6.48.6, 3.5
B β
OMe
β1β2
B αα
Atom
(chloroform)
S. Ralph SRIII-63-370mg2:1 isomeric mixture,
Notes:
133Compound Number
FPL/DFRC NMR Database -- April 2009
1-(4-hydroxy-3-methoxyphenyl)-2-[4-(1-hydroxyethyl)phenoxy]-propane-1,3-diol
13C
49
72
34
644345
4547919149
100100
2626
1917
21
25.08
56.00
61.24
69.8673.9483.28
109.42114.38116.47116.47119.99
126.88126.88
131.60139.39
145.68146.72
157.50
61.54
74.04
82.09
116.54
119.33
126.78
132.35
157.06
CDCl3
CS i
26.07
56.22
61.69
69.5273.3884.16
111.37115.19116.69116.69120.34
127.14127.14
134.18140.38
146.63147.92
158.92
62.04
73.99
83.75
116.81
120.47
127.10
134.44
158.55
52
53
34
523638
4548818142
100100
2531
2525
23
Acetone
CS i
25.78
55.45
60.00
67.6070.9583.14
110.90114.68115.39115.39118.96
126.14126.14
133.19139.20
145.33146.93
157.71
60.11
71.50
83.14
115.54
119.37
126.07
133.32
157.41
64
49
27
622429
2233787829
100100
3644
4240
33
CS i
DMSO
B β
OMe
γ
B ααβ
A2A5B3B5A6
B2B6
A1B1
A4A3
B4
minor isomershifts
γ
α
β
B3,5
A6
B2,6
A1
B4
Atom
1HJMultH Shifts
1.47
3.87
4.374.854.96
d
s
mqd
6.4
6.46.7
B β
OMe
βBαα
Atom
(chloroform)
major
S. Ralph SRIII-64-135mg
Notes:
134Compound Number
FPL/DFRC NMR Database -- April 2009
�1-(4-Hydroxy-3-methoxyphenyl)-2-[4-(1-hydroxyethyl)-2,6-dimethoxyphenoxy]propane-1,3-diol
13C
37
45100100
30393535
6969
363738
2615
232930
5050
25.39
55.9656.1456.14
60.5570.2974.1089.00
102.32102.32
109.90114.36120.34
131.89134.26
142.80145.44146.56
152.91152.91
CDCl3
CS i
26.27
56.2356.5456.54
61.3570.0174.1089.82
103.48103.48
111.51115.24120.75
133.67135.57
144.64146.79147.95
153.64153.64
42
49100100
41444240
8787
415448
2613
262425
4545
Acetone
CS i
25.81
55.4655.8055.80
60.0968.0771.4887.20
102.53102.53
110.97114.56119.14
132.82134.56
142.88145.23146.77
152.13152.13
51
51100100
27563437
6363
243237
3924
413937
7373
CS i
DMSO
B β
A OMeB OMeB OMe
γB α
αβ
B2B6
A2A5A6
A1B1
B4A4A3
B3B5
Atom
1HJMultH Shifts
1.47
3.86
3.89
4.83
5.00
6.63
6.956.856.91
d
s
s
q
d
s
sd
dd
6.4
6.4
8.8
8.38.3, 1.7
B β
A OMe
B OMe’s
B α
α
B2,6
A2A5A6
Atom
(chloroform)
threo
S. Ralph SRIII-64-230mg
Notes:
135Compound Number
FPL/DFRC NMR Database -- April 2009
3-(4-hydroxy-3-methoxyphenyl)-2-[4-(1-hydroxyethyl)-2,6-dimethoxyphenoxy]propan-1-ol
13C
35
36
58100100
343542
6262374637
2514
192520
4646
25.30
37.32
55.9456.1156.11
62.3170.4284.52
102.45102.45112.31114.27122.10
130.13134.64
142.09144.07146.38
153.29153.29
CDCl3
CS i
26.26
38.03
56.2356.4456.44
62.8470.0485.30
103.53103.53113.93115.51122.80
130.80135.57
144.15145.80148.04
154.08154.08
45
45
48100100
363948
6666384846
2511
141418
3939
Acetone
CS i
25.81
36.77
55.4655.7455.74
61.5868.1383.40
102.50102.50113.55115.01121.57
129.24133.95
142.83144.55147.03
152.61152.61
54
26
49100100
265136
5656313638
3821
383636
7474
CS i
DMSO
B β
α
A OMeB OMeB OMe
γB α
β
B2B6A2A5A6
A1B1
B4A4A3
B3B5
Atom
1HJMultH Shifts
1.47
2.973.20
3.853.83
4.824.18
6.61
6.746.806.82
d
dddd
ss
qm
s
dddd
6.4
13.6, 8.813.6, 5.4
6.4
8.0, 1.91.98.0
B β
α1α2
B OMeA OMe
B αβ
B2,6
A6A2A5
Atom
(chloroform)
J. Ralph30mg
Notes:
136Compound Number
FPL/DFRC NMR Database -- April 2009
Vinyl guaiacol2-methoxy-4-vinylphenol
4-vinylguaiacol
13C
100
51
78
85
88
24
78
20
22
55.86
108.14
111.38
114.40
120.03
130.26
136.62
145.64
146.63
CDCl3
CS i
56.17
109.85
111.09
115.69
120.58
130.59
137.70
147.55
148.38
83
50
100
42
86
22
86
9
14
Acetone
CS i
55.52
109.61
110.81
115.34
119.46
128.77
136.63
146.68
147.64
77
47
73
74
93
44
100
43
37
CS i
DMSO
OMe
2
β
5
6
1
α
A4
A3
Atom
1HJMultH Shifts
3.84
5.045.626.63
6.786.907.07
s
dddddd
dddd
10.9, 1.117.6, 1.117.6, 10.9
8.18.1, 1.9
1.9
OMe
β1β2α
A5A6A2
Atom
(acetone)
S. Ralph SRIII-65-A 52mgNotes:
137Compound Number
FPL/DFRC NMR Database -- April 2009
1,3-diacetoxy-1-(4-acetoxy-3-methoxyphenyl)-2-[4-(1-acetoxyethyl)phenoxy] propane
13C
65655450
44
65
36493625
3268684039100100
3224182217
20191822
20.6220.6220.9821.34
22.00
55.98
62.6471.8574.0078.08
111.64116.31116.31119.60122.96127.66127.66
134.86135.22140.05151.20157.97
168.71169.69170.29170.55
62.32
71.85
73.62
78.40
157.58
CDCl3
CS i
20.4520.5620.8621.14
22.34
56.31
63.2472.1775.0779.10
112.61117.08117.08120.37123.63128.27128.27
136.20136.39140.97152.25159.12
168.81169.99170.18170.65
62.88
72.17
74.21
78.86
158.59
52353941
38
42
28273222
3251514332100100
1822141819
18141414
Acetone
CS i
20.2820.3620.6120.92
21.78
55.82
62.1671.1474.0077.57
111.65116.01116.01119.45122.71127.30127.30
134.71135.25139.25150.73157.69
168.30169.35169.51169.82
61.73
71.14
72.81
76.99
157.03
1009381100
64
69
31574036
4598984045100100
4048364540
43454845
CS i
DMSO
Ac MeAc MeAc MeAc Me
B β
OMe
γB α
αβ
A2B5B3A6A5B2B6
B1A1A4A3B4
A4 Ac C=OAc C=OAc C=OAc C=O
erythro isomer:
γ
B α
α
β
B4
Atom
1HJMultH Shifts
1.982.052.052.291.513.81
4.044.27
5.836.074.69
1.506.035.82
ssssds
dddd
qdm
ddq
6.6
11.8, 6.111.8, 3.8
6.66.3
6.65.26.6
Ac MeAc MeAc MeAc Me
B βOMe
γ1γ2
B ααβ
erythro
B βα
B α
Atom
(chloroform)
threo
S. Ralph SRIII-65-B14mg
Notes:
138Compound Number
FPL/DFRC NMR Database -- April 2009
1-Acetoxy-1-(4-acetoxy-3-methoxyphenyl)2-[4-(1-acetoxyethyl)phenoxy] ethane
13C
524640
52
59
434343
3987875253100100
2930162725
202016
20.6521.1221.37
21.98
55.98
70.4971.9273.52
111.26114.72114.72119.09122.95127.62127.62
134.50135.85139.90151.20158.09
168.88169.98170.30
CDCl3
CS i
20.4520.9421.13
22.35
56.30
71.1872.2074.21
112.20115.45115.45119.70123.61128.27128.27
135.58137.17140.87152.28159.08
168.84170.13170.13
464236
50
52
444747
4210010043448888
2424132020
81414
Acetone
CS i
20.2820.7320.92
21.78
55.79
69.7671.1373.01
111.34114.55114.55118.71122.66127.29127.29
134.09135.84139.09150.69157.55
168.38169.49169.58
686464
64
64
365648
401001004452100100
4044323644
363632
CS i
DMSO
Ac MeAc MeAc Me
B β
OMe
βB α
α
A2B3B5A6A5B2B6
B1A1A4A3B4
A4 Ac C=OAc C=OAc C=O
Atom
1HJMultH Shifts
2.042.112.31
1.51
3.85
4.134.25
5.836.12
6.867.28
sss
d
s
dddd
qdd
mm
6.6
10.4, 3.910.4, 7.8
6.67.8, 3.9
8.78.7
Ac MeAc MeAc Me
Bβ
OMe
β1β2
B αα
B3,5B2,6
Atom
(chloroform)
S. Ralph SRIII-65-C 51mgerythro shifts from SRVII 138BB in acetone
Notes:
139Compound Number
FPL/DFRC NMR Database -- April 2009
G-β-S5
1,3-diacetoxy-1-(4-acetoxy-3-methoxyphenyl)-2-[4-(1-acetoxyethyl)-2,6-dimethoxyphenoxy] propane
13C
46412936
25
65100100
18293635
4747213939
2626222126
4343
19121519
20.6420.7021.0021.34
22.23
55.9956.0256.02
63.4872.3875.2580.59
103.21103.21111.92119.65122.51
135.96135.96137.54139.72150.91
152.91152.91
168.80169.71170.19170.54
CDCl3
CS i
20.4520.5820.9221.14
22.57
56.2856.3956.39
64.1772.7176.2581.38
104.01104.01112.64120.24123.34
136.92137.14138.78140.71152.02
153.79153.79
168.86169.85170.16170.57
63.28
72.68
75.06
81.26
103.91
112.17
119.99
123.36
53433843
32
57100100
42483242
6868385048
1730321827
5050
20232022
Acetone
CS i
20.3020.6020.9522.01
22.06
55.7855.7855.78
63.1471.7075.2880.11
102.88102.88111.53119.25122.53
135.25135.84137.44139.08150.58
152.30152.30
168.37169.25169.56169.89
46263719
19
100100100
13231318
3232152119
1925242126
4545
19202022
CS i
DMSO
Ac MeAc MeAc MeAc Me
B β
A OMeB OMeB OMe
γB α
αβ
B2B6A2A6A5
A1B1B4A4A3
B3B5
A4 Ac C=OAc C=OAc C=OAc C=O
erythro isomer
γ
Bα
α
β
B2,6
2
6
5
Atom
1HJMultH Shifts
1.992.062.072.30
1.51
3.823.77
3.954.344.545.796.15
6.547.086.996.99
ssss
d
ss
ddddmqd
sbsmm
6.6
11.8, 3.211.8, 4.7
6.66.3
Ac MeAc MeAc MeAc Me
B β
A OMeB OMe
γ1γ2β
B αα
B2,6A2A5A6
Atom
(chloroform)
threo
S. Ralph SRIII-65-D44mg
Notes:
140Compound Number
FPL/DFRC NMR Database -- April 2009
1,3-diacetoxy-1-(4-acetoxy-3-methoxyphenyl)-2-[4-(1-acetoxyethyl)-2-methoxyphenoxy] propane
13C
89716364
57
10086
41574141
294643566460
534339243643
37292731
20.6420.6821.0121.35
22.09
55.9255.97
62.9972.0674.4180.14
110.74111.74118.35118.67119.57122.80
135.24136.76139.94147.53150.65151.12
168.74169.66170.25170.53
63.0
73.7
80.1
146.7
CDCl3
CS i
20.4520.5820.9121.15
22.45
56.2956.29
63.5572.3975.3480.68
111.76112.64118.85119.19120.28123.51
136.60137.78140.88148.48151.57152.18
168.82169.94170.16170.62
62.5
74.5
80.2
147.7
51473853
39
100100
37463939
263228434441
372217172021
16141418
Acetone
CS i
20.2820.3520.6220.94
21.89
55.6655.78
62.4371.3774.2679.10
110.64111.62117.18118.09119.38122.63
135.36136.11139.21147.00149.92150.68
168.32169.31169.53169.91
61.8
73.1
78.3
146.1
921007487
58
8471
32713945
374550615047
555347506355
42474753
CS i
DMSO
Ac MeAc MeAc MeAc Me
B β
OMeOMe
γB α
αβ
B2A2B5B6A6A5
A1B1A4B4B3A3
A4 Ac C=OAc C=OAc C=OAc C=O
erythro isomer
γ
α
β
B4
Atom
1HJMultH Shifts
1.51
1.992.062.0652.30
3.823.83
4.044.304.615.826.11
d
ssss
ss
ddddmqd
6.6
11.9, 5.611.9, 4.6
6.66.3
B β
Ac MeAc MeAc MeAc Me
OMeOMe
γ1γ2β
B αα
Atom
(chloroform)
threo
S. Ralph SRIII-76B30mgin acetone 3 & α switch places
Notes:
141Compound Number
FPL/DFRC NMR Database -- April 2009
acetylated coniferylaldehyde4-acetoxy-3-methoxycinnamaldehyde
13C
57
95
67
78
100
89
45
20
26
52
21
50
20.57
55.98
111.55
121.82
123.49
128.74
132.97
142.30
151.66
151.74
168.52
193.27
CDCl3
CS i
20.43
56.44
112.65
122.68
124.25
129.68
134.17
143.22
152.77
152.55
168.72
193.89
62
91
62
71
100
98
38
18
24
51
16
49
Acetone
CS i
20.28
55.99
112.08
122.04
123.32
128.72
133.00
141.55
151.22
152.29
168.19
194.17
86
91
62
71
93
100
69
34
48
52
34
60
CS i
DMSO
Ac Me
OMe
2
6
5
β
1
4
3
α
Ac C=O
γ
Atom
1HJMultH Shifts
2.253.89
6.79
7.157.29
7.49
7.64
9.69
ss
dd
dd
d
d
d
15.9, 7.7
8.18.1, 1.9
1.9
15.9
7.7
Ac MeOMe
β
56
2
α
γ
Atom
(acetone)
M.Mozuch 177/95 47mgNotes:
142Compound Number
FPL/DFRC NMR Database -- April 2009
acetylated coniferyl alcohol4-acetoxy-3-methoxycinnamylacetate
13C
7556
100
84
73
92
97
90
97
43
21
35
3021
20.5920.92
55.88
64.84
110.34
119.37
122.88
123.61
133.52
135.30
139.76
151.21
168.83170.68
CDCl3
CS i
20.4520.76
56.24
65.13
111.23
119.92
123.74
124.90
133.62
136.26
140.82
152.43
168.89170.69
7248
91
82
51
100
96
93
97
39
18
25
2216
Acetone
CS i
20.2720.60
55.75
64.12
110.41
118.99
122.83
124.16
132.29
134.97
139.08
150.94
168.37170.02
9876
96
96
80
100
98
100
100
62
40
56
4933
CS i
DMSO
Ac MeAc Me
OMe
γ
2
6
5
β
α
1
4
3
A4 Ac C=Oγ Ac C=O
Atom
1HJMultH Shifts
2.042.23
3.8
4.69
6.36
6.68
7.01
7.01
7.21
ss
s
dd
dt
dt
m
m
s
Ac MeAc Me
OMe
γ
β
α
5
6
2
Atom
(acetone)
M.Mozuch 177/95 48mgNotes:
143Compound Number
FPL/DFRC NMR Database -- April 2009
Acetylated veratryl alcohol3,4-dimethoxybenzylacetate
13C
36
100100
58
50
52
66
24
18
17
12
21.03
55.9655.96
66.38
111.27
112.06
121.33
128.60
149.14
149.26
170.82
CDCl3
CS i
20.83
56.1856.18
66.53
112.76
113.50
121.90
129.99
150.38
150.45
170.85
33
100100
62
36
38
68
15
13
11
10
Acetone
CS i
20.66
55.5055.50
65.47
111.70
112.34
120.88
128.45
148.66
148.75
170.15
57
100100
82
54
61
84
36
30
28
25
CS i
DMSO
Ac Me
OMeOMe
α
2
5
6
1
3
4
Ac C=O
Atom
1HJMultH Shifts
2.01
3.793.80
5.00
6.91
6.91
6.98
s
ss
s
m
m
s
Ac Me
OMeOMe
α
5
6
2
Atom
(acetone)
Aldrich 40mgNote: In DMSO β and 1 are coincident
Notes:
144Compound Number
FPL/DFRC NMR Database -- April 2009
coniferaldehyde4-hydroxy-3-methoxycinnamaldehyde
13C
100
90
93
92
95
38
33
43
57
95
56.05
109.75
115.06
124.03
126.35
126.66
147.11
149.12
153.16
193.62
CDCl3
CS i
56.41
111.66
116.21
124.68
127.03
127.46
148.83
150.78
153.89
193.78
92
70
100
78
92
32
27
35
57
65
Acetone
CS i
55.74
111.59
115.68
123.86
125.69
125.69
148.02
150.15
153.83
193.84
63
44
59
56
100
100
37
39
46
50
CS i
DMSO
OMe
2
5
6
β
1
4
3
α
γ
Atom
1HJMultH Shifts
3.93
6.67
6.92
7.21
7.38
7.57
9.64
s
dd
d
dd
d
d
d
15.8, 7.8
8.2
8.2, 2.0
2.0
15.8
7.8
OMe
β
5
6
2
α
γ
Atom
(acetone)
M.Mozuch 199/16 25mgNote: only 8 mg was used for DMSO spec.and 1 and α switch places in CDCl3
Notes:
145Compound Number
FPL/DFRC NMR Database -- April 2009
3,4-dimethoxycinnamyl alcohol
13C
10097
71
53
58
97
77
94
33
21
23
55.8755.95
63.76
109.14
111.34
119.69
126.65
131.09
129.87
149.01
149.14
CDCl3
CS i
56.1256.18
63.34
110.59
112.92
120.24
128.90
130.14
131.40
150.10
150.55
10090
57
47
56
89
85
89
23
16
15
Acetone
CS i
55.5055.55
61.63
109.33
111.91
119.16
128.53
128.60
129.94
148.36
148.91
10086
81
58
58
81
81
91
47
93
40
CS i
DMSO
OMeOMe
γ
2
5
6
β
α
1
3
4
Atom
1HJMultH Shifts
3.793.82
4.20
6.26
6.49
6.88
6.89
7.06
ss
dd
dt
dt
m
m
d
5.4, 1.5
15.9, 5.4
15.9, 1.5
1.7
OMeOMe
γ
β
α
5
6
2
Atom
(acetone)
LLL XVII -19ANotes:
146Compound Number
FPL/DFRC NMR Database -- April 2009
2-(4-Acetyl-2-methoxyphenoxy)-1-(3,4-dimethoxyphenyl)ethanone
13C
54
77100100
48
5543
4338
6267
2226
2929
2223
29
23
26.16
56.0356.1056.10
71.39
110.30110.54
111.10112.57
122.74122.85
127.58131.52
149.40149.40
151.79154.14
192.22
196.56
CDCl3
CS i
26.29
56.2156.3056.36
71.71
111.63111.77
112.29113.55
123.45123.54
128.67132.02
150.32150.32
153.19155.19
192.90
196.36
56
8610082
61
4668
4548
8390
2324
3232
2524
24
20
Acetone
CS i
26.22
55.5955.6355.78
70.30
110.32110.92
111.03112.28
122.58122.58
127.08130.24
148.54148.69
151.73153.61
192.24
196.17
60
969680
56
5151
6456
100100
4440
4447
4038
44
33
CS i
DMSO
B β
OMeOMeOMe
β
A2A5
B2B5
B6A6
A1B1
A3B3
B4A4
α
B α
Atom
1HJMultH Shifts
2.50
3.873.893.90
5.56
6.94
7.07
7.75
s
sss
s
d
d
dd
8.9
8.4
8.4, 1.9
B β
OMeOMeOMe
β
B5
A5
A6
Atom
(acetone)
LLL V-59Bβ-carbon in CDCl3 was observed as shoulder on solvent.Very limited solubility in acetone; DEPT was run in DMSO.
Notes:
147Compound Number
FPL/DFRC NMR Database -- April 2009
1-(3,4-Dimethoxyphenyl)-2-(2-methoxyphenoxy)ethanol
13C
10010077
67
67
4144
4545
64
6767
23
17212017
55.9355.9356.01
72.17
76.53
109.67111.28
112.21116.28
118.67
121.15122.61
132.36
148.14148.89149.23150.30
CDCl3
CS i
56.1356.2656.36
72.59
76.22
111.63112.77
113.67115.82
119.44
121.86122.43
135.50
149.71149.71149.84150.30
8310063
67
76
5966
6457
100
7184
33
29292929
Acetone
CS i
55.3855.5755.57
70.68
74.07
110.48111.56
112.55113.79
118.32
120.73120.94
135.11
147.99148.20148.46149.11
5110098
47
40
3637
3733
48
5247
35
25262922
CS i
DMSO
OMeOMeOMe
α
β
A2A5
B2B5
A6
B6B1
A1
B3A3A4B4
Atom
1HJMultH Shifts
3.783.823.82
4.04.074.98
7.14
sss
ddddm
d
9.9, 7.79.9, 4.2
1.9
OMeOMeOMe
β1β2α
A2
Atom
(acetone)
J. Ralph P.S. 169.150mgcontains 30% unacetylated
Notes:
148Compound Number
FPL/DFRC NMR Database -- April 2009
acetylated methyl coumarate methyl 4-acetoxycinnamate
13C
100
11
11
2525
2424
9
12
4
4
4
21.02
51.66
118.04
122.23122.23
129.24129.24
132.13
143.80
152.31
167.31
169.05
CDCl3
CS i
20.93
51.70
118.75
123.10123.10
130.02130.02
132.81
144.21
153.34
167.36
169.36
40
45
48
100100
100100
40
48
18
17
17
Acetone
CS i
20.79
51.70
118.75
122.30122.30
129.50129.50
131.70
143.49
152.06
166.56
168.84
47
47
45
100100
100100
36
47
26
26
26
CS i
DMSO
Ac Me
OMe
β
35
26
1
α
4
γ
Ac C=O
Atom
1HJMultH Shifts
2.27
3.75
6.51
7.18
7.67
7.69
s
s
d
m
d
m
16.0
8.7
16.0
8.7
Ac Me
OMe
β
3,5
α
2,6
Atom
(acetone)
J. Ralph P.S. 171.1Notes:
149Compound Number
FPL/DFRC NMR Database -- April 2009
acetylated methyl ferulate methyl 4-acetoxy-3-methoxycinnamate
13C
68
73
100
71
85
87
98
47
27
85
37
32
27
20.54
51.62
55.94
111.52
118.13
120.20
123.30
133.41
141.66
144.12
151.57
167.15
168.59
CDCl3
CS i
20.46
51.69
56.44
112.59
118.95
122.04
124.12
134.25
142.73
144.68
152.72
167.41
168.76
70
85
100
78
85
89
100
33
22
100
30
33
26
Acetone
CS i
20.28
51.34
55.95
112.01
118.05
121.37
123.11
132.92
140.98
143.81
151.10
166.52
168.19
100
83
96
71
96
83
88
67
42
92
58
58
46
CS i
DMSO
Ac Me
γ OMe
OMe
2
β
6
5
1
4
α
3
γ
Ac C=O
Atom
1HJMultH Shifts
2.25
3.74
3.86
6.54
7.09
7.23
7.41
7.64
s
s
s
d
d
dd
d
d
16.0
8.1
8.1, 1.7
1.7
16.0
Ac Me
γ OMe
OMe
β
5
6
2
α
Atom
(acetone)
S. Ralph SRIII-8150mgDMSO nmr 20mg
Notes:
150Compound Number
FPL/DFRC NMR Database -- April 2009
3,4-dimethoxy cinnamaldehyde
13C
10095
49
63
80
81
34
20
17
51
56
56.0156.06
110.20
111.32
123.41
126.78
127.17
149.52
152.11
152.71
193.39
CDCl3
CS i
56.2656.32
111.66
112.61
124.30
127.57
128.28
150.73
153.24
153.64
193.83
100100
58
72
82
91
31
15
18
58
62
Acetone
CS i
55.5155.51
110.58
111.55
123.50
126.42
126.80
148.93
151.53
153.27
193.81
100100
42
58
61
67
42
30
30
45
55
CS i
DMSO
OMeOMe
2
5
6
β
1
3
4
α
γ
Atom
1HJMultH Shifts
3.883.90
6.70
7.05
7.28
7.38
7.62
9.67
ss
dd
d
dd
d
d
d
15.8, 7.7
8.3
8.3, 7.0
7.0
15.8
7.7
OMeOMe
β
5
6
2
α
γ
Atom
(acetone)
S. Ralph36mg
Notes:
151Compound Number
FPL/DFRC NMR Database -- April 2009
p-Coumaryl alcohol4-hydroxycinnamyl alcohol
13CCDCl3
CS i
63.47
116.19116.19
127.67
128.33128.33
129.73
130.29
157.78
36
100100
41
8989
14
42
22
Acetone
CS i
61.66
115.28115.28
127.06
127.27127.27
127.86
128.64
156.70
36
9696
42
100100
27
45
29
CS i
DMSO
γ
35
β
26
1
α
4
Atom
1HJMultH Shifts
4.20
6.21
6.51
6.80
7.31
bd
dt
bd
m
m
5.2
15.8, 5.5
15.9
8.7
8.7
γ
β
α
3,5
2,6
Atom
(acetone)
S. Ralph35mgorder of β & 1 are reversed in DMSO
Notes:
152Compound Number
FPL/DFRC NMR Database -- April 2009
p-Coumaraldehyde4-hydroxy cinnamaldehyde
13CCDCl3
CS i
116.84116.84
126.73
126.96
131.48131.48
153.64
161.24
193.81
9696
46
15
100100
37
19
40
Acetone
CS i
115.88115.88
125.34
125.15
130.81130.81
153.50
160.49
193.80
9797
51
29
100100
37
31
46
CS i
DMSO
35
1
β
26
α
4
γ
Atom
1HJMultH Shifts
6.62
6.94
7.58
7.61
9.64
dd
m
d
m
d
15.8, 7.7
8.7
15.8
8.7
7.7
β
3,5
α
2,6
γ
Atom
(acetone)
S. Ralph25mg
Notes:
153Compound Number
FPL/DFRC NMR Database -- April 2009
Sinapaldehyde3,4-dimethoxy-4-hydroxycinnamaldehyde
13C
100100
8080
22
50
15
3232
32
35
56.4556.45
105.73105.73
125.62
126.81
138.24
147.44147.44
153.09
193.32
CDCl3
CS i
56.7656.76
107.39107.39
126.15
127.28
140.26
149.02149.02
154.22
193.70
100100
8181
18
51
6
2323
38
26
Acetone
CS i
56.0856.08
106.71106.71
124.40
126.03
139.13
148.02148.02
154.12
193.75
100100
7777
26
46
14
4343
37
40
CS i
DMSO
OMeOMe
26
1
β
4
35
α
γ
Atom
1HJMultH Shifts
3.90
6.69
7.08
7.55
9.63
s
dd
s
d
d
15.8, 7.7
15.8
7.7
OMe
β
2,6
α
γ
Atom
(acetone)
S. RalphNotes:
154Compound Number
FPL/DFRC NMR Database -- April 2009
1-(4-hydroxy-3-methoxyphenyl)-2-(2-methoxyphenoxy)- ethanone
13C
96100
67
7463
9356
9396
8537
3322
2648
37
55.9556.12
72.08
110.31112.31
114.06114.88
120.86122.38
123.41127.62
146.86147.69
149.82151.02
193.17
CDCl3
CS i
56.2656.26
72.42
111.84113.68
115.42115.71
121.48122.55
123.94128.24
148.30149.14
150.86152.69
193.27
100100
51
5746
5743
6966
7123
2017
1417
23
Acetone
CS i
55.5455.62
70.46
111.21112.50
113.70115.00
120.46121.19
122.79126.18
147.56147.56
148.96152.18
192.60
83100
58
5858
5883
10083
8358
9292
4267
42
CS i
DMSO
OMeOMe
β
A2B2
A5B5
B6B1
A6A1
A3B3
B4A4
α
Atom
1HJMultH Shifts
3.833.92
5.36
ss
s
OMeOMe
β
Atom
(acetone)
Pearl Coll.40mgα and 3,5 change places in DMSO
Notes:
155Compound Number
FPL/DFRC NMR Database -- April 2009
Acetylated sinapaldehyde4-acetoxy-3,5-dimethoxycinnamaldehyde
13C
43
100100
8686
52
9
26
34
4747
17
36
20.39
56.2556.25
105.13105.13
128.79
131.23
132.30
152.20
152.63152.63
168.30
193.25
CDCl3
CS i
20.23
56.6856.68
106.26106.26
129.80
132.01
133.55
153.08
153.64153.64
168.37
193.94
40
100100
8888
48
8
22
36
3333
15
36
Acetone
CS i
20.05
56.2056.20
105.63105.63
128.93
130.20
132.39
15277
152.05152.05
167.76
194.18
50
100100
8484
47
13
39
66
3737
24
39
CS i
DMSO
Ac Me
OMeOMe
26
β
1
4
α
35
Ac C=O
γ
Atom
1HJMultH Shifts
2.26
3.87
6.81
7.12
7.61
9.68
s
s
dd
s
d
d
15.9, 7.6
15.9
7.6
Ac Me
OMe
β
2,6
α
γ
Atom
(acetone)
Aldrich48mg
Notes:
156Compound Number
FPL/DFRC NMR Database -- April 2009
3,4,5-Trimethoxyacetophenone
13C
43
100100
41
7575
23
9
4141
16
26.39
56.3456.34
60.91
106.00106.00
132.49
142.77
153.08153.08
196.79
CDCl3
CS i
26.52
56.5756.57
60.64
106.85106.85
133.51
143.62
154.16154.16
196.76
47
100100
44
8080
19
8
3333
15
Acetone
CS i
26.50
56.0156.01
60.07
105.80105.80
132.18
141.91
152.68152.68
196.70
51
100100
47
8787
30
11
6060
17
CS i
DMSO
β
OMe OMe
4 OMe
26
1
4
35
α
Atom
1HJMultH Shifts
2.56
3.80
3.89
7.29
s
s
s
s
β
4 OMe
3,5 OMe
2,6
Atom
(acetone)
N. Terashima15mg only DMSO solubleTerashima, Ralph, Landucci, Holzforschung, 50(1995)p. 151-155
Notes:
157Compound Number
FPL/DFRC NMR Database -- April 2009
p-Gluco cinnamyl alcohol4-(3-hydroxy-1-propenyl)phenyl-β-D-glucopyranoside
13CCDCl3
CS i
Acetone
CS i
60.63
61.49
69.6473.1476.5176.94100.32
116.23116.23
127.02127.02
127.97
128.71
130.58156.62
36
45
4541415041
9191
100100
50
45
3641
CS i
DMSO
B6
γ
B4B2B5B3B1
A3A5
A2A6
α
β
A1A4
Atom
1HJMultH Shifts
4.096.246.49
6.987.35
4.84
3.36-3.14
3.463.70
4.58
4.83
dddtbd
dd
d
nr
mddd
t
t
5.215.9, 5.0
16.0
8.78.7
7.3
11.7,6.011.7
5.7
5.4
γβα
A3,5A2,6
B1
B2,3,4,5
B6 αB6 β
B6 OH
γOH
Atom
(DMSO)
N. Terashima22mgβ + 3,5 switch places in CDCl3
Notes:
158Compound Number
FPL/DFRC NMR Database -- April 2009
acetylated p-gluco cinnamic acid
13C
100100100100
3242424548
39
9090
42
298181
39
29
29
32292926
20.5820.5820.5820.58
61.9768.2971.1772.2372.68
98.55
117.18117.18
116.31
129.38129.90129.90
145.76
158.52
169.25
169.39170.20170.51171.26
CDCl3
CS i
18.8618.8620.5220.58
62.7369.2971.9672.7573.33
98.86
117.81117.81
117.96
130.39130.60130.60
144.67
159.39
167.83
169.71170.02170.29170.62
1001007070
4743434347
40
8787
47
238383
40
33
27
23272727
Acetone
CS i
20.2220.2220.2820.37
61.5267.9670.6070.8471.86
96.67
116.48116.48
117.80
128.98129.76129.76
143.05
157.60
167.50
168.95169.17169.44169.82
91918166
4147475344
44
100100
47
41100100
53
38
41
44443847
CS i
DMSO
Ac MeAc MeAc MeAc Me
B6B4B2B5B3
B1
A3A5
β
A1A2A6
α
4
γ
Ac C=OAc C=OAc C=OAc C=O
Atom
1HJMultH Shifts
6.44
7.13
7.64
7.68
d
d
d
d
16.0
8.8
8.7
15.7
β
A3,5
α
A2,6
Atom
(acetone)
S. Ralph 15mgNotes:
159Compound Number
FPL/DFRC NMR Database -- April 2009
3,4-dimethoxycinnamyl acetate
13C
60
100100
87
60
67
87
100
47
87
33
40
27
21.01
55.8855.94
65.25
109.07
111.20
120.03
121.19
129.34
134.28
149.14
149.31
170.84
CDCl3
CS i
20.79
56.0856.08
65.48
110.48
112.67
120.78
122.28
130.37
134.54
150.54
150.62
170.72
44
100100
59
40
46
58
58
24
58
19
17
15
Acetone
CS i
20.64
55.4155.41
64.43
109.28
111.63
119.73
121.37
128.81
133.25
148.83
148.83
170.05
47
100100
47
33
37
50
50
30
43
43
43
20
CS i
DMSO
Ac Me
OMeOMe
γ
2
5
6
β
1
α
3
4
Ac C=O
Atom
1HJMultH Shifts
2.02
3.793.82
4.65
6.22
6.61
6.89
6.95
7.10
s
ss
dd
dt
bd
d
dd
q
6.5, 1.3
15.9, 6.4
15.9
8.3
8.3, 1.9
1.9
Ac Me
OMeOMe
γ
β
α
5
6
2
Atom
(acetone)
M. Mozuch 2mgNo DEPT run and not run in DMSO
Notes:
160Compound Number
FPL/DFRC NMR Database -- April 2009
Veratryl glycerol1-(3,4-dimethoxyphenyl)glycerol
13C
100100
50
47
53
33
33
50
27
23
27
55.9855.98
63.41
74.87
75.81
109.71
111.25
119.04
133.04
149.08
149.28
CDCl3
CS i
56.1056.20
63.98
74.70
77.21
111.82
112.54
119.91
136.24
149.70
150.16
9494
100
88
88
62
69
88
56
31
31
Acetone
CS i CS i
DMSO
OMeOMe
γ
β
α
2
5
6
1
3
4
Atom
1HJMultH Shifts
3.773.78
3.363.48
3.624.58
6.866.867.00
ss
dddd
md
mmbs
OMeOMe
γ1γ2
βα
562
Atom
(acetone)
M. Mozuch 17 mgNotes:
161Compound Number
FPL/DFRC NMR Database -- April 2009
1-(3,4-dimethoxyphenyl)-2,3-dihydroxypropan-1-one
13C
100100
93
93
79
71
100
43
50
36
50
56.1156.21
65.95
74.17
110.34
110.77
123.46
126.55
149.52
154.42
197.65
CDCl3
CS i
56.2056.28
66.30
75.28
111.64
112.03
124.23
128.45
150.28
155.09
199.22
7276
100
90
76
48
86
24
28
28
41
Acetone
CS i CS i
DMSO
OMeOMe
γ
β
2
5
6
1
3
4
α
Atom
1HJMultH Shifts
3.893.92
5.13
7.08
7.55
7.71
ss
m
d
d
dd
8.4
2.0
2.0, 8.4
OMeOMe
β
5
2
6
Atom
(acetone)
L.Landucci 30 mgNot run in DMSO
Notes:
162Compound Number
FPL/DFRC NMR Database -- April 2009
Erone diacetate3-acetoxy-1-(4-acetoxy-3-methoxyphenyl)-2-(2-methoxy
phenoxy)propan-1-one
13C
10065
7585
7060
85856580707580
4030253535
3530
40
20.6220.75
55.7556.08
64.3680.58
112.73112.73118.53121.04122.34122.97123.66
133.67144.38146.82150.43151.47
168.30170.82
194.59
CDCl3
CS i
20.4820.64
56.1656.46
64.6680.50
113.45113.93118.58121.67122.81124.04124.04
134.87145.35147.86151.40152.50
168.58170.90
195.10
10070
7985
7067
66645674678989
3920332539
2828
31
Acetone
CS i CS i
DMSO
Ac MeAc Me
OMeOMe
γβ
A2B2B5B6A6B1A5
A1A4B4B3A3
A4 Ac C=Oγ Ac C=O
α
Atom
1HJMultH Shifts
1.982.27
3.763.88
4.494.655.84
7.817.23
ss
ss
dddddd
md
6.5, 11.93.9, 11.93.9, 6.5
8.8
Ac MeAc Me
OMeOMe
γ1γ2β
A2,6A5
Atom
(acetone)
L.Landucci35 mg
Notes:
163Compound Number
FPL/DFRC NMR Database -- April 2009
Veratrone acetate
13C
84
1009593
8689
82848888938995
47
37463944
42
46
20.78
55.7955.9656.07
64.6280.28
110.22111.10112.67118.05120.96123.33123.76
128.04
146.92149.04150.32153.88
170.84
194.05
CDCl3
CS i
20.64
56.0556.1756.22
64.8580.00
111.59112.06113.85117.99121.57123.69124.27
128.96
147.95150.13151.25155.11
170.89
194.24
64
8210096
7982
82828679898286
39
32363236
32
39
Acetone
CS i
20.44
55.4055.5355.74
63.6079.08
110.70110.98112.88115.61120.53122.28123.23
127.29
146.33148.58149.37153.67
170.00
193.22
95
9310090
6767
74767674837979
57
55555557
55
62
CS i
DMSO
Ac Me
OMeOMeOMe
γβ
A2A5B2B5B6A6B1
A1
B4A3B3A4
Ac C=O
α
Atom
1HJMultH Shifts
1.98
3.773.853.89
4.47
4.62
5.81
7.06
7.66
7.84
s
sss
dd
dd
dd
d
d
dd
6.8, 11.9
3.9, 11.9
3.9
8.5
2.0
2.0, 8.4
Ac Me
OMeOMeOMe
γ1
γ2
β
A5
A2
A6
Atom
(acetone)
J.Pew15 mgAs this compound has a plane of symmetry the shifts for the other half areidentical.
Notes:
164Compound Number
FPL/DFRC NMR Database -- April 2009
Pinoresinol biphenyl
13C
8181
10091
6262
7272
4774
77
7251
34
5555
4751
4745
54.1354.18
55.9756.22
71.6671.82
85.8285.93
108.17108.64
114.28
118.98120.93
124.06
132.82132.82
142.31145.26
146.73147.40
CDCl3
CS i
55.2655.26
56.2556.48
72.1972.33
86.6786.67
109.38110.58
115.51
119.62121.96
125.96
133.50134.17
144.01146.82
148.28148.68
100100
6983
6059
9393
4957
58
6251
23
4131
2835
3338
Acetone
CS i
53.6053.60
55.5755.90
70.8670.98
85.1485.21
108.61110.39
115.08
118.60120.90
125.44
131.28132.16
142.96145.85
147.46147.63
9393
10077
5351
6656
3477
73
6836
26
4447
3854
6541
CS i
DMSO
A βBβ
OMeOMe
A γB γ
A αBα
A2B2
B5
B6A6
A5
A1B1
A4B4
B3A3
Atom
1HJMultH Shifts
3.82
3.87
4.21
4.67
s
s
dd
d
6.8, 9.0
4.5
OMe
OMe
A,B γ2
A,B α
Atom
(acetone)
J. Pew7 mg intensities for some peaks are irregularAs this compound has a plane of symmetrythe shifts for the other half are identical.
Notes:
165Compound Number
FPL/DFRC NMR Database -- April 2009
Pinoresinol biphenyl acetate
13C
6555
6552
7385
6645
100100
4146
54
5058
32
1828
2829
3135
2526
20.4720.67
54.2854.37
55.9656.17
71.9572.05
85.4985.49
109.40109.89
117.96
119.79122.76
131.38
136.93139.13
139.40140.02
151.24151.51
168.71169.08
CDCl3
CS i
20.4220.49
55.4055.40
56.2256.47
72.6272.62
86.1786.17
110.55111.09
118.62
120.26123.47
132.09
137.76140.12
141.07141.80
152.27152.59
168.83169.02
7792
8686
7164
100100
7272
4155
53
3860
26
2020
3135
3438
2634
Acetone
CS i
20.1921.16
54.5754.57
56.5256.82
72.0972.09
85.3285.42
110.80111.18
118.63
119.80123.36
131.16
136.84139.23
140.59141.24
151.52151.86
168.93169.32
66100
7474
9966
6969
4763
2061
65
2263
33
3142
4341
5548
2651
CS i
DMSO
Ac MeAc Me
A βB β
OMeOMe
A γB γ
A αB α
A2B2
B6
A6B5
A5
A4B4
A1B1
A3B3
A Ac C=OB Ac C=O
Atom
1HJMultH Shifts
2.00
2.21
3.80
3.84
3.14
4.28
4.80
s
s
s
s
m
m
m
Ac Me
Ac Me
OMe
OMe
A,B β
A,B γ2
A,Bα
Atom
(acetone)
M. Mozuch40 mgnot very soluble in CDCl3, not run in DMSO
Notes:
166Compound Number
FPL/DFRC NMR Database -- April 2009
1-(3,4-dimethoxyphenyl)-2-(4-hydroxyphenoxy)propan-1,3-diol
13CCDCl3
CS i
56.0356.09
61.5873.2985.37
111.84112.30
116.42116.42
118.70118.70
119.90
135.53
149.56149.97152.52153.12
61.96
73.94
85.17
6163
404048
4654
100100
100100
46
27
22252719
Acetone
CS i CS i
DMSO
OMeOMe
γαβ
A2A5
B2B6
B3B5
A6
A1
A3A4B1B4
minor isomer
γ
α
β
Atom
1HJMultH Shifts
3.49
3.77
3.77
4.26
4.95
dd
s
s
m
d
5.2, 11.3
5.0
γ1
OMe
OMe
β
α
Atom
(acetone)
M. Mozuch40 mgNot run in DMSO
Notes:
167Compound Number
FPL/DFRC NMR Database -- April 2009
Ethyl vanillin
13C
87
100
88
597365
33
2324
73
14.38
55.77
64.39
108.97111.07126.53
129.69
149.51153.71
190.60
CDCl3
CS i
14.92
56.00
65.02
110.36112.52126.65
130.98
150.72154.88
191.06
75
100
83
799370
30
2020
72
Acetone
CS i CS i
DMSO
Me
OMe
CH2
256
1
34
α
Atom
1HJMultH Shifts
1.42
3.89
4.15
7.08
7.41
7.49
9.85
t
s
q
d
d
dd
s
7.0
7.0
8.2
1.9
1.9, 8.2
Me
OMe
CH2
5
2
6
α
Atom
(acetone)
S. Kawai50 mg
Notes:
168Compound Number
FPL/DFRC NMR Database -- April 2009
1-(3,4-dimethoxyphenyl)-2-(4-carboxymethylphenoxy)propan-1,3-diol
13C
100
374138
3841
8484
37
27
7777
33192628
31
55.87
61.7174.0481.49
109.66111.06
116.00116.00
119.16
130.24
131.94131.94
132.82148.82149.00162.93
190.78
61.37
73.62
82.58
CDCl3
CS i
56.03
62.0073.5583.70
111.84112.22
116.94116.94
120.09
130.89
132.18132.18
135.16149.63149.93164.83
191.01
91
393638
4445
100100
36
27
8080
23171920
47
Acetone
CS i CS i
DMSO
OMe
γ α β
A2A5
B3B5
A6
A1
B2B6
B1A3A4B4
B α
Minor isomer
γ
α
β
Atom
1HJMultH Shifts
3.82
4.54
4.99
7.72
9.78
s
m
d
m
s
5.6
OMe
β
α
B 2,6
B α
Atom
(chloroform)
J. Pew50 mgAs this compound has a plane of symmetrythe shifts for the other half are identical.
Notes:
169Compound Number
FPL/DFRC NMR Database -- April 2009
Phenylcoumaran biphenyl acetate
13C
10075
77
858273
8881
66
40526838
4562
593362554056
26
13.7517.71
20.26
24.9237.9145.76
55.8556.00
92.66
109.60111.74115.33120.42
130.96132.48
136.36137.28138.51143.69145.07151.39
168.36
CDCl3
CS i
14.1018.49
20.30
25.7338.5346.82
56.4356.48
92.74
110.63113.65116.42120.46
132.00133.69
137.00138.28140.22144.86146.36152.72
168.66
9774
67
648661
10093
74
68698156
4668
472946312949
28
Acetone
CS i
13.7117.81
19.96
24.5637.2945.26
55.6656.04
91.15
110.13112.29115.42119.24
130.33132.47
135.76136.61138.84143.40144.73151.24
168.02
10057
49
836049
7964
43
38404523
4551
533647534347
26
CS i
DMSO
B γγ
Ac Me
B βB α
β
OMeOMe
α
B2A2B6A6
A1B1
A5A4B5B3A3B4
Ac C=O
Atom
1HJMultH Shifts
0.921.411.60
2.02
2.51
3.42
3.823.85
5.18
6.636.69
6.967.25
tdm
s
m
m
ss
d
ss
dd
7.36.87.5
7.3
8.7
1.81.9
B γγ
B β
Ac Me
B α
β
OMeOMe
α
B2B6
A2A6
Atom
(acetone)
J. Pew30 mgAs this compound has a plane of symmetry the shifts for the other half areidentical.
Notes:
170Compound Number
FPL/DFRC NMR Database -- April 2009
Phenyl coumaran biphenyl
13C
10070848479
8085
72
49546961
48
6457
6256493352
13.9117.4825.0838.0745.68
56.0056.20
93.52
108.42111.83115.44122.01
123.90
132.15132.96
136.28142.71143.82145.34147.41
CDCl3
CS i
14.1017.8725.7938.5446.48
56.4056.50
93.84
109.38113.57116.40122.57
125.82
132.38134.15
136.65144.74144.79146.58148.76
100781009374
8993
81
63708174
33
4856
4856563056
Acetone
CS i
13.7717.2824.6237.3244.80
55.6655.94
92.39
108.67112.19115.42121.57
125.33
129.98132.94
135.41143.32143.78144.91147.74
10076846450
8468
48
32465236
42
4656
5858484850
CS i
DMSO
B γγ
B βB α
β
OMeOMe
α
B2A2B6A6
A5
B1A1
B5B3A4A3B4
Atom
1HJMultH Shifts
0.92
1.371.612.523.44
3.803.89
5.09
6.636.68
7.027.11
t
dhtm
ss
d
ss
dd
7.3
6.87.47.4
9.4
1.81.9
B γ
γB βB αβ
OMeOMe
α
B2B6
A2A6
Atom
(acetone)
S. Ralph15 mgβ higher ppm than OMe's in acetone
Notes:
171Compound Number
FPL/DFRC NMR Database -- April 2009
1,2-diguaiacylpropane-1,3-diol
13C
46
100100
4951
5451
5651
5151
2732
3229
2727
55.60
55.9055.90
64.2575.78
109.06111.80
113.98114.58
119.70121.54
130.29133.99
144.97145.32
146.53146.63
CDCl3
CS i
56.46
56.0556.15
64.4274.86
111.18114.18
114.82115.01
119.92123.00
132.17136.59
145.91146.12
147.54147.60
85
90100
7870
7272
9288
8282
5260
4245
5245
Acetone
CS i
54.69
54.8755.06
62.2071.96
110.27113.46
113.98114.03
118.13121.32
130.96135.49
144.13144.36
146.05146.24
74
10095
6067
7174
9081
7471
6971
7464
6967
CS i
DMSO
β
OMeOMe
γα
A2B2
A5B5
A6B6
B1A1
B4A4
B3A3
Atom
1HJMultH Shifts
3.673.72
2.94
5.02
ss
m
d
OMeOMe
β
α
Atom
(acetone)
S. Ralph15 mg
Notes:
172Compound Number
FPL/DFRC NMR Database -- April 2009
1,2-diguaiacylpropane-1,3-diol tetraacetate
13C
92924849
43
100100
4242
414611475247
333321212724
28272626
20.6320.6320.7920.96
50.09
55.8855.88
64.0274.87
111.24113.32119.13120.98122.46122.58
135.77136.91139.04139.58150.71150.86
168.76168.84169.63170.74
CDCl3
CS i
20.4520.4520.6720.84
50.97
56.2056.20
64.8675.56
112.07114.49119.71121.91123.12123.29
137.41138.70140.02140.48151.78151.97
168.88168.94169.64170.74
50.70
64.71
76.50
68684346
48
100100
4246
434249485851
292617172220
23222020
Acetone
CS i
20.2820.2820.4420.53
49.08
55.6055.60
63.9474.49
111.00113.38118.69120.71122.15122.38
136.55137.52138.15138.71150.14150.40
168.32168.32169.19169.98
82825663
35
100100
2835
283739394134
343532323934
42423235
CS i
DMSO
Ac MeAc MeAc MeAc Me
β
OMeOMe
γα
A2B2A6B6B5A5
B1A1B4A4B3A3
Ac C=OAc C=O
α Ac C=O γAc C=O
Minor isomer
β
γ
α
Atom
1HJMultH Shifts
1.931.982.212.22
3.52
4.21
4.38
6.18
ssss
m
dd
dd
d
6.6, 11.0
6.8, 11.3
6.6
Ac MeAc MeAc MeAc Me
β
γ1
γ2
α
Atom
(acetone)
Jamie MilhauptJR-JMA 29.150 mg
Notes:
173Compound Number
FPL/DFRC NMR Database -- April 2009
4-acetoxy-acetophenone
13C
39
41
9292
100100
15
15
15
13
21.11
26.55
121.75121.75
129.91129.91
134.72
154.35
168.78
196.75
CDCl3
CS i
20.98
20.64
122.75122.75
130.53130.53
135.65
155.43
169.27
196.80
40
45
100100
9494
11
11
13
11
Acetone
CS i
20.51
26.62
122.02122.02
129.78129.78
134.39
154.08
168.73
196.75
47
46
9393
100100
23
22
19
15
CS i
DMSO
Ac Me
β
35
26
1
4
Ac C=O
α
Atom
1HJMultH Shifts
2.28
2.57
7.24
8.02
s
s
d
d
8.9
8.9
Ac Me
β
3
2
Atom
(acetone)
Jamie MilhauptJR-JMA 23.150mg
Notes:
174Compound Number
FPL/DFRC NMR Database -- April 2009
Vanillin acetate4-formyl-2-methoxy phenyl acetate
13C
72
100
85
98
87
40
24
30
28
92
20.58
56.06
110.92
123.40
124.59
135.23
144.93
151.96
168.26
190.97
CDCl3
CS i
20.45
56.46
112.31
124.39
124.44
136.43
145.83
153.03
168.57
191.76
62
86
79
100
100
25
18
20
18
71
Acetone
CS i
20.29
55.96
111.84
123.46
123.63
135.00
144.19
151.50
168.01
191.87
90
100
90
90
100
51
34
41
41
95
CS i
DMSO
Ac Me
OMe
2
6
5
1
4
3
Ac C=O
α
Atom
1HJMultH Shifts
2.27
3.91
7.57
7.29
7.55
9.97
s
s
d
d
dd
s
0.8
7.8
7.8, 0.8
Ac Me
OMe
2
5
6
α
Atom
(acetone)
Jamie MilhauptJR-JMA 25.125 mg
Notes:
175Compound Number
FPL/DFRC NMR Database -- April 2009
Syringic Acid Acetate4-acetoxy-3,5-dimethoxy benzoic acid
13C
47
100100
100100
12
14
5757
27
20
20.43
56.3456.34
106.90106.90
127.15
133.37
152.19152.19
168.17
171.25
CDCl3
CS i
20.23
56.6556.65
107.12107.12
129.34
133.63
153.21153.21
166.97
168.18
43
9898
100100
17
12
3333
21
19
Acetone
CS i
19.93
55.9255.92
105.72105.72
128.72
131.44
151.48151.48
166.44
167.52
50
100100
8383
33
17
6363
35
30
CS i
DMSO
Ac Me
OMeOMe
26
1
4
35
α
Ac C=O
Atom
1HJMultH Shifts
2.27
3.88
7.37
s
s
s
Ac Me
OMe
2,6
Atom
(acetone)
Jamie MilhauptJR-JMA 27.154 mg
Notes:
176Compound Number
FPL/DFRC NMR Database -- April 2009
Guaiacol acetate2-methoxyphenyl acetate
13C
64
100
93
97
95
95
19
22
21
20.64
55.78
112.39
120.72
122.78
126.86
139.75
151.10
168.99
CDCl3
CS i
20.48
56.12
113.41
121.30
123.66
127.50
141.01
152.36
168.93
68
95
94
100
98
97
15
19
17
Acetone
CS i
20.21
55.62
112.74
120.47
122.76
126.79
139.33
150.87
168.43
84
96
99
100
97
93
28
35
34
CS i
DMSO
Ac Me
OMe
2
5
1
6
4
3
Ac C=O
Atom
1HJMultH Shifts
2.22
3.79
6.93
7.20
7.05
7.05
s
s
m
m
m
m
Ac Me
OMe
2
5
1
6
Atom
(acetone)
Jamie MilhauptJR-JMA 31.150 mg
Notes:
177Compound Number
FPL/DFRC NMR Database -- April 2009
Acetosyringone acetate4-acetoxy-3,5-dimethoxy acetophenone
13C
43
44
100100
9494
9
23
4040
17
17
20.41
26.50
52.2856.28
105.10105.10
132.81
135.11
152.20152.20
168.14
196.75
CDCl3
CS i
20.23
26.68
56.6656.66
105.89105.89
133.70
136.19
153.28153.28
168.21
196.92
40
47
100100
100100
6
13
2626
13
13
Acetone
CS i
20.86
27.47
56.9456.94
105.79105.79
132.75
135.69
152.56156.56
168.43
197.64
50
50
100100
8888
13
31
5757
27
28
CS i
DMSO
Ac Me
β
OMeOMe
26
4
1
35
Ac C=O
α
Atom
1HJMultH Shifts
2.25
2.58
3.87
7.31
s
s
s
s
Ac Me
β
OMe
2,6
Atom
(acetone)
20 mgsample has a minor impurity
Notes:
178Compound Number
FPL/DFRC NMR Database -- April 2009
Sinapic acid acetate4-acetoxy-3,5-dimethoxy cinnamic acid
13C
51
100100
8787
41
11
31
44
5757
25
25
20.41
56.2756.27
105.19105.19
116.92
131.30
131.93
148.34
152.60152.60
162.19
168.33
CDCl3
CS i
20.23
56.6656.66
106.42106.42
117.90
132.15
132.95
149.06
153.60153.60
163.11
168.35
48
100100
100100
48
10
25
45
4040
15
20
Acetone
CS i
20.03
56.2056.20
105.93105.93
117.16
130.30
131.78
148.37
151.97151.97
162.61
167.74
60
100100
6868
38
19
34
34
6666
28
32
CS i
DMSO
Ac Me
OMeOMe
26
b
4
1
α
35
γ
Ac C=O
Atom
1HJMultH Shifts
2.29
3.86
7.13
6.66
7.79
s
s
s
d
d
5.9
5.9
Ac OMe
OMe
2,6
β
α
Atom
(acetone)
S. Lemke SLI 75B17.7mg
Notes:
179Compound Number
FPL/DFRC NMR Database -- April 2009
Guaiacylglycerol-β-syringyl ether
1-(4-hydroxy-3-methoxyphenyl)-2-(2,6-dimethoxyphenoxy)propane-1,3-diol
13C
58
100100
42
45
47
9898
44
45
47
47
26
15
27
24
3535
55.97
56.1656.16
60.49
74.13
89.06
105.36105.36
109.91
114.33
120.40
124.50
132.00
135.38
145.46
146.58
153.26153.26
60.59
72.52
87.03
CDCl3
CS i
56.23
56.5856.58
61.31
74.07
89.76
106.53106.53
111.51
115.23
120.76
124.90
133.71
137.16
146.81
147.95
154.19154.19
60.94
73.35
87.83
37
100100
46
44
51
9393
46
49
53
53
23
11
23
18
3535
Acetone
CS i
55.45
55.8555.85
60.08
71.40
86.96
105.64105.64
110.93
114.55
119.10
123.26
132.86
136.18
145.20
146.76
152.69152.69
59.71
72.04
86.12
49
100100
31
39
34
7272
36
39
37
39
36
22
36
33
5858
CS i
DMSO
OMe
OMeOMe
γ
α
β
B2B6
A2
A5
A6
B1
A1
B4
A4
A3
B3B5
erythro isomer
γ
α
β
Atom
1HJMultH Shifts
3.293.64
5.00
3.51
6.73
7.07
6.78
6.92
7.04
7.46
4.36
mm
dd
m
d
d
d
dd
t
s
dd
7.5, 2.6
8.4
1.8
8.0
8.0, 1.8
8.4
2.6, 1.1
γ1γ2
α
β
B2
A2
A5
A6
B1
A4
α OH
Atom
(acetone)
threo
Jamie MilhauptJR-JMA 43.150 mg
Notes:
180Compound Number
FPL/DFRC NMR Database -- April 2009
4-acetoxy-3-methoxy methyl benzoate
13C
73
77
96
88
93
100
34
22
28
33
29
20.61
52.26
56.07
113.44
122.60
122.78
128.82
143.64
151.07
166.33
168.43
CDCl3
CS i
20.45
52.45
56.40
113.96
123.05
123.85
129.67
144.81
152.30
166.53
168.59
72
74
100
82
88
88
30
20
24
20
22
Acetone
CS i
20.33
52.60
55.95
112.96
122.06
123.24
128.32
143.28
150.93
165.56
168.14
96
91
91
77
100
93
52
41
49
46
46
CS i
DMSO
Ac Me
α OMe
OMe
2
6
5
1
4
3
α
Ac C=O
Atom
1HJMultH Shifts
2.27
3.89
3.88
7.65
7.18
7.63
s
s
s
d
d
dd
1.9
8.0
8.0, 1.9
Ac Me
α OMe
OMe
2
5
6
Atom
(acetone)
S. Luque SLL 11C7mg Assignments from 360 MHz exps in acetone. Spectrum in CDCl3 weak3's,4's, and 1's uncertain Landucci, Luque and Ralph, J. Wood Chem. Tech., 15(4), 493-513 (1995)
Notes:
181Compound Number
FPL/DFRC NMR Database -- April 2009
G-b-S-c-CA
13C
48
86868080
332816
202915
4545
2921403330
231327
3131132512231710
39100
53.94
56.1056.1056.3456.34
60.6663.8164.21
72.6487.1988.18
103.26103.26
108.53110.67114.29114.89118.84
126.87130.15131.51
131.34131.34134.75137.86144.57144.94146.71148.76
153.53153.53
CDCl3
CS i
54.91
56.2456.5056.6156.61
60.9763.3664.62
73.3787.8788.36
104.10104.10
110.89111.89115.20116.06120.01
128.57130.15130.40
132.20133.73136.10139.09145.22146.44147.97148.82
154.26154.26
35
6152100100
384134
413828
6666
4131423539
351535
18188141120177
3030
Acetone
CS i
52.93
55.4255.9055.7155.71
59.6461.5262.71
71.9886.1486.93
103.24103.24
110.81110.88114.56114.82119.19
128.02128.78129.22
130.63133.15134.79136.59143.59145.18146.86146.86
152.60152.60
27
5573100100
243128
333119
4040
3939302221
222421
1927152125313636
4343
CS i
DMSO
B β
OMeOMeOMeOMe
γC γB γ
αβ
B α
B2B6
A2C2A5C6A6
C βC5C α
C1A1B1B4C3A4A3C4
B3B5
Atom
1HJMultH Shifts
3.823.843.89
5.00
5.62
6.83
6.256.54
sss
m
d
s
dtd
6.5
15.8, 5.415.9
OMeOMeOMe
α
B α
B2,6
C βC α
Atom
(acetone)
L. Landucci SR VII-9,8mg Assignments in d6-acetone based on 360MHz cosy df br HMBC and HMQCexps. Landucci, Luque and Ralph, J. Wood Chem. Tech., 15(4), 493-513 (1995)
Notes:
182Compound Number
FPL/DFRC NMR Database -- April 2009
G-b-S-c-CA (acetate)
13C
5652495656
30
48100100100
243928262128
575726292924
33
312423
31
111624212317214747
2122243737
20.68207820.8521.0721.07
50.51
55.9656.1056.1056.10
62.6465.1965.3374.0080.9588.55
103.08103.08110.72111.50115.33119.18
121.37
122.44127.52130.74
134.28
135.16136.12136.62139.51144.46148.19150.86153.38153.38
168.88169.50170.71170.85170.85
CDCl3
CS i
20.4920.6120.7720.8220.93
51.32
56.2856.4556.4556.51
63.2965.5165.9675.0381.3788.86
103.94103.94112.19112.30116.33120.01
122.30
123.29129.08131.60
134.70
136.15137.09138.02140.56145.41149.31152.03154.19154.19
168.97169.95170.70170.79170.98
5651586454
36
5610010078
264036323332
656529423635
35
442423
35
122226212214234545
2128242324
Acetone
CS i
20.3320.3120.5520.6720.71
49.37
55.7355.8255.8255.82
62.0664.5164.7673.6879.9487.60
103.13103.13111.07111.07115.24118.79
121.41
122.54127.99130.13
133.48
134.30135.63136.41138.89143.89147.55150.57152.65152.65
168.44169.32169.94170.12170.25
8080435051
22
53100100100
153521182221
393924242022
25
252527
27
232223222419274747
2525282330
CS i
DMSO
Ac MeAc MeAc MeAc MeAc Me
B β
OMeOMeOMeOMe
γC γB γ
αβ
Bα
B2B6C2A2C6A6
C β
A5C5C1
C α
B4A1B1A4 C3C4A3B3B5
Ac C=OAc C=OAc C=OAc C=OAc C=O
Atom
1HJMultH Shifts
4.164.65
6.064.735.54
6.767.14
6.246.64
dddd
dmd
sm
dtd
11.9, 4.06.5, 1.2
4.5
7.1
15.8, 6.515.9
γ1C γ
αβ
B α
B2,6C2
CβC α
Atom
(acetone)
S. Lugue SR VII 934mg Assignments in d6-acetone based on 360MHz HMBC and HMQC expsLanducci, Luque and Ralph, J. Wood Chem. Tech., 15(4), 493-513 (1995)
Notes:
183Compound Number
FPL/DFRC NMR Database -- April 2009
G-b-S-r-S
13C
2726
6680806262
36222529414127
100100100100343933
2218
141519
2827
3333
4444
54.3254.48
56.0056.2756.2756.4456.44
60.5771.7672.0872.5685.9885.9887.03
102.88102.88102.88102.88108.61114.28118.80
131.37131.91
134.36134.52137.80
144.94146.71
147.29147.29
153.45153.45
CDCl3
CS i
55.2355.39
56.2856.6056.6056.6756.67
60.9772.3872.5773.3886.5786.7287.78
104.09104.09104.50104.50110.93115.21120.04
133.10133.74
135.67136.20139.05
146.43147.96
148.67148.67
154.15154.15
32
36541001007979
34333339413042
70705555384139
1820
171624
2928
3333
4747
Acetone
CS i
53.6153.76
55.5355.9955.9955.9955.99
59.8471.1371.2772.1285.1285.3286.14
103.29103.29103.68103.67110.96114.65119.36
131.38133.26
134.77134.89136.89
145.32146.96
147.90147.90
152.61152.61
2227
53100100100100
22222527332332
46465151282828
2223
202023
3534
4444
4747
CS i
DMSO
B βC β
OMeOMeOMeOMeOMe
γC γB γ
αB αC α
β
B2B6C2C6A2A5A6
C1A1
B1C4B4
A3A4
C3C5
B3B5
Atom
1HJMultH Shifts
3.113.113.44
4.17
4.224.22
4.674.734.98
6.766.677.03
mmdd
m
mm
ddd
sss
72.0, 3.4
4.04.03.4
B βC βγ 2
β
C γB γ
C αB α
α
B2C2A2
Atom
(acetone)
L. Landucci XXI 3640mg Assign’ts in d6-acetone based on the HMBC exp't H assign’ts for 360 MHzspectra Landucci, Luque and Ralph, J. Wood Chem. Tech., 15(4), 493-513 (1995)
Notes:
184Compound Number
FPL/DFRC NMR Database -- April 2009
G-b-S-r-S (acetate)
13C
42464646
2535
448989100100
26252521213330
75755151282633
1418182626282649494949
25262828
20.3220.5120.6320.93
54.1654.33
55.7955.9655.9656.0956.09
62.5071.8771.9873.8280.6285.6385.77
102.12102.12102.64102.64111.37119.09122.26
127.87134.41135.97137.13139.35139.58150.68152.16152.16153.19153.19
168.64168.72169.36170.70
CDCl3
CS i
20.2420.4820.6120.94
55.3355.43
56.2656.3856.3856.4656.46
63.2972.6572.6575.0581.2886.4586.54
103.23103.23103.73103.73112.21120.04123.26
128.85135.48137.12138.89140.54141.44152.00153.21153.21154.04154.04
168.61168.94169.92170.67
33635256
3033
579090100100
36535330223133
55555454342537
813181721172331313737
15293031
Acetone
CS i
20.1120.3120.3120.66
53.6753.81
55.6955.7855.7855.9455.94
62.1071.3671.3673.7279.8684.9285.06
102.44102.44102.80102.80110.95118.80122.49
127.06133.63135.71137.53138.86140.14150.53151.64151.64152.54152.54
168.08168.41169.31169.94
45818145
3935
451001009797
26454523163232
68684242231623
1923193226352968684848
29293535
CS i
DMSO
Ac MeAc MeAc MeAc Me
B βC β
OMeOMeOMeOMeOMe
γB γC γ
αβ
B αC α
C2C6B2B6A2A6A5
C4B4A1B1A4C1A3C3C5B3B5
Ac C=OAc C=OAc C=OAc C=O
Atom
1HJMultH Shifts
3.90
4.184.274.39
4.724.76
6.056.686.74
6.967.147.01
dd
dddddddd
dd
ddss
dddd
11.9, 4.1, 1.8
11.8, 5.9, 0.8
4.44.4
4.7, 2.6
8.1, 1.81.87.4
B,C γ1
γ 1B,Cγ2
γ2
B αC α
αB2,6C2,6
A6A2A5
Atom
(acetone)
S. Ralph SRVII 15A67mg Landucci, Luque and Ralph, J. Wood Chem. Tech.15(4), 493-513 (1995)
Notes:
185Compound Number
FPL/DFRC NMR Database -- April 2009
S-b-SA (acetate)
13C
43434347
9696100100
34433537
65655757
35
1131
38
1830
51515353
18242727
20.4620.7620.9921.07
56.0256.0256.1756.17
62.7664.9274.2580.93
103.69103.69103.95103.95
122.95
128.49132.41
134.07
135.37135.53
151.93151.93153.22153.22
168.57169.57170.82170.82
CDCl3
CS i
20.2620.6320.8020.93
56.3956.3956.4956.49
63.2865.2575.2981.56
104.52104.52104.60104.60
124.09
129.32133.30
134.36
136.46136.62
153.02153.02154.14154.14
168.51169.95170.68170.74
49474447
1001009696
40484142
77777878
44
1126
48
1728
43434949
22252620
Acetone
CS i
20.0420.2920.6220.62
55.7355.7355.8655.84
62.0764.1673.8479.98
103.20103.20103.53103.53
123.32
127.47131.88
132.96
134.40135.19
151.44151.44152.58152.58
167.91169.24169.86170.00
47527575
1001009191
26409191
55555858
35
1929
37
2831
64646262
26313526
CS i
DMSO
Ac MeAc MeAc MeAc Me
OMeOMeOMeOMe
γB γαβ
A2A6B2B6
B β
A4B1
Bα
A1B4
A3A5B3B5
Ac C=OAc C=OAc C=OAc C=O
Atom
1HJMultH Shifts
3.813.85
4.194.434.686.074.74
3.786.80
6.33
6.63
ss
ddddddddt
ss
dt
d
11.8, 4.111.8, 6.17.4, 1.2
4.26.1, 4.2
15.8, 6.3
16.0
Ac MeAc Me
γ2γ1B γ
αβ
A6 or B6A2 or B2
B β
B α
Atom
(acetone)
S. Ralph SR VII 16D15mg Landucci, Luque and Ralph, J. Wood Chem. Tech., 15(4), 493-513 (1995)
Notes:
186Compound Number
FPL/DFRC NMR Database -- April 2009
S-b-CA (acetate)
13C
34374646
57100100
37434637
8383434346
49
1431
43
3129296060
23312623
20.5420.8621.1221.12
55.9156.2956.29
62.7356.1574.0580.21
104.52104.52110.41119.04119.89
122.36
128.85131.93
133.90
134.82147.37151.06152.13152.13
168.59169.55170.84170.90
CDCl3
CS i
20.2520.6420.8020.89
56.2956.5456.54
63.0965.3674.7880.17
105.14105.14111.40119.16120.49
123.52
129.61132.56
134.13
136.11148.33151.92153.06153.06
168.46169.89170.75170.75
45434147
54100100
43524643
8181454440
48
1127
48
2622213838
21222929
Acetone
CS i
20.0420.3820.6320.63
55.6155.9055.90
61.8864.3173.2078.01
103.94103.94110.26117.14119.43
122.30
127.66130.71
132.84
134.78146.56150.11151.38151.38
167.90169.18169.96170.03
45527575
56100100
29453532
6565333739
40
2331
40
3231336565
31323629
CS i
DMSO
Ac MeAc MeAc MeAc Me
OMeOMeOMe
γB γ
α β
A2A6B2B5B6
B β
A4B1
B α
A1B4B3A3A5
Ac C=OAc C=OAc C=OAc C=O
Atom
1HJMultH Shifts
3.863.81
4.384.264.68
4.89
6.056.30
6.63
6.877.15
ss
dddddd
m
ddt
d
sd
11.9, 5.911.9, 4.16.4, 1.2
5.115.8, 6.4
15.9
1.6
OMeOMe
γ1γ2
B γ
β
αB β
B α
A2,6B2
Atom
(acetone)
S. Ralph SR VII 21C8mgLanducci, Luque and Ralph, J. Wood Chem. Tech., 15(4), 493-513 (1995)
Notes:
187Compound Number
FPL/DFRC NMR Database -- April 2009
S-c-CA (acetate)
13C
454342
47
58100100
534242
81814345
47
341334
47
3630215353
253015
20.5320.9221.11
50.62
56.1856.3156.31
65.2665.4388.44
102.65102.65110.87115.42
121.44
127.51128.68130.85
134.33
135.97144.53148.26152.43152.43
168.69170.79170.93
CDCl3
CS i
20.2520.7420.82
51.37
56.5456.5456.54
65.5065.9688.76
103.51103.51112.38116.34
122.36
129.03129.52131.70
134.67
140.50145.55149.28153.40153.40
168.57170.75170.94
303030
32
100100100
353431
62623131
31
15616
31
1815102727
1288
Acetone
CS i
20.1320.5720.73
49.37
55.8456.0056.00
64.5164.4787.46
102.86102.86111.11115.24
121.46
127.98127.74130.22
133.46
138.92143.90147.49151.77151.77
168.02170.13170.28
465254
34
55100100
483437
73733334
39
361836
37
3434256969
282837
CS i
DMSO
Ac MeAc MeAc Me
β
OMeOMeOMe
B γγα
A2A6B2B6
B β
B5A4B1
B α
A1B3B4A3A5
Ac C=OAc C=OAc C=O
Atom
1HJMultH Shifts
4.484.374.67
5.59
6.256.65
6.84
7.057.07
ddddd
d
dtd
s
ss
11.1, 5.511.1, 7.3
6.4
7.1
15.9, 6.415.9
γ1γ2B γ
α
B βB α
A2
B2 or B6B2 or B6
Atom
(acetone)
S. Ralph SR VII - 17A16mgLanducci, Luque and Ralph, J. Wood Chem. Tech., 15(4), 493-513 (1995)
Notes:
188Compound Number
FPL/DFRC NMR Database -- April 2009
G-b-SA acetate
13C
55484957
58100100
32393536
6767323336
41
28
36
142619224545
19263838
20.7220.8121.0621.02
55.9956.0756.07
62.7465.0074.0981.03
103.76103.76111.56119.24122.51
122.97
132.46
134.16
135.38136.11139.56150.91153.29153.29
168.92169.55170.88170.88
CDCl3
CS i
20.4920.6120.8120.94
56.3156.4456.44
63.2465.2675.0781.57
104.71104.71111.46119.94123.34
124.14
133.39
134.40
136.46137.14140.60152.10154.23154.23
168.94169.92170.66170.66
55514754
64100100
43493839
8484473946
45
25
41
162814223939
18242222
Acetone
CS i
20.3520.3520.7020.70
55.7355.8255.82
62.0564.2473.6780.04
103.62103.62110.92118.72122.58
123.43
132.02
133.02
134.36135.66138.88150.59152.69152.69
168.45169.33169.95170.10
1001007979
629696
27372929
6060282843
34
28
35
242724295252
27333627
CS i
DMSO
Ac MeAc MeAc MeAc Me
OMeOMeOMe
γB γ
αβ
B2B6A2A6A5
B β
B1
B α
A1B4A4A3B3B5
Ac C=OAc C=OAc C=OAc C=O
Atom
1HJMultH Shifts
3.84
4.424.184.696.08
6.806.33
6.64
s
ddddddd
sdt
d
11.8, 6.011.8, 4.16.2, 1.1
4.3
15.9, 6.2
16.0
OMe
γ1γ2B γ α
B2,6B β
B α
Atom
(acetone)
Jamie MilhauptJR-JMA 35.140mg
Notes:
189Compound Number
FPL/DFRC NMR Database -- April 2009
2,6-dimethoxyphenol acetate
13C
36
100100
9090
47
5
2424
11
20.45
56.1256.12
104.91104.91
126.23
128.85
152.34152.34
168.71
CDCl3
CS i
20.27
56.4056.40
105.77105.77
126.92
129.94
153.43153.43
168.56
35
100100
9595
53
5
2222
10
Acetone
CS i
20.12
55.8955.89
105.00105.00
126.23
128.11
151.90151.90
168.04
47
9696
100100
53
9
4242
19
CS i
DMSO
Ac Me
OMeOMe
26
1
4
35
Ac C=O
Atom
1HJMultH Shifts
2.22
3.37
6.69
7.13
s
s
d
t
8.5
8.5
Ac Me
OMe
2,6
1
Atom
(acetone)
Jamie MilhauptJR-JMA 5554mg
Notes:
190Compound Number
FPL/DFRC NMR Database -- April 2009
phenol acetate
13C
33
8989
50
100100
10
10
21.12
121.58121.58
125.82
129.42129.42
150.74
169.48
CDCl3
CS i
20.94
122.57122.57
126.36
130.09130.09
151.96
169.61
36
9797
57
100100
10
10
Acetone
CS i
20.75
121.70121.70
125.63
129.35129.35
150.44
169.05
47
100100
59
100100
16
14
CS i
DMSO
Ac Me
35
1
26
4
Ac C=O
Atom
1HJMultH Shifts
2.23
7.12
7.22
7.40
s
m
m
m
Ac Me
3,5
1
2,6
Atom
(acetone)
Jamie MilhauptJR-JMA 41.140mg
Notes:
191Compound Number
FPL/DFRC NMR Database -- April 2009
methyl (4-acetoxy-3,5-dimethoxy) benzoate
13C
42
45
100100
9595
21
9
3939
16
17
20.40
52.34
56.3256.32
106.34106.34
128.10
132.63
152.10152.10
166.37
168.14
CDCl3
CS i
20.22
52.57
56.6856.68
106.87106.87
129.04
133.69
153.27153.27
166.61
168.17
43
45
9696
100100
17
8
2626
11
13
Acetone
CS i
20.06
52.36
56.1756.17
105.79105.79
127.70
131.96
151.81151.81
165.75
167.67
48
49
100100
9090
29
10
5858
25
26
CS i
DMSO
Ac Me
α OMe
OMeOMe
26
1
4
35
α
Ac C=O
Atom
1HJMultH Shifts
2.26
3.88
3.87
7.33
s
s
s
s
Ac Me
α OMe
OMe
2,6
Atom
(acetone)
Jamie MilhauptJR-JMA 39.141mg 2D short range XH corr confirms assignment of 5 and 6.
Notes:
192Compound Number
FPL/DFRC NMR Database -- April 2009
4-acetoxy-3-methoxy benzoic acid
13C
91
100
93
96
91
44
40
53
51
56
20.65
56.12
113.38
122.98
123.46
128.00
144.43
151.20
168.52
171.37
CDCl3
CS i
20.46
56.40
114.25
123.31
123.80
129.96
144.79
152.26
167.04
168.65
82
99
90
100
100
30
22
27
37
37
Acetone
CS i
20.37
55.90
113.18
122.16
123.05
129.58
142.98
150.82
166.66
168.21
88
100
84
90
85
52
46
56
59
54
CS i
DMSO
Ac Me
OMe
2
6
5
1
4
3
α
Ac C=O
Atom
1HJMultH Shifts
2.28
3.90
7.70
7.67
7.19
s
s
s
dd
dd
7.6, 1.8
7.7, 1.0
Ac Me
OMe
2
6
5
Atom
(acetone)
L.LanducciLLL XIV 148BA10 mg
Notes:
193Compound Number
FPL/DFRC NMR Database -- April 2009
S-b-S-b-SA (acetate)
13C
707056567373
100100100100100100
33332223233333
414144443535
17
111116
18
101213424229293333
151819172727
20.5320.5320.8520.8521.1521.15
56.1256.1256.2656.2656.2656.26
62.8862.8865.0074.3574.5080.8980.89
103.81103.81104.10104.10104.33104.33
123.04
128.54132.45133.24
134.12
135.40135.63135.81151.96151.96153.08153.08153.29153.29
168.68169.52169.66170.79170.94170.94
CDCl3
CS i
20.2620.2620.6720.8020.9520.95
56.4656.4656.4656.4656.4656.46
63.4463.4465.2675.4375.4381.4281.56
104.67104.67104.67104.67104.96104.96
124.09
129.36133.25134.06
134.38
136.54136.60136.64153.01153.01153.88153.88154.16154.16
168.50169.95169.95170.67170.67170.67
414127214646
100100100100100100
22221732321414
494949492020
12
799
12
999262621211919
182828232323
Acetone
CS i
20.0420.0420.2120.3020.6120.61
55.7255.7255.7255.7255.8555.85
62.2262.2264.1673.9773.9779.8979.89
103.35103.35103.35103.35103.53103.53
123.29
127.48131.80132.46
132.95
134.25134.45135.16151.40151.40152.29152.29152.54152.54
167.89169.23169.23169.83169.83169.98
505033357070
1001001001009292
26261920201717
464646463030
13
15118
15
9713434334342626
243333393912
CS i
DMSO
Ac MeAc MeAc MeAc MeAc MeAc Me
OMeOMeOMeOMeOMeOMe
γB γC γα
B αβ
B β
A2A6B2B6C2C6
C β
A4C1B1
C α
C4A1B4A3A5B3B5C3C5
A4 Ac C=O Ac C=O Ac C=O Ac C=O Ac C=O Ac C=O
Atom
1HJMultH Shifts
4.14
4.40
4.70
6.06,6.03
6.33
m
m
d
d
dt
11.2
4.0
15.6
A,B γ2
A,B γ1
C γ
A,B α
C β
Atom
(acetone)
S. Luque 12E8 mg Landucci, Luque and Ralph, J. Wood Chem. Tech., 15(4), 493-513 (1995)As this compound has a plane of symmetrythe shifts for the other half are identical.
Notes:
194Compound Number
FPL/DFRC NMR Database -- April 2009
G-b-S-r-S-b-G
13C
30
80100100
4327322530
6868
364143
2516
2330
32
5050
54.48
56.0056.2756.27
60.5672.0172.5585.8687.08
102.82102.82
108.45114.19118.75
131.31134.41
137.63144.89
146.64
153.49153.49
CDCl3
CS i
55.37
56.2656.6256.62
60.9772.6473.3886.5387.84
104.12104.12
110.93115.19120.05
133.77135.74
139.00146.45
147.96
154.20154.20
40
70100100
3438364045
7474
404938
1917
2126
26
4747
Acetone
CS i
53.56
55.4155.8955.89
59.7371.2172.0084.9786.05
103.22103.22
110.85114.54119.24
133.18134.69
136.68145.20
146.85
152.50152.50
31
69100100
2525252519
5050
252525
2525
2538
38
5656
CS i
DMSO
B,C β
OMeOMeOMe
A,D γB,C γA,D αB,C αA,D β
B,C 2B,C 6
A,D 2A,D 5A,D 6
A,D 1B,C 1
B,C 4A,D 4
A,D 3
B,C 3B,C 5
Atom
1HJMultH Shifts
3.833.87
3.71
4.98
4.75
6.77
7.04
ss
dd
d
d
s
d
12.0, 3.4
3.2
2.3
1.6
OMeOMe
A,D γ2
A,D α
B,C α
B,C 2,6
A,D 2
Atom
(acetone)
J. MilhauptA 5141mg
Notes:
195Compound Number
FPL/DFRC NMR Database -- April 2009
1-(4-acetoxy-3,5-dimethoxyphenyl)-1-acetoxy ethane
13C
4336
47
100100
51
8787
8
27
3939
1815
20.4721.36
22.24
56.1756.17
72.28
102.94102.94
128.24
140.03
152.12152.12
168.69170.15
CDCl3
CS i
20.2421.12
22.62
56.4456.44
72.64
103.51103.51
129.11
141.50
153.16153.16
168.52170.16
4138
52
9797
52
100100
6
23
2929
1414
Acetone
CS i
20.0320.90
22.02
56.8956.89
71.58
102.54102.54
127.25
140.23
151.57151.57
168.00169.54
5351
50
100100
51
8282
14
36
5656
2826
CS i
DMSO
Ac MeAc Me
β
OMeOMe
α
26
4
1
35
Ac C=Oα Ac C=O
Atom
1HJMultH Shifts
2.042.22
1.49
3.80
5.80
6.74
ss
d
s
q
s
6.6
6.6
Ac MeAc Me
β
OMe
α
2,6
Atom
(acetone)
J. MilhauptA 4547mg
Notes:
196Compound Number
FPL/DFRC NMR Database -- April 2009
Acetylated Sinapic acid methyl ester
13C
45
45
100100
100100
52
10
29
51
4949
24
22
20.36
51.68
56.1256.12
104.65104.65
118.05
130.40
132.64
144.51
152.38152.38
167.11
168.39
CDCl3
CS i
20.23
51.70
56.6156.61
105.83105.83
118.97
131.45
133.56
145.15
153.53153.53
167.44
168.38
39
48
9595
100100
46
7
26
52
3838
18
16
Acetone
CS i
20.00
51.34
56.0856.08
105.24105.24
118.18
129.60
132.30
144.26
151.90151.90
166.57
167.83
49
47
100100
8888
47
17
38
45
6363
30
29
CS i
DMSO
Ac Me
γ OMe
OMeOMe
26
β
4
1
α
35
γ
Ac C=O
Atom
1HJMultH Shifts
2.25
3.75
3.87
7.08
6.58
7.62
s
s
s
s
d
d
16.0
16.1
Ac Me
γ OMe
OMe
2,6
β
α
Atom
(acetone)
S. Luque SLL 13F, 11 mg1H data from 360 MHz spectrum. The β-O-4 units are erythro,Landucci, Luque and Ralph J. Wood Chem. Tech., 15(4), 493-513 (1995) As thiscompound has a plane of symmetry,the shifts for the other half are identical.
Notes:
197Compound Number
FPL/DFRC NMR Database -- April 2009
G-b-S-r-S-b-G (acetate)
13C
836959
22
72100100
2813262523
4848
272829
12161622
20
4343
282328
20.7420.8321.14
54.45
56.0056.1856.18
62.7872.0674.0180.8785.94
102.86102.86
111.58119.27122.48
134.60136.19137.35139.56
150.90
153.42153.42
168.92169.56170.91
CDCl3
CS i
20.4820.6120.94
55.38
56.2656.3956.39
63.2772.6075.0481.3086.52
103.71103.71
112.20120.03123.25
135.47137.15138.96140.54
152.01
154.05154.05
168.92169.90170.65
806264
31
69100100
3333312431
5858
332436
11182022
22
4444
332733
Acetone
CS i
20.2720.2720.61
53.65
55.6355.7355.73
62.0271.2473.6479.8384.93
102.69102.69
110.85118.72122.43
133.51135.61137.50138.79
150.46
152.46152.46
168.35169.24169.87
868643
22
66100100
1821172019
3131
161618
14151417
21
3434
323129
CS i
DMSO
Ac MeAc MeAc Me
B,C β
A,D OMeB,C OMeB,C OMe
A,D γB,C γA,D αA,D βB,C α
B,C 2B,C 6
A,D 2A,D 6A,D 5
B,C 4A,D 1B,C 1A,D 4
A,D 3
B,C 3B,C 5
4 Ac C=OαAc C=OγAc C=O
Atom
1HJMultH Shifts
3.10
3.803.82
3.914.164.254.40
4.68
4.726.06
6.69
6.967.027.15
m
ss
mmmdd
m
mm
s
ddds
B,C β
OMeOMe
B γ1A γ2B γ2A γ2
Aβ
B,C αA,D α
B,C 2,6
A 6A 5A 2
Atom
(acetone)
S. Luque SLL I 12E10 mg A4 was coincident with other shifts, the assignments were inferred fromother models and peak heights.Landucci, Luque and Ralph, J. Wood Chem. Tech., 15(4), 493-513 (1995)
Notes:
198Compound Number
FPL/DFRC NMR Database -- April 2009
S-b-S-r-S
13C
2721
68681001008888
27181614232318
454564645050
111618212118
434336363636
54.4354.57
56.3456.3456.4556.4556.4956.49
60.6571.8072.1772.7786.0186.0187.24
102.69102.69102.84102.84102.94102.94
130.46132.00134.05134.51134.51137.91
147.15147.15147.29147.29153.55153.55
CDCl3
CS i
55.2755.42
56.6356.6356.6356.6356.6356.63
61.0372.4072.6173.6386.6186.7387.87
104.10104.10104.51104.51104.91104.91
132.73133.13135.86135.86136.23139.07
148.38148.38148.68148.68154.16154.16
1919
100100100100100100
17212017202117
363643434040
111313131013
262621212020
Acetone
CS i
53.5953.73
55.8855.8856.0156.0156.0156.01
59.9071.1071.2672.3885.1085.3086.20
103.28103.28103.65103.65104.29104.29
131.36132.42134.42134.86134.86136.79
147.40147.40147.88147.88152.55152.55
2020
7676100100100100
14182120202221
333346463737
211821262613
393945453333
CS i
DMSO
B βC β
OMeOMeOMeOMeOMeOMe
γC γB γ
αB αC α
β
B2B6C2C6A2A6
A1C1B1A4C4B4
A3A5C3C5B3B5
Atom
1HJMultH Shifts
3.12
3.803.823.88
4.684.744.99
6.696.716.78
m
sss
ddm
sss
4.04.0
B,C β
OMeOMeOMe
B αC α
α
B 2,6C 2,6A 2,6
Atom
(acetone)
S. Luque SLL 13F15mgLanducci, Luque and Ralph, J. Wood Chem. Tech., 15(4), 493-513 (1995)
Notes:
199Compound Number
FPL/DFRC NMR Database -- April 2009
S-b-S-r-S (acetate)
13C
52523130
1723
65658888100100
18212116152120
484832324141
71113111316
333331312525
18161616
20.5320.5320.8621.16
54.3954.52
56.1756.1756.2356.2356.2956.29
62.8172.0772.1974.2580.7885.8285.98
102.30102.30102.84102.84104.07104.07
128.05128.51134.67135.66137.27139.74
151.92151.92152.34152.34153.35153.35
168.63168.85169.53170.94
CDCl3
CS i
20.2620.2620.6320.94
55.3355.44
56.3856.3856.4656.4656.4656.46
63.4172.6672.6675.3381.2986.4586.56
103.23103.23103.71103.71104.68104.68
128.85129.34135.61136.65138.83141.45
152.95152.95153.22153.22153.98153.98
168.48168.58169.91170.76
49492626
2023
6464100100100100
19444415112520
474735353434
779101215
202024242222
15151415
Acetone
CS i
20.0620.0620.2920.63
53.6153.85
55.7255.7255.8755.8755.8755.87
62.1671.3171.3173.9279.7684.8585.00
102.36102.36102.70102.70103.30103.30
126.98127.45133.69135.21137.38140.08
151.38151.38151.58151.58152.41152.41
167.91168.02169.26169.89
45453234
2323
6868100100100100
13343413121918
444426262626
91212121418
323239392626
22191919
CS i
DMSO
Ac MeAc MeAc MeAc Me
B βCβ
OMeOMeOMeOMeOMeOMe
γC γB γ
αβ
B αC α
C2C6B2B6A2A6
C1A4B4A1B1C4
A3A5C3C5B3B5
Ac C=OAc C=OAc C=OAc C=O
Atom
1HJMultH Shifts
3.11
4.734.766.05
6.706.76
m
ddm
ss
B,C β
B αC α α
2,62,6
Atom
(acetone)
S. Ralph35mg
Notes:
200Compound Number
FPL/DFRC NMR Database -- April 2009
Vanillyl alcohol diacetate4-hydroxy-3-methoxybenzyl alcohol diacetate
13C
7659
100
91
91
89
95
45
26
33
29
23
20.5720.93
55.84
65.86
112.50
120.67
122.77
134.80
139.62
151.07
168.84
170.66
CDCl3
CS i
20.4520.78
56.20
66.10
113.32
121.04
123.57
136.23
140.64
152.19
168.93
170.79
7555
92
99
83
96
100
37
20
24
24
19
Acetone
CS i
20.2520.59
55.68
65.10
112.58
120.16
122.67
134.99
138.97
150.69
168.42
170.15
9778
100
90
92
92
89
64
43
52
49
36
CS i
DMSO
Ac MeAc Me
OMe
α
2
6
5
1
4
3
4 Ac C=O
α Ac C=O
Atom
1HJMultH Shifts
2.042.23
3.80
5.06
6.96
7.03
7.11
ss
s
s
dd
d
d
8.1,1.8
8.0
1.7
Ac MeAc Me
OMe
α
6
5
2
Atom
(acetone)
J. Milhaupt A 5335 mgSample has impurity
Notes:
201Compound Number
FPL/DFRC NMR Database -- April 2009
Syringyl alcohol diacetate3,5-dimethoxy-4-hydroxy benzyl alcohol diacetate
13C
5931
100100
48
8989
7
21
3939
16
12
20.4721.05
56.2156.21
66.37
105.13105.13
128.58
134.42
152.21152.21
168.67
170.77
CDCl3
CS i
20.2320.79
56.4656.46
66.46
105.67105.67
129.43
135.77
153.19153.19
168.50
170.80
4927
100100
44
9393
6
19
2727
12
9
Acetone
CS i
20.0520.63
55.9155.91
65.45
104.84401.84
127.57
134.49
151.59151.59
167.97
170.14
6242
100100
42
8080
12
32
5353
28
17
CS i
DMSO
Ac MeAc Me
OMeOMe
α
26
4
1
35
4 Ac C=O
α Ac C=O
Atom
1HJMultH Shifts
2.062.22
3.80
5.05
6.76
ss
s
s
s
Ac MeAc Me
OMe
α
2,6
Atom
(acetone)
J. MilhauptA 49.135mg
Notes:
202Compound Number
FPL/DFRC NMR Database -- April 2009
1-(4-acetoxy-3-methoxyphenyl)-1-acetoxyethane
13C
7965
91
100
89
88
95
89
26
44
31
31
30
20.6921.37
22.21
55.93
71.96
110.60
118.44
122.75
139.33
140.52
151.05
169.01
170.21
CDCl3
CS i
20.4721.12
22.57
56.21
72.31
111.30
118.73
123.51
140.32
141.88
152.18
168.95
170.17
7964
86
88
91
78
98
100
17
36
24
22
19
Acetone
CS i
20.2820.90
22.00
55.70
71.26
110.46
117.74
122.60
138.62
140.60
150.66
168.44
169.55
9687
87
100
96
82
87
96
42
58
42
49
42
CS i
DMSO
Ac MeAc Me
β
OMe
α
2
6
5
1
4
3
4 Ac C=O
α Ac C=O
Atom
1HJMultH Shifts
1.49
2.032.22
3.82
5.83
6.95
7.02
7.11
d
ss
s
q
dd
d
d
6.6
6.6
8.1,1.8
8.1
1.8
β
Ac MeAc Me
OMe
α
6
5
2
Atom
(acetone)
Aldrich60mg
Notes:
203Compound Number
FPL/DFRC NMR Database -- April 2009
4-methoxy benzaldehyde
13C
51
100100
14
9797
14
45
55.51
114.26114.26
129.90
131.88131.88
164.55
190.68
CDCl3
CS i
56.03
115.16115.16
131.11
132.43132.43
165.44
191.09
58
100100
11
9090
11
42
Acetone
CS i
55.51
114.35114.35
129.57
131.65131.65
164.10
191.01
38
8787
18
100100
18
51
CS i
DMSO
OMe
35
1
26
4
α
Atom
1HJMultH Shifts
3.89
7.08
7.85
9.86
s
d
d
s
8.8
8.8
OMe
3,5
2,6
α
Atom
(acetone)
J. MilhauptA 14138mg
Notes:
204Compound Number
FPL/DFRC NMR Database -- April 2009
1-(3,4-dimethoxyphenyl)-1-acetoxyethane
13C
39
55
100100
51
46
49
53
24
16
18
15
21.39
21.99
55.9155.91
72.20
109.69
111.06
118.64
134.19
148.76
148.96
170.29
CDCl3
CS i
21.18
22.41
56.1356.13
72.51
111.16
112.63
119.25
135.54
150.01
150.29
170.21
38
57
100100
54
43
46
54
17
12
12
13
Acetone
CS i
20.93
21.82
55.4355.43
71.42
109.93
111.57
118.12
134.02
148.32
148.58
169.51
62
72
100100
73
67
70
70
45
35
36
31
CS i
DMSO
Ac Me
β
OMeOMe
α
2
5
6
1
4
3
Ac C=O
Atom
1HJMultH Shifts
1.47
2.00
3.783.81
5.78
6.90
6.97
d
s
ss
q
m
s
6.6
6.6
β
Ac Me
OMeOMe
α
5,6
2
Atom
(acetone)
J. MilhauptA 13956mg
Notes:
205Compound Number
FPL/DFRC NMR Database -- April 2009
4-methoxybenzyl alcohol acetate
13C
32
51
53
100100
17
9999
14
11
21.01
55.23
66.07
113.94113.94
128.10
130.08130.08
159.65
170.85
CDCl3
CS i
20.85
55.53
66.25
114.60114.60
129.43
130.78130.78
160.57
170.85
33
61
57
100100
14
100100
12
10
Acetone
CS i
20.61
54.98
65.18
113.70113.70
128.03
129.85129.85
159.07
170.13
36
50
45
100100
24
9898
13
13
CS i
DMSO
Ac Me
OMe
α
35
1
26
4
Ac C=O
Atom
1HJMultH Shifts
2.00
3.78
5.01
6.91
7.31
s
s
s
d
d
8.7
8.7
Ac Me
OMe
α
3,5
2,6
Atom
(acetone)
J. MilhauptA 14742mg
Notes:
206Compound Number
FPL/DFRC NMR Database -- April 2009
Syringaldehyde acetate3,5-dimethoxy-4-acetoxy-benzaldehyde
13C
39
100100
9292
7
22
3232
14
45
20.41
56.3556.35
106.09106.09
133.82
134.36
152.88152.88
168.01
191.00
CDCl3
CS i
20.21
56.7256.72
106.72106.72
134.60
135.62
153.91153.91
168.15
191.82
37
100100
8484
5
10
2222
11
31
Acetone
CS i
20.01
56.2056.20
106.00106.00
132.83
134.20
152.35152.35
167.58
191.89
50
100100
9292
12
34
5151
23
48
CS i
DMSO
Ac Me
OMeOMe
26
4
1
35
Ac C=O
α
Atom
1HJMultH Shifts
2.28
3.90
7.28
9.93
s
s
s
s
Ac Me
OMe
2,6
α
Atom
(acetone)
J. milhaupt137.542mg
Notes:
207Compound Number
FPL/DFRC NMR Database -- April 2009
4-Acetoxy benzaldehyde
13C
39
100100
9292
16
12
12
38
21.06
122.32122.32
131.12131.12
133.93
155.30
168.62
190.88
CDCl3
CS i
20.98
123.43123.43
131.68131.68
135.13
156.42
169.27
191.83
39
100100
100100
13
11
9
34
Acetone
CS i
20.78
122.63122.63
130.85130.95
133.75
154.99
168.64
191.84
42
9898
100100
19
16
16
42
CS i
DMSO
Ac Me
35
26
1
4
Ac C=O
α
Atom
1HJMultH Shifts
2.30
7.35
7.97
10.01
s
d
d
s
8.6
8.6
Ac Me
3,5
2,6
α
Atom
(acetone)
J. Milhaupt27mg
Notes:
208Compound Number
FPL/DFRC NMR Database -- April 2009
4-Acetoxy benzoic acid
13C
48
100100
20
9696
26
22
13
21.25
121.84121.84
126.96
131.95131.95
155.09
168.89
171.38
CDCl3
CS i
20.98
122.76122.76
128.81
131.91131.91
155.55
167.00
169.28
48
9595
15
100100
18
17
15
Acetone
CS i
20.80
121.96121.96
128.31
130.78130.78
153.86
166.55
168.75
48
100100
21
9999
25
20
25
CS i
DMSO
Ac Me
35
1
26
4
α
Ac C=O
Atom
1HJMultH Shifts
2.29
7.26
8.08
s
d
d
8.8
8.8
Ac Me
3,5
2,6
Atom
(acetone)
J. MilhauptJMA 14542mg
Notes:
209Compound Number
FPL/DFRC NMR Database -- April 2009
4-Methoxy benzyl alcohol
13C
52
48
44
9191
100100
17
14
25.04
55.27
69.84
113.82113.82
126.67126.67
138.12
158.90
CDCl3
CS i
26.20
55.43
69.50
114.20114.20
127.27127.27
140.18
159.49
54
62
42
100100
9292
11
13
Acetone
CS i
25.89
54.92
67.60
113.25113.25
126.34126.34
139.34
157.90
15
15
15
100100
100100
7
6
CS i
DMSO
β
OMe
α
35
26
1
4
Atom
1HJMultH Shifts
1.37
3.76
4.79
6.86
7.29
d
s
m
d
d
6.5
8.7
8.6
β
OMe
α
3,5
2,6
Atom
(acetone)
J. MilhauptJMA 14923mg
Notes:
210Compound Number
FPL/DFRC NMR Database -- April 2009
1-(4-acetoxyphenyl)-1-acetoxy ethane
13C
35
56
48
47
100100
100100
19
13
12
21.44
22.01
55.32
72.06
113.90113.90
127.64127.64
133.82
159.34
170.38
CDCl3
CS i
21.16
22.35
55.51
72.28
114.52114.52
128.26128.26
134.94
160.22
170.20
34
57
44
46
100100
9292
15
11
10
Acetone
CS i
20.92
21.76
54.98
71.18
113.63113.63
127.28127.28
133.52
158.69
169.49
44
51
46
48
100100
100100
25
20
19
CS i
DMSO
Ac Me
β
OMe
α
35
26
1
4
Ac C=O
Atom
1HJMultH Shifts
1.46
1.98
3.78
5.79
6.90
7.30
d
s
s
q
d
d
6.6
6.6
8.8
8.8
β
Ac Me
OMe
α
3,5
2,6
Atom
(acetone)
J.MilhauptJMA 11120mg
Notes:
211Compound Number
FPL/DFRC NMR Database -- April 2009
Sinapyl alcohol diacetate
13C
4633
100100
50
8888
49
8
49
26
4242
21
14
20.5121.05
56.2156.21
64.90
103.38103.38
123.71
128.75
134.01
134.71
152.28152.28
168.71
170.85
CDCl3
CS i
20.2620.79
56.4756.47
65.13
104.18104.18
124.99
129.68
134.04
135.67
153.36153.36
168.51
170.72
4433
100100
51
9393
44
5
44
17
3232
16
9
Acetone
CS i
20.0520.62
55.9055.90
64.06
103.22103.22
124.32
127.69
132.55
134.33
151.73151.73
167395
170.01
4945
100100
45
7878
41
14
42
30
5858
25
20
CS i
DMSO
Ac MeAc Me
OMeOMe
γ
26
β
4
α
1
35
4 Ac C=O
γ Ac C=O
Atom
1HJMultH Shifts
2.04
2.22
3.82
4.69
6.84
6.38
6.66
s
s
s
dd
s
dt
d
6.2, 1.2
15.8, 6.2
15.9
Ac Me
Ac Me
OMe
γ
2,6
β
α
Atom
(acetone)
T. DuchI-5725mg
Notes:
212Compound Number
FPL/DFRC NMR Database -- April 2009
Syringylgycerol-β-vanillyl alcohol ether
1-(4-Hydroxy-3,5-dimethoxyphenyl)-2-[4-(1-hydroxymethyl)-2-methoxyphenoxy]propane-1,3-diol
13C
54100100
44544745
7373
484945
3229
2938
5151
27
55.9056.3456.34
61.0564.8774.1689.20
103.82103.82
110.98119.98120.50
130.66134.61
137.06146.93
147.10147.10
151.16
CDCl3
CS i
56.2856.6056.60
61.9564.5474.0688.56
105.41105.41
111.95119.60120.02
132.82136.17
137.97148.42
148.50148.50
151.54
59100100
41465149
9494
515248
3232
2849
3030
27
Acetone
CS i
55.4455.7455.74
60.0062.7470.8884.44
104.13104.13
110.97115.43118.58
131.93134.31
135.45146.93
147.34147.34
149.39
70100100
51685754
7676
575457
5446
4946
7070
49
CS i
DMSO
B OMeA OMeA OMe
γ
Bααβ
A2A6
B2B5B6
A1A4
B1B4
A3A5
B3
Atom
1HJMultH Shifts
3.803.86
3.503.694.184.564.87
6.78
6.84
7.03
7.12
ss
mmmdm
s
dd
d
d
5.6
8.2,2.0
1.9
8.2
A OMeB OMe
γ1γ2β
B αα
A 2,6
6
2
5
Atom
(acetone)
T.DuchI-5540 mg
Notes:
213Compound Number
FPL/DFRC NMR Database -- April 2009
Syringylgycerol-β-vanillyl alcohol ether tetra-acetate
1-(4-acetoxy-3,5-dimethoxyphenyl)-1,3-diacetoxy-2-[4-(1-acetoxymethyl)-2-methoxyphenoxy]
13C
45576868
34100100
27665048
8989
52485220
3639
3436
6161
30323425
20.3620.6420.9720.97
55.8056.1456.14
62.9166.0874.5780.14
104.02104.02
112.70118.12121.15128.79
130.88134.63
147.90150.60
152.14152.14
168.42169.60170.48170.79
CDCl3
CS i
20.2420.6320.8320.95
56.3156.5556.55
63.5966.3575.6480.72
105.13105.13
113.94118.67121.77129.70
132.09136.18
148.97151.57
153.21153.21
168.46170.02170.72170.88
51754550
60100100
46575055
9999
59555622
3037
2934
5757
30342424
Acetone
CS i
20.0320.3820.6520.65
55.6055.9855.98
63.3765.2874.4879.02
103.94103.94
112.86116.91120.69127.92
130.30134.92
147.38149.79
151.55151.55
167.88169.32167.94170.15
6662100100
66100100
48575353
9090
60606252
5757
5559
7878
50575940
CS i
DMSO
Ac MeAc MeAc MeAc Me
B OMeA OMeA OMe
γB α
αβ
A2A6
B2B5B6A4
B1A1
B4B3
A3A5
A4 Ac C=Oα Ac C=Oγ Ac C=OBα Ac C=O
Atom
1HJMultH Shifts
1.982.032.092.21
3.803.83
4.054.274.815.026.08
6.86
6.917.037.05
ssss
ss
ssssd
s
dddd
12.3,5.911.9,4.0
6.5
8.3,1.88.41.6
Ac MeAc MeAc Me
A4 Ac Me
A OMeB OMe
γ1γ2β
B αα
A 2,6
B6B5B2
Atom
(acetone)
S. RalphMixture is 65/35 erythro/threo35mg
Notes:
214Compound Number
FPL/DFRC NMR Database -- April 2009
Guaiacylglycerol-β-guaiacyl ether acetate
1-(4-acetoxy-3-methoxyphenyl)-1,3-diacetoxy-2-(2-methoxyphenoxy)propane
13C
1006671
9185
576071
546179568660
593222212424
262623
20.5720.6620.93
55.7855.90
62.5573.7980.15
112.02112.70119.51119.71120.98122.52
123.58135.41139.80147.18150.97151.11
168.69169.44170.68
CDCl3
CS i
20.4620.5920.86
56.2656.32
63.0374.6380.37
112.83113.90119.88120.46121.68123.36
124.08136.71140.85148.33152.11152.11
168.89169.89170.74
846957
100100
555559
556259596961
604121183232
262520
Acetone
CS i
20.2220.2920.53
55.5455.66
61.8473.1078.36
111.61112.89117.93119.28120.61122.43
122.83135.30139.05146.61150.30150.52
168.31169.16169.94
10010073
8181
444947
585151597158
494432293134
363727
CS i
DMSO
Ac MeAc MeAc Me
OMeOMe
γα
β
A2B2B5A6B6A5
B1A1A4B4B3A3
Ac C=OAc C=OAc C=O
Atom
1HJMultH Shifts
1.942.082.233.813.83
4.224.394.836.09
sssss
ddddmd
11.9,4.211.9,5.8
5.0
Ac MeAc MeAc MeOMeOMe
γ1γ2βα
Atom
(acetone)
erythro
Pew Collection50 mg
Notes:
215Compound Number
FPL/DFRC NMR Database -- April 2009
p-Methoxy cinnamaldehyde
13C
46
100100
46
22
9292
44
15
46
55.34
114.48114.48
126.33
126.67
130.28130.28
152.72
162.13
193.66
CDCl3
CS i
55.81
115.35115.35
127.37
127.91
131.26131.26
153.22
163.08
193.81
52
100100
47
16
9595
41
11
44
Acetone
CS i
55.35
114.51114.51
126.31
126.69
130.65130.65
153.10
161.75
194.00
43
100100
51
23
9898
40
20
43
CS i
DMSO
OMe
35
β
1
26
α
4
γ
Atom
1HJMultH Shifts
3.86
6.65
7.02
7.60
7.68
9.66
s
dd
d
d
d
d
15.9,7.7
8.9
15.9
8.9
7.7
OMe
β
3,5
α
2,6
γ
Atom
(acetone)
S.RalphVII-70AAssignments in acetone are based on360MHZ HMBC and HMQC expts.
Notes:
216Compound Number
FPL/DFRC NMR Database -- April 2009
G-b-G-c-CA (acetate)
13C
11110799141141
59
10012169
467643405741
86678175457667
80
795872
94
4253656642517171
4856759259
20.6320.7420.7920.9621.00
50.37
55.8855.9156.00
62.4565.1865.2973.6680.2588.23
110.28110.60111.88115.31118.69119.18119.60
121.24
122.59127.49130.60
134.30
135.30135.80139.75144.41147.19148.20150.96151.19
168.80169.49170.74170.76170.88
CDCl3
CS i
20.4520.6020.6820.8020.86
51.24
56.2856.2856.28
63.0465.4965.9574.4880.3088.54
111.50112.17112.71116.33119.14119.41120.45
122.23
123.33129.01131.53
134.71
136.60137.06140.78145.39148.14149.31151.95152.08
168.92169.89170.77170.95170.95
10488928686
65
130130130
65100737110559
76956985567792
100
997290
111
6850707859537271
67681079494
Acetone
CS i
20.3220.4020.5120.6220.70
49.34
55.7155.7155.71
61.8564.4964.7673.0178.3087.17
110.74110.93111.62115.26117.49118.30119.33
121.34
122.50127.89130.04
133.49
135.05135.26139.06143.84146.54147.53150.16150.54
168.43169.26170.04170.15170.28
9784687373
25
125125125
335031323129
16282927211537
40
352532
35
2028393823292849
4746614147
CS i
DMSO
A4 Ac MeA αAc MeB γAC MeC γAc MeA γAc Me
B β
OMeOMeOMe
γC γB γαβ
B α
B2C2A2C6B6B5A6
C β
A5C5C1
C α
A1B1A4C3B4C4B3A3
A4 C=OA αC=OC γC=OB γC=OA γC=O
Atom
1HJMultH Shifts
1.932.042.062.213.753.813.894.224.364.324.434.654.865.556.056.236.646.917.007.077.23
ssssmss
ddddddddddmdddtdddddm
4.1,12.05.9,12.07.6,11.15.4,11.11.3,6.5
6.85.2
6.5,15.815.8
2.0,8.38.32.0
C γAc MeA,Bγ Ac MeA α Ac MeA4 Ac Me
B βA,B OMeC OMe
A γ1Aγ2B γ1B γ2C γβ
B αα
C βC αB6B5B2A2
Atom
(acetone)
T. DuchTDI-143, 39mgAssignments in acetone are based onHMBC and HMQC expts.
Notes:
217Compound Number
FPL/DFRC NMR Database -- April 2009
3-(4-hydroxy-3-methoxyphenyl)-2-[2,6-dimethoxyphenoxy]propan-1-ol
13C
43
619191
3745
8383
44454346
30212827
4141
37.30
55.9056.0956.09
62.2184.48
105.42105.42
112.31114.28122.09123.95
130.13135.66144.12146.44
153.60153.60
CDCl3
CS i
37.97
56.1956.4556.45
62.7885.29
106.49106.49
113.89115.52122.81124.51
130.76137.09145.71148.05
154.61154.61
23
274040
2024
3838
22222424
17131515
1818
Acetone
CS i
36.86
55.5255.8655.86
61.6983.46
105.65105.65
113.58115.11121.68123.41
129.32135.65144.64147.15
153.29153.29
22
346161
2231
3636
29313031
26222525
3838
CS i
DMSO
α
OMeOMeOMe
γβ
B2B6
A2A5A6B1
A1B4A4A3
B3B5
Atom
1HJMultH Shifts
3.033.50
3.823.83
4.17
6.69
6.74
6.907.01
7.39
ddm
ss
m
d
m
sdd
s
13.6,5.4
8.4
8.8
αγ
A OMeB OMe
β
B 2,6
A 5,6
A2B1
Ar OH
Atom
(acetone)
T. Duch TDI-143 Ac'd,32mg Assignments in acetone are based on HMBC and HMQC expts.A1,B4, and A4 are too close to positively identify.
Notes:
218Compound Number
FPL/DFRC NMR Database -- April 2009
Acetic acid 3-(4-acetoxy-3-methoxyphenyl)-2-[2,6-dimethoxyphenoxy] propyl ester
13C
4231
31
767676
3135
6868
33393634
182821
23
3535
2222
20.7020.85
38.26
55.9755.9755.97
65.3580.49
105.20105.20
113.95121.64122.30123.92
135.89137.13138.26
150.69
153.66153.66
169.17170.92
CDCl3
CS i
20.4920.65
38.82
56.1256.3056.30
65.7280.86
106.29106.29
114.77122.34123.12124.53
137.12137.89139.37
151.85
154.65154.65
169.08170.80
4435
33
407777
3333
5959
32333836
172217
20
2626
2118
Acetone
CS i
20.3720.46
37.51
55.6055.7455.74
64.7879.44
105.39105.39
113.76121.30122.27123.74
137.28136.71137.69
150.35
153.16153.16
168.60170.16
3838
23
355353
2225
4242
25232726
182319
21
3232
2121
CS i
DMSO
Ac MeAc Me
α
OMeOMeOMe
γβ
B2B6
A2A6A5B1
B4A1A4
A3
B3B5
Ac C=Oγ Ac C=O
Atom
1HJMultH Shifts
3.06
3.763.79
4.114.51
6.64
6.866.956.987.07
t
ss
dm
d
dddddd
11.5,6.5
4.8
8.3
8.0,1.88.2
8.2,8.01.8
α
B OMeOMe
γβ
B 2,6
A6A5B1A2
Atom
(acetone)
S.Ralph 55mgSRVIII-45CDCl3 1H shifts in ( )’s
Notes:
219Compound Number
FPL/DFRC NMR Database -- April 2009
p-Methoxy coumaryl alcohol4-methoxy cinnamyl alcohol
13C
45
42
7878
8282
44
32
14
12
55.30
63.76
113.99113.99
127.69127.69
126.43
130.82
129.57
159.32
CDCl3
CS i
55.48
63.36
114.73114.73
128.24128.24
128.61
129.76
130.78
160.05
37
33
6767
6767
33
34
9
8
Acetone
CS i
55.00
61.62
113.96113.96
127.27127.27
128.20
128.27
129.51
158.57
26
33
6262
6666
43
32
15
13
CS i
DMSO
OMe
γ
35
26
β
α
1
4
Atom
1HJMultH Shifts
3.76 (3.78)
4.20 (4.25)
6.24 (6.19)
6.53 (6.52)
6.86 (6.83)
7.33 (7.28)
s
bs
dt
d
d
d
15.9, 5.4
15.9
8.7
8.7
OMe
γ
β
α
3,5
2,6
Atom
(acetone)
trans
S.Ralph30mg gHSQC, gHMBC Acetone shifts confirmed
Notes:
220Compound Number
FPL/DFRC NMR Database -- April 2009
p-Methoxy coumaryl alcohol acetate4-methoxy cinnamyl alcohol acetate
13C
27
48
46
8686
40
8585
11
41
13
10
21.07
55.35
65.39
114.13114.13
121.00
127.94127.94
130.17
134.10
159.73
170.90
CDCl3
CS i
20.82
55.59
65.52
114.91114.91
122.21
128.69128.69
130.80
134.32
160.71
170.77
19
31
32
5555
33
6565
7
28
5
6
Acetone
CS i
20.64
55.05
64.48
114.02114.02
121.17
127.74127.74
129.86
133.00
159.13
170.07
21
26
26
5050
25
5353
7
24
10
8
CS i
DMSO
Ac Me
OMe
γ
35
β
26
1
α
4
Ac C=O
Atom
1HJMultH Shifts
2.01
3.78
4.65
6.19
6.89
7.38
s
s
dd
dt
d
d
6.4,1.2
15.7, 6.4
8.8
8.8
Ac Me
OMe
γ
β
3,5
2,6
Atom
(acetone)
trans
S.Ralph 51mgSRVII-104HMBC and HMQC in acetonegamma's and A3 and A4 are very close and may be switched
Notes:
221Compound Number
FPL/DFRC NMR Database -- April 2009
V-c-CA4-methoxy phenyl coumaran diacetate
13C
2925
29
626234
312928
3027302831
30
131418
29
1711
2626
1610
20.7820.99
50.32
55.9755.9756.08
65.1965.3588.61
109.39110.81111.21115.35118.78
121.22
127.76130.56132.94
134.35
144.45148.35
149.30149.30
170.73170.73
CDCl3
CS i
20.7020.83
51.16
56.2056.2056.48
65.5265.9688.84
110.95112.29112.77116.35119.35
122.21
129.18131.46134.53
134.75
145.40149.40
150.48150.55
170.79170.94
2620
38
505028
292927
2625262828
28
131514
28
138
1110
712
Acetone
CS i
20.5020.67
49.36
55.5355.5355.75
64.5164.7787.44
109.96111.05111.76115.29118.47
121.34
128.06130.03132.88
133.55
143.90147.67
148.87148.87
170.12170.26
2927
21
474729
271922
2319242125
23
202020
22
1712
3030
1420
CS i
DMSO
Ac MeAc Me
β
OMeOMeOMe
Bγγα
A2B2A5B6A6
Bβ
B5B1A1
Bα
B3B4
A3A4
Ac C=OAc C=O
Atom
1HJMultH Shifts
2.002.02
3.793.803.88
4.384.43
4.66
5.54
6.23
6.64
ss
sss
dddd
dd
d
dt
d
11.1, 7.411.1, 5.6
7.4, 0.9
7.0
15.8, 6.4
15.9
Ac MeAc Me
OMeOMeOMe
γ1γ2
Bγ
Aα
Bβ
Bα
Atom
(acetone)
S.Ralph 37mgNotes:
222Compound Number
FPL/DFRC NMR Database -- April 2009
4-hydroxy cinnamyl alcohol diacetateCoumaryl alcohol acetate
13C
31
47
39
7878
36
7575
36
13
12
14
10
20.98
21.12
64.95
121.79121.79
123.58
127.62127.62
133.19
134.08
150.52
169.32
170.78
CDCl3
CS i
20.78
20.96
65.17
122.85122.85
124.89
128.29128.29
133.28
134.99
151.70
169.55
170.74
27
38
36
6262
31
6565
30
13
9
10
8
Acetone
CS i
20.63
20.86
64.18
121.97121.97
123.97
127.43127.43
132.05
133.64
150.13
169.03
170.07
30
40
28
5858
28
5757
28
15
13
13
9
CS i
DMSO
γ Ac Me
4 Ac Me
γ
35
β
26
α
1
4
4 Ac C=O
γ Ac C=O
Atom
1HJMultH Shifts
2.03
2.24
4.69
6.32
6.69
7.08
7.47
s
s
dd
dt
d
d
d
6.2, 1.3
16.0, 6.2
16.0
8.6
8.6
γ Ac Me
4 Ac Me
γ
β
α
3,5
2,6
Atom
(acetone)
trans
S.Ralph27mg
Notes:
223Compound Number
FPL/DFRC NMR Database -- April 2009
4-acetoxy cinnamaldehydeCoumaryl aldehyde acetate
13C
70
125125
86
125125
27
72
25
22
65
21.11
122.43122.43
128.73
129.70129.70
131.75
151.44
152.90
168.97
193.44
CDCl3
CS i
20.98
123.40123.40
129.60
130.60130.60
132.91
152.21
154.01
169.40
193.95
25
6464
27
6262
10
25
9
6
26
Acetone
CS i
20.65
122.33122.33
128.41
129.81129.81
131.59
151.73
152.41
168.70
193.97
45
100100
47
9898
20
44
18
17
49
CS i
DMSO
Ac Me
35
β
26
1
α
4
Ac C=O
γ
Atom
1HJMultH Shifts
2.27
6.73
7.22
7.66
7.76
9.70
s
dd
d
d
d
d
16.0, 7.6
8.6
16.0
8.5
7.6
Ac Me
β
3,5
α
2,6
γ
Atom
(acetone)
trans
S.Ralph SRVII 109D44mg2D HMBC in CDCL3A4and A1 identical chemical shift and B4 very closeAs compound has a plane of symmetry thru A5 only half the shifts are reported
Notes:
224Compound Number
FPL/DFRC NMR Database -- April 2009
S-b-G-5,5-G-b-S (α = CH2)
13C
3037
24
919191
2528
6868
2423
32
18
152929
204242
819
20.3420.80
38.29
56.0056.0056.00
65.2680.43
105.31105.31
113.43128.48
123.92
131.10
136.00136.19136.19
151.02153.17153.17
168.68170.82
CDCl3
CS i
20.3220.68
38.90
56.3356.3356.33
65.6980.91
106.27106.27
114.11124.07
124.57
131.92
137.04137.04137.04
152.12154.64154.64
168.80170.80
1820
15
717171
1718
4040
1411
14
8
171717
122222
610
Acetone
CS i
19.8820.35
37.58
55.7155.7155.84
64.7079.49
105.42105.42
113.29122.66
123.70
130.30
135.36135.42135.84
150.67153.17153.17
167.98170.02
3459
22
12012040
2831
8181
2020
36
23
313129
266969
1935
CS i
DMSO
Ac MeAc Me
α
OMeOMeOMe
γβ
B2B6
A2A6
B1
A5
B4A1A4
A3B3B5
4 Ac C=Oγ Ac C=O
Atom
1HJMultH Shifts
1.93
1.99
3.07
3.74
3.82
4.14
4.51
6.62
6.76
7.09
s
s
m
s
s
d
bt
d
s
d
4.8
4.9
8.4
1.4
Ac Me
Ac Me
α
OMe
OMe
γ
β
B2,6
A6
A2
Atom
(acetone)
S.RalphSRVII-139E3 18mggHMQC and gHMBC in acetone
Notes:
225Compound Number
FPL/DFRC NMR Database -- April 2009
H-b-S
13C
39404736
34
7878
26362920
6767
57574242
141921
19
4040
17161717
20.7820.1221.1921.44
22.26
56.0856.08
62.6672.3873.9480.88
103.29103.29
121.36121.36128.06128.06
134.69134.96137.91
150.37
153.22153.22
169.36169.62170.29170.29
CDCl3
CS i
20.5520.9520.9521.16
22.60
56.3856.38
63.1972.6874.9081.26
103.98103.98
122.33122.33128.89128.89
135.64135.84139.17
151.53
154.08154.08
169.61169.93170.21170.66
18313118
21
4444
18171513
3838
37373030
71711
8
1717
79610
Acetone
CS i
20.2220.6020.7420.95
21.99
55.7555.75
61.9471.5973.4979.79
102.85102.85
121.56121.56128.72128.72
134.26135.05137.40
149.96
152.52152.52
169.08169.08169.55169.90
27283228
25
5454
15221516
3939
45453737
101515
14
2929
19191819
CS i
DMSO
Ac MeAc MeAc MeAc Me
Bβ
OMeOMe
γBααβ
B2B6
A3A5A2A6
A1B4B1
A4
B3B5
A4 Ac C=OAα Ac C=OBα Ac C=OAγ Ac C=O
Atom
1HJMultH Shifts
1.47
1.842.032.122.25
3.79
4.154.384.695.786.07
6.687.117.45
d
ssss
s
ddddmqd
sdd
6.6
11.9, 4.211.9, 5.9
6.64.6
8.58.5
Bβ
Ac MeAc MeAc Me
A4 Ac Me
OMe
γ1γ2β
Bαα
B2,6A3,5A2,6
Atom
(acetone)
erythro
S.Ralph SRVII-140C230mggHSQC and gHMBC in acetone
Notes:
226Compound Number
FPL/DFRC NMR Database -- April 2009
G-bt-S-bt-G
13C
4450437070
44447171
272829281821
515116333719312530121016161625252727
1718172019
20.6920.7520.7921.0921.09
55.8055.9056.0456.04
62.7463.1673.9974.8780.3680.78
104.30104.30111.60112.49118.50119.24120.98122.37123.24132.59135.35136.03139.49148.00150.77150.77153.14153.14
168.84169.49169.76170.51170.82
CDCl3
CS i
20.4820.5820.6720.9220.96
56.1956.2456.4356.43
63.3663.7275.0775.7180.7681.38
105.27105.27112.26113.68118.95120.01121.66123.26123.61133.70136.40137.04140.53149.14151.74152.01153.96153.96
168.95169.92169.99170.61170.61
999696103116
115119127127
637169546970
12512547756060817889371941333437356868
3749496060
Acetone
CS i
20.2820.2822.4122.4120.65
55.4855.6255.7855.78
62.1962.5673.7474.6079.1579.94
104.13104.13110.95112.61117.23118.78120.60122.46122.46132.42134.48135.59138.85147.58150.03150.53152.43152.43
168.40169.29169.29169.92169.92
5555415050
45436666
222125192423
434321342323344343171618212122213737
2026363939
CS i
DMSO
γ Ac MeγAc Me
α Ac MeαAc Me4 Ac Me
OMeOMeOMeOMe
AγBγAαBαBβAβ
B2B6A2C2C5A6C6A5C1B1B4A1A4C4C3A3B3B5
A4 Ac C=Oα Ac C=Oα Ac C=Oγ Ac C=OγAc C=O
Atom
1HJMultH Shifts
1.841.982.002.102.22
3.80
4.034.224.41
4.714.79
6.07
6.79
mmdd
mm
bd
d
11.8, 6.05
6.31
2.8
γ Ac Meγ Ac Meα Ac MeαAc Me
A4 Ac Me
OMe
γγ1,γ2
γ
AβBβ
A,Bα
B2,6
Atom
(acetone)
threo
S.RalphSRVII-141-1 31mg gHSQC and gHMBC in acetone
Notes:
227Compound Number
FPL/DFRC NMR Database -- April 2009
G-b-G
13C
664848
58
7457
434559
464663495346272820222425
232422
20.6120.7420.99
21.09
55.7055.89
62.4873.7080.57
111.84113.49119.54119.69121.21122.55133.53135.62139.69144.76150.86150.95
168.79169.50170.78
63.04
74.54
80.59
CDCl3
CS i
20.4720.6220.89
21.07
56.1456.27
62.9574.5880.63
112.63114.61120.07120.30121.85123.36133.79136.82140.73145.94151.83152.11
168.92169.91170.76
63.58
75.38
80.98
615145
45
6255
454445
675044515445202714151517
181715
Acetone
CS i
20.3120.4020.62
20.68
55.4755.69
61.8073.1078.71
111.50113.60118.21119.17120.77122.50132.26135.45138.98144.24150.12150.53
168.41169.26170.03
303042
20
2320
121719
211515172314171712131615
141412
CS i
DMSO
Ac MeAc MeAc Me
Bα
OMeOMe
γ
αβ
A2B2B5A6B6A5B1A1A4B4B3A3
A4 Ac C=Oα Ac C=OγAc C=O
threo isomer
γ
α
β
Atom
1HJMultH Shifts
1.942.082.222.253.793.834.204.374.746.06
6.656.826.85
7.047.23
3.994.256.10
ssssss
ddddmd
bdbsd
ms
11.9, 4.211.9, 5.8
5.0
8.1
8.2
Ac MeAc Me
BαAc MeOMeOMe
γ1γ2β
α
B6B2B5
A5,6A2
γ1 isomerγ2 isomerα isomer
Atom
(acetone)
erythro
L.Landucci LLL XXII-134C35mggHSQC and gHMBC in acetone
Notes:
228Compound Number
FPL/DFRC NMR Database -- April 2009
S-b-S
13C
211513
49494949
111212
22222424
3894
15151414
796
12
20.4420.7021.04
56.1856.1856.1856.18
62.9074.1780.87
104.07104.07106.50106.50
128.61132.08135.04140.89
151.95151.95153.46153.46
168.60169.46170.76
191.01
CDCl3
CS i
20.2420.5820.89
56.5056.5056.5856.58
63.4075.1781.67
104.61104.61107.18107.18
129.41133.26136.27141.81
153.06153.06154.43154.43
168.52169.94170.66
191.69
14710898
270270279279
969398
181181183183
21545328
86868686
485046
98
Acetone
CS i
20.0920.3120.63
55.9355.9355.9955.99
62.2673.8180.21
103.39103.39106.37106.37
127.60131.82134.94140.06
151.54151.54152.95152.95
168.03169.35169.96
191.82
453437
79798787
182220
37374242
10182016
43434646
212523
22
CS i
DMSO
A4 Ac Meα AcMeγ Ac Me
A OMeA OMeB OMeB OMe
γαβ
A2A6B2B6
A4B1A1B4
A3A5B3B5
A4 Ac C=Oα Ac C=Oγ Ac C=O
Bα
Atom
1HJMultH Shifts
1.872.142.22
3.823.95
4.22
4.47
4.956.09
6.817.25
9.90
sss
ss
dd
dd
dtd
ss
s
11.9, 3.8
11.9, 6.2
6.6, 4.24.2
γ Ac Meα Ac Me
A4 Ac Me
OMeOMe
γ 1
γ 2
βα
A 2,6B 2,6
Bα
Atom
(acetone)
S.Ralph SRIX-17D18mggHSQC and gHMBC in acetone
Notes:
229Compound Number
FPL/DFRC NMR Database -- April 2009
S-b-S
13C
1378892106
178178239239
71677565
127127132132
21492948
89897777
44432734
20.4820.7721.0621.10
56.0556.0556.1756.17
62.7366.4574.1980.79
103.92103.92105.47105.47
128.44132.02135.09135.59
151.90151.90153.19153.19
168.64169.54170.84170.92
CDCl3
CS i
20.3520.7120.9321.04
56.5056.5056.5856.58
63.4266.7175.4181.55
104.61104.61106.29106.29
129.41133.40136.29136.76
153.12153.12154.13154.13
168.64170.09170.81170.97
42292030
58587979
23222325
43434242
411813
25252020
1313126
Acetone
CS i
20.0620.2920.6420.66
55.7455.7455.8855.88
62.0965.5873.8879.96
103.18103.18105.20105.20
127.45131.90134.12135.26
151.47151.47152.47152.47
168.10169.35169.97170.20
54405251
70708888
18272422
38384040
12191718
52523838
26282716
CS i
DMSO
A4 Ac Meγ Ac Me
Bα Ac Meα Ac Me
OMeOMeOMeOMe
γBααβ
A2A6B2B6
A4B1B4A1
A3A5B3B5
A4 Ac C=Oα Ac C=OγAc C=O
BαAc C =O
Atom
1HJMultH Shifts
1.862.052.142.22
3.813.82
4.184.434.745.026.08
6.716.78
ssss
ss
dddddtsd
ss
11.9, 4.211.9, 6.06.2, 4.2
4.3
γ Ac MeBαAc Mea Ac Me
A4 Ac Me
OMeOMe
γ1γ2β
Bαα
B 2,6A 2,6
Atom
(acetone)
erythro
S.Ralph SRIX-17E40mg threo isomer shifts from SRIX-104DgHSQC and gHMBC in acetone
Notes:
230Compound Number
FPL/DFRC NMR Database -- April 2009
S-b-S
13C
292321
21
45454949
181719
36363434
561313
21212222
10119
20.4320.7621.06
21.82
55.9055.9156.1256.12
62.6974.2080.80
103.81103.81105.95105.95
128.33132.79134.13135.77
151.86151.86152.87152.87
168.62169.54170.94
63.53
75.60
80.87
CDCl3
CS i
20.2420.6220.93
21.76
56.2556.2556.4656.46
63.2275.3381.45
104.43104.43106.85106.85
129.25134.15134.52136.80
153.01153.01153.84153.84
168.54169.98170.72
64.13
76.58
81.65
412827
28
63638282
292931
54546060
691617
27272929
141513
Acetone
CS i
20.0420.3020.61
21.32
55.5755.5755.8455.84
62.0073.8879.94
103.08103.08105.77105.77
127.39132.12133.35135.39
151.45151.45152.27152.27
167.99169.33169.95
796361
56
117117126126
323738
70708282
20293738
73737171
354241
CS i
DMSO
A4 Ac Meγ Ac MeαAc Me
Bα
OMeOMeOMeOMe
γα
β
A2A6B2B6
A4B4B1A1
A3A5B3B5
A4 Ac C=Oα Ac C=Oγ Ac C=O
threo isomer
γ
α
β
Atom
1HJMultH Shifts
1.872.142.22
2.27
3.783.81
4.184.404.66
6.06
6.49
6.76
sss
s
ss
dddddt
d
s
s
11.9, 4.411.9, 6.25.8, 4.4
4.4
γ Ac MeαAc Me
A4 Ac Me
Bα
OMeOMe
γ1γ2β
α
B 2,6
A 2,6
Atom
(acetone)
erythro
J.Ralph10mggHSQC and gHMBC in acetonegHSQC in DMSO
Notes:
231Compound Number
FPL/DFRC NMR Database -- April 2009
cis-coniferyl alcohol
13C
23
21
20
21
22
6
20
20
7
5
55.97
59.75
111.53
114.33
122.25
129.04
129.51
131.10
145.17
146.38
CDCl3
CS i
56.13
59.73
113.19
115.55
122.78
129.73
130.19
131.44
146.69
147.93
91
77
82
82
86
26
82
82
29
22
Acetone
CS i
55.47
58.16
112.84
115.15
121.56
128.06
128.62
130.95
145.74
147.13
96
86
81
79
83
46
82
75
50
39
CS i
DMSO
OMe
γ
2
5
6
1
α
β
4
3
Atom
1HJMultH Shifts
3.834.415.736.396.726.826.87
CDCl3
3.894.445.796.496.746.786.89
sddtddddd
sdddtddddd
5.811.9, 6.2
11.78.2, 2.0
8.22.0
6.4, 1.411.5, 6.6
11.98.2, 1.8
1.8 8.2
OMeγβ
α652
CDCl3
OMeγβ
α652
Atom
(acetone)
cis
S.Ralph SRIX-43G55 mgHSQC and HMBC in d6-DMSO
Notes:
232Compound Number
FPL/DFRC NMR Database -- April 2009
G-b-S
13C
211188174
170
494494494
157160173
314314
150157179
5911211872
88183183
758579
20.6720.7821.09
21.87
55.9455.9455.94
62.6474.0280.92
106.02106.02
111.46119.10122.43
132.81134.16136.35139.44
150.84152.96152.96
168.91169.56170.92
CDCl3
CS i
20.4620.5920.92
21.77
56.2556.2556.25
63.1075.0481.40
106.87106.87
112.07119.81123.29
134.03134.56137.26140.56
152.02153.86153.86
168.94169.93170.67
138116119
111
329329329
122125126
224224
101115122
33657540
53104104
505650
Acetone
CS i
20.3420.3420.67
21.40
55.6655.6655.70
61.9873.7280.03
105.90105.90
110.83118.66122.61
132.13133.51135.87138.86
150.63152.42152.42
168.51169.39170.03
16616697
85
200200135
596668
140140
646571
47626350
60128128
565764
CS i
DMSO
Ac Me Ac Me Ac Me
Bα
OMeOMeOMe
γαβ
B2B6
A2A6A5
B4B1A1A4
A3B3B5
A4 Ac C=Oα Ac C=Oγ Ac C=O
Atom
1HJMultH Shifts
1.852.122.22
2.27
3.763.82
4.164.434.676.10
6.51
6.997.067.18
sss
s
ss
dddddtd
s
dddd
11.8, 4.411.7, 5.85.8, 4.2
4.2
8.3, 1.88.21.8
Ac MeAc MeAc Me
Bα
B OMeA OMe
γ1γ2βα
B 2,6
A6A5A2
Atom
(acetone)
erythro
S.Lempke I-31HSQC and HMBC in d6-acetone
Notes:
233Compound Number
FPL/DFRC NMR Database -- April 2009
G-b1-G
13C
474721
21
4949
19
2122
12423
2522
1513
1011
1211
111011
13
20.6720.6720.92
52.08
56.0356.03
65.58
111.99112.32
120.95122.22
122.94123.54
133.94135.02
139.64144.13
151.54151.72
168.46168.83170.89
195.95
CDCl3
CS i
20.4320.4320.66
52.37
56.2956.40
65.94
113.14113.66
121.30122.88
123.95124.21
135.54135.77
140.53145.10
152.52152.70
168.58168.87170.75
196.63
464620
21
2728
21
2323
2423
2424
1411
88
1110
91010
11
Acetone
CS i
20.3220.3220.55
50.52
55.8055.95
64.74
112.35112.95
120.26122.14
123.28123.28
134.26134.42
138.79143.59
151.11151.11
138.10168.41170.10
195.91
24249
8
1113
6
88
88
1616
78
66
1313
776
7
CS i
DMSO
Ac MeAc MeAc Me
β
OMeOMe
γ
A2B2
A6B6
A5B5
B1A1
B4A4
B3A3
A4 Ac C=OB4 Ac C=Oγ Ac C=O
α
Atom
1HJMultH Shifts
1.932.202.24
3.813.96
4.334.765.19
6.987.03
7.167.22
7.737.77
sss
ss
dddddd
ddd
dd
dd
10.5, 5.810.5, 8.58.5, 5.7
8.0, 2.08.0
8.21.8
6.2, 1.81.8
Ac MeAc MeAc Me
OMe OMe
γ1γ2β
B6B5
A5B2
A6A2
Atom
(acetone)
S.RalphSRIX-46E31mgHSQC and HMBC in d6-acetone
Notes:
234Compound Number
FPL/DFRC NMR Database -- April 2009
G-c-G
13C
3934
31
37
4546
3838
3429383839
2021
1122
169
16
1315
21.5121.67
22.13
51.63
56.7756.77
66.4988.49
110.89114.11117.76119.09123.68
127.71132.29
140.42140.73
144.89146.62
152.09
169.81171.66
CDCl3
CS i
20.4720.70
21.18
51.65
56.2356.41
66.1987.85
111.02114.79117.92118.61123.72
128.29131.92
140.61141.40
145.00146.96
152.36
168.97170.96
4135
32
42
4140
4443
4032404443
1720
1022
1310
13
1314
Acetone
CS i
20.3320.54
20.80
49.82
55.6655.73
65.0386.41
110.39113.50116.90117.81122.87
127.22130.68
138.98139.88
143.48145.26
150.83
168.47170.29
117121
111
89
118129
7580
8557849789
7278
5277
7144
66
5166
CS i
DMSO
Ac Me Ac Me
Bα
β
OMeOMe
γα
A2B2B6A6A5
B5B1
A4A1
B3B4
A3
A4 Ac C=Oγ Ac C=O
Atom
1HJMultH Shifts
2.012.22
2.26
3.74
3.803.83
4.294.42
5.55
6.706.736.997.057.18
ss
s
m
ss
dddd
d
ss
dddd
11.1, 8.010.9, 5.6
6.6
8.2, 1.88.21.8
Ac MeAc Me
Bα
β
A OMeB OMe
γ1γ2
α
B6B2A6A5A2
Atom
(acetone)
S. Ralph SRIX-44D670mg HSQC and HMBC in d6-acetoneBβ,Aβ,A2,A6,B5,B1,A1,and B4 appear as split signalsThe shift reported is the average.
Notes:
235Compound Number
FPL/DFRC NMR Database -- April 2009
S-b-G-b1-G
13C
262424252727
9
24254949
101415138
1919111610121620
6109101059122424
8101281112
20.1920.3920.5220.5620.7320.76
49.86
55.5955.6755.9755.97
62.3764.0473.7474.8279.64
104.20104.20111.11112.95118.27119.26120.99122.25
128.50133.19134.81136.11138.85146.81150.44150.59151.84151.84
168.23168.61169.27169.50170.42170.50
CDCl3
CS i
20.2520.4920.6320.6820.8720.87
50.93
56.2256.2256.5156.51
63.0765.0274.7775.6679.97
105.11105.11112.37114.30118.61120.13122.06123.12
129.52134.59136.05137.79139.98147.93151.43151.80153.01153.01
168.49168.98169.93169.93170.74170.77
393737375151
17
68687171
2019222219
3737182211192025
8912131379173131
161529291921
Acetone
CS i
19.9920.2420.3020.3820.5020.50
49.21
55.5455.5955.8755.87
61.9564.0773.3974.6278.10
104.04104.04111.22113.27116.86119.06120.84122.10
127.83133.00134.76136.85138.27146.40149.76150.26151.47151.47
167.81168.27169.07169.12169.89169.89
10611810899133133
40
97125179179
4136464225
9393335719405659
4025334748373365120120
59535768111111
CS i
DMSO
γAc MeγAc Me
α Ac Meα Ac Me4 Ac Me4 Ac Me
Bβ
OMeOMeOMeOMe
AγBγ
AαBαAβ
A2A6B2C2B5B6C6C5
A4B1A1C1C4B4B3C3A3A5
A4 Ac C=OC4 Ac C=Oα Ac C=Oα Ac C=Oγ Ac C=Oγ Ac C=O
Atom
1HJMultH Shifts
1.891.902.042.172.18
3.463.693.723.753.764.224.314.364.384.825.996.086.806.97
sssss
mssssmmmmmddss
5.87.2
Ac MeAc MeAc MeAc MeAc Me
BβOMeOMeOMeOMeBγ1Aγ1Bγ2Aγ2Aβ
AαBα
A2,6C2
Atom
(acetone)
SRIX-47C221 mgBβ,Aβ,A2,B5,B1,B4 appear assplit signals, the shift reported is the average.HSQC and HMBC in d6-acetone
Notes:
236Compound Number
FPL/DFRC NMR Database -- April 2009
G-b-G-b1-G
13C
4444242533336
213335
121415127
14815111511151918745995111410
101210101111
20.6920.6920.7820.8521.0321.0350.07
55.8355.9455.97
62.5264.2973.7275.0780.01
111.36111.98113.12118.74119.48119.73121.22122.50122.62133.41135.34136.29139.06139.82147.00150.75150.80151.02
168.84168.90169.55169.78170.74170.80
CDCl3
CS i
20.4920.4920.6220.6920.8720.8750.96
56.2556.2556.30
63.0465.0574.5575.7080.16
112.43112.78114.34118.93120.14120.46122.10123.13123.36134.76136.60137.84140.02140.80147.92151.55151.83152.11
168.92168.98169.93169.93170.75170.75
90905355848424
969677
2932302634
31223717353428413713161617159152217
212429293131
Acetone
CS i
20.3520.3520.3520.5020.6120.6149.13
55.6355.6855.72
61.9464.1773.1474.6878.15
111.27111.68113.32116.97119.12119.40120.89122.19122.51133.13135.26137.02138.21139.10146.35149.81150.26150.57
168.46168.46169.23169.28170.06170.06
99999953888822
456762
2020222117
192028112426262827152025272518213124
393933325555
CS i
DMSO
γ Ac Meγ Ac Meα Ac Meα Ac Me4 Ac Me4 Ac Me
Bβ
OMeOMeOMe
AγBγAαBαAβ
B2A2C2B5B6A6C6C5A5B1A1C1C4A4B4B3C3A3
4 Ac C=O4 Ac C=Oα Ac C=Oα Ac C=Oγ Ac C=Oγ Ac C=O
Atom
1HJMultH Shifts
1.952.072.153.503.743.783.834.214.274.334.374.856.066.13
6.816.826.967.027.05
7.25, 7.26
sssmsssmmmmmdd
smmdm
5.07.0
2 signals
γ Ac Meα Ac Me4 Ac Me
BβOMeOMeOMeBγ 1Aγ 1Bγ 2Aγ 2AβAαBα
B2B,C 6B,C 5
C2A 5,6A2
Atom
(acetone)
SRIX-46DB33mgHSQC and HMBC in d6-acetoneShifts for B and C α's,2's and 6's were too close to assign with confidence
Notes:
237Compound Number
FPL/DFRC NMR Database -- April 2009
G-a-G-b-G
13C
2424
2323
254949
212121
212827212423242522
15151610
1212
121213
1112
20.6920.82
21.0521.12
55.7155.9655.96
63.5680.4182.44
111.53113.37113.41116.77119.45119.72121.01121.21122.36
131.97133.11138.62139.42
145.22145.32
149.95150.79151.02
168.85170.91
CDCl3
CS i
20.4620.65
20.9621.05
56.1156.1956.28
65.6281.0982.14
112.70114.51114.54117.73119.80120.54121.64121.80123.13
132.54133.32138.11140.48
146.01146.37
151.12151.69152.03
168.89170.81
2927
2828
333632
302432
213429243129303030
1415179
1011
111114
1012
Acetone
CS i
20.3420.44
20.5620.61
55.4855.6355.63
62.4679.0880.19
111.79113.58113.58116.22117.84119.51120.67120.77122.30
131.23131.83136.70138.81
144.25144.77
149.52150.00150.45
168.39170.13
129134
136136
131193193
869398
861901901091188811712587
93899379
8988
858689
6570
CS i
DMSO
Ac MeAc Me
CαBα
OMeOMeOMe
γα
β
A2B2C2C5B5A6B6C6A5
C1B1A1A4
C4B4
C3B3A3
A4 Ac C=Oγ Ac C=O
Atom
1HJMultH Shifts
1.902.202.202.243.753.793.834.434.544.745.55
6.536.616.766.786.836.987.057.33
sssssss
ddddmd
dddddsddddd
11.7, 3.811.7, 5.8
5.4
8.2, 1.68.0, 1.4
8.08.0
8.0, 1.81.8
Ac MeAc Me
B or C αB or C α
OMeOMeOMe
γ1γ2βα
C6B6C5
B,C 2B5A5A6A2
Atom
(acetone)
SRIX-51D-C13mg HMBC,HSQC,selective INEPT in acetone 1H in acetone (threo isomer) γ1 3.96, dd J = 11.8,5.6 γ2 4.24, dd J = 11.8,4.2α 6.12,d J = 6.8
Notes:
238Compound Number
FPL/DFRC NMR Database -- April 2009
H-b−G
13C
212147
47
28
181921
201925
4141
3939
1012898
10109
20.8221.0621.18
21.18
55.79
62.4873.6780.80
113.60120.09121.27
121.53121.53
128.41128.41
133.72134.44144.75150.59151.03
169.29169.60170.87
63.10
74.53
80.73
CDCl3
CS i
20.5920.8820.95
21.07
56.13
62.8474.4380.84
114.65120.44121.85
122.41122.41
129.25129.25
133.96135.53145.86151.71151.95
169.57169.90170.73
63.56
75.24
81.06
464588
48
57
454646
474660
9696
8686
2023142017
201716
Acetone
CS i
20.3420.5820.58
20.73
55.46
61.6772.9378.98
113.64118.60120.77
121.56121.56
128.13128.13
132.43134.05144.14150.11150.23
169.05169.21169.97
62.38
74.03
79.39
669494
78
58
323737
424251
8383
7777
3234302835
323130
CS i
DMSO
γAc Meα Ac Me
A4 Ac Me
Bα
OMe
γαβ
B2B5B6
A3A5
A2A6
B1A1B4A4B3
A4 Ac C=Oα Ac C=Oγ Ac C=O
minor isomer
γ
α
β
Atom
1HJMultH Shifts
1.922.072.24
2.25
3.77
4.174.37
4.696.06
6.646.857.127.50
sss
s
s
dddd
md
mmmm
11.9, 4.411.9, 5.6
5.0
γ Ac Meα Ac Me
A4 Ac Me
Bα
OMe
γ1γ2
βα
B6B 2,5A 3,5A 2,6
Atom
(acetone)
erythro
SRIX-53E 2mgHSQC and HMBC in acetone
Notes:
239Compound Number
FPL/DFRC NMR Database -- April 2009
H-c-G
13C
2536
33
21
30
2221
232353534545
91210759
109
20.8921.21
21.35
50.94
56.11
65.8387.46
113.35117.04121.81121.81127.10127.10
128.30131.59138.76144.09145.86150.54
169.44170.88
CDCl3
CS i
20.6820.95
21.18
51.78
56.38
66.2987.57
114.79118.02122.82122.82127.64127.64
128.12131.95140.15145.03146.96151.66
169.62170.94
5377
49
54
43
5753
5251112112107107
262122141116
1918
Acetone
CS i
20.4820.73
20.73
49.85
55.56
65.0285.95
113.40116.88121.90121.90126.83126.83
127.67130.59138.55143.38145.14150.07
169.08170.21
2656
56
19
19
2020
182146464747
8141611711
1712
CS i
DMSO
γAc MeA4 Ac Me
Bα
β
OMe
γα
B2B6A3A5A2A6
B5B1A1B3B4A4
A4 Ac C=Oγ Ac C=O
Atom
1HJMultH Shifts
2.002.242.263.73
3.83
4.274.415.58
6.70
6.73
7.11
7.44
sssm
s
ddddd
bs
bs
d
d
10.9, 8.010.9, 5.6
6.4
8.5
8.5
γ Ac MeA4 Ac Me
Bαβ
OMe
γ1γ2α
B2
B6
A3,5
A2,6
Atom
(acetone)
SRIX-69E7mggHSQCand gHMBC d6-acetone
Notes:
240Compound Number
FPL/DFRC NMR Database -- April 2009
13C
167167126111
134
93
95
96
106
102
104
62
36
41
40
39
44
40
20.6720.6720.8020.96
56.02
62.11
72.22
73.43
111.30
119.75
123.10
134.70
140.20
151.37
168.77
169.65
170.04
170.43
CDCl3
CS i
20.4420.5220.6620.79
56.34
62.81
72.92
74.15
112.29
120.15
123.72
136.28
140.98
152.30
168.95
170.08
170.30
170.73
62.31
72.92
73.53
216182173172
192
156
167
151
169
161
155
74
45
54
61
70
63
66
Acetone
CS i
20.3620.4120.4620.66
55.84
61.93
71.68
72.90
111.25
119.00
122.81
135.20
139.19
150.72
168.40
169.44
169.44
169.97
57544741
41
24
27
25
27
26
29
22
21
22
22
39
39
22
CS i
DMSO
Ac MeAc MeAc MeAc Me
OMe
γ
β
α
2
6
5
1
4
3
4 Ac C=O
α Ac C=O
β Ac C=O
γAc C=O
minor isomer
γ
β
α
Atom
1HJMultH Shifts
1.981.992.082.22
3.83
3.904.245.425.97
7.007.067.17
ssss
s
ddddmd
dddd
11.9, 6.211.9, 4.0
6.6
8.2, 1.68.21.6
Ac MeAc MeAc MeAc Me
OMe
γ1γ2βα
652
Atom
(acetone)
SRIX-8435mg
Notes:
241Compound Number
FPL/DFRC NMR Database -- April 2009
H-b-G
13C
16
19
11
13
14
17
3131
19
16
2828
6
11
7
8
9
21.16
55.81
60.79
73.72
89.12
113.07
115.53115.53
120.78
121.96
128.42128.42
131.29
133.99
145.21
150.97
156.37
60.79
72.72
87.06
CDCl3
CS i
21.08
56.24
61.73
73.84
89.41
114.18
115.62115.62
120.73
122.21
129.10129.10
133.16
133.35
147.33
151.67
157.63
61.64
73.55
87.53
21
28
22
21
22
19
4646
23
25
4545
10
11
7
5
11
Acetone
CS i
20.51
55.55
60.00
70.94
85.34
113.46
114.35114.35
116.69
120.75
127.75127.75
130.38
132.21
146.17
149.60
156.19
59.89
71.41
84.57
31
37
17
19
20
25
4444
24
31
4747
20
17
17
17
20
CS i
DMSO
B α
OMe
γ
α
β
B2
A3A5
B5
B6
A2A6
A1
B1
B4
B3
A4
erythro isomer
γ
α
β
Atom
1HJMultH Shifts
2.273.433.64
3.85
4.034.83
6.666.796.857.077.28
8.26
smm
s
mdd
mdddd
s
6.9, 3.2
8.72.08.08.7
B αγ2γ1
OMe
βα
B6A3,5B2B5
A2,6
A4 OH
Atom
(acetone)
threo
SRIX-86B,C40 mg
Notes:
242Compound Number
FPL/DFRC NMR Database -- April 2009
G-b-S
13C
36
58111111
30
32
33
9595
33
37
34
18
10
23
17
16
2929
21.99
56.0156.1456.14
60.51
74.20
89.20
106.10106.10
109.92
114.36
120.47
132.06
133.04
134.67
145.46
146.58
152.75152.75
60.63
72.49
87.13
CDCl3
CS i
21.77
56.1656.4656.46
61.19
74.08
89.83
107.09107.09
111.45
115.22
120.73
133.60
134.65
134.82
146.75
147.90
153.60153.60
60.86
73.26
87.90
39
468686
35
38
37
7676
36
43
38
22
14
22
24
19
3434
Acetone
CS i
21.31
55.4855.8255.82
60.11
71.53
87.29
106.28106.28
111.01
114.62
119.22
132.79
132.90
133.80
145.29
146.83
152.27152.27
59.57
71.93
86.11
74
93168168
29
37
41
100100
44
43
47
44
34
27
33
32
5959
CS i
DMSO
B α
OMeOMeOMe
γ
α
β
B2B6
A2
A5
A6
A1
B4
B1
A4
A3
B3B5
erythro isomer
γ
α
β
Atom
1HJMultH Shifts
2.293.283.64
3.803.883.855.00
6.556.796.927.07
sdddd
smsd
sdddd
12.5, 3.212.6, 3.6
7.6
8.348.3, 1.8
1.8
B αγ1γ2
OMeβ
OMeα
B2,6A5A6A2
Atom
(acetone)
threo
SRIX-88SSB54mg B1,B4,A4,A1gHSQC, gHMBC in acetone
Notes:
243Compound Number
FPL/DFRC NMR Database -- April 2009
S-b-S
13C
42
9494
9494
33
39
40
7777
8787
27
18
26
28
5454
4646
21.85
56.0256.02
56.2556.25
60.37
74.33
89.04
104.04104.04
105.99105.99
131.04
132.90
134.43
134.58
146.99146.99
152.63152.63
60.50
72.50
87.03
CDCl3
CS i
21.78
56.4856.48
56.5656.56
61.31
74.29
89.56
105.39105.39
107.05107.05
132.54
134.55
134.78
136.00
148.23148.23
153.52153.52
61.23
73.43
86.32
78
173173
175175
47
52
62
150150
169169
37
28
47
35
6868
7474
Acetone
CS i
21.31
55.8855.88
55.9055.90
60.18
71.59
87.18
104.30104.30
106.34106.34
132.13
132.88
133.92
134.32
147.37147.37
152.34152.34
91
252252
266266
49
62
61
124124
155155
59
57
46
43
112112
113113
CS i
DMSO
B α
OMeOMe
OMeOMe
γ
α
β
A2A6
B2B6
A1
B1
B4
A4
A3A5
B3B5
erythro isomer
γ
a
β
Atom
1HJMultH Shifts
2.29
3.803.86
4.99
6.546.77
7.08
s
ss
d
ss
s
6.8
B α
OMeOMe
α
A2,6B2,6
A4 OH
Atom
(acetone)
threo
SRIX-88GHB36mg A1 and B1 may be interchangedgHSQC, gHMBC in acetone and CDCl3
Notes:
244Compound Number
FPL/DFRC NMR Database -- April 2009
G-b-H
13C
27
34
18
20
21
21
24
4747
21
4949
13
14
14
13
11
20.53
55.98
61.11
73.81
83.38
109.56
114.43
116.57116.57
120.00
130.18130.18
131.43
131.76
145.59
146.75
155.98
61.44
73.94
81.22
CDCl3
CS i
20.46
56.20
61.67
73.36
84.30
111.36
115.17
117.08117.08
120.36
130.47130.47
130.55
134.24
146.66
147.93
157.98
62.03
74.03
83.98
42
49
36
36
36
48
43
7979
40
8989
30
20
19
17
15
Acetone
CS i
20.05
55.49
60.04
70.92
83.25
110.95
114.73
115.88115.88
119.01
129.55129.55
128.97
133.25
145.41
146.99
156.93
60.17
71.55
83.37
125
119
63
75
74
79
83
199199
80
210210
83
66
67
68
67
CS i
DMSO
Bα
OMe
γ
α
β
A2
A5
B3B5
A6
B2B6
B1
A1
A4
A3
B4
erythro isomer
γ
α
b
Atom
1HJMultH Shifts
2.22
3.79
3.543.784.394.94
6.777.08
7.44
s
s
mmmm
dbs
s
8.2
Bα
OMe
γ1γ2βα
A5A2
A4 OH
Atom
(acetone)
threo
SRIX-95BRHSQC and HMBC in CDCl3
Notes:
245Compound Number
FPL/DFRC NMR Database -- April 2009
S-b-G
13C
21
244848
15
19
21
3939
232222
121410
10232311
21.73
55.8556.3456.34
60.99
74.18
89.51
103.86103.86
113.06120.90121.96
130.82134.17134.58
145.25147.12147.12150.93
60.76
72.87
87.70
CDCl3
CS i
21.06
56.2656.6056.60
61.89
74.05
88.73
105.41105.41
114.20120.10122.19
132.84133.10136.15
147.36148.40148.40151.50
61.75
73.98
87.09
41
499797
40
42
45
9595
454548
232218
18383818
Acetone
CS i
20.57
55.5055.8055.80
60.05
70.90
84.58
104.15104.15
113.34115.95120.76
130.21132.00134.33
145.98147.39147.39149.46
59.94
71.90
83.97
38
467777
27
28
27
5656
333134
252725
25525225
CS i
DMSO
Bα
B OMeA OMeA OMe
γ
α
β
A2A6
B2B5B6
A1B1A4
B4A3A5B3
erythro shifts
γ
α
β
Atom
1HJMultH Shifts
2.253.48
3.783.84
4.104.484.85
6.656.766.837.04
sm
ss
mddd
msdd
3.83.6, 6.4
1.88.2
Bαγ1
A OMeB OMe
γ2βα
B6A2,6B2B5
Atom
(acetone)
threo
SRTSII-131-Ac 12mgA2,6 and B2,6 ; A1 and B1 switch in DMSOHSQC and HMBC in Acetone, CDCl3 and DMSO
Notes:
246Compound Number
FPL/DFRC NMR Database -- April 2009
13C
252120
49494848
22
24
48484646
6151414
2525
2424
1111
13
20.4320.7521.82
55.8655.8656.2956.29
64.15
81.65
105.93105.93106.25106.25
133.03133.50133.57134.31
152.09152.09
152.49152.49
168.14170.75
194.84
CDCl3
CS i
20.2220.6021.73
56.1956.1956.6056.60
64.34
81.24
106.75106.75106.80106.80
133.82134.25134.72134.88
153.11153.11
153.51153.51
168.20170.73
195.23
129113109
268268249249
117
119
280280283283
33356367
110110
107107
5552
57
Acetone
CS i
20.0820.4221.32
55.6555.6556.1256.12
63.26
79.70
105.93105.93105.58105.58
132.20132.74133.61133.33
151.75151.75
152.05152.05
167.79170.03
194.40
149139130
293293272272
88
97
196196191191
4068100102
193193
180180
8199
87
CS i
DMSO
A4 Ac Meγ Ac Me
Bα
B OMeB OMeA OMeA OMe
γ
β
B2B6A2A6
A4B4A1B1
A3A5
B3B5
A4 Ac C=Oγ Ac C=O
α
Atom
1HJMultH Shifts
1.90
2.08
2.26
3.703.85
4.495.50
6.477.49
s
s
s
ss
mt
ss
5.4
A4 Ac Me
Bα
γ Ac Me
B OMeA OMe
γβ
B2,6A2,6
Atom
(acetone)
LLL-XXIII-76DA37mgAs this dimer contains a plane of symmetry the CSs are reported for one unit.
Notes:
247Compound Number
FPL/DFRC NMR Database -- April 2009
13C
2424
36
23
27
9
414
12
9
20.5421.51
56.08
112.75
123.17
131.30
135.39136.02
150.95
168.96
CDCl3
CS i
20.3621.32
56.28
113.52
123.44
132.13
136.48136.48
152.17
168.67
8482
114
98
95
29
5858
31
21
Acetone
CS i
20.1020.87
55.83
112.90
122.22
130.49
134.74135.52
150.64
168.00
6364
67
55
48
34
2146
38
26
CS i
DMSO
Ac Meα
OMe
2
6
5
41
3
Ac C=O
Atom
1HJMultH Shifts
2.00
2.33
3.81
6.60
6.92
s
s
s
bdd
bd
2.0, 0.8
1.6
Ac Meα
OMe
6
2
Atom
(acetone)
SRIX-98 27mgB5 and A6 may be switchedHSQC and HMBC in CDCl3
Notes:
248Compound Number
FPL/DFRC NMR Database -- April 2009
G-b-G
13C
31
3941
172423
283228302833
151814151513
21.21
55.8555.93
60.9673.9689.52
109.59113.05114.39120.22120.87121.94
131.64134.08145.31145.58146.75150.86
60.69
72.71
87.33
CDCl3
CS i
21.06
56.1956.26
61.8273.9588.90
111.40114.17115.23120.23120.57122.19
133.16133.82146.80147.82148.02151.47
61.69
73.78
87.08
36
4454
262833
343637373841
191616141612
Acetone
CS i
20.63
55.4555.58
60.1070.9684.95
111.05113.43114.69116.28119.04120.84
130.36133.01145.44146.13147.00149.57
59.97
71.72
84.21
80
7993
475244
545256485671
495257445345
CS i
DMSO
Bα
OMeOMe
γα
β
A2B2A5B5A6B6
A1B1B4A4A3B3
erythro isomer
γ
α
β
Atom
1HJMultH Shifts
2.273.513.683.813.854.074.886.666.877.37
smmssmdbdbds
6.07.38.0
Bαγ1γ2
OMeOMe
βα
B6B5
A4 OH
Atom
(acetone)
threo
SRIX-101B 21mgHSQC acetoneHSQC & HMBC CDCl3
Notes:
249Compound Number
FPL/DFRC NMR Database -- April 2009
H-b-S
13C
25
5858
182323
484848484545
171115
2727
18
22.01
56.1956.19
60.5074.1089.14
106.16106.16115.56115.56128.75128.75
131.26133.02134.77
152.69152.69
156.28
60.6
72.4
87.0
CDCl3
CS i
21.78
56.4856.48
61.0673.9589.98
107.12107.12115.58115.58129.22129.22
133.06134.67134.84
153.67153.67
157.68
60.8
73.1
87.8
21
5050
212223
424248484646
10710
1515
12
Acetone
CS i
21.34
55.8655.86
60.0871.5387.36
106.33106.33114.37114.37127.88127.88
132.21132.86133.93
152.32152.32
156.23
35
7777
232728
575759596161
232417
4242
26
CS i
DMSO
Bα
OMeOMe
γα
β
B2B6A3A5A2A6
A1B4B1
B3B5
A4
erythro isomer
γ
α
β
Atom
1HJMultH Shifts
2.283.213.603.823.854.986.556.787.27
CDCl32.363.323.573.873.905.036.476.727.26
sddddmsdsdd
12.3, 3.212.3, 3.2
7.8
8.58.5
Bαγ1γ2β
OMeα
B2,6A3,5A2,6
CDCl3Bαγ1γ2β
OMeα
B2,6A3,5A2,6
Atom
(acetone)
threo
SRIX-105 30mgOrder of Ac Me changes in CDCl3HSQC and HMBC in CDCl3 and d6-acetone The first β-O-4 linkage appears to beerythro and the second linkage appears to be threo.
Notes:
250Compound Number
FPL/DFRC NMR Database -- April 2009
G-b-S-b-S
13C
4746417575
39
10910910910984
212523295757
53537070172433
2025181125192341414141
2023212121
20.8520.6720.7321.0821.08
21.85
55.9955.9955.9955.9956.07
62.7663.7474.0675.9980.8980.89
104.44104.44106.05106.05111.60119.23122.42
133.37133.74134.40135.22136.15139.50150.85152.65152.65153.06153.06
168.89169.55169.85170.54170.88
CDCl3
CS i
20.4820.5920.7420.9321.02
21.74
56.3256.3256.4556.4556.86
63.3964.3075.1576.7581.4581.76
105.27105.27106.99106.99112.30120.02123.30
134.17134.36135.56136.33137.10140.57152.05153.67153.67153.91153.91
168.96169.90169.95170.69170.69
5548415348
47
9191123123104
393644283428
79798989332541
2727141824202549495353
2329344545
Acetone
CS i
20.2720.3520.4820.6720.73
21.37
55.7155.7155.7155.7155.85
62.2563.2073.8375.7780.0080.50
104.01104.01105.89105.89111.04118.85122.57
133.02133.02133.79134.35135.67138.92150.59152.13152.13152.43152.43
168.49169.29169.38169.99169.99
3547364140
35
11511511511572
191522131715
36365353211321
3939132019232748484242
2628293434
CS i
DMSO
A4 Ac Meγ Ac Meγ Ac Meα Ac Meα Ac Me
Cα
B OMeB OMeC OMeC OMeA OMe
AγBγAαBαAβBβ
B2B6C2C6A2A6A5
C1B1C4B4A1A4A3C3C5B3B5
A4 Ac C=Oα Ac C=Oα Ac C=Oγ Ac C=OγAc C=O
Atom
1HJMultH Shifts
1.841.932.002.112.212.283.773.793.813.834.164.224.404.524.706.066.066.496.747.007.16
ddddsssssmdddddddmmddsdmd
1.61.43.01.0
11.7, 4.211.7, 3.8, 1.8
11.7, 6.0
overlappingoverlapping
1.61.4
γ Ac Meα Ac Meγ Ac MeαAc Me
A4 Ac MeCα
OMeOMeOMeBγ 1Aγ 1Bγ 2Aγ 2BβAβAαBα
C2,6B2,6A5,6A2
Atom
(acetone)
L.Landucci XXIII-143 39mg.HSQC and HMBC in acetone d-6
Notes:
251Compound Number
FPL/DFRC NMR Database -- April 2009
13CCDCl3
CS i
21.00
31.1532.42
56.13
64.9871.56
113.72115.39121.14122.79122.79128.40128.40128.40128.72129.11129.11131.62131.62135.56138.76147.68150.88155.53
166.03
169.26
21
1215
18
1411
121112363633333362323292964447
4
8
Acetone
CS i CS i
DMSO
Ac Me
βα
OMe
γBα
A2A5A6C3C5B2B6B4C1B3B5C2C6A1B1A4A3C4
Cα
Ac C=O
Atom
1HJMultH Shifts
2.082.282.743.794.315.056.756.917.257.357.478.05
sdbtsbtsmmdmbdd
< 1.08.0
6.4
8.5
7.48.5
βAc Me
αOMe
γBαA6
A2,5C3,5
B3,4,5B2,6C2,6
Atom
(acetone)
L.Landucci XXIII-127G 48 mgHSQC and HMBC in acetone d-6
Notes:
252Compound Number
FPL/DFRC NMR Database -- April 2009
13CCDCl3
CS i
56.16
63.26
71.47
110.73115.12120.11128.46128.46128.54129.19129.19
129.19130.01131.94
138.60148.98151.02
34
17
30
2928326161387777
773113
13710
Acetone
CS i CS i
DMSO
OMe
γ
Bα
A2A5A6B2B6B4B3B5
βα
A1
B1A4A3
Atom
1HJMultH Shifts
3.844.195.096.266.526.886.967.08
7.3-7.5
sddsdtdtddddm
5.4, 1.4
16.1, 5.49.9, 1.78.3, 2.0
8.32.0
OMeγ
Bαβα
A6A5A2
B2-6
Atom
(acetone)
L.Landucci XXIII-114B 16 mgHSQC and HMBC in acetone d-6
Notes:
253Compound Number
FPL/DFRC NMR Database -- April 2009
13CCDCl3
CS i
20.9820.98
56.30
66.01
111.31120.16122.93122.93123.16123.16123.95
124.89
127.72128.57131.77131.77132.34132.34
134.01
136.55140.81152.54155.72156.13
164.23165.84
169.29169.29
3939
32
22
21174545484823
21
8748484646
23
1514161115
46
1919
Acetone
CS i CS i
DMSO
Ac MeAc Me
OMe
γ
A2A6C3C5B3B5A5
β
B1C1C2C6B2B6
α
A1A4A3C4B4
BαCα
Ac C=OAc C=O
Atom
1HJMultH Shifts
2.292.313.845.006.556.857.137.207.287.337.358.118.21
sss
bddtbdddddbsddd
6.016.0, 6.0
16.08.3, 1.8
8.38.7
8.78.78.7
Ac MeAc MeOMe
γβα
A6A5
C3,5A2
B3,5C2,6B2,6
Atom
(acetone)
L.Landucci XXIII-129B 57mgHSQC and HMBC in acetone d-6
Notes:
254Compound Number
FPL/DFRC NMR Database -- April 2009
13CCDCl3
CS i
21.00
56.31
66.3471.53
111.16115.17120.82
122.39
122.83122.83128.45128.45128.57128.69129.20129.20131.00131.74131.74
134.95
138.49149.70151.13155.68
165.93
169.25
39
30
3426
181837
34
7878787838146868147373
36
15131213
13
13
Acetone
CS i CS i
DMSO
Ac Me
OMe
γBa
A2A5A6
β
C3C5B2B6B4C1B3B5A1C2C6
α
B1A4A3C4
Cα
Ac C=O
Atom
1HJMultH Shifts
2.283.854.955.106.386.746.977.167.26
7.31-7.417.478.09
ss
ddsdtdmbsdmbdd
6.4, 1.3
15.9, 6.415.9
8.7
7.48.7
Ac MeOMe
γBαβα
A5,6A2
C3,5B3,4,5B2,6C2,6
Atom
(acetone)
L.Landucci XXIII-114D2 8mgHSQC and HMBC in acetone d-6
Notes:
255Compound Number
FPL/DFRC NMR Database -- April 2009
13CCDCl3
CS i
20.98
56.24
66.47
110.24115.83121.33
121.33
122.90122.90128.70129.35131.73131.73
135.40
147.91148.55155.68
165.90
169.29
32
28
28
232247
47
62629106262
26
1169
8
11
Acetone
CS i CS i
DMSO
Ac Me
OMe
γ
A2A5A6
β
B3B5B1A1B2B6
α
A4A3B4
Bα
Ac C=O
Atom
1HJMultH Shifts
2.283.864.946.336.726.796.937.147.278.09
ss
dddtddddddd
6.6, 1.216.0, 6.6
16.08.3
8.3, 2.12.18.98.9
Ac MeOMe
γβα
A5A6A2
B3,5B2,6
Atom
(acetone)
L.Landucci XXIII-114D1 4mgHSQC and HMBC in acetone d-6
Notes:
256Compound Number
FPL/DFRC NMR Database -- April 2009
13CCDCl3
CS i
20.99
56.22
63.10
111.04119.58123.15123.15123.81127.80
129.30131.61
132.32132.32137.50140.16152.44156.10
164.29
169.30
35
39
29
373676763816
3637
737317111613
8
13
Acetone
CS i CS i
DMSO
Ac Me
OMe
γ
A2A6B3B5A5B1
αβ
B2B6A1A4A3B4
Bα
Ac C=O
Atom
1HJMultH Shifts
2.313.843.904.256.436.647.057.157.237.348.20
sstdtdtddddddd
5.2, 1.415.9, 5.2
15.98.3, 1.9
8.31.98.98.9
Ac MeOMeOH
γβα
A6A5A2
B3,5B2,6
Atom
(acetone)
L.Landucci XXIII-93CC 17mgHSQC and HMBC in acetone d-6
Notes:
257Compound Number
FPL/DFRC NMR Database -- April 2009
13CCDCl3
CS i
56.2757.07
62.98
106.32108.77111.75120.19122.94
128.91132.31
138.15140.96151.65159.23160.39181.63182.05
2627
26
2826242727
2426
13696997
Acetone
CS i CS i
DMSO
A OMeB OMe
γ
B2B5A2A6A5
αβ
A1A4A3B6B3B4B1
Atom
1HJMultH Shifts
3.853.864.245.406.026.446.637.097.27
ssbsssdtdtmbs
15.9, 5.016.1, 1.7
A OMeB OMe
γB2B5βα
A5,6A2
Atom
(acetone)
SRIX-116E 3mggHSQC and gHMBC in acetoneproton CS's for A6,C5 and A2 determined by simulation (Acorn MacNuts)
Notes:
258Compound Number
FPL/DFRC NMR Database -- April 2009
Vanillin-a-G-b-CA
13C
323119
283842
23252323
24242321222624
22
25221413
21
16121213111211
111210
25
20.7420.8221.10
55.8456.0956.13
63.1265.1779.9882.11
109.93110.29111.14114.77119.31119.46119.93
122.39
122.94126.32130.99132.03
133.93
136.05139.89147.31150.68151.13151.43152.81
168.86170.82170.95
190.96
CDCl3
CS i
20.4620.6220.80
56.2456.2956.51
63.3265.3880.5581.82
111.36111.36112.68115.94119.62120.33120.53
123.35
123.53126.04132.08132.61
134.20
136.78140.85148.54151.58152.02152.28153.36
168.87170.77170.77
191.26
292722
363131
26292627
51512627262728
27
27261414
25
17111212121212
111818
30
Acetone
CS i CS i
DMSO
A4 Ac MeγAc Me
BγAc Me
OMeOMeOMe
γ
Bγαβ
B2C2A2C5B5A6B6
Bβ
A5C6C1B1
Bα
A1A4B4C3A3B3C4
A4 Ac C=OγAc C=OγAc C=O
Cα
Atom
1HJMultH Shifts
1.91, 2.03, 2.073.813.833.974.454.564.674.915.846.276.636.937.017.037.147.157.157.367.397.469.81
s’ssss
ddddddmddtddddddddddddds
11.9, 4.011.9, 5.86.4, 1.2
5.215.9, 6.4
15.98.2, 1.6
8.38.2
8.2, 1.82.08.32.4
8.2, 1.81.8
Ac Me’sOMeOMeOMe
γ1γ2Bγβα
BβBαB6B5A5A6B2C5A2C6C2Cα
Atom
(acetone)
L.LanducciXXIII-52H 25 mgAs this dimer contains a plane of symmetry the CSs are reported for one unit.
Notes:
259Compound Number
FPL/DFRC NMR Database -- April 2009
dihydrodiconiferyl alcohol
13C
37
35
52
34
32
40
13
16
17
18
31.94
34.45
56.20
62.38
110.71
123.04
124.52
133.76
140.83
147.33
CDCl3
CS i
32.53
35.75
56.42
61.85
111.75
123.94
126.47
134.15
142.49
148.64
33
31
45
22
31
32
11
19
13
14
Acetone
CS i
31.34
34.59
55.85
60.24
110.77
122.73
125.89
132.26
141.36
147.61
34
39
63
48
28
32
18
30
24
20
CS i
DMSO
α
β
OMe
γ
2
6
5
1
4
3
Atom
1HJMultH Shifts
1.81
2.64
3.58
3.85
6.726.82
m
m
t
s
dd
6.6
2.12.0
β
α
γ
OMe
62
Atom
(acetone)
L.LanducciXXIII-146ACHAs this dimer contains a plane of symmetry the CS's are reported for one unit.
Notes:
260Compound Number
FPL/DFRC NMR Database -- April 2009
13C
3227
1919
34
21
1315
8
7
10
11
89
20.3920.91
30.3032.15
56.02
63.72
111.95122.27
131.36
135.76
139.28
151.13
168.76171.08
CDCl3
CS i
20.4620.78
30.9932.61
56.34
64.04
112.93122.80
132.20
136.81
140.33
152.37
168.76171.00
4437
2833
44
30
2119
9
8
12
14
1211
Acetone
CS i
19.9920.56
29.5831.32
55.79
63.10
112.16121.46
130.51
135.09
139.20
150.82
167.98170.25
1112
87
10
9
44
4
4
4
5
45
CS i
DMSO
Ac MeAc Me
αβ
OMe
γ
26
5
4
1
3
4 Ac C=Oγ Ac C=O
Atom
1HJMultH Shifts
1.97
1.982.01
2.70
3.83
4.07
6.66
6.99
m
ss
bt
s
t
d
d
8.0
6.4
1.8
1.8
β
Ac MeAc Me
α
OMe
γ
6
2
Atom
(acetone)
S.RalphSRIX-115BAc 30 mg CS's indicate A-threo-B-erythro-CgHSQC and gHMBC in acetone, some signals split due to isomers
Notes:
261Compound Number
FPL/DFRC NMR Database -- April 2009
S-b(t)-G-b(e)-S5
13C
3226352629
317070706161151519181821
30305050101618981015158828283535
1416121414
20.4820.7520.8421.0821.14
21.9055.9755.9755.9756.2856.2862.8263.0974.3374.4880.2080.84
104.16104.16106.09106.09111.59118.00119.52128.90132.33132.90134.14134.78147.69150.46152.26152.26152.98152.98
168.52169.75169.79170.62170.91
CDCl3
CS i
20.2420.6420.6420.9620.96
21.7756.2856.2856.2856.2856.5563.3563.6375.2275.6880.6581.16
104.97104.97106.92106.92112.49118.39120.29129.69132.98134.16134.48136.15148.70151.38153.20153.20153.88153.88
168.45169.96170.01170.70170.70
4681816868
5112512512512584261927271533
464688881613161210132019141435354848
1827273232
Acetone
CS i
20.0520.3520.3520.6220.62
21.3555.6155.6155.6155.9855.9862.1262.4673.7674.5978.9679.94
103.97103.97105.87105.87110.87116.75118.89127.84131.07132.16133.32134.92147.19149.68151.58151.58152.34152.34
167.91169.26169.33169.94169.94
2738383737
246666663838151214101016
23234141971096814128822222929
1117172525
CS i
DMSO
A4 Ac Meγ Ac Meγ Ac Meα Ac MeαAc Me
CαOMeOMeOMeOMeOMe
BγAγBαAαAβBβ
A2A6C2C6B2B5B6A4B1C4C1A1B4B3A3A5C3C5
A4 Ac C=Oα Ac C=OαAc C=Oγ Ac C=Oγ Ac C=O
Atom
1HJMultH Shifts
1.881.972.012.122.212.27
3.77, 3.80, 3.844.054.134.264.394.654.816.016.086.486.856.907.027.06
ssddss
s’sddddmmmmddssmdm
11.9, 5.411.5, 3.2
4.26.6
8.3
γ Ac Meγ Ac Meα Ac MeαAc Me
A4 Ac MeCα
OMe’sAγ 1Bγ 1Aγ 2Bγ 2BβAβBαAα
C 2,6A 2,6
B6B5B2
Atom
(acetone)
SRVII-91D 8mg HSQC and HMBC in acetone and CDCl3A1 and A4 tentative assignments, some signals split due to isomers
Notes:
262Compound Number
FPL/DFRC NMR Database -- April 2009
13C
8282826846
23
4238
2313221722
21131319311414
1110107
15
1514151518
20.7620.7620.7620.8521.07
50.64
56.0256.26
62.3664.9872.4773.9588.20
110.13111.74115.87118.40122.97127.58129.80
139.29139.84144.61148.54
151.39
168.96169.87170.10170.45170.75
CDCl3
CS i
20.4720.5620.7320.7320.89
51.45
56.2956.59
63.0065.7973.2774.5588.40
111.11113.19116.84118.78123.80128.83131.06
140.82140.92145.31149.38
152.46
168.96170.01170.26170.63170.95
6756606449
43
6252
3819361727
28202027541314
141597
21
2417172023
Acetone
CS i CS i
DMSO
Ac MeAc MeAc MeAc Me
A4 Ac Me
Aβ
A OMeB OMe
BγAγBβ BαAα
A2B2B6A6A5B5B1
A1A4B3B4
A3
A4 Ac C=OBα Ac C=OBβ Ac C=OBγ Ac C=OAγ Ac C=O
Atom
1HJMultH Shifts
1.982.002.032.042.213.783.793.823.874.174.385.385.615.926.997.047.18
mmsssmsmsmmmdddmdbs
6.87.2, 2.8
8.2
Ac MeAc MeAc MeAc Me
A4 Ac MeAβ
A OMeB γ1
B OMeB γ2AγBβAαBα
B2,6,A6A5A2
Atom
(acetone)
SRVII-143D 13 mgErythro isomer shirts reportedsample contains small amt of 5,5 resinol tetramer.
Notes:
263Compound Number
FPL/DFRC NMR Database -- April 2009
13CCDCl3
CS i
20.4820.4820.6320.89
55.2755.41
56.2156.2656.28
63.0372.5072.6274.5480.3186.1786.17
111.08111.58112.74118.61119.03119.42120.48123.33123.47
136.69136.69140.12141.08141.88147.48151.88152.27152.27
168.92169.05169.91170.77
63.58
75.33
80.74
71712917
2323
413819
14404013154242
321816161710101414
1212131415772121
142077
Acetone
CS i CS i
DMSO
C4 Ac MeA4 Ac MeAα Ac MeAγ Ac Me
BβCβ
OMeOMeOMe
AγBγCγAαAβBαCα
C2B2A2C6B5B6A6A5C5
A1B1C4A4C1B4B3C3A3
A4 Ac C=OC4 Ac C=OAαAc C=OAγ Ac C=O
threo isomer
Aγ
Aα
Aβ
Atom
1HJMultH ShiftsAtom
(acetone)
FPL - Pearl collection25 mgHSQC and HMBC in acetone
Notes:
264Compound Number
FPL/DFRC NMR Database -- April 2009
alpha,4-dihydroxy-3-methoxypropiophenone
13C
48
50
46
47
48
49
15
15
19
16
22.91
56.19
68.89
110.64
114.30
124.08
125.91
147.10
151.41
200.75
CDCl3
CS i
22.69
56.33
69.42
112.20
115.60
124.65
127.08
148.48
152.84
201.10
58
68
50
56
68
75
17
18
24
18
Acetone
CS i
21.17
55.57
68.10
111.74
114.89
123.51
126.15
147.48
151.73
199.72
37
36
30
23
34
35
20
21
25
20
CS i
DMSO
γ
OMe
β
2
5
6
1
3
4
α
Atom
1HJMultH Shifts
1.353.914.105.136.947.577.608.61
1.463.965.136.616.987.487.54
dsdmddddbs
dsmbsdddd
6.8
6.4
8.22.0
8.2, 2.0
6.6
8.28.2, 2.0
2.0
γOMeβ-OH
β526
4-OH
CDCl3
γOMe
β4-OH
562
Atom
(acetone)
FPL - Pearl Collection25 mgHSQC and HMBC in acetone
Notes:
265Compound Number
FPL/DFRC NMR Database -- April 2009
alpha,4-diacetoxy-3-methoxypropiophenone
13C
63
5557
67
61
62
66
66
25
19
24
2223
23
17.16
20.5620.66
56.02
71.23
112.09
121.55
122.97
133.03
144.22
151.66
168.31170.32
195.65
CDCl3
CS i
17.41
20.4720.54
56.46
72.21
112.79
122.34
124.10
134.07
145.25
152.72
168.62170.54
196.21
76
6162
82
69
71
73
76
23
17
21
2222
24
Acetone
CS i
16.90
20.2620.26
55.94
71.26
111.85
121.56
123.32
132.46
143.69
151.23
168.02169.74
195.52
26
4949
27
23
21
22
23
14
12
14
1113
13
CS i
DMSO
γ
β Ac Me4 Ac Me
OMe
β
2
6
5
1
4
3
4 Ac C=Oβ Ac C=O
α
Atom
1HJMultH Shifts
1.482.062.273.906.007.237.647.66
1.532.142.333.893.937.147.557.59
dsssqd
O/LapO/Lap
dsssqdddd
7.0
7.08.0
7.0
7.08.1
8.1, 2.02.0
γβ Ac Me4 Ac Me
OMeβ526
CDCl3
γβAc Me4 Ac Me
OMeβ562
Atom
(acetone)
SRIX-138A23mg 1H CDCl3 shifts in ( )sHSQC and HMBC in acetone. A and C OMe shifts may be switched, B and CCH3's may be switchd
Notes:
266Compound Number
FPL/DFRC NMR Database -- April 2009
S-a-S-b-S
13C
34363542
797993938686
303134
656569696767
82027271820
353533333434
1816
20.5620.8721.7621.82
55.8755.8755.9655.9656.1256.12
64.4481.5281.89
105.52105.52105.81105.81106.22106.22
128.10133.01133.48133.48133.62138.02
150.94150.94152.47152.47152.87152.87
168.75168.75
CDCl3
CS i
20.2720.6921.6121.68
56.2756.2756.3556.3556.3956.39
64.6482.6883.16
105.94105.94107.01107.01107.26107.26
129.11133.61133.87134.38135.03138.47
152.21152.21153.62153.62153.87153.87
168.52170.78
37293130
868694949090
333637
696972726969
7191510820
272730303030
1316
Acetone
CS i
20.0520.3021.1821.25
55.4655.4655.6255.6255.6755.67
62.9880.9281.36
104.49104.49105.74105.74106.08106.08
127.23132.21132.47132.72132.75136.90
150.59150.59151.95151.95152.22152.22
167.91167.91
13131213
252532322929
898
171720201818
56810107
151516161616
78
CS i
DMSO
A4 Ac Meγ Ac Me
B αC α
B OMeB OMeA OMeA OMeC OMeC OMe
γβα
A2A6B2B6C2C6
A4C1B1C4B4A1
A3A5C3C5B3B5
A4 Ac C=Oγ Ac C=O
Atom
1HJMultH Shifts
1.83 (1.95)2.17 (2.30)2.18 (2.24)2.22 (2.23)3.69 (3.58)3.73 (3.67)3.74 (3.71)4.53 (4.64)4.63 (4.72)4.73 (4.72)5.72 (5.60)6.37 (6.26)6.40 6.25)6.81 (6.76)
sssssss
ddmmdsss
11.7, 2.8
6.2
γ Ac MeA4 Ac Me
C αB α
B OMeA/C OMeC/A OMe
γ1γ2βα
C 2,6B 2,6A 2,6
Atom
(acetone)
LLL XXV-17A-E 11mg1H CDCl3 shifts in ( )sNote: B5 and Bγ C=O move in CDCl3 to lower ppm relative to acetone shiftsHSQC and HMBC run in Acetone
Notes:
267Compound Number
FPL/DFRC NMR Database -- April 2009
13C
403458
40424040
40
41
9494388888234221
38
19
1514
171220
20.8921.1121.19
50.2665.3565.6887.22
109.86
121.03
121.98121.98122.89126.89126.89126.49128.55129.87
134.16
138.63
150.64159.85
169.44170.96170.84
CDCl3
CS i
20.6720.8120.94
51.0665.5166.1087.85
110.20
122.13
122.88122.88123.88127.70127.70127.98129.19130.82
134.43
139.84
151.77160.77
169.62170.77170.94
292341
30333132
29
33
5858305555142914
30
12
1210
13813
Acetone
CS i CS i
DMSO
Ac MeAc MeAc Me
βBγAγα
B3
Bβ
A3A5B6A2A6B5B2B1
Bα
A1
A4B4
A4 C=OBγ C=OAγC=O
Atom
1HJMultH Shifts
2.00 (2.07)2.01 (2.10)2.24(2.30)
3.74 (3.70)4.34 (4.29)4.46 (4.46)4.66 (4.71)5.64 (5.54)
6.23 (6.14)6.66 (6.61)6.85 (6.85)7.13 (7.09)7.33 (7.27)7.45 (7.27)7.45 (7.37)
sss
mddddddd
dtdddddd
11.1, 7.811.1, 5.46.4, 1.4
6.4
15.9, 6.415.98.38.5
8.3, 2.08.5
Ac MeAc MeAc Me
βγ1γ2Bγα
BβBαB3
A 3,5B2
A 2,6B6
Atom
(acetone)
S. Ralph SRIX-6224mg, 70% erythroA4 and B4 switch in CDCl3, B1 falls between A and B 2,6 in DMSOHSQC and HMBC in all solvents
Notes:
268Compound Number
FPL/DFRC NMR Database -- April 2009
H-b-H5e
13C
58343540
83839090
81819898
2727
2823
20.5861.3273.8982.25
115.52115.52116.79116.79
127.71127.71130.18130.18
131.41132.13
155.78155.53
CDCl3
CS i
20.4561.9073.8184.15
115.50115.50117.33117.33
128.89128.89130.44130.44
130.61133.98
157.43157.65
28222027
64644949
80806060
1411
138
Acetone
CS i
20.0760.0771.3683.58
114.46114.46116.22116.22
128.01128.01129.52129.52
129.03132.76
156.25156.67
43262627
64646464
58586868
2622
3020
CS i
DMSO
Bαγα
β
A3A5B3B5
A2A6B2B6
B1A1
A4B4
Atom
1HJMultH Shifts
2.19
3.773.854.344.896.786.997.28
2.253.803.904.284.986.747.027.20
s
ddddmd
sddddmd
dd
11.7, 4.411.7, 5.2
5.6
8.58.5
11.9, 4.011.9, 4.4
5.2
8.38.3
Bα
γ1γ2βα
A,B 3,5B 2,6A 2,6
CDCl3
Bαγ1γ2βα
A,B 3,5A 2,6B 2,6
Atom
(acetone)
erythro
SRIX-62 20mg75% threo, HSQC and HMBC in DMSOB1 falls between A and B 2,6 in DMSOA4 and B4 may be switched in CDCl3
Notes:
269Compound Number
FPL/DFRC NMR Database -- April 2009
H-b-H5t
13C
44272628
68687979
66668787
2025
2026
20.5360.9573.6483.32
115.61115.61116.64116.64
128.38128.38130.19130.19
131.17131.42
155.95156.21
CDCl3
CS i
20.4661.5473.1584.43
115.52115.52117.15117.15
128.87128.87130.47130.47
130.56133.58
157.51159.00
28241925
63634747
75756161
1613
1510
Acetone
CS i
20.0559.9970.7983.41
114.45114.45115.96115.96
127.68127.68129.55129.55
128.99132.50
156.22156.95
45182527
62627171
63637474
2819
2420
CS i
DMSO
Bαγα
β
A3A5B3B5
A2A6B2B6
B1A1
A4B4
Atom
1HJMultH Shifts
2.213.483.784.354.946.786.877.027.27
2.253.463.734.284.916.726.847.017.18
sddddmd
sddddmd
11.5, 5.411.5, 4.2
5.2
12.1, 3.812.1, 4.0
6.8
Bαγ1γ2βα
A 3,5B 3,5B 2,6A 2,6
CDCl3
Bαγ1γ2βα
A 3,5B 3,5A 2,6B 2,6
Atom
(acetone)
threo
SRIX-62 25mg1H CDCl3 shifts in ( )s70% erythroHSQC and HMBC in acetone
Notes:
270Compound Number
FPL/DFRC NMR Database -- April 2009
H-b-H5e
13C
64
526774
495053
103103110110
133133148148
2530
2322
222220
20.31
20.5020.7720.88
62.1573.3378.69
116.76116.76121.44121.44
128.30128.30129.88129.88
131.39133.83
150.54155.77
168.99169.31170.48
CDCl3
CS i
20.49
20.5820.8620.94
62.8674.1279.27
117.56117.56122.49122.49
129.31129.31130.74130.74
131.85135.33
151.79157.04
169.53169.86170.76
46
414152
363452
68687474
9292107107
1218
1212
161111
Acetone
CS i
20.04
20.4020.6320.77
61.7772.7477.41
116.37116.37121.66121.66
128.31128.31130.33130.33
130.51134.09
150.23155.46
169.05169.21170.04
42
424248
212423
61615252
54547171
2124
1919
191918
CS i
DMSO
Bα
Aγ Ac MeAα Ac MeA4 Ac Me
γα
β
B3B5A3A5
A2A6B2B6
B1A1
A4B4
A4 Ac C=Oα Ac C=Oγ Ac C=O
Atom
1HJMultH Shifts
1.94 (2.02)2.06 (2.09)2.23 (2.28)2.23 (2.28)
4.23 (4.20)4.34 (4.37)4.83 (4.66)6.04 (6.04)
6.85 (6.77)7.08 (7.07)7.08 (7.07)7.51 (7.42)
ssss
ddddmd
mmmd
11.9, 4.211.9, 6.0
5.4
8.7
Aγ Ac MeAα Ac Me
BαA4 Ac Me
γ1γ2βα
B 3,5B 2,6A 3,5A 2,6
Atom
(acetone)
erythro
SRIX-62 25mg75% threo1H CDCl3 shifts in ( )s
Notes:
271Compound Number
FPL/DFRC NMR Database -- April 2009
H-b-H5t
13C
65
546575
565564
124124118118
141141154154
2933
2824
212424
20.49
20.6420.9721.08
62.6873.9478.49
116.48116.48121.78121.78
128.47128.47130.04130.04
131.37133.81
150.84156.33
169.15169.73170.57
CDCl3
CS i
20.49
20.5520.8820.94
63.2774.8879.27
117.24117.24122.67122.67
129.33129.33130.74130.74
131.66135.22
151.94157.59
169.52170.04170.68
59
545772
535576
104104109109
124124137137
2225
2120
211917
Acetone
CS i
20.03
20.3920.6420.77
62.2373.7777.74
116.09116.09121.81121.81
128.37128.37129.81129.81
130.33134.04
150.36156.12
169.04169.41169.98
CS i
DMSO
Bα
Aγ Ac MeAα Ac MeA4 Ac Me
γα
β
B3B5A3A5
A2A6B2B6
B1A1
A4B4
A4 Ac C=Oα Ac C=Oγ Ac C=O
Atom
1HJMultH Shifts
1.94 (1.98)2.01 (2.05)2.24 (2.28)2.24 (2.28)
4.01 (4.00)4.23(4.26)4.83 (4.64)6.10 (6.09)
6.90 (6.85)7.10 (7.07)7.10 (7.07)7.51 (7.42)
ssss
ddddmd
d
11.9, 5.811.9, 4.2
6.4
8.5
Aγ Ac MeAα Ac Me
BαA4 Ac Me
γ1γ2βα
B 3,5B 2,6A 3,5A 2,6
Atom
(acetone)
threo
L. Landucci XXII-138D7 19mg2:1 mix of isomers
Notes:
272Compound Number
FPL/DFRC NMR Database -- April 2009
13C
82567471
166166
454647
9797
930
4545
20222419
20.4820.7220.8521.01
56.3156.31
62.1772.2473.78
104.05104.05
129.13134.19
152.45152.45
168.51169.67170.09170.43
61.42
72.48
73.03
103.75
134.19
152.27
CDCl3
CS i
20.2320.5520.7120.83
56.5856.58
62.8572.9974.45
104.76104.76
129.79135.85
153.30153.30
168.42170.00170.21170.65
62.34
72.99
73.76
104.67
135.63
153.19
94738081
179179
657360
125125
828
4848
22232221
Acetone
CS i
20.0820.3920.4620.65
56.0356.03
61.9271.7373.17
103.59103.59
127.83134.79
151.64151.64
167.93169.43169.43169.95
33312933
6262
141616
3333
815
2929
13232311
CS i
DMSO
A4 Ac Meγ Ac Meβ Ac Meα Ac Me
OMeOMe
γβ
α
26
41
35
A4 Ac C=Oα Ac C=Oβ Ac C=Oγ Ac C=O
minor isomer
γ
β
α
2, 6
1
3, 5
Atom
1HJMultH Shifts
1.992.012.082.213.813.914.235.415.956.80
2.062.082.102.333.833.834.265.425.926.61
sssss
ddddmds
sssss
ddmds
12.1, 6.212.1, 3.8
6.8
hidden12.1, 3.6
7.6
γ Ac Meβ Ac Meα Ac Me
A4 Ac MeOMe
γ1γ2βα
2,6
CdCl3γ Ac Meβ Ac Meα Ac Me
A4 Ac MeOMe
γ1γ2βα
2,6
Atom
(acetone)
FPL Collection 11mgBoth A5 and A1 change order in CDCl3 compared to acetone-d6B4 and A4 assignments taken from 2D in CDCl3gHSQC and gHMBC in all solvents
Notes:
273Compound Number
FPL/DFRC NMR Database -- April 2009
G-5-O-4-G
13C
3847373437
3634
30
3334343335
12181710111313
mult
ttmbtssbtdmdd
10.1613.8524.6131.8337.87
55.9556.29
75.94
104.43109.38112.88119.57120.77
136.18135.83139.42143.63144.59148.01150.27
CDCl3ppm
0.860.951.672.563.853.914.436.536.696.796.88
CDCl3
CS i
10.4814.0525.4133.2038.33
56.2756.56
75.40
105.66109.81114.27119.64121.35
137.28137.69139.25145.23145.44149.29151.45
CDCl3J =
7.67.6
7.6
6.61.8
2.08.1
5149474350
4949
27
4749494850
9232118181820
Acetone
CS i
10.0613.6824.1532.0538.50
55.5755.91
73.36
104.81108.57113.19118.00120.25
135.77136.52137.60143.69144.24148.46149.79
4040393034
3737
30
2728282931
23242420202221
CS i
DMSO
AγBγBβAβBα
B OMeA OMe
Aα
A2A6B2B5B6
A4A1B1B4A5A3B3
Protonshifts inCDCl3
AγBγ
Aβ,BβBα
OMeOMeAαA6
A2,B6B2B5
Atom
1HJMultH Shifts
0.830.931.622.563.813.864.396.456.706.756.766.947.39
ttmbtssbtdddddds
J = 7.3J = 7.3
J = 7.6
J = 6.1J = 1.5
J = 8.1, 1.5J = 8.1J = 1.5J = 1.5
AγBγ
Aβ,BβBα
OMeOMeAαA6B6B5A2B2
A4-OH
Atom
(acetone)
FPL Collection 6 mggHSQC and gHMBC in CDCl3 and acetone-d6A4 upon acetylation appears as cluster of signalsin acetone-d6 B5 and B6 too close to assign definitively
Notes:
274Compound Number
FPL/DFRC NMR Database -- April 2009
G-5-O-4-G diacetate
13C
37363331373636363635333334343782018131414151215
ttmmssbtssbtdddddd
9.9013.8120.4221.1924.6229.3137.8755.9856.2276.92104.58108.53113.11120.49120.86129.59138.79139.73142.84150.39150.72152.46168.48170.26
CDCl3
0.840.951.651.762.032.242.573.803.855.526.386.636.696.786.84
CDCl3
CS i
10.1214.0020.2220.9425.3630.1138.3656.1856.5677.23104.97107.93114.36121.58121.73129.57140.24141.00143.37151.63152.15153.60168.46170.25
CDCl3
J = 7.6J = 7.6
J = 7.6
J = 6.8J = 1.7J = 2.02.0, 8.1J = 1.7J = 8.1
63645450646064616360585859646783028171921201919
Acetone
CS i
9.7513.6320.0920.7824.1428.9137.0555.6456.1776.07104.20106.52113.48120.55120.68128.30139.23139.90141.62150.02150.66152.18168.05169.76
353232313427313630221925232526112222201611171917
CS i
DMSO
AγBγ
A4 Ac MeAα Ac Me
BβAβBα
B OMeA OMe
AαA2A6B2B6B5A4A1B1B4A5B3A3
A4 Ac C=OAα Ac C=O
Protonshifts inCDCl3
AγBγBβAβ
Aα Ac MeA4 Ac Me
BαB OMeA OMe
AαA6A2B6B2B5
Atom
1HJMultH Shifts
0.820.931.641.731.962.182.583.763.845.486.326.756.776.846.96
ttmmssbtssmmmmdd
J = 7.3J = 7.3
J = 7.3
overlappedoverlappedoverlapped
J = 8.1J = 1.7
AγBγBβAβ
Aα Ac MeA4 Ac Me
BαB OMeA OMe
AαA6B6A2B5B2
Atom
(acetone)
FPL Collection SRX-84 5 mggHSQC and gHMBC in all solvents, A5 is coincident with A6 in acetone-d6B5 and A4 change order in CDCl3, A6 and A5 change order in DMSOA and B OMe not definitively assigned in 13C DMSO-d6
Notes:
275Compound Number
FPL/DFRC NMR Database -- April 2009
13C
2824
2428
22
2625142626
19161417151217
tmsmdddsss
10.2131.90
56.1956.39
75.72
107.16109.43118.56120.19135.42
136.30143.07142.53146.78159.02180.27187.51
0.821.583.804.335.066.146.616.646.968.81
CDCl3
CS i
10.6433.21
56.4656.84
75.40
107.77110.91120.61120.61135.34
138.14144.12144.79148.08160.27180.63188.03
J = 7.1
J = 3.9J = 1.7J = 1.7
4538
4544
30
4243636338
32242425261925
Acetone
CS i
10.3032.03
55.8756.57
73.45
107.06110.48120.06119.35134.11
136.85144.04142.84147.29159.09179.87187.39
2924
2827
26
2320222220
2314191818316
CS i
DMSO
γβ
B OMeA OMe
α
B2A2A5A6B6
A1A4B5A3B3B4B1
Protonshifts inDMSO
γβ
OMeα
α OHB2B6A6A2
A4-OH
Atom
1HJMultH Shifts
0.911.703.883.894.506.076.696.777.077.76
0.931.763.863.934.545.935.986.746.836.98
tmssbtdddds
tmssbt
dbddbd
J = 7.4
J = 6.4J = 2.2J = 2.2J = 1.7J = 1.7
J = 7.6
J = 6.9
J = 2.2J = 1.2J = 2.2J = 1.2
γβ
A OMeB OMe
αB2B6A6A2
A4-OHCDCl3
γβ
B OMeA OMe
αα OH
B2A6B6A2
Atom
(acetone)
FPL Collection SRX-84 5 mgbeta carbon shift taken from DEPT-135, obscured by solvent in 13C acetone-d6Compound began to degrade after being taken up in CDCl3, shifts taken frommixture with unknown for CDCl3 and DMSO-d6
Notes:
276Compound Number
FPL/DFRC NMR Database -- April 2009
13C
605555616159605450514651275439494746464145
10.0620.5621.2829.3356.2656.5377.29107.40112.23120.36126.86135.67137.30139.15141.95151.44158.88168.19170.44179.90186.98
CDCl3
CS i
10.2220.3121.0230.1356.5556.9177.01108.00112.42120.65128.45135.94138.05140.40142.79152.38159.98168.42170.38180.40187.46
29272601392827272627928516913101010711
Acetone
CS i
9.8420.1320.8828.8556.1556.6075.82107.33111.63119.58127.00134.85136.35139.08141.15150.83158.74167.88169.95179.51186.80
131315999676757375546835
CS i
DMSO
γA4 Ac MeAαAc Me
βA OMeB OMe
αB2A2A6A5B6A4A1B5A3B3
A4 Ac C=OAα Ac C=O
B4B1
Atom
1HJMultH Shifts
0.911.882.062.113.873.895.686.106.596.947.19
0.931.862.102.183.865.665.996.706.817.00
tmsssstdddd
tdddd
J = 7.3
J = 6.9J = 2.2J = 2.2J = 1.7J = 1.7
J = 6.9J = 2.5J = 2.5J = 2.2J = 2.0
γβ
Aα Ac MeA4 Ac Me
A OMeB OMe
αB2B6A6A2
CDCl3γβ
Aα Ac MeA4 Ac Me
A OMeα
B2B6A6A2
Atom
(acetone)
SRVII-81 16mgNotes:
277Compound Number
FPL/DFRC NMR Database -- April 2009
dibenzodioxicin
13C
979741481081051054763633839235454524122524515232120225656452238
10.3410.3831.8832.0855.7855.8556.0062.9775.8475.8484.8286.93108.86109.47109.47114.41118.92119.35120.90130.01133.19132.12141.36141.74144.75145.98145.98146.80151.72152.24
0.971.813.553.763.843.924.144.59
0.901.663.223.863.844.474.81
CDCl3
CS i
10.7110.7733.2333.3056.0656.2956.3362.9775.5275.5285.1887.71110.17110.55111.94115.56119.26119.57121.33131.38133.24133.91143.38143.72145.95146.73147.43148.16152.75153.15
606045455075903251512927192238423120413014111816162135341530
Acetone
CS i
10.3910.4932.1132.1155.5455.6955.8060.6673.6373.6383.3485.57109.45109.57111.82115.14117.93117.93120.11129.59131.87132.08142.41142.41144.87145.04146.31147.18151.68151.68
323134343139351632321313161518222121171310712129920192121
CS i
DMSO
B or C γB or C γB or C βB or C β
OMeA OMeOMeAγ
B or C αB or C α
AαA βB2C2A2A5C6B6A6A1C5B5C1B1B4C4A4A3B3C3
Protonshifts inCDCl3
B,C γB,C β
AγOMeOMeOMeA β
A,B,C α
DMSO
B,C γB,C βAγ1Aγ2A β
B,C αAα
Atom
1HJMultH Shifts
0.961.753.483.703.773.833.924.034.604.776.846.896.967.017.05
7.06, 7.087.14, 7.16
mmmmsssmmddddmdmd'sd's
J = 10.0J = 8.1
J = 8.1, 1.7
J = 1.7
J = 2.0J = 2.0
B,C γB,C βAγ1Aγ2OMeOMeOMeA β
B,C αAαA5A6C6A2B6C2B2
Atom
(acetone)
SRVII-81AcgHSQC and gHMBC in d6-acetone and CDCl3
Notes:
278Compound Number
FPL/DFRC NMR Database -- April 2009
13C
9090987585853133847084412424242520203214144943232345262639181633273646272644
10.1910.1920.7420.8421.4021.4029.2829.3856.1056.1756.2263.9377.2677.5182.7684.45110.27111.03111.51119.26119.74119.91122.76132.63132.63137.13137.28137.28139.95146.17146.57151.32152.32152.52168.84170.48170.58170.76
CDCl3
0.941.881.972.082.122.303.743.823.904.084.144.494.855.706.87-7.05
CDCl3
CS i
10.4310.4320.5020.5821.1021.1030.0830.4356.1956.3256.3864.3377.4977.6283.4185.33110.79111.19112.78119.35120.00120.74123.46133.22133.42138.06138.57138.75140.80146.86147.24152.14153.35153.53168.94170.45170.45170.74
6666716163632018537762333130252715143412163339131320141422141327221933282830
Acetone
CS i
10.0210.0220.3620.4220.9020.9028.7529.2255.7455.9456.0263.1476.3476.3981.8084.06109.96110.43112.08118.00118.71119.98122.61131.58131.77136.45137.33137.60139.23145.13145.55150.63151.98152.16168.47169.89169.92170.07
4040423734342623556147283232172118162610122635101429151234172239192043444450
CS i
DMSO
BγCγ
A4 Ac MeAαAc MeB Ac MeC Ac MeB or C βB or C β
OMeOMeOMeAγ
B or CαB or Cα
A βAα
B or C2B or C2
A2B or C6B or C6
A6A5
B or C5B or C5
A1B or C1B or C1
A4B4C4A3
B or C3B or C3
A4 Ac C=OBorCAcC=OBorCAcC=OAγ Ac C=O
Protonshifts inCDCl3
B,C γB,C βAc MeAc MeAc MeAc MeOMeOMeOMe
γ1 βγ2α
B,C αaromatic H
Atom
1HJMultH Shifts
0.931.911.912.072.243.793.944.054.304.434.935.71
7.00-7.067.097.137.17
mmsssss
ddmdddmmmmm
J = 12.0, 3.4
J = 12.0, 3.4J = 10.0
from HSQCfrom HSQCfrom HSQCfrom HSQC
B,C γB,C β
γAc MeB,C α AcMeA4 Ac Me
OMeOMe
γ1 βγ2α
B,C αA5,A,B,C6
B or C 2B or C 2
A2
Atom
(acetone)
J. Ralph 16 mggHSQC, gHMBC in d6-acetone
Notes:
279Compound Number
FPL/DFRC NMR Database -- April 2009
dihydro-coniferyl alcohol
13C
2424
25
25
222524
111210
31.7234.43
55.84
62.22
111.03114.27120.90
133.70143.72146.43
CDCl3
CS i
32.4435.85
56.21
61.83
112.87115.59121.55
134.61145.47148.17
3327
31
28
283032
141410
Acetone
CS i
32.6235.99
56.95
61.58
113.96116.67121.71
134.38145.77148.77
2626
30
28
242626
192017
CS i
DMSO
αβ
OMe
γ
256
143
Atom
1HJMultH Shifts
1.78 (1.86)2.60 (2.63)3.55 (3.67)3.82 (3.86)6.64 (6.68)6.73 (6.70)6.81 (6.81)
1.662.483.403.734.406.556.656.728.60
mbtbts
dddd
J = 8.0J = 5.4
J = 8.1, 1.7J = 8.1J = 1.7
βαγ
OMe652
DMSOβαγ
OMeγ OH
652
phenolic OH
Atom
(acetone)
JRalph 25mggHSQC, gHMBC in d6-acetone
Notes:
280Compound Number
FPL/DFRC NMR Database -- April 2009
dihydro-coniferyl alcohol diacetate
13C
6552
8079
81
79
618379
254736
2723
20.4920.78
30.0232.03
55.68
63.63
112.45120.30122.43
137.84140.06150.77
169.01170.94
CDCl3
CS i
20.7920.50
31.0832.63
56.14
64.10
113.63121.05123.39
139.17141.27152.14
169.07171.00
3644
5054
52
54
465452
142718
1815
Acetone
CS i
20.3120.61
29.6731.34
55.59
63.21
112.76120.06122.41
137.45140.14150.60
168.56170.38
4647
4541
48
48
424446
253332
2925
CS i
DMSO
A4 Ac Meγ Ac Me
βα
OMe
γ
265
413
A4 Ac C=OγAc C=O
Atom
1HJMultH Shifts
1.941.992.212.683.794.056.786.946.97
1.952.052.292.673.814.106.756.786.93
mssbtst
dddd
mssbtst
bddbsd
J = 7.8
J = 6.6J = 8.1, 1.7
J = 8.1J = 1.7
J = 7.8
J = 6.68.1, 1.5
J = 8.1
βγ Ac Me
A4 Ac Meα
OMeγ652
CDCl3β
γ Ac MeA4 Ac Me
αOMe
γ625
Atom
(acetone)
FPL Collection 10 mgCompound has plane of symmetry
Notes:
281Compound Number
FPL/DFRC NMR Database -- April 2009
13C
45
39
49
39
35
36
20
32
22
25
10.40
31.89
56.22
76.08
108.03
121.13
124.15
136.76
142.08
147.47
CDCl3
CS i
10.70
33.21
56.43
75.70
109.18
121.81
126.11
138.09
143.38
148.56
52
44
60
30
39
43
15
31
16
22
Acetone
CS i
10.33
32.06
55.81
73.71
108.28
120.58
125.54
136.43
142.10
147.36
36
25
37
21
17
19
16
22
18
21
CS i
DMSO
γ
β
OMe
α
2
6
5
1
4
3
Atom
1HJMultH Shifts
0.911.713.884.506.856.99
0.931.793.924.546.876.93
0.841.603.814.344.986.666.878.20
tmstdd
tmstdd
tmsbssdds
J = 7.3
J = 6.36J = 2.0J = 2.0
J = 7.3
J = 6.36J = 2.0J = 2.0
J = 7.34
J = 1.71J = 1.71
γβ
OMeα62
CDCl3γβ
OMeα62
DMSOγβ
OMeα
α OH62
4-OH
Atom
(acetone)
FPL Collection 8mg 1H DMSO shifts in ( )s. Compound has plane of symmetrybeta shifts in acetone taken from DEPT 135 spectrumg-HSQC, g-HMBC all solvents
Notes:
282Compound Number
FPL/DFRC NMR Database -- April 2009
13C
46
55
43
34
48
49
29
19
20
14
21
24
15
25
10.01
20.37
21.23
29.46
56.10
76.86
110.14
120.24
131.15
137.00
138.66
151.37
168.76
170.36
CDCl3
CS i
10.27
20.33
21.04
30.20
56.46
77.29
110.87
120.41
131.87
137.91
140.04
152.64
168.99
170.46
61
71
63
70
66
56
44
24
26
17
31
38
18
35
Acetone
CS i
9.81
19.99
20.82
28.90
56.04
76.03
110.20
118.88
130.12
136.15
138.82
151.14
168.33
169.84
41
52
42
30
40
30
19
13
22
18
23
27
14
30
CS i
DMSO
γ
4 Ac Me
α Ac Me
β
OMe
α
2
6
5
4
1
3
Ac C=O
α Ac C=O
Atom
1HJMultH Shifts
0.91 (0.86)1.87 (1.81)2.03 (2.02)2.07 (2.07)3.87 (3.81) 5.63 (5.58)6.79 (6.67)7.11 (7.11)
0.901.852.082.093.865.636.816.90
tmssst
bsbs
tmssstdd
J = 7.34
J = 6.6
J = 7.34
J = 6.7J = 1.7J = 1.7
γβ
4 Ac Meα Ac Me
OMeα62
CDCl3γβ
4 Ac Meα Ac Me
OMeα62
Atom
(acetone)
FPL Collection 20 mg1H CDCl3 shifts in ( )s. Plane of symmetry runs through moleculeCH2 shift obscured by solvent in acetone, taken from Dept 1352 and 6 switch places in 1H in CDCl3
Notes:
283Compound Number
FPL/DFRC NMR Database -- April 2009
biphenyl methane
13C
39
32
20
38
43
39
33
22
18
13
21
13.78
24.79
29.39
27.80
55.93
109.14
122.36
126.13
134.02
141.01
146.41
CDCl3
CS i
14.04
25.57
29.56
38.42
56.27
110.18
123.13
127.59
133.74
142.84
147.75
47
45
34
49
49
37
45
31
31
30
29
Acetone
CS i
13.59
24.34
28.74
37.10
55.73
109.62
121.77
127.08
132.02
141.72
147.05
23
20
10
21
23
17
18
17
18
14
15
CS i
DMSO
γ
β
CH2
α
OMe
2
6
5
1
4
3
Atom
1HJMultH Shifts
0.87 (0.91)1.53 (1.57)2.41 (2.46)3.79 (3.85)3.94 (3.93)6.57 (6.55)6.63 (6.61)7.23 (6.00)
0.821.472.353.753.746.376.598.22
tmddsbsbdbdbs
tmbtss
bdbds
J = 7.34J = 7.34J = 7.34
J = 1.71J = 1.71
J = 7.34J = 7.34
J = 1.71J = 1.71
γβα
OMeCH2
62
OH
DMSO
γβα
OMeCH2
62
OH
Atom
(acetone)
FPL Collection 5 mg1H--CDCl3 shifts in ( )s. g-HSQC and g-HMBC all solventsObscured 1H shifts taken from g-HSQC in CDCl3A1 and B4 may switch order in CDCl3
Notes:
284Compound Number
FPL/DFRC NMR Database -- April 2009
13C
8410088
596966
10810875
747456
171727473535
11141620156222013
222119
10.1510.2510.30
31.4231.4832.00
56.1556.1556.30
75.8075.8076.02
103.82106.66108.03109.45120.98121.20
123.38132.06134.74135.22136.04141.12142.24142.01145.59
146.79147.44152.39
0.660.881.401.654.134.456.026.456.596.826.887.047.938.14
CDCl3
CS i
10.5110.5910.59
32.9733.1133.27
55.3455.3456.52
75.4275.5775.66
104.50106.31109.13110.37121.58122.17
124.87133.71135.37136.74137.33141.12143.44143.71147.29
148.14148.53153.21
647474
454456
818143
464540
323031363646
13161419269171919
231617
Acetone
CS i
9.9510.0610.26
32.0632.0632.06
55.6855.7455.83
73.5173.6073.66
103.06104.51108.35109.50120.18121.16
124.13132.72133.50135.41135.91139.14142.18142.47146.54
147.28147.59151.70
463943
616161
605165
403935
162017201917
181624182114172319
192318
CS i
DMSO
γγγ
B βC βA β
OMeOMeOMe
A αB αC α
C2C6B2A2B6A6
B5A5C4C1B1A4B4A1C5
B3C3A3
1H--DMSO
B,C γA γ
B,C βAβ
B,C αA αC6C2B6B2A6A2
C4 OHB4 OH
Atom
1HJMultH Shifts
0.760.961.531.743.753.81
4.23 (4.25)4.35 (4.40)4.60 (4.63)6.18 (6.14)6.52 (6.41)6.75 (6.76)6.86 (6.78)6.98 (6.97)7.11 (7.04)
mtmmsstttdbddddd
J = 6.36J = 6.36J = 6.36J = 1.7J = 1.7J = 1.7J = 1.7J = 1.7J = 1.7
B,C γA γ
B,C βA β
OMeOMeC αB αA αC6C2B6B2A6A2
Atom
(acetone)
FPL Collection 20 mgMarginally soluble in CDCl3 and acetone-d6, g-HSQC and g-HMBC in all solvents1H shifts for β and γ taken from HSQC in DMSOβ and α 13C shifts change order in DMSO (HSQC data)
Notes:
285Compound Number
FPL/DFRC NMR Database -- April 2009
α-(4-hydroxy-3,5-dimethoxyphenyl)-glycerol
13C
4747
19
20
22
4242
10
10
2020
56.4056.40
63.24
74.69
75.99
103.03103.03
131.60
134.57
147.28147.28
CDCl3
CS i
56.6056.60
64.24
76.26
76.26
105.32105.32
133.98
135.90
148.32148.32
1313
6
9
9
1212
4
3
77
Acetone
CS i
55.9955.99
63.10
75.49
74.24
104.72104.72
133.58
134.31
147.42147.42
4949
20
20
20
3939
18
19
3434
CS i
DMSO
OMeOMe
γ
β
α
26
1
4
35
Atom
1HJMultH Shifts
3.633.723.814.606.717.09
3.773.813.914.776.64
3.423.493.724.346.58
dmsdsbs
J = 6.11
J = 6.11
γβ
OMeα
2,64 OH
CDCl3γβ
OMeα
2,6
DMSOγβ
OMeα
2,6
Atom
(acetone)
SRX-11012 mgα,β,γ and B3, A5 are too close to assign with certaintyHSCQ and HMBC all solvents
Notes:
286Compound Number
FPL/DFRC NMR Database -- April 2009
13C
2932
2832
3529
3330
22
27
27
23
27
28
5
15
14
9
9
10
10
13.6713.78
24.4224.57
37.8037.99
55.9556.04
60.94
107.18
111.16
113.01
119.20
120.55
137.70
138.19
138.63
143.82
150.37
150.48
153.27
0.880.951.551.652.432.563.833.876.266.476.686.79
0.820.901.471.602.372.533.673.733.796.096.586.706.756.94
CDCl3
CS i
13.9314.04
25.2625.39
38.3638.58
56.2456.38
60.67
108.19
111.12
114.37
120.54
121.41
138.59
138.86
139.80
144.64
151.82
151.94
154.67
1011
1011
1210
1010
7
10
10
9
10
10
2
4
4
3
3
3
3
Acetone
CS i
13.5413.70
24.0824.18
37.0837.28
55.7055.88
60.21
107.36
109.83
113.43
119.39
120.50
136.89
137.90
138.71
142.89
150.31
150.31
153.26
3836
3334
3330
3131
26
25
26
27
28
28
11
20
20
17
34
34
18
CS i
DMSO
AγBγ
AβBβ
BαAα
OMeOMe
A4 OMe
A2
A6
B2
B5
B6
A4
A1
B1
B4
B3
A5
A3
1H-CDCl3γγ
AβBβAαBα
B3 OMeA 3,4 OMe
A6A2B6
B 2,5
1H-DMSOγγββ
AαBα
A4 OMeB3 OMeA3 OMe
A6A2B6B5B2
Atom
1HJMultH Shifts
0.850.931.521.642.412.573.743.783.836.176.586.726.786.95
ttmmbtbtsssdddddd
7.37.37.37.37.37.3
2.02.0
1.7, 8.18.11.7
AγBγAβBβAαBα
A4 OMeB3 OMeA3 OMe
A6A2B6B5B2
Atom
(acetone)
FPL Collection12 mgA5 and B4 may be switched in acetone but confirmed in CDCl3 by 4-OHcorrelation to A5
Notes:
287Compound Number
FPL/DFRC NMR Database -- April 2009
4-O-5
13C
6361
7273
120120
6359
57
58
60
30
61
24
20
29
19
18
20
22
13.4913.63
24.4424.47
37.6737.67
55.8156.04
107.05
111.46
112.75
119.17
120.53
133.56
134.79
138.87
143.84
144.28
147.59
150.10
0.800.861.471.562.352.473.783.805.946.306.416.606.716.78
0.800.871.451.572.342.493.743.766.116.536.576.646.898.39
CDCl3
CS i
13.9114.04
25.4225.42
38.3438.34
56.2856.57
108.23
112.07
114.27
119.60
121.37
133.80
136.58
139.23
145.27
145.58
149.43
151.43
3839
5353
6060
3736
36
37
34
34
33
21
10
18
14
12
13
16
Acetone
CS i
13.4813.67
24.1724.17
36.9636.98
55.5755.90
107.39
110.95
113.17
117.84
120.27
132.29
135.22
137.53
143.77
144.34
148.71
149.71
3132
5959
3739
2829
23
23
24
24
25
20
19
19
16
18
19
18
CS i
DMSO
γγ
ββ
αα
OMeOMe
A2
A6
B2
B5
B6
A1
A4
B1
B4
A5
A3
B3
1H CDCl3γγ
A βB βA αB α
B OMeA OMe4 OHA6A2B6B5B2
1H DMSOγγ
A βB βA αB α
B OMeA OMe
A6A2B6B5B2
4 OH
Atom
1HJMultH Shifts
0.850.981.521.622.412.553.803.836.256.586.696.746.92
ttmmbtbtssdddddd
7.37.37.37.37.37.3
2.02.0
1.7, 8.38.31.7
γγ
A βB βA αB α
B OMeA OMe
A6A2B6B5B2
Atom
(acetone)
SRX-110BAc12 mgα, β, γ shifts are too close to assign with absolute certaintyB2 and B5 change order in CDCl3 1H
Notes:
288Compound Number
FPL/DFRC NMR Database -- April 2009
4-O-5
13C
4338
32
3837
3637
6262
36
36
35
36
36
9
2021
15
16
1717
14
13.7313.78
20.39
24.3324.57
37.8338.23
56.0856.08
106.59
110.36
113.16
120.40
120.82
128.18
139.36141.02
143.25
150.12
150.73152.11
168.70
0.890.951.551.652.242.452.563.823.826.256.496.686.786.85
0.810.881.471.582.152.392.513.703.746.096.626.696.746.92
CDCl3
CS i
13.9414.02
20.25
25.2225.37
38.3738.73
56.2456.44
107.26
110.24
114.39
121.55
121.55
129.04
140.62141.66
143.86
151.45
152.14153.44
168.57
3432
27
3133
3232
3032
31
30
28
63
63
5
1415
9
9
1110
9
Acetone
CS i
13.5213.61
20.05
24.0024.09
37.0337.36
55.6355.96
106.58
108.99
113.39
120.23
120.53
127.29
139.39140.63
142.07
149.76
150.53151.94
168.04
4040
36
3638
3232
3736
26
26
28
30
21
15
1628
22
23
2525
19
CS i
DMSO
A γB γ
Ac Me
A βB β
B αA α
B OMeA OMe
A2
A6
B2
B5
B6
A4
B1A1
B4
A5
B3A3
OAc C=O
1H--CDCl3γγ
A βB β
Ac MeA αB α
B OMeA OMe
A6A2B6B2B5
1H--DMSOγγ
A βB β
Ac MeA αB α
B OMeA OMe
A6A2B6B5B2
Atom
1HJMultH Shifts
0.860.931.531.642.202.452.573.773.816.186.636.736.826.96
ttmmsbtbtssdddddd
7.37.37.37.3
7.37.3
1.71.7
2.0, 8.38.32.0
γBγA βB β
Ac MeA αB α
B OMeA OMe
A6A2B6B5B2
Atom
(acetone)
FPL Collection 2 mgCOSY, HSQC and HMBC in acetone at 600MHz1H in CDCl3 some shifts taken from HSQC and HMBCAromatic carbon shifts in DMSO are weak, no 2D spectra in DMSO
Notes:
289Compound Number
FPL/DFRC NMR Database -- April 2009
13C
3935403226253629171225464632272727811161512143812671616689202089121717
9.799.859.9020.2120.3221.1221.1621.2228.9429.2129.4656.0056.0056.0776.8376.8876.88103.60105.82110.40110.70120.30120.78128.02130.86131.77136.95137.84138.16138.16140.05150.42151.11152.20152.20167.92168.77170.30170.40170.40
1H
0.720.790.891.721.721.861.992.072.102.162.213.713.743.795.455.545.636.136.466.826.766.816.87
CDCl3
CS i
10.1910.1910.1920.1820.1820.4621.2521.3629.7729.9730.1856.3856.3856.6577.2877.2877.28104.30106.11110.99111.63119.42120.81128.90131.83133.47137.91139.40139.65139.65140.78151.59152.36153.33153.33167.62169.09169.09170.37170.50
65656527272040272020204646323535351210141212157867101313810914147891215
Acetone
CS i
9.579.579.5719.7719.8820.5920.6820.8028.5028.6828.8455.8955.8955.8975.9475.9475.94103.38106.53110.12110.88119.39119.64127.11130.23130.83136.20138.03138.31138.50138.96149.99150.84151.80151.80167.29168.23169.71169.71169.71
1H
0.710.780.861.671.671.841.92
|||
2.153.673.723.765.425.495.616.036.626.706.706.997.13
636363272318272922152434343437373788811615786101015109413141489181818
CS i
DMSO
γγγ
C4AcMeB4AcMeAαAcMeCαAcMeBαAcMe
ββ
B βOMeOMeOMe
ααα
C2C6A2B2B6A6C4A5B5A4B1A1C1B4C5A3B3C3
C4AcC=OB4AcC=OAαAcC=OCαAcC=OBαAcC=O
1H CDCl3
γγ
B γββ
B βAcMe CαAcMe AαAcMe BαAcMe B4AcMe C4
OMeOMeOMeCαAαBαC6C2B6A6A2B2
Atom
1HJMultH Shifts
0.780.820.911.731.881.952.042.052.102.163.733.763.815.465.555.656.206.646.816.836.997.13
γγ
B γA,C βB β
AcMe CαAcMe AαAcMe BαAcMe B4AcMe C4
OMeOMeOMeCαAαBαC6C2B6A6A2B2
Atom
(acetone)
FPL Collection22 mgHSQC and HMBC in acetone
Notes:
290Compound Number
FPL/DFRC NMR Database -- April 2009
1-(3,5-dimethoxy-4-hydroxy)-propanol
13C
27
27
5757
24
4545
11
16
2323
10.19
31.87
56.2356.23
76.20
102.60102.60
133.91
135.87
146.91146.91
CDCl3
CS i
10.61
33.24
56.5956.59
75.81
104.32104.32
135.66
137.56
148.41148.41
47
36
9393
29
8787
11
22
2525
Acetone
CS i
10.32
32.16
55.9555.95
73.92
103.33103.33
134.10
136.44
147.65147.65
25
21
4848
20
3535
14
17
3131
CS i
DMSO
γ
β
OMeOMe
α
26
4
1
35
Atom
1HJMultH Shifts
0.871.663.794.446.636.99
0.911.753.884.506.57
0.791.563.724.306.548.08
tmsbtss
7.3
6.4
γβ
OMeα
2,64 OH
CDCl3γβ
OMeα
2,6
DMSOγβ
OMeα
2,64 OH
Atom
(acetone)
SRX-115G 26 mgHSQC in acetone and CDCl3, HMBC in acetoneHSQC shows that C2 is downfield of C5 for acetone and CDCl3C2 = C5 in DMSO
Notes:
291Compound Number
FPL/DFRC NMR Database -- April 2009
13C
60
6860
57
59
52
62
8
8
7
10
22.77
55.9756.06
68.78
110.13
110.68
123.32
126.16
149.25
153.96
200.73
1.273.813.845.055.217.067.487.69
CDCl3
CS i
22.59
56.1456.24
69.53
111.62
111.95
124.22
127.80
150.30
155.01
201.30
67
8981
46
80
77
81
9
9
7
8
Acetone
CS i
21.09
55.5455.75
68.31
110.89
110.89
123.31
127.38
148.61
153.11
200.09
67
6362
62
105
105
68
15
12
10
15
CS i
DMSO
γ
OMeOMe
β
5
2
6
1
3
4
α
1H--DMSO
γOMeOMe
ββ OH
526
Atom
1HJMultH Shifts
1.353.873.905.147.067.547.68
1.433.923.935.106.897.497.49
dssqdddd
6.85
6.858.62.0
8.6, 2.0
γOMeOMe
β526
CDCl3
γOMeOMe
β526
Atom
(acetone)
SRX-115S39 mgHSQC and HMBC in acetone
Notes:
292Compound Number
FPL/DFRC NMR Database -- April 2009
1-(3,4,5-trimethoxyphenyl)-1-propanol
13C
46
66
9797
24
34
113113
3
9
1616
10.06
31.84
55.8655.86
60.57
75.80
102.68102.68
136.84
140.60
152.96152.96
CDCl3
CS i
10.58
33.20
56.3256.32
60.44
75.69
104.06104.06
137.95
142.75
154.08154.08
79
83
142142
38
55
144144
3
12
1414
Acetone
CS i
10.29
32.08
55.7855.78
59.98
73.81
103.00103.00
136.05
142.09
152.55152.55
90
91
183183
60
92
179179
9
30
3838
CS i
DMSO
γ
β
OMeOMe
4 OMe
α
26
4
1
35
Atom
1HJMultH Shifts
0.891.673.683.794.124.486.65
0.931.763.823.864.526.58
0.811.563.603.734.355.086.59
tmssdbts
7.3
4.06.4
γβ
4 OMeOMe
αα OH
2,6CDCl3
γβ
4 OMeOMe
α2,6
DMSOγβ
4 OMeOMe
ααOH2,6
Atom
(acetone)
FPL Collection 20 mgg-HSQC and g-HMBC in d6-acetone2 isomers 1H minor shifts and j's in ( )
Notes:
293Compound Number
FPL/DFRC NMR Database -- April 2009
13C
5567464952535410107
19671917252622444
18.3456.8372.2578.37110.18115.09120.61133.49146.17147.55
19.6756.8373.1580.27110.12115.16120.90134.08146.40147.61
CDCl3
CS i
18.0856.2072.0378.15111.20115.09120.32134.95146.39147.81
19.3056.2072.6879.80111.27115.21120.66134.90146.77148.02
8274656670707414118
33742526343129944
Acetone
CS i
18.4255.5670.6776.83111.04114.65119.26134.56145.16146.97
19.0055.5670.8977.79111.12114.76119.50133.98145.46147.04
41523840303436222016
165216141517141099
CS i
DMSO
major
γOMe
βα256143
minor isomer
γOMe
βα256143
Atom
1HJMultH Shifts
1.02 (0.92)3.81 (3.69)3.80 (3.80)4.45 (4.20)6.73 (6.73)6.77 (6.77)6.98 (6.95)
1.03 (0.96)3.87 (3.74)3.81 (3.81)4.49 (4.20)
0.93 (0.77)3.56 (3.56)3.69 (3.69)4.20 (4.09)6.64 (6.64)6.83 (6.81)
dmsddddd
6.4
5.1 (7.3)8.1
8.1, 1.71.7
γβ
OMeα562
CDCl3γβ
OMeα
DMSOγβ
OMeα
5,62
Atom
(acetone)
SRX-115SSMAc19 mgC4 has very long T1, D1 set to 6 sec.
Notes:
294Compound Number
FPL/DFRC NMR Database -- April 2009
13C
40
3226
50
8888
49
9797
311
1717
65
10.01
20.4121.20
29.30
56.1056.10
77.26
103.29103.29
128.18138.92
152.01152.01
168.65170.25
CDCl3
CS i
10.29
20.2621.04
30.13
56.4556.45
77.61
103.86103.86
129.21140.45
153.13153.13
168.55170.39
66
4737
112
135135
71
121121
314
1414
108
Acetone
CS i
9.93
20.1420.90
28.96
55.9855.98
76.49
102.85102.85
127.27139.33
151.60151.60
168.14169.89
59
5754
50
116116
52
9393
1138
5555
2724
CS i
DMSO
γ
4 Ac Meα Ac Me
β
OMeOMe
α
26
41
35
4 Ac C=Oα Ac C=O
Atom
1HJMultH Shifts
0.881.832.052.213.805.616.71
0.911.852.092.333.825.626.58
0.851.802.072.223.745.566.68
tmsss
dds
7.3
7.3
γβ
α Ac Me4 Ac Me
OMeα
2,6CDCl3
γβ
Ac Me Ac MeOMe
α2,6
DMSOγβ
Ac Me Ac MeOMe
α2,6
Atom
(acetone)
SRX-115GAc12 mgg-HSQC and g-HMBC in d6-acetone
Notes:
295Compound Number
FPL/DFRC NMR Database -- April 2009
13C
60
42
6859
57
58
56
61
14
10
10
11
12
17.40
20.69
55.9256.03
70.95
110.10
110.66
122.92
127.29
149.23
153.70
170.35
195.21
CDCl3
CS i
17.70
20.60
56.1256.25
71.98
111.66
111.69
123.75
128.23
150.39
154.98
170.47
195.54
61
38
6558
53
75
75
61
10
8
8
7
7
Acetone
CS i
17.32
20.42
55.5555.80
71.13
110.45
111.05
123.08
126.48
148.83
153.57
169.78
194.95
48
38
4643
45
37
44
44
11
10
10
10
11
CS i
DMSO
γ
AcMe
OMeOMe
β
5
2
6
1
3
4
Ac C=O
α
Atom
1HJMultH Shifts
1.462.053.863.905.977.067.507.67
1.532.15
3.93, 3.965.966.917.527.59
1.402.06
3.81, 3.855.997.087.437.68
dsssqdddd
6.85
6.858.62.0
8.6, 2.0
γAcMe3 OMe4 OMe
β526
CDCl3γ
AcMe OMe
β526
DMSOγ
AcMe OMe
β526
Atom
(acetone)
SRX-115SAc29mgg-HMBC in d6-acetone
Notes:
296Compound Number
FPL/DFRC NMR Database -- April 2009
13C
60
38
59
120120
38
63
117117
185
2424
10
9.92
21.13
29.20
55.9855.98
60.63
77.41
103.58103.58
136.12137.45
153.08153.08
170.26
CDCl3
CS i
10.30
21.05
30.13
56.4356.43
60.45
77.75
104.71104.71
137.56138.71
154.32154.32
170.37
53
29
53
9696
31
49
7676
114
1414
6
Acetone
CS i
9.90
20.89
28.90
55.8655.86
59.91
76.60
103.49103.49
136.39136.85
152.80152.80
169.83
46
32
42
8383
29
44
7777
164
2020
9
CS i
DMSO
γ
α Ac Me
β
3 OMe5 OMe
4 OMe
α
26
14
35
α Ac C=O
Atom
1HJMultH Shifts
0.861.822.033.693.815.566.64
0.901.852.093.833.875.596.55
0.821.772.053.633.765.526.60
tmsssbts
7.3
6.6
γβ
α Ac Me4 OMe
3,5 OMeα
2,6CDCl3
γβ
α Ac Me4 OMe
3,5 OMeα
2,6DMSO
γβ
α Ac Me4 OMe
3,5 OMeα
2,6
Atom
(acetone)
S. RalphCarbon pairs 2 & 5 and 3 & 4 are to close for definitive assignment
Notes:
297Compound Number
FPL/DFRC NMR Database -- April 2009
Veratryl alcohol methyl ether
13C
6157
27
44
4949
51
7
44
55.8055.89
57.86
74.61
110.84110.99
120.29
130.73
148.58149.02
CDCl3
CS i
56.0356.12
57.74
74.86
112.49112.60
120.95
132.16
149.89150.34
5856
28
45
4746
48
8
55
Acetone
CS i
55.3755.46
57.15
73.55
111.45111.50
120.03
130.65
148.23148.64
126117
60
106
141146
128
19
1213
CS i
DMSO
OMeOMe
α OMe
α
2 or 55 or 2
6
1
3 or 44 or 3
Atom
1HJMultH Shifts
3.273.783.794.336.836.896.91
4.376.816.856.87
4.316.836.896.90
ssss
dddd
8.1, 2.08.12.0
α OMeOMeOMe
α-CH2652
CDCl3α-CH2
562
DMSOα-CH2
625
Atom
(acetone)
FPL - Pearl Collection30 mg, beta under B3,5 shift from APT experiment, HSQC and HMBC all solventsSome 1H shifts taken from HSBC expt.s
Notes:
298Compound Number
FPL/DFRC NMR Database -- April 2009
3-Methoxy-4-hydroxy stilbene carboxylic acid
13C
29
36
37
41
14
39
75
75
75
73
73
8
30
7
11
6
55.25
112.07
114.19
126.78
126.73
127.90
128.91
128.91
128.91
130.03
130.03
136.18
142.49
145.76
147.37
172.08
CDCl3
CS i
55.42
113.60
115.58
126.69
127.30
128.25
129.48
129.48
130.55
130.81
130.81
138.15
141.18
147.68
148.91
169.12
31
30
34
34
7
34
64
64
7
65
65
5
30
5
8
7
Acetone
CS i
54.61
113.05
115.11
125.35
125.35
127.28
128.59
128.59
129.64
129.66
129.66
137.15
139.52
146.88
148.05
168.58
36
29
29
30
20
30
63
63
9
76
76
15
25
14
18
16
CS i
DMSO
OMe
A2
A5
A6
A1
B4
B3
B5
β
B2
B6
B1
α
A3
A4
γ
Atom
1HJMultH Shifts
3.386.506.716.807.277.367.437.80
6.416.776.837.29
7.37, 7.417.87
6.416.646.667.19
7.35, 7.417.66
sddddmmms
2.08.1
8.1, 2.0
OMeA2A5A6
B 2,6B4
B 3,5α
CDCl3 A2A5A6
B 2,6B4, B 3,5
α
DMSOA2A5A6
B 2,6B4, B 3,5
α
Atom
(acetone)
SR X 125D1-2B5 and B6 change order in CDCl31H shifts in CDCl3 in ( )s after acetone shiftC6, C5 and B2 shifts from HSQC
Notes:
299Compound Number
FPL/DFRC NMR Database -- April 2009
beta-O-4, 5-O-4 trimer
13C
6453
89895551
797687
708283
56756855
5539445862578175
393838283124
27313232
29323230
9.8313.85
20.6820.6821.0321.19
24.6329.2737.89
55.6355.7556.01
62.7774.2277.0380.66
104.53108.03111.51112.97119.46120.75120.43122.30
135.88136.35136.35139.38139.64142.32
150.58150.78150.98153.40
168.98169.67170.28170.93
CDCl3
CS i
10.0814.04
20.4620.5320.8920.95
25.3830.0238.39
56.1156.1156.42
63.3975.2077.3081.27
105.23107.60112.18114.27120.06121.57121.75123.25
136.38136.94137.60140.66140.90143.02
152.04152.04152.12154.40
168.91169.96170.17170.66
4338
55324441
559862
626249
55375141
3926466255573158
61284105
1717810
9877
Acetone
CS i CS i
DMSO
AγBγ
C4 Ac MeCγ Ac Meα Ac Meα Ac Me
BβAβBα
OMeOMe
A OMe
CγCαAαCβ
A2A6C2B2C6B6B5C5
A4C1A1C4B1B4
B3C3A5A3
C4 Ac C=OCα Ac C=OAα Ac C=OCγ Ac C=O
Atom
1HJMultH Shifts
0.79 (0.79)0.94 (0.97)
1.6-1.75 (1.66-1.76)1.78 (1.86)1.93 (2.01)2.08 (2.10)2.20 (2.28)2.60 (2.59)3.70 (3.69)3.74 (3.72)3.82 (3.76)4.21 (4.26)4.41 (4.47)4.98 (4.90)5.44 (5.44)6.13 (6.14)6.24 (6.27)6.69 (6.52)6.80 (6.70)6.90 (6.80)6.97 (6.92)6.98 (6.91)6.99 (6.77)7.15 (7.02)
ttmdsssmdss
ddddmtdbsbsddd
bs
7.37.3
1.0
2.2
4.2, 11.75.9, 11.7
7.34.4
2.0, 8.18.1
AγBγ
Bβ--AβCγ Ac MeAα Ac MeCα Ac MeC4 Ac Me
BαC OMeB OMeA OMe
Cγ1Cγ2CβAαCαA6A2B6B5C6C5B2C2
Atom
(acetone)
SRX-146CA4-OH has strong HMBC correlations in DMSO to A3,4 ,5
Notes:
300Compound Number
FPL/DFRC NMR Database -- April 2009
5-O-4 diacetovanillone
13C
4946
6866
6547
614775
1696
1010910
109
25.9226.09
56.1756.50
107.30112.30
114.80116.82122.48
129.24133.33142.21
142.41148.16150.08150.43
195.70196.37
CDCl3
CS i
26.3326.47
56.3656.76
108.56112.68
115.45116.80123.22
129.73133.65143.16
144.09149.67150.73151.69
195.93196.55
4443
4949
4544
474447
13128
7998
1110
Acetone
CS i
26.3226.51
55.7956.23
108.09111.65
114.62115.44122.51
127.91132.01141.97
143.37148.83149.09150.44
195.87196.50
5544
4947
3534
343438
261815
19172014
1817
CS i
DMSO
AβBβ
B OMeA OMe
A2B2
A6B5B6
A1B1A5
A4A3B3B4
AαBα
Atom
1HJMultH Shifts
2.49 (2.48)2.53 (2.56)3.93 (3.95)3.95 (3.99)6.78 (6.85)7.30 (7.28)7.47 (7.41)7.56 (7.49)7.64 (7.63)
2.492.553.903.926.677.257.427.547.5910.00
ssssdddddd
8.32.02.0
8.3, 2.02.0
AβBβ
OMeOMeB5A6A2B6B2
DMSO
AβBβ
OMeOMeB5A6A2B6B2
A4-OH
Atom
(acetone)
FPL collectionA2 and B2 change order in DMSO1H DMSO chemical shifts in ( )’s13C C6 shift assignments not confirmed, also C5s in CDCl3
Notes:
301Compound Number
FPL/DFRC NMR Database -- April 2009
guaiacyl chalcone
13C
108122
126125121126
122
130146
1812
122
15152022
13
55.9956.09
110.07110.50113.71114.85
119.25
123.13123.49
127.62131.22
144.33
146.79146.85148.12150.21
188.62
CDCl3
CS i
56.3456.40
111.95112.05115.36116.14
119.87
124.15124.21
128.33131.84
144.36
148.54148.74150.10152.17
187.90
4542
50493533
47
5654
77
47
5454
7
Acetone
CS i
55.7055.84
111.79111.57114.92115.60
118.71
123.55123.70
126.51129.85
143.60
147.78147.96149.41151.66
187.02
4545
26253133
33
3235
2521
36
17172322
19
CS i
DMSO
OMeOMe
B2A2A5B5
β
66
B1A1
γ
A3B3B4A4
α
Atom
1HJMultH Shifts
3.93 (3.87)6.83 (6.83)6.93 (6.97)7.29 (7.28)7.49 (7.49)7.61 (7.61)7.63 (7.63)7.76 (7.76)7.80 (7.80)
3.933.956.936.977.107.207.377.617.627.73
bsdddddddddd
ssdddddddddd
8.38.3
1.7, 8.31.71.715.415.4
1.7, 8.3
8.38.31.96
1.96, 8.315.4
obscuredobscured
15.4
OMeB5A5B6B2A2γβ
A6
CDCl3
OMeOMe
55
B2B6β
A2A6γ
Atom
(acetone)
S. RalphNotes:
302Compound Number
FPL/DFRC NMR Database -- April 2009
3,4,5-trimethoxy cinnamyl alcohol
13C
145145
45
70
109109
7066
164
2626
55.9955.99
60.85
63.47
103.47103.47
128.04130.92
132.40137.78
153.22153.22
CDCl3
CS i
56.3356.33
60.53
63.17
104.55104.55
130.11130.32
133.87138.76
154.41154.41
140140
37
67
146146
7166
113
2222
Acetone
CS i
55.7855.78
59.99
61.43
103.43103.43
128.55130.16
132.65136.83
152.94152.94
7070
28
31
6060
3131
176
2626
CS i
DMSO
3 OMe5 OMe
4 OMe
γ
26
αβ
14
35
Atom
1HJMultH Shifts
3.69 (3.81)3.82 (3.83)
3.894.21 (4.28)6.32 (6.24)6.53 (6.50)6.72 (6.57)
3.643.784.106.336.476.72
sstdtdtbts
5.41.5, 5.415.9, 5.215.9, 1.5
4 OMe3,5 OMe
OHγβα
2,6
DMSO
4 OMe3,5 OMe
γβα
2,6
Atom
(acetone)
R. HelmNotes:
1001Compound Number
FPL/DFRC NMR Database -- April 2009
3-(4-Hydroxyphenyl)acrylic acid3-hydroxy-1-(4-hydroxy-3-methoxyphenyl)-2-(2-methoxyphenoxy)propyl ester
13CCDCl3
CS i
56.2556.31
61.7675.8885.20
112.04113.58115.58
115.81
116.64116.64119.36121.23121.78
123.24127.04130.16130.91130.91
145.39
147.48148.18149.82151.87160.48
166.51
Acetone
CS i CS i
DMSO
OMeOMe
γα
β
A2B2A5
C β
C3C5B5A6B6
B1C1A1C2C6
C α
A4A3B4B3C4
C γ
Atom
1HJMultH Shifts
3.51
3.68
4.58
6.16
6.30
7.51
dd
dd
m
d
d
d
7.2, 5.3
7.2, 3.7
7.3
16.0
15.6
γ1
γ2
β
α
C β
C α
Atom
(acetone)
threo
R. HelmNotes:
1002Compound Number
FPL/DFRC NMR Database -- April 2009
3-(4-Hydroxyphenyl)acrylicacid 3-hydroxy-1-(4-hydroxy-3-methoxyphenyl)-2-(2-methoxyphenoxy)propyl ester
13CCDCl3
CS i
56.2956.29
61.4975.0884.09
112.57113.67115.21
115.62
116.67116.67119.18121.75121.79
123.31126.97129.64130.96130.96
145.65
147.35147.99149.22151.86160.59
166.32
Acetone
CS i CS i
DMSO
OMeOMe
γα
β
A2B2A5
C β
C3C5B5B6A6
B1C1A1C2C6
C α
A4A3B4B3C4
C γ
Atom
1HJMultH Shifts
3.68
3.79
4.66
6.12
6.35
7.56
dd
dd
m
d
d
d
11.7, 4.8
11.8, 5.7
4.8
16.0
16.0
γ1
γ2
β
α
C β
C α
Atom
(acetone)
erythro
R. HelmNotes:
1003Compound Number
FPL/DFRC NMR Database -- April 2009
3-(4-Hydroxy-3-methoxyphenyl)acrylicacid3-hydroxy-1-(4-hydroxy-3-methoxyphenyl)-2-(2-methoxyphenoxy)propyl ester
13CCDCl3
CS i
56.2256.3156.31
61.7475.8785.13
111.26112.04113.54115.59
115.99
116.03119.25121.20121.76123.21123.91127.44130.15
145.77
147.50148.19148.70149.78150.02151.82
166.55
Acetone
CS i CS i
DMSO
OMeOMeOMe
γα
β
C2A2B2A5
C β
C5B5A6B6B1C6C1A1
C α
A4A3C3B4C4B3
C γ
Atom
1HJMultH Shifts
3.52
3.69
4.58
6.16
6.34
7.49
dd
dd
m
d
d
d
11.9, 5 .3
11.9, 3.8
2.3
15.9
15.9
γ1
γ2
β
α
C β
C α
Atom
(acetone)
threo
R. HelmCDCl3 column is D2O/Acetone-d6
Notes:
1004Compound Number
FPL/DFRC NMR Database -- April 2009
3-(4-Hydroxy-3-methoxyphenyl)acrylic acid3-hydroxy-1-(4-hydroxy-3-methoxyphenyl)-2-(2-methoxyphenoxy)propyl ester
13C
Acet/D2O56.3056.3156.33
61.3875.1084.00
111.32112.64113.68115.17
115.84
116.01119.07121.77121.82123.28124.00127.40129.62
146.02
147.32147.97148.72149.23150.08151.85
166.35
CDCl3
CS i
56.2856.3056.32
61.4875.0984.02
111.29112.60113.66115.22
115.83
116.04119.10121.96121.80123.30123.99127.40129.63
146.02
147.36147.98148.71149.19150.09151.84
166.34
Acetone
CS i CS i
DMSO
OMeOMeOMe
γα
β
C2A2B2A5
Cβ
C5B5B6A6B1C6C1A1
C α
A4A3C3B4C4B3
C γ
Atom
1HJMultH Shifts
3.60
3.79
4.67
6.13
6.39
7.55
dd
dd
m
d
d
d
11.7, 4.8
11.5, 5.8
4.8
15.9
15.9
γ 1
γ 2
β
α
C β
C α
Atom
(acetone)
erythro
R. HelmNotes:
1005Compound Number
FPL/DFRC NMR Database -- April 2009
3-(4-Acetoxyphenyl)acrylic acid 3-acetoxy-1-(4-acetoxy-3-methoxyphenyl)-2-(2-methoxyphenoxy)propyl ester
13CCDCl3
CS i
20.4420.6020.9456.1656.32
63.7075.8180.87
112.71113.66
118.76
119.33120.31121.65123.21123.21123.61123.78130.22130.22132.82136.74140.95
144.91
149.12151.89152.24153.52
165.90
168.86169.42170.69
Acetone
CS i CS i
DMSO
Ac MeAc MeAc MeOMeOMe
γα
β
A2B2
Cβ
B5A6B6C3C5A5B1C2C6C1A1A4
C α
B4B3A3C4
C γ
Ac C=OAc C=OAc C=O
Atom
1HJMultH Shifts
4.08
4.31
4.89
6.24
6.52
7.63
dd
dd
m
d
d
d
11.9, 5.6
11.9, 4.1
6.6
16.0
16.0
γ1
γ2
β
α
C β
C α
Atom
(acetone)
threo
R. HelmNotes:
1006Compound Number
FPL/DFRC NMR Database -- April 2009
3-(4-Acetoxyphenyl) acrylic acid 3-acetoxy-1-(4-acetoxy-3-methoxyphenyl)-2-(2-methoxyphenoxy) propyl ester
13CCDCl3
CS i
20.4520.6120.94
56.2256.30
63.1674.9680.44
112.79113.80
118.67
119.89120.45121.68123.24123.24123.40124.08130.28130.28132.82136.63140.83
145.12
148.39152.06152.14153.58
165.79
168.89169.42170.75
Acetone
CS i CS i
DMSO
Ac MeAc MeAc Me
OMeOMe
γα
β
A2B2
C β
B5A6B6C3C5A5B1C2C6C1A1A4
C α
B4B3A3C4
C γ
Ac C=OAc C=OAc C=O
Atom
1HJMultH Shifts
4.29
4.41
4.93
6.22
6.61
7.71
dd
dd
m
d
d
d
11.9, 4.4
11.9, 6.1
4.7
16.1
16.1
γ 1
γ2
β
α
C β
C α
Atom
(acetone)
erythro
R. Helm16mg
Notes:
1007Compound Number
FPL/DFRC NMR Database -- April 2009
3-(4-Acetoxy-3-methoxyphenyl) acrylic acid 3-acetoxy-1-(4-acetoxy-3-methoxyphenyl)-2-(2-methoxyphenoxy) propyl ester
13CCDCl3
CS i
20.4420.4420.60
56.1656.3256.40
63.7075.8280.88
112.42112.72113.65
118.85
119.30120.30121.65122.27123.61123.77124.12134.15136.77140.95142.76
145.36
149.13151.88152.24152.67
165.96
168.79168.86170.69
Acetone
CS i CS i
DMSO
Ac MeAc MeAc Me
OMeOMeOMe
γα
β
C2A2B2
C β
B5A6B6C6A5B1C5C1A1A4C4
C α
B4B3A3C3
C γ
Ac C=OAc C=OAc C=O
Atom
1HJMultH Shifts
4.09
4.30
4.89
6.24
6.56
7.60
dd
dd
m
d
d
d
11.9, 5.6
11.9, 4.1
6.5
15.8
γ1
γ2
β
α
C β
C α
Atom
(acetone)
threo
R. Helm19mgAcetone run at 300 K
Notes:
1008Compound Number
FPL/DFRC NMR Database -- April 2009
3-(4-Acetoxy-3-methoxyphenyl) acrylic acid 3-acetoxy-1-(4-acetoxy-3-methoxyphenyl)-2-(2-methoxyphenoxy) propyl ester
13CCDCl3
CS i
20.4420.4420.61
56.2256.3056.41
63.1674.9780.39
112.46112.79113.79
118.75
119.85120.43121.68122.35123.41124.08124.14134.13136.61140.83142.82
145.57
148.37152.05152.14152.69
165.89
168.79168.90170.76
Acetone
CS i CS i
DMSO
Ac MeAc MeAc Me
OMeOMeOMe
γα
β
C2A2B2
C β
B5A6B6C6A5B1C5C1A1A4C4
C α
B4B3A3C3
C γ
Ac C=OAc C=OAc C=O
Atom
1HJMultH Shifts
4.28
4.40
4.96
6.22
6.65
7.68
dd
dd
m
d
d
d
11.8, 4.4
11.8, 6.1
4.7
16.0
16.0
γ1
γ2
β
α
C α
C β
Atom
(acetone)
erythro
R. Helm25.5mgacetone-d6 at 300 K
Notes:
1009Compound Number
FPL/DFRC NMR Database -- April 2009
3-(4-Acetoxyphenyl) acrylic acid 3-(4-acetoxy-3- methoxyphenyl)-2-(2-methoxyphenoxy)-3-oxopropyl ester
13CCDCl3
CS i
20.4520.94
56.1056.42
64.9780.56
113.46113.84
118.32
118.69121.64122.88123.24123.24124.02124.07130.27130.27132.68134.86
145.09
145.34147.84151.42152.49153.58
166.76
168.58169.42
195.13
Acetone
CS i CS i
DMSO
Ac MeAc Me
OMeOMe
γ
β
A2B2
C β
B5B6A6C3C5A5B1C2C6C1A1
C α
A4B4B3A3C4
C γ
Ac C=OAc C=O
α
Atom
1HJMultH Shifts
4.62
4.81
5.91
6.48
7.60
dd
dd
dd
d
d
12.0, 6.5
12.0, 3.8
6.5, 3.8
16.0
16.0
γ1
γ2
β
C β
C α
Atom
(acetone)
R. Helm25mg300k, acetone-d6
Notes:
1010Compound Number
FPL/DFRC NMR Database -- April 2009
3-(4-Acetoxy-3-methoxyphenyl) acrylic acid 3-(4-acetoxy-3-methoxyphenyl)-2-(2-methoxyphenoxy)-3-oxopropyl ester
13CCDCl3
CS i
20.4420.44
56.1056.4056.43
64.9380.54
112.41113.48113.83
118.44
118.62121.64122.35122.87124.03124.06124.15134.01134.85142.83145.35
145.50
147.82151.40152.50152.69
166.81
168.58168.80
195.11
Acetone
CS i CS i
DMSO
Ac MeAc Me
OMeOMeOMe
γ
β
C2A2B2
C β
B5B6C6A6A5B1C5C1A1C4A4
C α
B4B3A3C3
C γ
Ac C=OAc C=O
α
Atom
1HJMultH Shifts
4.61
4.81
5.91
6.52
7.58
dd
dd
dd
d
d
12.0, 6.5
12.0, 3.8
6.5, 3.8
16.0
16.0
γ1
γ2
β
Cβ
C α
Atom
(acetone)
R. HelmNotes:
1011Compound Number
FPL/DFRC NMR Database -- April 2009
3-(4-Acetoxyphenyl) acrylic acid 3-(4-acetoxy-3-methoxyphenyl)-3-hydroxy-2-(2-methoxyphenoxy) propyl ester
13CCDCl3
CS i
64.28
73.58
83.80
118.73
144.57
166.68
Acetone
CS i CS i
DMSO
γ
α
β
C β
C α
C γ
Atom
1HJMultH Shifts
5.08
4.75
4.64
4.17
4.44
6.46
7.54
d
m
dd
dd
d
d
4.3
11.9, 6.3
11.9, 3.7
16.1
16.0
α
α OH
β
γ1
γ2
C β
C α
Atom
(acetone)
threo
R. HelmNotes:
1012Compound Number
FPL/DFRC NMR Database -- April 2009
3-(4-Acetoxyphenyl) acrylic acid 3-(4-acetoxy-3-methoxyphenyl)-3-hydroxy-2-(2-methoxyphenoxy) propyl ester
13CCDCl3
CS i
63.95
73.16
83.22
118.83
144.36
166.79
Acetone
CS i CS i
DMSO
γ
α
β
C β
C α
C γ
Atom
1HJMultH Shifts
5.09
4.80
4.70
4.45
4.52
6.41
7.50
d
m
dd
dd
d
d
4.4
11.8, 3.7
11.8, 6.3
16.1
16.1
α
α OH
β
γ1
γ2
C β
C α
Atom
(acetone)
erythro
R. HelmNotes:
1013Compound Number
FPL/DFRC NMR Database -- April 2009
3-(4-Acetoxy-3-methoxyphenyl) acrylic acid 3-(4-acetoxy-3-methoxyphenyl)-3-hydroxy-2-(2-methoxyphenoxy) propyl ester
13CCDCl3
CS i
64.27
73.56
83.73
118.81
144.94
166.72
Acetone
CS i CS i
DMSO
γ
α
β
C β
C α
C γ
Atom
1HJMultH Shifts
5.08
4.75
4.64
4.17
4.44
6.49
7.51
d
m
dd
dd
d
d
4.2
11.9, 6.2
11.9, 3.7
16.0
16.0
α
α OH
β
γ1
γ2
Cβ
C α
Atom
(acetone)
threo
R. HelmNotes:
1014Compound Number
FPL/DFRC NMR Database -- April 2009
3-(4-Acetoxy-3-methoxyphenyl) acrylic acid 3-(4-acetoxy-3-methoxyphenyl)-3-hydroxy-2-(2-methoxyphenoxy) propyl ester
13CCDCl3
CS i
63.93
73.14
83.18
118.91
144.79
166.83
Acetone
CS i CS i
DMSO
γ
α
β
C β
C α
C γ
Atom
1HJMultH Shifts
5.08
4.79
4.70
4.45
4.58
6.44
7.47
d
m
dd
dd
d
d
4.4
11.8, 3.7
11.8, 6.2
16.0
16.0
α
α OH
β
γ1
γ2
C β
C α
Atom
(acetone)
erythro
R. HelmNotes:
1015Compound Number
FPL/DFRC NMR Database -- April 2009
3-(4-Hydroxyphenyl) acrylic acid 3-hydroxy-3-(4- hydroxy-3-methoxyphenyl)-2-(2-methoxyphenoxy) propyl ester
13CCDCl3
CS i
56.1956.25
64.1873.9584.52
111.46113.59
115.22
115.34116.66116.66119.42120.56121.81123.55126.89130.94130.94133.16
145.57
147.02148.09149.36151.79160.63
167.15
Acetone
CS i CS i
DMSO
OMeOMe
γα
β
A2B2
C β
A5C3C5B5A6B6B1C1C2C6A1
C α
A4A3B4B3C4
C γ
Atom
1HJMultH Shifts
4.10
4.36
4.56
4.59
4.97
6.29
7.47
dd
dd
m
d
dd
d
d
12.0, 6.2
12.0, 3.5
3.9
6.2, 3.9
16.0
16.0
γ1
γ2
β
α OH
α
C β
C α
Atom
(acetone)
threo
R. HelmNotes:
1016Compound Number
FPL/DFRC NMR Database -- April 2009
3-(4-Hydroxyphenyl) acrylic acid 3-hydroxy-3-(4- hydroxy-3-methoxyphenyl)-2-(2-methoxyphenoxy) propyl ester
13CCDCl3
CS i
56.2056.22
63.9873.2883.54
111.20113.64
115.24
115.34116.64116.64119.67120.32121.71123.51126.91130.88130.88133.59
145.39
146.72148.02148.86152.02160.52
167.28
Acetone
CS i CS i
DMSO
OMeOMe
γα
β
A2B2
C β
A5C3C5B5A6B6B1C1C2C6A1
C α
A4A3B4B3C4
C γ
Atom
1HJMultH Shifts
4.39
4.46
4.66
4.91
6.24
7.42
dd
dd
m
d
d
d
11.8, 3.6
11.8, 6.6
4.9
16.0
16.0
γ1
γ2
β
α
C β
C α
Atom
(acetone)
erythro
R. HelmNotes:
1017Compound Number
FPL/DFRC NMR Database -- April 2009
3-(4-Hydroxy-3-methoxyphenyl) acrylic acid 3-hydroxy-3-(4-hydroxy-3-methoxyphenyl)-2-(2-methoxyphenoxy) propyl ester
13CCDCl3
CS i
56.2056.2656.32
64.1673.9484.48
111.37111.46113.60115.33
115.47
116.05119.39120.56121.81123.54123.90127.35133.16
145.91
147.01148.08148.71149.36150.09151.80
167.14
Acetone
CS i CS i
DMSO
OMeOMeOMe
γα
β
C2A2B2A5
C β
C5B5A6B6B1C6C1A1
C α
A4A3C3B4C4B3
C γ
Atom
1HJMultH Shifts
4.96
4.56
4.36
4.10
6.33
7.45
d
m
dd
dd
d
d
6.3
12.0, 3.5
12.0, 6.2
16.0
16.0
α
β
γ2
γ1
C β
C α
Atom
(acetone)
threo
R. Helm27mg300K, acetone-d6
Notes:
1018Compound Number
FPL/DFRC NMR Database -- April 2009
3-(4-Hydroxy-3-methoxyphenyl) acrylic acid 3-hydroxy-3-(4-�hydroxy-3-methoxyphenyl)-2-(2-methoxyphenoxy) propyl ester
13CCDCl3
CS i
56.2356.2356.31
63.9473.2683.57
111.21111.29113.66115.25
115.59
116.03119.63120.31121.73123.49123.86127.37133.63
145.74
146.74148.05148.70148.86150.04152.04
167.28
Acetone
CS i CS i
DMSO
OMeOMeOMe
γα
β
A2C2B2A5
C β
C5B5A6B6B1C6C1A1
C α
A4A3C3B4C4B3
C γ
Atom
1HJMultH Shifts
4.40
4.46
4.66
4.97
6.28
7.40
dd
dd
m
d
d
d
3.7,
6.7,
4.9
15.9
15.9
γ1
γ2
β
α
C α
C β
Atom
(acetone)
erythro
R. Helm18mg
Notes:
1019Compound Number
FPL/DFRC NMR Database -- April 2009
3-(4-acetoxyphenyl) acrylic acid 3-acetoxy-3-(4-acetoxy-3-methoxyphenyl)-2-(2-methoxyphenoxy) propyl ester
13CCDCl3
CS i
20.4520.9420.94
56.2056.28
63.9475.5480.89
112.70113.73
118.57
119.36120.32121.69123.21123.21123.59123.81130.25130.25132.81136.71140.91
144.75
149.12151.90152.22153.52
166.61
168.87169.43170.02
Acetone
CS i CS i
DMSO
Ac MeAc MeAc Me
OMeOMe
γα
β
A2B2
C β
B5A6B6C3C5A5B1C2C6C1A1A4
C α
B4B3A3C4
C γ
Ac C=OAc C=OAc C=O
Atom
1HJMultH Shifts
4.17
4.40
4.88
6.18
6.51
7.57
dd
dd
m
d
d
d
5.6,
4.0,
6.5
16.0
16.1
γ1
γ2
β
α
C β
C α
Atom
(acetone)
threo
R. HelmNotes:
1020Compound Number
FPL/DFRC NMR Database -- April 2009
3-(4-acetoxyphenyl) acrylic acid 3-acetoxy-3-(4-acetoxy-3-methoxyphenyl)-2-(2-methoxyphenoxy) propyl ester
13CCDCl3
CS i
20.4620.8920.94
56.1956.26
63.3374.7180.52
112.74113.76
118.54
119.99120.44121.64123.20123.20123.37124.10130.21130.21132.78136.73140.77
144.71
148.30152.09152.11153.49
166.60
168.89169.41169.92
Acetone
CS i CS i
DMSO
Ac MeAc MeAc Me
OMeOMe
γα
β
A2B2
C β
B5A6B6C3C5A5B1C2C6C1A1A4
C α
B4B3A3C4
C γ
Ac C=OAc C=OAc C=O
Atom
1HJMultH Shifts
4.40
4.48
4.92
6.13
6.45
7.56
dd
dd
m
d
d
d
11.9, 4.2
11.9, 5.9
5.1
16.0
16.1
γ1
γ2
β
α
C β
C α
Atom
(acetone)
erythro
R. Helm18.5mg300K
Notes:
1021Compound Number
FPL/DFRC NMR Database -- April 2009
3-(4-acetoxyphenyl) acrylic acid 3-acetoxy-3-(4-acetoxy-3-methoxyphenyl)-2-(2-methoxyphenoxy) propyl ester
13CCDCl3
CS i
20.4520.4520.95
56.2056.2956.42
63.9675.5780.88
112.45112.69113.73
118.64
119.33120.32121.69122.30123.60123.80124.12134.13136.69140.92142.76
145.20
149.10151.89152.23152.68
166.68
168.82168.89170.05
Acetone
CS i CS i
DMSO
Ac MeAc MeAc Me
OMeOMeOMe
γα
β
C2A2B2
C β
B5A6B6C6A5B1C5C1A1A4C4
C α
B4B3A3C3
C γ
Ac C=OAc C=OAc C=O
Atom
1HJMultH Shifts
4.16
4.40
4.88
6.18
6.55
7.54
dd
dd
m
d
d
d
12.0, 5.6
12.0, 3.9
6.6
16.0
16.0
γ1
γ2
β
α
C β
C α
Atom
(acetone)
threo
R. Helm18.5mg300K
Notes:
1022Compound Number
FPL/DFRC NMR Database -- April 2009
3-(4-acetoxyphenyl) acrylic acid 3-acetoxy-3-(4-acetoxy-3-methoxyphenyl)-2-(2-methoxyphenoxy) propyl ester
13CCDCl3
CS i
20.4520.4520.89
56.1956.2856.40
63.3374.7080.50
112.44112.74113.77
118.63
119.97120.44121.65122.25123.38124.41124.41134.11136.73140.79142.74
145.16
148.30152.10152.12152.67
166.67
168.80168.90169.94
Acetone
CS i CS i
DMSO
Ac MeAc MeAc Me
OMeOMeOMe
γα
β
C2A2B2
C β
B5A6B6C6A5B1C5C1A1A4C4
C α
B4B3A3C3
C γ
Ac C=OAc C=OAc C=O
Atom
1HJMultH Shifts
4.40
4.49
4.92
6.13
6.48
7.53
dd
dd
m
d
d
d
11.9, 4.2
11.9, 5.9
5.1
16.0
16.0
γ1
γ2
β
α
C β
C α
Atom
(acetone)
erythro
R. Helm20.6mg
Notes:
1023Compound Number
FPL/DFRC NMR Database -- April 2009
3-(4-acetoxyphenyl) acrylic acid 4-[1,3-diacetoxy-2- (2-methoxyphenoxy) propyl] phenyl ester�
13CCDCl3
CS i
20.5920.9220.96
56.3056.20
63.6075.4080.70
112.70113.74
117.92
119.23120.34121.68123.31123.31123.64123.72130.44130.44132.72136.78140.83
146.05
149.08151.84152.30153.74
164.91
169.42170.01170.68
Acetone
CS i CS i
DMSO
Ac MeAc MeAc Me
OMeOMe
γα
β
A2B2
C β
B5A6B6C3C5A5B1C2C6C1A1A4
C α
B4B3A3C4
C γ
Ac C=OAc C=OAc C=O
Atom
1HJMultH Shifts
7.84
6.74
6.14
4.81
4.28
4.04
d
d
d
m
dd
dd
16.1
16.1
6.5
11.9, 4.2
11.9, 5.6
C α
C β
α
β
γ1
γ 2
Atom
(acetone)
threo
R. Helm25mg
Notes:
1024Compound Number
FPL/DFRC NMR Database -- April 2009
3-(4-acetoxyphenyl) acrylic acid 4-[1,3-diacetoxy-2- (2-methoxyphenoxy) propyl] phenyl ester�
13CCDCl3
CS i
20.6120.8720.96
56.2056.28
63.0074.6080.32
112.77113.79
117.95
119.82120.45121.64123.31123.31123.45124.06130.44130.44132.73136.78140.71
146.02
148.27152.06152.19153.74
164.95
169.42169.92170.76
Acetone
CS i CS i
DMSO
Ac MeAc MeAc Me
OMeOMe
γα
β
A2B2
C β
B5A6B6C3C5A5B1C2C6C1A1A4
C α
B4B3A3C4
C γ
Ac C=OAc C=OAc C=O
Atom
1HJMultH Shifts
7.84
6.74
6.10
4.85
4.39
4.24
d
d
d
m
dd
dd
15.7
16.1
5.1
11.9, 5.9
11.9, 4.2
C α
C β
α
β
γ1
γ2
Atom
(acetone)
erythro
R. Helm20.6mg std conditions
Notes:
1025Compound Number
FPL/DFRC NMR Database -- April 2009
3-(4-acetoxy-3-methoxyphenyl) acrylic acid 4-[1,3-diacetoxy-2-(2-methoxyphenoxy) propyl] phenyl ester�
13CCDCl3
CS i
20.4620.5920.93
56.2056.3056.44
63.6175.4080.70
112.61112.70113.75
118.03
119.23120.34121.68122.52123.64123.72124.20134.04136.77140.83142.98
146.46
149.08151.84152.30152.76
164.97
168.79170.01170.69
Acetone
CS i CS i
DMSO
Ac MeAc MeAc Me
OMeOMeOMe
γα
β
C2A2B2
C β
B5A6B6C6A5B1C5C1A1A4C4
C α
B4B3A3C3
C γ
Ac C=OAc C=OAc C=O
Atom
1HJMultH Shifts
7.81
6.77
6.14
4.81
4.28
4.04
d
d
d
m
dd
dd
15.9
16.0
6.5
11.9, 4.2
11.9, 5.6
C α
C β
α
β
γ1
γ2
Atom
(acetone)
threo
R. Helm20.9mg
Notes:
1026Compound Number
FPL/DFRC NMR Database -- April 2009
3-(4-acetoxy-3-methoxyphenyl) acrylic acid 4-[1,3-diacetoxy-2-(2-methoxyphenoxy) propyl] phenyl ester�
13CCDCl3
CS i
20.4620.6020.86
56.2056.2756.44
63.0074.6080.32
112.60112.77113.79
118.06
119.82120.45121.64122.52123.44124.06124.20134.04136.77140.70142.97
146.44
148.27152.06152.19152.76
165.00
168.80169.92170.76
Acetone
CS i CS i
DMSO
Ac MeAc MeAc Me
OMeOMeOMe
γα
β
C2A2B2
C β
B5A6B6C6A5B1C5C1A1A4C4
C α
B4B3A3C3
C γ
Ac C=OAc C=OAc C=O
Atom
1HJMultH Shifts
7.81
6.78
6.10
4.85
4.39
4.24
d
d
d
m
dd
dd
15.8
16.0
5.1
11.9, 5.6
11.9, 4.2
C α
C β
α
β
γ1
γ2
Atom
(acetone)
erythro
R. Helmcrystalline
Notes:
1027Compound Number
FPL/DFRC NMR Database -- April 2009
Acetic acid 2-methoxy-4-[2-(2-methoxyphenoxy) acetyl] phenyl ester
13CCDCl3
CS i
20.44
56.2156.44
72.50
112.66113.63115.72121.54122.13122.79123.99134.59145.22148.97150.88152.58
168.63
194.31
Acetone
CS i CS i
DMSO
Ac Me
OMeOMe
β
A2B2B5B6A6B1A5A1A4B4B3A3
Ac C=O
α
Atom
1HJMultH Shifts
5.43β
Atom
(acetone)
R. Helm20mg300K acetone-d6
Notes:
1028Compound Number
FPL/DFRC NMR Database -- April 2009
Acetic acid 4-[3-hydroxy-2-(2-methoxyphenoxy) propionyl]-2-methoxyphenyl ester
13CCDCl3
CS i
20.44
56.1256.35
63.9084.22
113.43113.73117.45121.60122.81123.34123.80
135.27145.05148.29151.13152.36
168.60
196.80
Acetone
CS i CS i
DMSO
Ac Me
OMeOMe
γβ
A2B2B5B6A6B1A5
A1A4B4B3A3
Ac C=O
α
Atom
1HJMultH Shifts
5.55
4.09
β
γ's
Atom
(acetone)
R. Helm19.6mgacetone-d6
Notes:
1029Compound Number
FPL/DFRC NMR Database -- April 2009
Acetic acid 3-acetoxy-3-(4-hydroxy-3-methoxyphenyl) -2-(2-methoxyphenoxy) propyl ester
13CCDCl3
CS i
20.5820.97
56.2156.30
63.8675.8780.99
111.89113.77115.64119.13121.19121.67123.57
129.17147.71148.26149.31151.83
169.95170.66
Acetone
CS i CS i
DMSO
Ac MeAc Me
OMeOMe
γα
β
A2B2A5B5A6B6B1
A1A4A3B4B3
Ac C=OAc C=O
Atom
1HJMultH Shifts
6.04
4.77
4.21
3.95
d
m
dd
dd
7.13
11.9, 3.6
11.9, 5.6
α
β
γ1
γ2
Atom
(acetone)
threo
R. Helm15mgstd conditions
Notes:
1030Compound Number
FPL/DFRC NMR Database -- April 2009
Acetic acid 3-acetoxy-3-(4-hydroxy-3-methoxyphenyl) -2-(2-methoxyphenoxy) propyl ester
13CCDCl3
CS i
20.6020.90
56.2056.29
63.3074.8980.40
112.01113.78115.41119.56121.28121.61123.83
129.07147.53148.15148.49152.00
169.90170.75
Acetone
CS i CS i
DMSO
Ac MeAc Me
OMeOMe
γα
β
A2B2A5B5A6B6B1
A1A4A3B4B3
Ac C=OAc C=O
Atom
1HJMultH Shifts
5.99
4.81
4.34
3.98
d
m
dd
dd
4.99
11.9, 6.2
11.9, 4.0
α
β
γ1
γ2
Atom
(acetone)
erythro
S. QuideauAssignments confirmed in all three solventsJAFC 1992-40(7), 1108-1110
Notes:
2001Compound Number
FPL/DFRC NMR Database -- April 2009
coniferyl alcohol4-hydroxy-3-methoxy cinnamyl alcohol
13C
100
67
59
69
81
92
48
80
53
31
55.78
63.66
108.40
114.48
120.18
126.05
129.18
131.23
145.51
146.64
CDCl3
CS i
56.09
63.37
109.91
115.73
120.55
127.96
130.16
130.41
147.07
148.36
92
100
71
99
100
90
40
97
45
34
Acetone
CS i
55.56
61.73
109.72
115.47
119.43
127.49
128.52
129.00
146.17
147.72
100
64
67
68
70
65
52
69
54
55
CS i
DMSO
OMe
γ
2
5
6
β
1
α
4
3
Atom
1HJMultH Shifts
3.783.854.18
6.22
6.49ຶ
6.766.84
7.047.63
tstd
dt
dtຶddd
ds
5.65
1.5, 5.6
15.9, 5.5
15.9, 1.5
8.1 8.1, 1.9
1.9
γ OHOMe
γ
β
α
56
2Ar OH
Atom
(acetone)
trans
S. QuideauNote A1 and β change places in DMSO. Assignments confirmed in CDCl3 andAcetone. JAFC 1992-40(7), 1108-1110
Notes:
2002Compound Number
FPL/DFRC NMR Database -- April 2009
sinapyl alcohol4-hydroxy-3,5-dimethoxy cinnamyl alcohol
13C
100100
52
9494
49
22
50
20
41
41
56.2756.27
63.76
103.35103.35
126.58
128.22
131.50
134.80
147.13
147.13
CDCl3
CS i
56.4856.48
63.33
104.65104.65
128.27
128.99
130.62
136.52
148.71
148.71
3939
21
3232
19
10
100
8
16
16
Acetone
CS i
55.9255.92
61.62
103.79103.79
127.89
127.40
129.17
135.17
148.01
148.01
100100
42
7676
41
28
42
14
50
50
CS i
DMSO
OMe OMe
γ
26
β
1
α
4
3
5
Atom
1HJMultH Shifts
3.883.824.20
6.24
6.48
6.71
7.30
tstd
dt
dt
s
s
5.65
5.6, 1.5
15.8, 5.5
15.8, 1.5
γ OHOMe
γ
β
α
2,6
4 OH
Atom
(acetone)
S. QuideauJAFC-1992-40(7), 1108-1110
Notes:
2003Compound Number
FPL/DFRC NMR Database -- April 2009
p-coumaryl alcohol4-hydroxy-cinnamyl alcohol
13C
46
100100
46
9898
24
48
31
63.79
115.50115.50
125.74
127.73127.73
128.90
131.08
156.12
CDCl3
CS i
63.41
116.15116.15
127.71
128.33128.33
129.68
130.13
157.76
41
8484
42
100100
18
44
18
Acetone
CS i
61.72
115.37115.37
127.15
127.38127.38
127.92
128.70
156.80
49
8585
50
100100
27
50
27
CS i
DMSO
γ
35
β
26
1
α
4
Atom
1HJMultH Shifts
3.854.19
6.19
6.50
6.787.25
8.40
ttd
dt
dt
mm
s
5.65 5.6, 1.6
15.9, 5.6
15.9, 1.6
γ OHg's
β
α
3,52,6
4 OH
Atom
(acetone)
S. Quideau-Ag2O oxidation of coniferyl alcohol. Assignments confirmed in acetone.
Notes:
2004Compound Number
FPL/DFRC NMR Database -- April 2009
4-[3-Hydroxymethyl-5-(3-hydroxypropenyl)-7-methoxy-2,3-dihydrobenzofuran-2-yl]-2-methoxyphenol
13C
70
97100
897272
7373
78
7275
70
50
80
47
49
42
52
44
28
53.53
55.9956.01
63.8364.0088.24
108.75110.54
114.33
114.78119.43
126.45
128.09
131.33
130.87
132.87
144.47
145.74
146.68
148.38
CDCl3
CS i
54.73
56.2656.38
63.3964.6088.51
110.48111.72
115.67
116.08119.57
128.33
130.40
130.54
131.91
134.36
145.14
147.27
148.36
148.84
73
94100
7968100
9985
60
9799
85
59
100
54
55
50
26
32
32
Acetone
CS i
53.02
55.6855.73
61.7062.9887.26
110.37110.37
115.00
115.37118.58
128.02
129.52
129.04
130.56
132.39
143.72
146.42
147.13
147.60
41
46100
773245
5959
38
5255
46
48
73
78
69
70
87
56
78
CS i
DMSO
β
A OMeB OMe
B γγ
α
A2B2
A5
B6A6
B β
B5
B α
B1
A1
B3
A4
A3
B4
Atom
1HJMultH Shifts
3.53
3.78-3.883.813.85
4.16
4.195.566.236.52
6.806.876.946.977.03
7.73
br q
mss
t
tdddtdt
ddddbr sbr sd
br s
5.0
5.2, 1.56.5
15.8, 5.515.8, 1.5
8.18.1, 2.0, 0.5
2.0
β
γ + γ OHA3 OMeB3 OMe
B γ OH
B γα
B βB α
A5A6B2B6A2
A4 OH
Atom
(acetone)
S.Quideau-Ag2O oxidation of coniferyl alcohol + acetylation. Assignmentsconfirmed in CDCl3 and acetone A1 and A4 switch places in CDCl3
Notes:
2005Compound Number
FPL/DFRC NMR Database -- April 2009
Acetic acid 4-[3-acetoxymethyl-5-(3-acetoxypropenyl)- 7-methoxy-2,3-dihydrobenzofuran-2-yl]-2-methoxyphenyl ester
13C
918184
71
10095
836172
77606978
72
796360
76
4658563957
525343
20.5120.6820.90
50.36
55.7955.92
65.0665.2287.91
109.84110.56115.23118.08
121.16
122.79127.21130.59
134.13
139.56139.30144.30148.03151.16
168.82170.63170.76
CDCl3
CS i
20.4320.6720.78
51.33
56.2456.41
65.4765.9688.34
111.07112.20116.32118.67
122.30
123.76128.82131.65
134.64
140.70140.99145.39149.21152.38
168.98170.97170.80
949277
85
9792
1007589
88797690
86
946158
87
3854533744
444332
Acetone
CS i
20.4120.6120.79
49.53
55.8455.84
64.5764.9087.01
110.59111.08115.36118.00
121.53
123.01127.84130.28
133.52
139.14139.59143.96147.55150.92
168.60170.41170.27
687884
46
100100
603747
50354050
45
505047
47
4046473553
425144
CS i
DMSO
A4 Ac MeγAc Me
BγAc Me
β
A OMeB OMe
Bγγα
A2B2B6A6
B β
A5B5B1
B α
A4A1B3B4A3
A4 Ac C=Oγ C=O
B γ C=O
Atom
1HJMultH Shifts
2.02.012.22
3.783.793.88
4.344.464.665.616.246.63
7.07.037.0497.0547.18
sss
mss
ddddddddtdt
br ddbr sbr sdd
11.1, 7.611.1, 5.46.5, 1.3
6.715.8, 6.515.8, 1.3
8.1, 1.8
8.11.8
γ Ac MeB γ Ac MeA4 Ac Me
βA3 OMeB3 OMe
γ1γ2B γα
BβB α
A6B6B2A5A2
Atom
(acetone)
S. Quideau-Ag2O oxidation of ethyl ferulate.Notes:
2006Compound Number
FPL/DFRC NMR Database -- April 2009
�5-(2-Ethoxycarbonylvinyl)-2-(4-hydroxy-3-methoxyphenyl)-7-methoxy-2,3-dihydrobenzofuran-3-carboxylic acid ethyl ester
13C
9596
77
10094
8785
80
907195
78
7593
657067
77
63636542
5864
14.2414.31
55.54
55.9856.08
61.8360.37
87.46
108.74111.93114.49
115.93
117.86119.44
125.85128.61131.44
144.50
144.69146.69146.03149.90
167.18170.20
CDCl3
CS i
14.4814.63
56.06
56.3156.49
62.2060.56
88.34
110.74113.30115.82
116.69
118.91120.18
127.41129.46132.10
145.22
145.82148.56147.97150.99
167.28171.10
9492
88
98100
8989
89
798364
87
9091
575942
85
50353434
5353
Acetone
CS i
14.1214.32
54.33
55.7856.04
61.4959.99
87.36
110.86112.55115.48
115.84
118.31119.41
126.35128.23129.97
144.66
147.83144.44149.50147.19
166.65170.42
10091
42
9678
8067
45
593757
45
4158
535357
43
66604759
5765
CS i
DMSO
A CH3B CH3
β
A OMeB OMe
A CH2B CH2
α
A2B2A5
B β
B6A6
B5B1A1
B α
B3A3A4B4
B γγ
Atom
1HJMultH Shifts
1.271.273.823.91
4.184.25
4.436.036.41
6.846.917.087.27
7.317.627.87
ttss
qm
ddd
dddd
br s
br sds
7.17.1
7.1
8.08.015.9
8.18.1, 1.9
1.9
15.9
CH3CH3
A3 OMeB3 OMe
CH2CH2
βα
B β
A5A6A2B6
B2B α
A4 OH
Atom
(acetone)
S. QuideauFrom LiBH4 red. of dilactoneAs this compound has a plane of symmetry the shifts for the other half areidentical.
Notes:
2007Compound Number
FPL/DFRC NMR Database -- April 2009
1,4-bis-(4-hydroxy-3-methoxypheny)l-1,3-butadiene
13C
100
90
90
93
87
48
88
57
53
55.89
107.95
114.55
120.29
127.35
130.25
131.72
145.45
146.69
CDCl3
CS i
56.21
109.76
115.96
120.95
128.07
130.81
132.49
147.41
148.60
100
84
77
96
85
41
80
44
42
Acetone
CS i
55.55
109.38
115.55
119.81
126.90
128.96
131.37
146.43
147.80
100
61
57
67
49
35
59
45
52
CS i
DMSO
OMe
2
5
6
β
1
α
4
3
Atom
1HJMultH Shifts
3.87
6.56
6.78
6.85-6.92
7.12
7.71
s
m
d
m
d
s
8.1
1.9
OMe
α
A5
β, A6
A2
Ar OH
Atom
(acetone)
trans
S. QuideauAs this compound has a plane of symmetry the shifts for the other half areidentical.
Notes:
2008Compound Number
FPL/DFRC NMR Database -- April 2009
dilactone from ferulic acid3,6-Bis-(4-hydroxy-3-methoxyphenyl) tetrahydrofuro [3,4-c]
furan-1,4-dione
13C
83
95
86
100
92
92
52
53
47
48
48.39
56.13
81.90
107.52
114.98
117.41
129.81
146.35
147.06
174.94
CDCl3
CS i
49.11
56.39
83.22
110.40
116.00
119.57
130.82
148.17
148.72
175.99
95
95
94
88
81
100
49
42
36
48
Acetone
CS i
48.11
55.81
82.06
110.64
115.46
119.22
129.00
147.36
147.88
175.40
83
74
75
98
85
100
73
70
85
75
CS i
DMSO
β
OMe
α
2
5
6
1
4
3
γ
Atom
1HJMultH Shifts
3.85
4.095.77
6.866.927.05
7.90
s
tbr s
dddd
s
1.0
8.28.2, 1.8
1.8
OMe
βα
562
4 OH
Atom
(acetone)
S. QuideauNotes:
2009Compound Number
FPL/DFRC NMR Database -- April 2009
coniferyl p-coumarate3-(4-Hydroxyphenyl) acrylic acid 3-(4-hydroxy-3-methoxyphenyl) llyl
ester
13C
55
43
51
53
4710010054
52
3230
9696
5041
3231
32
28
55.87
65.35
108.44
114.45
114.98115.93115.93120.62
120.89
126.81128.83
130.00130.00
134.43145.07
145.84146.63
158.26
167.57
CDCl3
CS i
56.20
65.49
110.20
115.45
115.83116.68116.68121.19
121.72
126.90129.39
130.91130.91
134.90145.49
147.80148.53
160.65
167.27
47
55
47
43
40676746
44
2422
100100
4543
2217
17
23
Acetone
CS i
55.61
64.62
109.91
114.13
115.46115.81115.81120.12
120.61
125.12127.59
130.37130.37
133.9144.90
146.87147.79
159.89
166.46
77
34
52
44
51969653
49
3843
100100
4943
3947
37
40
CS i
DMSO
OMe
γ
A2
B β
A5B3B5A6
β
B1A1
B2B6
αBα
A4A3
B4
B γ
Atom
1HJMultH Shifts
3.86
4.786.256.376.65
6.796.88
6.917.117.54
7.63
7.769.03
s
dddtddt
dm
dddm
d
ss
6.5, 1.315.8, 6.5
15.915.8, 1.3
8.1
8.1, 2.02.0
15.9
OMe
γβ
B βα
A5B3,5
A6A2
B2,6
B α
ArOHArOH
Atom
(acetone)
S. Quideauisolated from gum s.am
Notes:
2010Compound Number
FPL/DFRC NMR Database -- April 2009
coniferyl benzoate3-Phenyl-acrylic acid 3-(4-hydroxy-3-methoxyphenyl)allyl ester
13C
43
45
414043
44
9595
21
100100
1345
44
2023
16
55.86
65.74
108.39114.44120.64
120.81
128.32128.32
128.76
129.61129.61
130.24132.93
134.50
146.63145.91
166.46
CDCl3
CS i
56.21
66.35
110.25115.84121.29
121.32
129.37129.37
129.31
130.17130.17
131.30133.86
135.34
148.54147.89
166.58
59
60
574364
64
100100
100
9494
1759
60
1818
16
Acetone
CS i
55.61
65.55
109.96115.45120.23
120.23
128.82128.82
127.52
129.20129.20
129.78133.39
134.29
147.79146.93
165.62
58
45
464480
80
9696
30
100100
2450
50
3631
25
CS i
DMSO
OMe
γ
A2A5A6
β
B3B5
A1
B2B6
B1B4
α
A3A4
B α C=O
Atom
1HJMultH Shifts
3.86
4.946.346.72
6.806.937.147.507.62
8.03 - 8.06
7.76
s
dddtdt
ddddmmm
s
6.5, 1.315.8, 6.515.8, 1.3
8.18.1, 2.0
2.0
OMe
γβ
α
A5A6A2
B3,5B4
B2,6
ArOH
Atom
(acetone)
S. QuideauNotes:
2011Compound Number
FPL/DFRC NMR Database -- April 2009
Guaiacylglycerol-β-coniferyl ether peracetate
13C
20.6320.6820.9921.02
55.8155.93
63.0265.0874.4080.19
110.17111.66118.31119.54119.82
122.13
122.83131.54
133.87
135.18139.92148.02150.71151.12
168.76169.65170.54170.84
CDCl3
CS i
20.4420.5820.7820.91
56.2456.29
63.5665.3675.3280.56
111.31112.64118.74120.30120.54
123.26
123.56132.35
134.16
136.61140.92149.09151.75152.22
168.89170.00170.68170.77
Acetone
CS i
20.3820.4620.7520.72
55.6755.84
62.4964.4574.2878.95
110.22111.65116.99119.46119.56
122.35
122.74130.64
132.99135.40139.23147.56150.09150.73
168.48169.45170.05170.21
CS i
DMSO
A4 Ac Meα Ac MeγAc Me
Bγ Ac Me
A3 OMeB3 OMe
γB γα
β
B2A2B5A6B6
Bβ
A5B1
B α
A1A4B4B3A3
A4 Ac C=OαAc C=OγAc C=O
BγAc C=O
Atom
1HJMultH ShiftsAtom
(acetone)
threo
S. QuideauNotes:
2012Compound Number
FPL/DFRC NMR Database -- April 2009
Guaiacyl glycerol-β-coniferyl ether peracetate
Acetic acid 4-{1,3-diacetoxy-2-[4-(3-acetoxypropenyl)-2-methoxyphenoxy] propyl}-2-methoxyphenyl ester
13C
20.6420.7420.9920.99
55.8055.91
62.5365.0773.7080.17
110.24111.94119.11119.65119.80
122.23
122.60131.86
133.85
135.28139.78147.23150.98151.02
168.80169.49170.76170.83
CDCl3
CS i
20.4520.5920.7720.85
56.2556.27
62.9865.3474.4980.27
111.38112.73119.36120.39120.48
123.37
123.35132.63
134.12
136.59140.79148.27151.98152.11
168.90169.88170.74170.74
87928690
100100
71938388
8676828080
97
9749
82
6338444646
38457777
Acetone
CS i
20.3920.4720.6920.75
55.7255.78
61.9264.4373.0778.29
110.40111.69117.51119.37119.56
122.48
122.58130.93
132.96
135.34139.11146.63150.32150.60
168.51169.33170.12170.21
CS i
DMSO
A4 Ac Meα Ac Meγ Ac Me
B γ Ac Me
A3 OMeB3 OMe
γB γα
β
B2A2B5A6B6
B β
A5B1
B α
A1A4B4B3A3
A4 Ac C=Oα Ac C=Oγ Ac C=O
B γ Ac C=O
Atom
1HJMultH Shifts
1.932.022.072.213.823.854.224.364.664.856.066.266.62
6.936.977.027.057.137.25
ssssss
ddddddmddtdt
dddddddd
11.9, 4.111.9, 5.96.4, 1.4
5.115.9, 6.415.9, 1.4
8.3, 2.08.38.1
8.1, 1.82.01.8
γ Ac MeB γ Ac Meα Ac Me
A4 Ac MeA3 OMeB3 OMe
γ1γ2B γβα
B βB α
B6B5A5A6B2A2
Atom
(acetone)
erythro
S. Quideauα (e/t) and γ shifts (e/t) interchange from sample to sample, probably due to H-exchange of OH's in d6-acetone. CDCl3 and DMSO shifts not substantiated.
Notes:
2013Compound Number
FPL/DFRC NMR Database -- April 2009
Guaiacylglycerol-β-coniferyl ether
1-(4-Hydroxy-3-methoxyphenyl)-2-[4-(3-hydroxypropenyl)-2-methoxyphenoxy]propane-1,3-diol
13C
83100
22572154
446832635553
6767
192826163335
55.9756.03
61.2163.5674.0789.47
108.94110.00114.37120.15120.29120.83
128.24130.53
131.55133.15144.75145.71147.47151.33
CDCl3
CS i
56.1956.31
61.8863.2573.8388.37
110.85111.42115.21119.57120.31120.54
129.63129.85
132.96133.82146.83148.03149.15151.69
10090
601005080
504030906080
7090
404030304040
Acetone
CS i
55.4455.83
60.1661.6571.0184.36
109.84111.05114.71115.53119.05119.10
128.58128.60
130.18132.97145.46147.03147.88149.70
7569
501003536
423839422951
8383
464364484225
CS i
DMSO
A3 OMeB3 OMe
γB γα
β
B2A2A5B5B6A6
B βB α
B1A1A4A3B4B3
Atom
1HJMultH Shifts
3.483.67
3.80-3.903.803.88
4.204.204.454.876.286.52
6.766.88-6.91
7.087.097.11
7.50
dddd
ss
br ddmd
br ddtdt
dmddd
br s
11.9, 5.711.9, 3.7
5.3, 1.6
3.95.5
15.9, 5.415.9, 1.6
8.1
1.91.98.4
γ1γ2
A,B γ OHA3 OMeB3 OMe
B γβ
α OHα
B βB α
A5A,B 6
A2B2B5
A4 OH
Atom
(acetone)
threo
S. Quideauα (e/t) and γ shifts (e/t) interchange from sample to sample, probably due to H-exchange of OH's in d6-acetone. CDCl3 and DMSO shifts not substantiated.
Notes:
2014Compound Number
FPL/DFRC NMR Database -- April 2009
Guaiacylglycerol-β-coniferyl ether
1-(4-Hydroxy-3-methoxyphenyl)-2-[4-(3-hydroxypropenyl)-2-methoxyphenoxy]propane-1,3-diol
13C
84100
16581143
446832424554
6361
1034
20142522
55.9756.03
60.8763.5672.9687.34
108.82110.05114.37119.14120.09120.79
128.19130.56
131.86133.11
143.98145.27146.75151.62
CDCl3
CS i
56.2156.29
61.8263.2573.8186.63
110.99111.44115.13119.27120.23120.46
129.54129.87
132.84134.24
146.65147.96148.55151.88
100100
60997049
879243586286
5592
3535
21272931
Acetone
CS i
55.6455.64
60.1661.6571.6783.75
109.93111.47114.60115.60119.05119.54
128.52128.60
130.08133.23
145.46147.00147.60149.75
100100
92922423
292426382727
3478
3428
60402944
CS i
DMSO
A3 OMeB3 OMe
γB γα
β
B2A2A5B5B6A6
B βB α
B1A1
A4A3B4B3
Atom
1HJMultH Shifts
3.693.81
3.80-3.903.803.84
4.194.294.574.896.266.50
6.756.86-6.89
6.917.057.10
7.47
dddd
ss
br ddmd
br ddtdt
dmddd
br s
11.8, 4.011.8, 6.2
5.4, 1.6
4.65.2
15.9, 5.415.9, 1.6
8.1
1.91.98.4
γ1γ2
A,B γ OHA3 OMeB3 OMe
B γβ
α OHα
B βB α
A5A,B6B5B2A2
A4 OH
Atom
(acetone)
erythro
S. Quideau Shifts for α and β's and A,B,C 1's change places in CDCl3 and DMSOS. Quideau, and J. Ralph, A biomimetic route to lignin model compounds via silver(I) oxide oxidation. 2. NMR characterization of non-cyclic benzyl aryl ethers,Holzforschung, 1994, 48(2), 124-132.
Notes:
2015Compound Number
FPL/DFRC NMR Database -- April 2009
Guaiacylglycerol-α,β-bis-coniferyl ether
4-{3-Hydroxy-1,2-bis-[4-(3-hydroxypropenyl)-2-methoxyphenoxy]propyl}-2-methoxyphenol
13C
8292100
4061645256
615662545758646155
68706262
496645504744454746
55.7655.8555.93
62.1763.5663.6381.6885.42
109.38109.54109.77114.26115.94119.13119.49119.74120.33
127.10127.60130.59130.79
130.43130.85132.09145.49146.64146.85147.08149.80150.81
CDCl3
CS i
56.1856.2056.32
61.7563.2563.2581.1585.31
110.74110.93112.11115.23117.02119.04119.90120.15121.49
129.22129.45129.85129.85
130.39132.05132.74147.18147.77148.10148.61151.17151.71
838376
461001004957
505153465459676657
5661100100
413841323331364140
Acetone
CS i
55.4155.6155.80
59.7461.5261.5879.0182.53
109.93109.93111.91114.74115.71116.15118.87119.00120.34
128.32128.47130.49130.49
128.24128.71128.82146.07146.27147.11147.36149.73149.80
88100100
3171723940
626241314841585335
72587979
405858455845586161
CS i
DMSO
A3 OMeB3 OMeC3 OMe
γB γC γα
β
C2B2A2A5C5B5C6B6A6
C βB βB αC α
A1C1B1A4C4A3B4C3B3
Atom
1HJMultH Shifts
5.46
4.56
3.81ຶ3.93
d
m
dddd
5.5
11.7, 7.111.7, 4.1
A α
A β
A γ1A γ2
Atom
(acetone)
erythro
S. Quideau Shifts substantiated in d6-acetone but not CDCL3 or DMSO. γ and Bγ
Ac C=O shifts may be interchanged S. Quideau, and J. Ralph, A biomimetic routeto lignin model compounds via silver (I) oxide oxidation. 2. NMR characterizationof non-cyclic benzyl aryl ethers, Holzforschung, 1994, 48(2), 124-132.
Notes:
2016Compound Number
FPL/DFRC NMR Database -- April 2009
3-(4-{3-Acetoxy-1-(4-acetoxy-3-methoxyphenyl)-2-[4-(3-acetoxypropenyl)-2-methoxyphenoxy]propoxy}-3-methoxyphenyl) acrylic acid ethyl ester
13C
90948488
618210075
44874250
72654854
47
58426275
75
685250
79
5657
58
3952535543
52482755
14.3320.6520.7421.00
55.7355.9655.9860.39
63.2265.0979.9981.98
110.14110.73111.17115.87
116.51
119.10119.34119.82122.08
122.15
122.66128.62131.71
133.90
136.48139.64
144.28
147.35149.33150.23150.96151.20
167.13168.78170.77170.86
CDCl3
CS i
14.5720.4320.6020.77
56.1656.2056.4460.56
63.4165.3780.4781.70
111.19111.92112.80116.69
117.15
119.28120.33120.47122.57
123.17
123.36129.41132.37
134.18
137.19140.63
144.96
148.51150.06151.36151.86152.12
167.23168.90170.81170.82
8510062100
92626262
38543846
38384638
46
69546262
69
464646
69
3146
46
2331462338
69543169
Acetone
CS i
14.1920.3320.4320.71
55.6755.8055.9559.79
62.3364.4178.4579.57
110.22111.40111.89115.28
116.25
117.18119.35119.50122.33
122.24
122.49127.56130.59
133.00
135.93138.94
144.23
146.96148.42149.75150.12150.49
166.40168.36170.09170.14
737781100
97546153
24592733
37413834
39
40284539
43
253943
53
3151
42
5047445338
53444854
CS i
DMSO
MeA4 Ac Meγ Ac Me
B γAc Me
A OMeB OMeC OMe
CH2
γB γα
β
B2C2A2C5
C β
B5A6B6C6
B β
A5C1B1
B α
A1A4
C α
B4C4C3B3A3
C γ C=OA4 Ac C=O
γAc C=OB γ Ac C=O
Atom
1HJMultH Shifts
4.454.534.664.885.716.256.396.617.53
ddddddmddtddtd
11.8, 3.811.9, 6.06.4, 1.3
5.315.8, 6.4
15.915.8, 1.3
15.9
γ1γ2B ຶ
γβα
B βC ຶ
βB αC ຶ
α
Atom
(acetone)
erythro
S. Quideau Run only in Acetone:D2O (9:1) S. Quideau, and J. Ralph,,Holzforschung, 1994, 48(2), 124-132. Note: Two erythro isomers!! Resolvablepairs are:80.10, 80.05 54.28, 54.21 136.08, 136.05 110.98, 110.89147.31, 147.30 116.41, 116.42 118.42, 118.40
Notes:
2017Compound Number
FPL/DFRC NMR Database -- April 2009
Veratryglycerol-α-dehydrodiconifyl-β-con.ether
13CCDCl3
CS i
Note*54.28
55.8355.8056.0956.2056.33
61.2062.7762.8564.1880.1083.8687.80
110.71110.98111.35111.67112.04115.96116.41117.55118.42119.99120.96
127.73128.64130.02
129.64
130.57
130.94131.83132.11136.08144.75147.31147.98148.27149.45149.48150.58150.83
30
1007210010086
46945052294655
6629464447592449496436
656485
33
39
395346246125482453535050
Acetone
CS i CS i
DMSO
C β
A3 OMeA4 OMeB OMeD OMeC OMe
γB γD γC γα
βC α
B2C2D2A5A2D6C5B5C6B6A6
D βB βB α
D5
D α
A1D1B1C1D3C4B4D4A3A4C3B3
Atom
1HJMultH Shifts
5.48
4.62
3.80ຶ3.91
5.51
3.43
3.69ຶ3.80
d
m
dddd
d
m
ss
5.8
11.9, 6.511.9, 4.9
5.8
A α
A β
A γ1A γ2
C α
C β
C γ1C γ2
Atom
Acetone/D2O
erythro
S. QuideauB α changes in CDCl3JCS Perkin 1, 3485-98 (1994)Cmpd 13
Notes:
2018Compound Number
FPL/DFRC NMR Database -- April 2009
beta-5-dehydrodiferulic acid
13C
5547
4624
931820
79
2610024
2629
46
80304628
2831
56.0356.15
53.7687.53
108.77112.26114.53
114.91
118.63119.49125.93
128.29131.44
146.74
144.71146.06146.74150.32
171.34173.67
CDCl3
CS i
56.3156.49
56.2288.56
110.72113.34115.78
116.75
118.95120.08128.05
129.38132.49
145.59
145.73147.81148.53150.96
168.18172.55
8270
10049
574157
42
426035
3431
41
34303124
4238
Acetone
CS i
55.6155.85
55.1087.72
110.61112.10115.30
116.43
117.93119.50127.82
130.69137.46
144.09
144.19146.79147.60149.16
167.79171.66
8080
2029
703861
100
497343
2415
49
49316049
4942
CS i
DMSO
A3 OMeB3 OMe
β
α
A2B2A5
B β
B6A6B5
B1A1
B α
B3A4A3B4
B γγ
Atom
1HJMultH Shifts
6.054.39
7.086.836.91
3.83
7.626.397.297.33
3.91
dd
dddd
s
dd
br sbr s
s
7.87.8
2.08.1
8.1, 2.0
15.915.9
αβ
A2A5 A6
A3 OMe
B αB βB2B6
B3 OMe
Atom
(acetone)
S. QuideauB5,B6 and A6 switch in acetone and DMSO
Notes:
2019Compound Number
FPL/DFRC NMR Database -- April 2009
�3-(4-Hydroxy-3-methoxyphenyl)-2-[2-hydroxy-3-methoxy-5-(2-propoxycarbonylvinyl)phenyl] acrylic acid ethyl ester
13C
100100
7472
7169
586165
6341
4362614850
5360
45445144
4334
14.2814.28
55.2456.12
60.3561.09
108.68111.57114.29
116.00123.29
124.76124.82125.82126.81126.94
141.45144.30
145.86146.05147.11147.31
167.11167.46
CDCl3
CS i
14.6114.62
55.5156.58
60.4761.05
110.25113.28115.63
116.31124.92
126.56125.71126.37127.31127.58
141.37145.25
147.87148.03148.99149.10
167.29167.77
100100
8188
7974
768181
7638
4576815050
7174
45435245
4033
Acetone
CS i
14.1414.16
54.6656.05
59.6260.15
110.05112.92115.02
115.17123.97
125.09124.61125.16125.56125.66
140.11144.49
147.02147.11148.16148.23
166.44166.83
10094
7874
6461
384845
5044
4542485149
3942
58465259
5243
CS i
DMSO
CH3CH3
A3 OMeB3 OMe
CH2CH2
B2A2A5
B ββ
B5B6A6B1A1
αB α
A3B4A4B3
B γγ
Atom
1HJMultH Shifts
1.211.24
3.443.96
4.164.17
6.38
6.6966.7026.837.007.38
7.567.76
tt
ss
d
dddddd
ds
7.17.1
7.17.1
15.9
2.18.2
8.2, 2.12.02.0
15.9
CH3CH3
A3 OMeB3 OMe
CH2CH2
B β
A2A5A6B6B2
B αA α
Atom
(acetone)
S. QuideauAs this compound has a plane of symmetry the shifts for the other half areidentical.
Notes:
2020Compound Number
FPL/DFRC NMR Database -- April 2009
Pinoresinol
13C
98
98
98
98
95
93
100
51
59
48
54.15
55.94
71.66
85.86
108.60
114.27
118.95
132.91
145.24
146.70
CDCl3
CS i
55.23
56.24
72.20
86.62
110.60
115.52
119.59
134.17
146.86
148.32
86
93
88
83
80
69
100
46
47
32
Acetone
CS i
53.59
55.62
70.91
85.17
110.43
115.15
118.64
132.26
145.91
147.53
72
100
70
72
72
73
75
61
66
66
CS i
DMSO
β
OMe
γ
α
2
5
6
1
4
3
Atom
1HJMultH Shifts
3.08
3.80
3.83
4.19
4.66
6.786.836.98
7.48
m
dd
s
dd
d
dddd
s
9.1, 3.8
9.0, 7.0
4.25
8.18.1, 1.8
1..8
β
γ1
OMe
γ 2
α
A5A6A2
Ar OH
Atom
(acetone)
S. QuideauNotes:
2021Compound Number
FPL/DFRC NMR Database -- April 2009
3-[2-(4-Hydroxy-3-methoxyphenyl)-3-hydroxymethyl-7-methoxy-2,3-dihydrobenzofuran-5-yl] prop-2-enal
13CCDCl3
CS i
54.25
56.2956.46
64.3289.39
110.59113.56115.76119.64119.73
127.14
129.00131.24133.75145.65147.55148.46152.41
154.10
193.77
59
10081
5482
9467618583
76
59414041312322
77
87
Acetone
CS i CS i
DMSO
β
A3 OMeB3 OMe
γα
A2B2A5B6A6
B β
B5B1A1B3A4A3B4
B α
B γ
Atom
1HJMultH Shifts
3.61
3.823.91
3.87-3.915.656.65
6.816.887.047.297.32
7.599.63
br q
ss
mddd
dddd
brobro
dd
6.615.8, 7.7
8.18.1, 2.0
2.0
15.87.7
β
A3 OMeB3 OMe
γα
B β
A5A6A2B2B6
B αB γ
Atom
(acetone)
erythro
S. Quideauα and β of B and C can interchange in CDCl3S. Quideau, and J. Ralph, Holzforschung, 1994, 48(2), 124-132.
Notes:
2022Compound Number
FPL/DFRC NMR Database -- April 2009
Guaiacylglycerol-α,β-bis coniferyl ether acetate
13C
454010077
374444
2035412524
2929252828263737
31
31
262424
32
35
24212626252322
23292929
20.6320.7320.9820.98
55.7355.9155.94
63.3765.0865.1280.1781.92
109.94110.11111.29116.41118.92119.49119.77119.79
121.69
122.03
122.50130.61131.55
133.92
134.02
136.80139.53147.45147.47150.18150.90151.09
168.76170.76170.83170.83
CDCl3
CS i
20.4420.6220.7620.78
56.2356.2356.39
63.5665.3765.3780.8581.74
111.16111.32112.74117.41119.23120.45120.50120.51
122.99
123.18
123.26131.73132.34
134.22
134.22
137.52140.65148.20148.66151.43151.91152.12
168.85170.72170.74170.77
57575855
100100100
2855553136
3641353544515151
44
47
393841
91
91
40263929404032
35323240
Acetone
CS i
20.3320.4220.70
20.7055.5955.6455.78
62.3964.3964.3978.6879.56
110.15110.21111.87115.81117.06119.43119.48119.50
122.12
122.19
122.38130.12130.51
133.00
133.00
136.19138.88146.38146.99149.75150.09150.45
168.34170.07170.10170.12
878792
92898994
311001003831
5252385248707070
58
59
314550
76
76
57494854495852
50737373
CS i
DMSO
A4 Ac Meγ Ac Me
C γ Ac MeB γAc Me
A3 OMeB3 OMeC3 OMe
γC γB γα
β
C2B2A2C5B5C6B6A6
C β
B β
A5C1B1
C α
B α
A1A4C4B4C3B3A3
A4 Ac C=OA γ Ac C=OD γ Ac C=OC γ Ac C=O
Atom
1HJMultH Shifts
5.62
4.87
4.454.53
A α
A β
A γ1A γ2
Atom
(acetone)
erythro
S. Quideau S. QuideauS. Quideau, and J. Ralph, A biomimetic route to lignin model compounds via silver(I) oxide oxidation. 2. NMR characterization of non-cyclic benzyl aryl ethers,Holzforschung, 1994, 48(2), 124-132.
Notes:
2023Compound Number
FPL/DFRC NMR Database -- April 2009
Guaiacylglycerol-α-dehydrodiconiferyl-bis-ether peracetate
diastereomeric mixture
13C
88881008989
3535848443344730
75755532394129623870
6067
52324145
6965
65394342454527274736
20.5220.6120.7420.9820.98
50.2563.3665.0665.1665.2880.1381.8788.38
110.09110.17110.61111.33115.31116.39118.64118.89119.51119.77
121.13122.01
122.47127.53130.49131.52
133.90134.31
134.49136.76139.52144.36147.36147.45148.22150.35150.87151.06
168.72170.74170.74170.80170.83
CDCl3
CS i
20.4320.6120.6520.7820.78
56.3956.3156.1756.15
51.0463.5265.3665.4865.8480.7381.6388.61
111.17111.36112.02112.69116.24117.29119.11119.11120.45120.46
122.13123.10
123.24128.99131.41132.23
134.20134.69
135.94137.49140.56145.32147.96148.56149.22151.33151.82152.05
168.84170.74170.74170.76170.90
9789899595
7877100100
4950853555424838
30573045323131318181
6674
57424849
7474
27284744374646305546
Acetone
CS i
20.3220.4220.4820.7020.70
49.1662.3864.4064.4968.4278.6279.4987.25
110.20110.74110.93111.89115.24115.76118.35117.00119.43119.49
121.31122.18
122.38127.93129.99130.48
133.00133.50
134.13136.18138.88143.83146.31146.95147.51149.63150.07150.44
168.33170.12170.12170.12170.23
CS i
DMSO
A4 Ac MeA γAc MeC γ Ac MeB γ Ac MeD γ Ac Me
OMeOMeOMeOMe
C βγ
B γD γC γαβ
C α
B2C2D2A2D6C5C6B5A6B6
D βB β
A5D5D1B1
B αD α
C1A1A4D3C4B4D4C3B3A3
A4 Ac C=OB γ Ac C=OD γ Ac C=OA γ Ac C=OC γ Ac C=O
Atom
1HJMultH Shifts
5.62
4.88
4.464.53
5.49
3.72
4.284.40
d
m
dtdt
d
s
dddd
5.4
11.9, 3.811.9, 5.8
6.9
11.1, 7.511.1, 5.4
A α
A β
A γ1A γ2
C α
C β
C γ1C γ2
Atom
(acetone)
erythro
S. QuideauA3 and A4, C and D OMe's, and B and D γ's can be interchanged in allsolvents Shifts are confirmed for AcetoneS. Quideau, and J. Ralph, Holzforschung, 1994, 48(2), 124-132.
Notes:
2024Compound Number
FPL/DFRC NMR Database -- April 2009
Veratrylglycerol-α-dehydrodiconiferyl-β-coniferyl-bis-ether
peracetate, diastereomeric mixture
13C
7272100100
89949464
2828798750333128
5629435642382351515757
4847
30243236
58
38
64
4328333532312537
20.7520.7520.9820.98
55.7555.8255.8656.0655.97
50.1863.6765.0965.1765.2880.1481.8088.43
110.02110.33110.17110.56110.79115.29116.53118.47118.59119.73119.95
121.16121.91
127.57130.18130.49131.24
133.94
134.12
134.32
144.37147.38147.71148.21148.83148.93150.39150.78
170.70170.77170.82170.85
CDCl3
CS i
20.6420.6420.7920.79
55.9756.0656.2256.38
51.0863.8665.3865.4965.9080.8981.7388.65
111.28111.45112.16112.22112.31116.31117.46118.91119.11120.48120.98
122.19123.04
129.06130.90131.46132.08
134.26
135.74
134.71
145.37148.11148.83149.29150.20150.23151.42151.81
170.76170.76170.79170.90
98989898
9410010085
3952989859465344
8139696969522948407328
7665
38284940
75
28
81
4932404044443147
Acetone
CS i
20.4520.4520.7020.70
55.3355.5955.7055.79
49.1662.6464.4164.5064.7178.7779.5787.28
110.17110.63110.93111.25111.12115.24115.95116.79118.27119.49119.81
121.32122.09
127.93129.46129.99130.30
133.03
133.92
133.51
143.83146.38147.12147.51148.37148.48149.69150.02
170.05170.10170.13170.23
97979797
99999999
544010010049293852
6329584532462646286625
6158
53305851
76
39
67
6334515151483358
CS i
DMSO
A γ Ac MeC γAc MeB γ Ac MeD γAc Me
A4 OMeA3 OMeB3 OMeC3 OMeD3 OMe
C βγ
B γD γC γα
βC α
B2C2D2A5A2D6C5B5C6B6A6
D βB β
D5A1D1B1
B α
C 1
D α
D3C4B4D4A3A4C3B3
D γ Ac C=OB γ Ac C=OA γ Ac C=OC γ Ac C=O
Atom
1HJMultH Shifts
5.54
4.87
4.444.52
5.48
3.70
4.284.39
d
s
tdtd
d
s
dtdt
5.2
11.8, 3.711.8, 6.2
6.9
11.1, 7.511.1, 5.5
A α
A β
A γ1A γ2
C α
C β
C γ1C γ2
Atom
(acetone)
threo
S. Quideau Only run in acetoneS. Quideau, and J. Ralph, A biomimetic route to lignin model compounds via silver(I) oxide oxidation. 2. NMR characterization of non-cyclic benzyl aryl ethers,Holzforschung, 1994, 48(2), 124-132.
Notes:
2025Compound Number
FPL/DFRC NMR Database -- April 2009
Guaiacylglycerol-α-pinoresinol-β-coniferyl-bis-ether
diastereomeric mixture
13CCDCl3
CS i
55.1555.15
56.2256.2556.2556.44
61.8263.2772.2372.2381.2185.3886.3786.58
110.59111.05111.43112.21115.28115.50116.83118.96119.06119.61120.17121.53
129.50129.88
130.53132.78134.10136.29146.85147.24147.61148.15148.30151.12151.75
100100
75757452
2844717128365136
524322193245242043614223
3742
2733322226122316221721
Acetone
CS i CS i
DMSO
D βC β
D3 OMeA3 OMeB3 OMeC3 OMe
γB γD γC γαβ
C αD α
D2B2C2A2A5D5C5C6B5D6B6A6
B βB α
A1B1D1C1D4A4C4A3D3C3B3
Atom
1HJMultH Shifts
5.45
4.55
3.823.92
4.63
3.04
3.774.17
d
m
dddd
5.6
11.5, 6.511.5, 5.2
A α
A β
A γ1A γ2
C α
C β
C γ1C γ2
Atom
(acetone)
erythro
S. QuideauRef: S. Quideau and John Ralph. J. Chem Soc. Perkin Trans. 1 1993 - issue 6 - 653 -659.
Notes:
2026Compound Number
FPL/DFRC NMR Database -- April 2009
11-hydroxy-(4-hydroxy-3methoxyphenyl)-10-methoxy-3a,4,6,6a-tetrahydro 3H-3,4-benzenofuro [3,4-c]f uran-1-one
13C
10088
9093
878891
8491838790
403737
40424044
43
50.4053.87
56.1455.95
82.3883.3385.74
106.87108.61110.88114.39118.82
131.09132.06133.95
145.52146.60148.42148.69
176.43
CDCl3
CS i
51.1354.58
56.3856.25
84.1884.2286.62
108.57110.78112.10115.56119.80
132.41133.24135.28
147.28148.30150.03150.43
177.32
8681
9492
9010087
7890667290
413443
35334229
46
Acetone
CS i
49.7853.16
55.6755.58
83.1483.2785.15
108.24110.60111.46115.12118.98
130.35131.52133.78
146.38147.50149.01149.63
176.86
5450
99100
625861
5065546665
586351
65606357
65
CS i
DMSO
B ββ
B3 OMeA3 OMe
αB αB γ
B2A2B5A5A6
A1B1B6
A4A3B4B3
γ
Atom
1HJMultH Shifts
3.36
4.24
4.72
5.73
5.60
dd
dddd
dquin
br d
dq
10.7, 6.4
10.6, 7.5, 6.9, 0.6
6.3, 0.6
β
B β
α
B α
B γ
Atom
(acetone)
S. QuideauS. Quideau and John Ralph. J. Chem. Soc. Perkin Trans. 1 1993 issue 6 653-659.Cmpd 14
Notes:
2027Compound Number
FPL/DFRC NMR Database -- April 2009
4-cis-8-trans-bis (4-hydroxy-3-methoxyphenyl)-3,7-dioxabicyclo[3-3-0] octan-2-one
13C
8991
92100
919390
9692999710098
4648
60584643
30
51.3151.67
55.9756.11
71.6384.0085.65
107.89108.78114.43114.59118.83119.65
127.88131.26
145.81146.15146.60146.99
174.51
CDCl3
CS i
52.0252.43
56.2856.35
72.0884.4386.32
110.68111.21115.39115.80120.06120.32
129.78132.60
147.15147.82147.99148.62
174.93
9793
9493
879589
9689768610093
4953
35383542
38
Acetone
CS i
50.4251.54
55.8155.91
71.0683.0785.45
110.88110.96115.28115.54119.27119.48
128.41130.80
146.24147.03147.35147.96
174.99
5873
10061
585461
606755686897
5461
57657184
62
CS i
DMSO
B ββ
A3 OMeB3 OMe
B γα
B α
B2A2A5B5B6A6
A1B1
A4B4A3B3
γ
Atom
1HJMultH Shifts
3.63
3.35
5.05
5.23
3.88
4.28
t
ddd
br d
br d
dd
br d
8.8
9.0, 6.6, 4.6
8.6
6.6
9.5, 4.8
9.5
β
B β
α
B α
B γ cis
B γ trans
Atom
(acetone)
S. QuideauS. Quideau and J. Ralph. J. Chem Soc . Perkin Trans. 1 1993 (6) 653-659
Notes:
2028Compound Number
FPL/DFRC NMR Database -- April 2009
4-trans-8-cis-bis( 4-hydroxy-3-methoxyphenyl)-3,7-dioxabicyclo [3-3-0]octan-2-one
13C
9099
8293
86
8988
8591100828897
534463454449
54
45.4354.80
56.0056.13
68.66
80.3783.70
107.47108.17114.41114.65117.76118.11
127.90132.46145.33145.56146.67146.80
177.07
CDCl3
CS i
46.1455.35
56.2656.34
69.98
81.0984.56
109.50110.24115.65115.87118.57119.17
129.22133.48147.10147.24148.39148.54
177.77
7778
10082
78
7881
737437427485
364117191415
38
Acetone
CS i CS i
DMSO
B ββ
A3 OMeB3 OMe
B γ
B γγ
B2A2A5B5B6A6
B1A1A4B4A3B3
γ
Atom
1HJMultH Shifts
3.65
3.71
5.16
5.82
3.80
3.47
dd
m
br d
br d
m
dd
8.7, 2.6
2.6
5.9
9.2, 6.7
β
B β
γ
B α
B γ cis
B γ trans
Atom
(acetone)
S. Quideau S.Quideau and J. Ralph. J. Chem. Soc. Perkin Trans. 1 1993 (6) 653-659.
Notes:
2029Compound Number
FPL/DFRC NMR Database -- April 2009
3,6-bis(4-hydroxy-3-methoxyphenyl)-tetrahydro-furo[3,4-c]furan-1-one
4-cis-8-cis-bis (4-hydroxy-3-methoxyphenyl)-3,7-dioxabicylclo[3-3-0] octan-2-one
13C
8489
8892
907591
1008788859599
414144464047
54
49.9953.31
56.0256.08
72.7083.3884.59
107.77108.11114.42114.71118.02118.40
131.11132.31145.34146.07146.73146.94
176.92
CDCl3
CS i
50.3853.71
50.2650.34
73.4484.4385.78
110.35110.45115.64115.87119.30119.66
132.47133.17147.12147.80148.35148.63
177.72
9386
9993
969092
9697737110095
474722262830
39
Acetone
CS i
48.6252.32
55.6155.71
72.1582.9184.83
110.30110.54115.16115.34118.50118.88
130.58131.08146.19146.85147.55147.73
177.14
6972
10098
667773
787768668578
615737476159
67
CS i
DMSO
B ββ
A3 OMeB3 OMe
B γα
B α
A2B2A5B5A6B6
B1A1A4B4A3B3
γ
Atom
1HJMultH Shifts
3.65
3.39
5.20
5.39
4.30
4.02
ddd
ddddd
dquin
br d
ddd
ddt
9.2, 3.7, 0.5
9.2, 7.0, 4.6, 3.6, 0.6
3.7, 0.6
3.6
9.4, 7.0, 0.5
9.4, 4.6, 0.5
β
B β
α
B α
B γ cis
B γ trans
Atom
(acetone)
S. QuideauRalph, Helm, Quideau. J. Chem. Soc. Perkin Trans. 1 1992 2971-2980
Notes:
2030Compound Number
FPL/DFRC NMR Database -- April 2009
4-cis-8-cis-bis (4-hydroxy-3-methoxyphenyl)-3,7-dioxabicylclo[3-3-0] octan-2-one diacetate
13C
9898
8495
92100
908088
868690869597
534140364854
4850
54
20.6120.63
49.8953.14
55.9956.06
72.8082.9983.89
109.13109.35117.14117.22122.98123.38
138.04139.26139.32139.96151.35151.66
169.04168.90
176.66
CDCl3
CS i
20.4520.45
50.3353.59
56.2456.35
73.7284.0184.93
110.86111.05118.40118.53123.65123.96
139.95140.40140.68140.96152.38152.62
168.98168.94
177.49
100100
7676
7675
818278
827781837982
392743233028
2828
36
Acetone
CS i
20.3920.39
48.6252.19
55.8255.95
72.5182.4983.93
110.37110.69117.87118.00122.80123.07
138.71138.80139.21139.30150.88151.05
168.57168.53
176.98
CS i
DMSO
Ac MeAc Me
B ββ
A3 OMeB3 OMe
B γα
B α
A2B2A6B6A5B5
B1A4A1B4A3B3
Ac C=OAc C=O
γ
Atom
1HJMultH Shifts
3.72
3.45
4.12
4.39
5.52
5.29
ddd
ddddd
ddt
ddd
br d
dquin
9.25, 3.8, 0.5
9.15, 7.1, 4.8, 3.0,0.6
9.5, 4.8, 0.5
9.5, 7.1, 0.5
3.6
3.8, 0.6
β
B β
B γ trans
B γ cis
B α
α
Atom
(acetone)
S. QuideauJCS Perkin 1, 3485-98 (1994)Cmpd 18As this compound has a plane of symmetry only one set of shifts are reported.
Notes:
2031Compound Number
FPL/DFRC NMR Database -- April 2009
4,4'-dihydroxy-3,3'-dimethoxy-β,β'-bicinnamic acid
13CCDCl3
CS i
56.05
113.51115.93125.60
126.15
127.94
142.26
148.19149.25
168.46
100
915795
24
57
59
3124
28
Acetone
CS i
55.28
113.23115.47124.11
125.12
126.13
140.40
147.29148.37
168.06
100
605967
15
62
18
7761
40
CS i
DMSO
OMe
256
β
1
α
34
γ
Atom
1HJMultH Shifts
3.74
6.78
7.11
7.31
7.83
s
d
dd
d
s
8.2
8.2, 2.0
2.0
OMe
5
6
2
α
Atom
(acetone)
S. QuideauNotes:
2032Compound Number
FPL/DFRC NMR Database -- April 2009
γ'-methoxy-4,4'-dihydroxy-3,3'-dimethoxy-β,β'-bicinnamic acid
13CCDCl3
CS i
52.2856.0456.04
113.40113.54115.95115.97125.60
125.67125.67
125.73
127.78127.81
142.36142.47
148.19148.20149.32149.37
168.22168.53
54100100
5659585956
5656
66
3636
5144
33332721
2719
Acetone
CS i CS i
DMSO
B gOMeB3 OMeA3 OMe
A2B2A5B5A6
βBβ
B6
A1B1
B αα
B3A3A4B4
Bγγ
Atom
1HJMultH Shifts
3.66
3.723.73
6.78
7.117.097.257.30
7.817.84
s
ss
d
dddddd
ss
8.2
8.3, 2.08.3, 2.0
2.02.0
B γ OMe
A3 OMeB3 OMe
A,B 5
B6A6A2B2
B αα
Atom
(acetone)
S. QuideauJCS Perkin 1, 3485-98 (1994)Cmpd 12b (R=H)
Notes:
2033Compound Number
FPL/DFRC NMR Database -- April 2009
13CCDCl3
CS i
54.03
56.2756.27
81.24
110.17113.95116.04116.20119.17
120.45
126.54126.58132.37
140.46
147.97148.54148.63150.20
171.66172.12
56
100100
66
7267585766
37
686842
59
30293034
2334
Acetone
CS i
52.64
55.5455.67
80.17
110.31113.67115.61115.70118.21
119.08
124.72125.56130.42
139.48
147.07147.72147.76149.54
171.02171.72
49
90100
48
6353585865
68
575062
42
59676751
5576
CS i
DMSO
B β
A3 OMeB3 OMe
B α
B2A2B5A5B6
β
A1A6B1
α
B4A3B3A4
γB γ
Atom
1HJMultH Shifts
3.813.87
4.305.75
6.826.896.987.217.37
7.61
ss
td
md
br sddd
d
2.52.8
8.2
8.2, 2.02.0
2.1
B3 OMeA3 OMe
B βB α
B 5,6A5B2A6A2
α
Atom
(acetone)
S. QuideauNotes:
2034Compound Number
FPL/DFRC NMR Database -- April 2009
13C
51
50
100100
52
5650625154
38
385135
45
37323341
3826
52.98
53.49
55.9755.97
80.22
107.65112.04114.78114.92118.22
118.38
125.66125.59131.08
141.06
146.12146.77146.89148.39
170.77171.23
CDCl3
CS i
53.16
53.78
56.2356.26
80.97
110.12113.78116.04116.24119.23
120.03
126.38126.42132.08
140.75
147.99148.52148.61150.24
171.45171.56
82
89
100100
87
8988898993
52
639352
81
56484858
3352
Acetone
CS i
51.98
52.75
55.4655.62
79.74
110.26113.48115.53115.68118.26
118.34
124.48125.44130.02
139.93
147.11147.69147.71149.62
170.53170.70
56
74
88100
54
6352474267
41
455047
48
33495041
6848
CS i
DMSO
B γOMe
B β
B3 OMeA3 OMe
B α
B2A2B5A5B6
β
A1A6B1
α
B4A3B3A4
γB γ
Atom
1HJMultH Shifts
3.733.813.88
4.395.72
6.79 - 6.856.96.977.177.28
7.62
sss
td
md
br dddd
d
2.63.0
8.21.5
8.2, 2.02.0
2.1
B γ OMeB3 OMeA3 OMe
B βB α
B 5,6A5B2A6A2
α
Atom
(acetone)
S. QuideauNotes:
2035Compound Number
FPL/DFRC NMR Database -- April 2009
Dimethyl 7-hydroxy-6-methoxy-1-(4-hydroxy-3-methoxyphenyl)-trans-1,2-dihydronaphtlalene-2,3-dicarboxylate
13C
8281
969310096
9182908689
57
586061
77
69596072
4760
45.6047.20
51.8752.4055.8356.03
110.12111.21114.17115.58120.35
122.37
123.85131.19134.28
137.74
144.42145.78146.40147.69
167.10172.93
CDCl3
CS i
46.3348.09
51.8752.3456.2156.38
112.03113.27115.59116.85120.83
122.96
124.37132.09135.31
138.45
146.29147.63148.20149.68
167.49173.17
9292
94889996
10091989398
53
585459
87
58535365
4458
Acetone
CS i
44.6946.74
51.6752.1155.6255.74
111.65113.25115.24116.06119.48
120.89
122.47130.74133.56
137.92
145.31146.72147.39148.88
166.52172.31
5348
778410092
6653644761
55
485054
50
66556466
5969
CS i
DMSO
αβ
B γ OMeA γOMeA3 OMeB3 OMe
A2B2A5B5A6
B β
B1B6A1
B α
A4B3A3B4
B γγ
Atom
1HJMultH Shifts
3.563.68
3.753.88
3.944.53
6.396.656.666.767.10
7.65
ss
ss
dd
dddsds
s
3.03.0
8.2, 2.08.2
2.0
A γ OMeB γ OMe
A3 OMeB3 OMe
β
α
A6A5B5A2B2
B α
Atom
(acetone)
S. QuideauJCS Perkin 1, 3485-98 (1994)Cmpd 19Not very soluble in CDCl3
Notes:
2036Compound Number
FPL/DFRC NMR Database -- April 2009
β-β-coupled dehydrodiferulic acid
7-hydroxy-6-methoxy-1-(4-hydroxy-3-methoxyphenyl)-trans-1,2-dihydronapthlalene-2,3-dicarboxylic acid
13CCDCl3
CS i
46.0048.08
56.1956.39
111.98113.06115.48116.92120.67
124.34
124.64132.35136.12
137.58
146.06147.48148.10149.29
169.32173.62
7243
10099
8875736590
19
534839
44
33464438
1431
Acetone
CS i
44.2547.80
55.5955.76
111.57112.63115.13116.23119.30
123.07
124.67130.85134.50
135.09
145.04146.46147.28147.99
169.23173.27
3513
10087
6337604561
43
5425
18
47425129
951
CS i
DMSO
α
β
A3 OMeB3 OMe
A2B2A5B5A6
B β
B1B6A1
B α
A4B3A3B4
B γγ
Atom
1HJMultH Shifts
3.743.86
3.884.61
6.426.646.716.797.04
7.60
ss
dbr d
dddsds
s
1.81.8
8.2, 2.08.2
2.0
A3 OMeB3 OMe
βα
A6A5B5A2B2
B α
Atom
(acetone)
S. QuideauNotes:
2037Compound Number
FPL/DFRC NMR Database -- April 2009
13CCDCl3
CS i
15.4521.28
56.4356.66
63.26
104.47
108.94112.46114.45119.32125.46
133.26134.22143.42150.68151.42151.95155.59
191.23191.48
9190
10095
83
91
8183808984
46442631333336
9496
Acetone
CS i CS i
DMSO
'CH3CH3
B OMeA OMe
CH2
CH
A2B2A6B5B6
B1A1A4A3B3B4A5
αB α
Atom
1HJMultH Shifts
1.081.38
3.56 -3.89
3.953.995.53
7.047.117.427.537.629.859.95
tdm
ssq
ddddddss
7.055.1
5.1
8.11.81.88.11.9
'CH3CH3CH2
OMeOMeCH
B5A6A2B6B2α
B α
Atom
(acetone)
S. QuideauNotes:
2038Compound Number
FPL/DFRC NMR Database -- April 2009
4-0-5-coupled dehydrodivanillin3-{3-[4-(2-carboxyvinyl)-2-methoxy-phenoxy]-4-hydroxy-5-
methoxy-phenyl} acrylic acid
13C
100100
6885679090
5754374446
4539
96100
56.0756.56
106.80110.85116.92117.31125.55
128.69132.76142.55143.30148.60
150.61151.08
190.05190.84
CDCl3
CS i
56.4156.80
108.48112.26116.99117.63125.55
129.54133.56143.79145.22150.37
151.49152.48
190.75191.43
10097
6685619388
4747303639
3632
997
Acetone
CS i
55.8556.24
108.09111.60116.27116.31124.80
127.64131.84142.52144.52149.47
149.82151.24
190.84191.57
100100
5163868568
7069725667
7864
3927
CS i
DMSO
B3 OMeA3 OMe
A2B2A6B5B6
A1B1A5A4A3
B3B4
αB α
Atom
1HJMultH Shifts
3.953.98
6.947.227.407.487.58
9.809.92
ss
dddddd
ss
8.21.81.8
8.2, 2.02.0
B OMeA OMe
B5A6A2B6B2
αB α
Atom
(acetone)
S. QuideauNotes:
2039Compound Number
FPL/DFRC NMR Database -- April 2009
4-0-5 coupled dehydrovanillin / vanillyl alcohol
13C
5897
88
62976010099
59604844424348
83
55.9456.47
64.91
106.40111.55114.09119.49120.46
128.30138.45142.58143.95145.16148.45150.87
190.44
CDCl3
CS i
56.1956.73
64.34
107.98112.52112.62119.78121.17
129.00140.84143.92144.30146.98149.86152.00
190.91
9499
35
55985410094
48413132313134
92
Acetone
CS i
55.6156.15
62.59
107.74111.09111.54118.81119.98
127.04139.77142.63143.03145.90148.93150.45
190.97
10097
90
5234758160
46574230434271
67
CS i
DMSO
B3 OMeA3 OMe
B α
A2B2A6B6B5
A1B1A4B4A5A3B3
α
Atom
1HJMultH Shifts
3.793.95
4.63
6.916.94 - 6.97
7.167.27
9.71
ss
s
dm
br dd
s
1.8
1.8
B3 OMeA3 OMe
B α
A6B 5,6B2A2
α
Atom
(acetone)
S. QuideauJCS Perkin 1, 3485-98 (1994)Cmpd 15
Notes:
2040Compound Number
FPL/DFRC NMR Database -- April 2009
13CCDCl3
CS i
55.9256.47
112.39113.77114.39115.96
117.50
122.92125.31126.06
128.49
130.10
138.28145.25
148.30148.90149.46150.23
164.51167.91
10091
80837970
77
825480
63
56
2777
46403752
1322
Acetone
CS i
55.0955.86
111.55112.98113.30115.53
117.52
122.02123.44124.62
127.09
128.74
137.01143.71
147.24147.42148.59148.59
164.11167.70
10085
38414536
57
424439
34
52
4446
50478988
5672
CS i
DMSO
A3 OMeB3 OMe
B2A2B5A5
B β
B6A1A6
α
B1
βB α
A3B4A4B3
γB γ
Atom
1HJMultH Shifts
3.734.00
6.43
6.826.837.137.23
7.42
7.447.52
7.59
ss
d
dddddd
s
dd
d
15.9
8.28.3
8.3, 2.08.2, 2.0
2.02.0
15.9
A3 OMeB3 OMe
B β
A5B5B6A6
α
B2A2
B α
Atom
(acetone)
S. QuideauToward β-O-4 dehydro diferulic acid(steryl ether, Z isomer)
Notes:
2041Compound Number
FPL/DFRC NMR Database -- April 2009
13C
95
8310097
92
83978987
82
80
5584
71
60
5190
53674759
4362
14.14
51.6555.5956.21
61.42
111.24112.03114.14114.47
116.32
122.12
124.74125.54
127.80
129.31
137.73144.42
146.43147.44147.80149.16
163.41167.50
CDCl3
CS i
14.47
51.5855.9256.49
61.72
112.45113.78114.53115.99
117.10
122.92
125.19126.03
128.05
130.09
138.39145.02
148.29148.89149.48150.24
163.75167.63
100
789390
74
70707170
71
78
971
10
45
4272
40354043
3247
Acetone
CS i
14.05
51.3255.1155.93
60.96
111.79113.17113.46115.57
116.29
122.27
123.18124.79
127.43
128.78
136.44144.23
147.27147.43148.67148.67
162.67166.80
100
627559
61
41343526
42
46
3235
49
39
4142
33264646
3348
CS i
DMSO
CH3
B γ OMeA3 OMeB3 OMe
CH2
B2A2B5A5
B β
B6
A1A6
α
B1
β
B α
A3B4A4B3
γB γ
Atom
1HJMultH Shifts
1.213.713.733.994.17
6.45
6.796.817.127.22
7.37
7.447.497.59
8.12
tsssq
d
dddddd
s
ddd
br s
7.1
7.1
16.0
8.38.3,
8.3, 2.08.3, 2.0
2.02.016.0
CH3B γ OMeA3 OMeB3 OMe
CH2
B β
B5A5B6A6
α
B2A2
B α
Ar OH
Atom
(acetone)
S. QuideauToward β-O-4 dehydro diferulic acid(steryl ether, Z isomer)
Notes:
2042Compound Number
FPL/DFRC NMR Database -- April 2009
13C
98
10094
91
78807879826277
85756257
57615261
80
4891
14.06
56.1555.47
61.37
111.31112.06114.11114.57122.87124.41125.42
127.19127.90128.83137.35
146.51147.59148.54149.21
152.33
163.19193.42
CDCl3
CS i
14.48
56.5555.94
61.76
112.58113.81114.66116.03123.76125.16126.08
128.29128.16130.13138.31
148.31149.53149.58150.38
153.18
163.70193.89
12
1316
92
93919382995453
1001005443
43514650
96
3899
Acetone
CS i
14.05
55.9755.11
60.99
111.82113.35113.44115.59123.13123.13124.85
128.89127.35127.53136.34
147.45147.90148.78148.86
152.98
162.62194.19
100
1073
74
4953534098352
65553945
41485960
57
4972
CS i
DMSO
CH3
B3 OMeA3 OMe
CH2
B2A2B5A5B6A1A6
B βα
B1β
A3A4B4B3
B α
γB γ
Atom
1HJMultH Shifts
1.213.734.004.21
6.706.816.837.187.23
7.38
7.497.50
7.589.65
8.14
tssq
ddddddddd
s
dd
dd
s
7.1
7.1
15.9, 7.78.38.3
8.3, 2.08.3, 2.0, 0.4
2.02.0
15.97.7
CH3A3 OMeB3 OMe
CH2
B βA5B5B6A6
α
A2B2
B αB γ
Ar OH
Atom
(acetone)
S. Quideau Compds 2043 and 2044 were run as a mixture and the differentisomers were assigned. Relative intensities reflect the spectrum of themixture.e isomer for synthesis of β-O-4 dehydro diferulic acid
Notes:
2043Compound Number
FPL/DFRC NMR Database -- April 2009
13C
97
10098
84
6971
737271717382
81
806470585459
74
6490
13.86
55.7255.78
61.33
73.7082.29
109.63111.09113.93115.99119.80122.72
127.15
128.79130.89145.48146.36149.72150.11
152.38
168.80193.53
CDCl3
CS i
Acetone
CS i CS i
DMSO
CH3
OMeOMe
CH2
αβ
A2B2A5B5A6B6
B β
B1A1A3A4B3B4
B α
γB γ
Atom
1HJMultH Shifts
1.163.853.864.15
4.815.16
6.587.379.61
6.07
tssq
dd
dddd
7.2
7.1
5.45.4
15.8, 7.715.87.7
CH3OMeOMeCH2
βa
B βB αB γ
Ar OH
Atom
(acetone)
erythro
S.Quideau Compounds 2043 and 2044 were run as a mixture and the differentisomers were assigned. Relative intensities reflect the spectrum of the mixture.threo isomer for synthesis of β-O-4 dehydro diferulic acid
Notes:
2044Compound Number
FPL/DFRC NMR Database -- April 2009
13C
100
3334
28
1415
161617151682
29
801315131813
17
2790
13.73
55.6755.82
61.28
74.4983.43
109.51110.98114.02115.56119.91122.72
127.19
128.79129.94145.73146.55149.74149.92
152.32
168.73193.53
CDCl3
CS i
Acetone
CS i CS i
DMSO
CH3
OMeOMe
CH3
αβ
A2B2A5B5A6B6
B β
B1A1A3A4B3B4
B α
γB γ
Atom
1HJMultH Shifts
1.083.853.87
4.04-4.11
4.675.10
6.597.389.62
6.10
tssm
dd
dddd
7.2
6.26.2
15.8, 7.715.87.7
CH3OMeOMeCH2
βα
B βB αB γ
Ar OH
Atom
(acetone)
threo
S. Quideauintermediate toward β--O-4 dehydro diferulic acid
Notes:
2045Compound Number
FPL/DFRC NMR Database -- April 2009
13C
47
5736
5437
5032100100
3325
3557
40272731344343301818441621931
35
13.82
14.9320.10
55.5455.63
61.0161.8464.8264.82
73.5783.09
100.92103.59
110.04110.76117.40118.63119.09120.07124.08131.25133.82133.84134.08145.39147.22150.12150.40
169.03
CDCl3
CS i
Acetone
CS i CS i
DMSO
A γ CH3
CH3CH3
OMeOMe
4 CH2A CH2B CH2B CH2
αβ
γ
Atom
1HJMultH Shifts
1.47
4.564.725.065.13
5.32
5.366.036.66
d
dd
br dbr s
q
dddd
5.1
6.65.46.3
5.2
6.015.9, 6.0
16.0
CH3
β tβ eα tα e
A 4 CH
B γB βB α
Atom
(chloroform)
erythro
S. Quideauintermediate toward b--O-4 dehydro diferulic acid
Notes:
2046Compound Number
FPL/DFRC NMR Database -- April 2009
13C
10010055
222161
12481455
7412
62
17241656
---
55.5955.5961.86
74.5184.39100.94
109.98110.69116.92118.70
124.14132.73
134.06
145.67147.26149.92150.00
CDCl3
CS i
Acetone
CS i CS i
DMSO
CH3CH3CH3OMeOMeCH2CH2CH2
αβ
Atom
1HJMultH Shifts
4.56
5.06
d
br d
6.6
6.3
β
α
Atom
(chloroform)
threo
S. QuideauFor synthesis of b--O-4 dehydro diferulic acid
Notes:
2047Compound Number
FPL/DFRC NMR Database -- April 2009
13C
100
72
63949460
71
676766
6839
663134
30
14.09
55.84
61.2765.0165.0166.42
103.90
109.88113.88120.14
123.75130.39
134.47147.58149.56
168.78
CDCl3
CS i
Acetone
CS i CS i
DMSO
CH3
OMe
CH2CH2CH2CH2
γ
256
βα
134
C=O
Atom
1HJMultH Shifts
1.263.87
3.90-4.054.244.67
5.396.056.69
6.766.906.99
ts
mqs
dddd
dddd
7.1
7.1
6.115.9, 6.1
15.9
8.38.3, 2.0
2.0
CH3OMe
CH2CH2CH2
γβα
562
Atom
(chloroform)
S. QuideauIntermediate for synthesis of β--O-4 dehydro diferulic acid
Notes:
2048Compound Number
FPL/DFRC NMR Database -- April 2009
13C
8598
94
85
92
7910081
473737
91
15.0319.95
55.90
61.72
100.61
109.81116.59126.06
130.97150.78151.64
190.89
CDCl3
CS i
Acetone
CS i CS i
DMSO
'CH3CH3
OMe
CH2
CH
256
134
α
Atom
1HJMultH Shifts
1.211.58
3.50-3.85
3.92
5.54
7.21-7.43
9.87
td
m
s
q
s
7.15.3
5.3
'CH3CH3
CH2
OMe
CH
Aromatics
α
Atom
(chloroform)
S. Quideau5-O-4 trimer
Notes:
2049Compound Number
FPL/DFRC NMR Database -- April 2009
13CCDCl3
CS i
56.0756.7556.89
64.25
108.03108.40109.92110.17112.36119.76122.66
128.73134.75138.25142.09142.49143.04147.16149.70152.34153.71155.04
191.02191.69
1009790
33
70506750409387
3753204737332730373347
5555
Acetone
CS i CS i
DMSO
C3 OMeA3 OMeB3 OMe
C α
B2A2B6A6C2C6C5
A1B1B4C1C4A4A5A3C3B5B3
αB α
Atom
1HJMultH Shifts
3.723.903.94
4.62
6.886.947.007.017.147.267.40
9.749.86
sss
s
dddddddd
ss
1.78.1, 1.7
8.11.71.71.71.7
C3 OMeB3 OMeA3 OMe
C α
B6C6C5A6C2A2B2
αB α
Atom
(acetone)
S. QuideauSterochemistry determined from NOESYexperimentsαβ-/α6 model
Notes:
2050Compound Number
FPL/DFRC NMR Database -- April 2009
13C
9388
577566
10099
67
8078
6880779175
58434963605259
5455
14.1914.22
36.9042.1551.31
55.9356.10
58.66
60.4760.63
106.61110.87110.99114.29121.39
134.34135.12137.10144.54145.61146.04146.50
172.30172.43
CDCl3
CS i
14.5214.47
37.5043.0652.35
56.2356.39
59.09
60.7960.95
108.23112..04112.60115.76121.75
135.02ຶ135.58137.90146.45147.43147.92148.37
172.45173.00
9189
808580
99100
87
8484
7582939296
55504756574648
5861
Acetone
CS i
13.9714.07
36.4141.7450.93
55.5655.64
56.96
59.9460.07
107.86111.25112.08115.32120.35
133.25133.61136.47145.36146.34147.08147.51
171.45172.10
100100
445446
7497
53
8876
4542414548
53464953585255
7761
CS i
DMSO
A CH3B CH3
B β B α
α
A3 OMeB3 OMe
β
B CH2A CH2
B2B5A2A5A6
A1B1B6A4B4B3A3
B γγ
Atom
1HJMultH Shifts
2.432.61
3.433.904.56
dddd
ddbrqd
16.0, 8.016.0, 7.0
9.85, 8.208.010.1
B β1B β2
βB α
α
Atom
(acetone)
S. Quideauveratryl phenylcoumaran
Notes:
2051Compound Number
FPL/DFRC NMR Database -- April 2009
4-[3-Hydroxymethyl-5-(3-hydroxypropenyl)-7-methoxy-2,3-dihydrobenzofuran-2-yl]-1,2-dimethoxyphenyl
13CCDCl3
CS i
54.81
56.1256.1256.39
63.3864.6588.34
110.84111.74112.67116.08119.02
128.42
130.30
130.49
132.00135.59145.18148.93150.15150.45
63
1009584
716171
7972847383
69
41
74
544538263031
Acetone
CS i CS i
DMSO
β
A3 OMeA4 OMeB3 OMe
B γγα
A2B2A5B6A6
B β
B5
B α
B1A1B3B4A4A3
Atom
1HJMultH Shifts
3.52
3.773.783.86
3.80-3.924.144.195.586.236.52
6.916.94-9.67
7.03
br q
sss
mttdddtdt
dmd
5.505.7, 1.7
6.415.8, 5.515.8, 1.7
8.1
1.8
β
A3 OMeA4 OMeB3 OMe
γ 'sB γ OH
B γα
B βB α
A5A,B6 + B2
A2
Atom
(acetone)
S. QuideauNotes:
2052Compound Number
FPL/DFRC NMR Database -- April 2009
13CCDCl3
CS i
14.63
55.4356.3056.47
60.51
88.70
110.70113.20115.72
116.46
119.08120.05128.35129.20132.64
145.36
145.70147.70148.47151.03
167.31172.24
85
4697100
79
59
796891
76
6986325452
76
53384434
6020
Acetone
CS i CS i
DMSO
CH3
β
A3 OMeB3 OMe
CH2
α
A2B2A5
B β
B6A6B5B1A1
B α
B3A4A3B4
B γγ
Atom
1HJMultH Shifts
4.376.06
6.387.60
br dd
dd
7.87.9
15.915.9
βα
B βB α
Atom
(acetone)
S. QuideauNotes:
2053Compound Number
FPL/DFRC NMR Database -- April 2009
13CCDCl3
CS i
56.2556.56
109.15110.16115.99
116.50120.61
120.84121.14125.47126.98
130.68
130.90
146.00
146.96147.61148.61148.83
168.22
10080
748383
7678
74884856
81
58
69
50554654
47
Acetone
CS i CS i
DMSO
A3 OMeB3 OMe
B2A2A5
B ββ
B6A6B5B1
α
A1
B α
B4A4A3B3
B γ
Atom
1HJMultH Shifts
3.913.95
6.44
6.837.057.227.23
7.317.33
7.54
7.63
ss
d
ddddd
dddd
d
d
15.9
8.18.1, 2.0
2.01.9
16.5, 7.3816.5, 7.38
1.9
15.9
A3 OMeB3 OMe
B β
A5A6A2B2
α
β
B6
B α
Atom
(acetone)
S. QuideauJCS Perkin 1, 3485-98 (1994)Cmpd 14Not soluble in CDCl3
Notes:
2054Compound Number
FPL/DFRC NMR Database -- April 2009
13CCDCl3
CS i
55.4856.55
110.27113.26115.63
116.23
125.14125.60
126.34
126.36127.26127.58
141.81145.80
147.86148.01148.98149.10
168.56169.15
10095
677874
67
4071
57
806262
6266
54435053
4136
Acetone
CS i
54.6256.06
109.76112.79115.63
115.92
124.57124.38
125.90
124.95125.66125.88
139.75144.28
145.82147.00148.05148.12
167.86168.38
10090
364747
48
4242
67
484967
3443
32646546
8068
CS i
DMSO
A3 OMeB3 OMe
B2A2A5
B β
B5B6
β
A6B1A1
αB α
A3B4A4B3
B γγ
Atom
1HJMultH Shifts
3.453.95
6.38
6.716.736.857.037.37
7.607.81
ss
d
dddddd
ds
15.4
8.21.9
8.2, 2.01.91.9
15.9
A3 OMeB3 OMe
B β
A5A2A6B6B2
B αα
Atom
(acetone)
S. Quideauintermediate for systhesis of β-O-4 dehydro diferulic acid
Notes:
2055Compound Number
FPL/DFRC NMR Database -- April 2009
13C
91
97
8688
939497
99
544640
84
44100
14.06
55.95
61.4465.99
110.77113.40122.75
127.17
128.31149.74149.96
152.36
168.25193.41
CDCl3
CS i
Acetone
CS i CS i
DMSO
CH3
OMe
CH2CH2
256
α
134
β
C=Oγ
Atom
1HJMultH Shifts
1.25
3.89
4.234.69
6.57
6.787.06-7.08
7.369.62
t
s
qs
dd
dm
dd
7.1
7.1
15.8, 7.7
7.9
15.87.7
CH3
OMe
CH2CH2
β
52,6
α
γ
Atom
(acetone)
S. Quideau JCS Perkin 1, 3485-98 (1994) Cmpd 16Note chemical shift differences of 5,6,1 between solvents. Shifts were verified inboth solvents As this compound has a plane of symmetry the shifts for the otherhalf are identical.
Notes:
2056Compound Number
FPL/DFRC NMR Database -- April 2009
5-5, Dehydrodiferulic Acid
13CCDCl3
CS i
56.52
109.97
116.28
125.62126.07126.60
145.89
147.38148.92
168.36
100
89
94
549664
100
4058
59
Acetone
CS i
56.04
109.44
115.82
125.20125.05124.83
144.56
146.43147.90
167.94
55
56
64
606074
55
7199
100
CS i
DMSO
OMe
2
β
561
α
43
γ
Atom
1HJMultH Shifts
3.97
6.42
7.217.35
7.64
s
d
dd
d
15.4
2.02.0
15.9
OMe
β
62
α
Atom
(acetone)
S. QuideauAs this compound has a plane of symmetry the shifts for the other half areidentical.
Notes:
2057Compound Number
FPL/DFRC NMR Database -- April 2009
5-5 Dehydrodiferulate diethyl ester
13C
100
84
79
61
71
346851
70
3746
47
14.31
56.17
60.34
108.78
116.21
123.59124.81126.73
144.46
145.10147.27
167.14
CDCl3
CS i
14.64
56.56
60.46
109.95
116.23
125.59126.22126.64
145.58
147.47148.93
167.39
Acetone
CS i
14.22
56.03
59.63
109.47
114.70
125.20125.35124.58
144.98
146.84147.94
166.59
CS i
DMSO
CH3
OMe
CH2
2
β
561
α
43
γ
Atom
1HJMultH Shifts
1.264.18
3.97
6.43
7.207.36
7.62
tq
s
d
dd
d
7.17.1
15.9
2.02.0
15.9
CH3CH2
OMe
β
62
α
Atom
(acetone)
S. Quideau Run only in acetone, no HMBC run. Assignment of quatenary carbonsbased on shift assignments of diacid/diester parents. Poor solubility on CDCl3...sample degraded, no DMSO data.As this compound has a plane of symmetrythe shifts for the other half are identical.
Notes:
2058Compound Number
FPL/DFRC NMR Database -- April 2009
5,5 Dehydrodiconiferyl Alcohol
13CCDCl3
CS i
56.52
63.49
108.97123.16126.15
128.53
129.69
130.57
144.53148.87
100
68
697921
71
45
80
2627
Acetone
CS i CS i
DMSO
OMe
γ
265
β
1
α
43
Atom
1HJMultH Shifts
3.89
4.216.266.54
6.927.06
7.42
s
br ddtdt
dd
s
5.415.8, 5..515.8, 1.6
2.02.0
A3 OMe
γβ
α
A6A2
ArOH
Atom
(acetone)
S.Quideaunot substantiated in CDCl3 & d6 DMSOPeracetate/diastereomeric mixture
Notes:
2059Compound Number
FPL/DFRC NMR Database -- April 2009
Guaiacylglycerol-α-pinoresinol-β-coniferyl-bis-ether (Ac'd)
13C
99997070
6674
7010010056
3669707043435145
8959593530793139595957
497640
59
3535293744223029393939
30403636
20.5920.5920.7020.93
53.9154.39
55.8255.9555.9556.11
63.4565.0571.8871.8880.3481.8785.5385.64
110.01110.35110.39111.55116.58117.93118.19118.87119.65119.65122.08
122.45122.73131.55
133.93
135.13136.93139.19139.62140.23146.94147.63150.46150.93151.12151.27
168.71168.98170.68170.76
CDCl3
CS i
20.4520.4520.6220.78
55.1155.36
56.1956.2356.2356.40
63.6265.3872.3772.4880.8881.7386.2086.27
111.07111.31111.47112.77117.29118.62118.90119.11120.51120.51123.14
123.25123.43132.27
134.23
136.85137.72140.08140.62141.84147.42148.67151.27151.86152.10152.24
168.90169.05170.78170.81
99995070
6460
100100100100
4059484830435151
7474542829712951757555
797934
57
2539313144233019363134
35354040
Acetone
CS i
20.3520.3520.4320.70
53.4953.74
55.5955.6555.7155.79
62.4464.4071.0771.1878.6979.5684.6784.75
110.38110.20110.71111.89115.64116.96118.18117.83119.43119.43122.17
122.37122.55130.46
133.01
135.21136.37138.42138.86140.50145.70147.00149.61150.06150.43150.72
168.36168.54170.08170.12
99994949
6163
7474100100
3661525233324747
4482823437417676525243
868633
51
2931173033192117242422
27252525
CS i
DMSO
Ac MeAc MeAc MeAc Me
C βB β
A3 OMeB3 OMeD3 OMeC3 OMe
A γB γC ຶ
γD γA ຶ
αA βD ຶ
αC α
D2B2C2A2C5D6C6B5A6B6B ຶ
β
A5D5B1
B α
C1A1D4A4D1C4B4C3B3A3D3
A4 AcC=OD4 AcC=OB γ AcC=OA γ AcC=O
Atom
1HJMultH Shifts
5.60
4.86
4.454.53
4.66
3.06
3.834.17
4.74
4.23
d
m
dddd
s
m
mm
d
m
5.6
11.9, 3.811.9, 5.9
4.5
α
β
γ1γ2
C α
C α
C γ1C γ2
D α
D γ
Atom
(acetone)
S. QuideauC3,4,5 and D3,4,5 Can be interchangednot substantiated in CDCl3 & DMSO
Notes:
2060Compound Number
FPL/DFRC NMR Database -- April 2009
13C
30
10010033
312534
412642
3943
329696969643
36
292935343497973433
36
33
4037
2638383131
3429
50.40
55.9055.9056.03
65.1965.3888.86
109.31110.67111.06
114.53115.14
115.39115.93115.83115.96115.96118.91
121.37
126.75126.98127.79130.00130.00130.06130.06130.62132.86
134.27
144.40
144.94145.40
148.27149.14149.17158.05158.23
167.20167.37
CDCl3
CS i
51.33
56.0956.1356.41
65.4265.9289.15
110.93112.25112.65
115.08115.49
116.36116.68116.68116.70116.70119.44
122.40
126.85126.97129.21130.94130.94131.02131.02131.51134.52
134.78
145.42
145.50145.91
149.42150.43150.51160.61160.71
167.23167.23
39
563255
403342
473350
5151
4010010010010052
41
3337361001001001002734
44
36
5045
2525282525
3838
Acetone
CS i
49.47
55.4855.7655.82
64.4664.8087.87
110.01111.03111.67
113.68114.05
115.31115.77115.77115.77115.77118.66
121.56
124.94125.08128.08130.34130.34130.34130.34130.06133.61
132.79
143.91
144.89145.13
147.65148.72148.81159.87159.94
166.38166.38
15
572255
211220
291128
2132
1610010010010028
18
2429221001001001002418
29
22
2923
2336213427
514
CS i
DMSO
β
A3 OMeA4 OMeB3 OMe
B γγα
A2B2A5
D βC β
B6D3D5C3C5A6
B β
D1C1B5C2C6D2D6B1A1
B α
B3
C αD α
B4A3A4D4C4
C γD γ
Atom
1HJMultH Shifts
3.773.853.884.454.584.785.616.316.336.376.706.886.937.007.077.117.517.547.637.53
sms
ddddddddtdddtmdd
br dbr smmdd
11.1, 7.611.1, 5.46.5, 1.2
7.115.8, 6.5
15.915.9
15.8, 1.2
8.38.3, 2.0
2.0
15.915.9
A3,4 OMeβ
B3 OMeγ1γ2B γa
B βD βC βB α
C,D 3,5A5A6
A,B 2B6
D 2,6C 2,6C αD α
Atom
(acetone)
S. QuideauC4,D4 and Cg,Dg Can be interchangedNot substantiated in CDCl3 & DMSO
Notes:
2061Compound Number
FPL/DFRC NMR Database -- April 2009
13C
8585
30
524747
302335
32254030
3741
42
34
100100100100275757242426232328
314037
2418301717
3023
3030
21.0821.08
50.45
55.9756.0056.13
65.3165.5688.94
109.53110.96111.26115.41
117.59118.21
118.94
121.34
122.14122.14122.19122.19127.79129.21129.21129.42129.42130.66131.92132.16132.96
134.47143.91144.39
144.53148.45149.36152.21152.36
166.47166.61
168.97169.01
CDCl3
CS i
20.9420.94
51.21
56.0856.1456.41
65.7166.1589.17
110.97112.28112.63116.35
118.61119.01
119.53
122.17
123.23123.23123.23123.23129.17130.16130.16130.21130.21131.47132.77132.91134.41
134.99144.43144.79
145.42149.44150.45153.46153.53
166.80166.80
169.45169.45
9191
31
463142
322334
38263930
4141
38
31
100100100100279696939326252528
313937
2619252121
4848
3434
Acetone
CS i
20.7620.76
49.36
55.5055.5055.76
64.6664.9887.72
110.11111.18111.77115.30
117.65118.01
118.65
121.32
122.24122.24122.28122.28128.02129.49129.49129.53129.53130.01131.47131.62132.74
133.72143.59143.81
143.87147.67148.81151.99152.03
165.84165.87
168.87168.87
100100
32
959585
312631
48304832
4957
49
33
96969696474444969641474641
412455
4732454747
4545
5252
CS i
DMSO
C4 AcMeD4 AcMe
β
A3 OMeA4 OMeB3 OMe
B γγα
A2B2A5B6
D βC β
A6
B β
D3D5C3C5B5C2C6D2D6B1D1C1A1
B αC αD α
B3B4A3C4D4
C γD γ
C4 C=OD4 C=O
Atom
1HJMultH Shifts
2.263.763.88
~3.884.484.614.815.616.326.436.506.546.717.007.087.087.11
7.16-7.217.687.707.72
sssmddddddddtddddtddd
br sbr smmdm
11.1, 7.511.1, 5.46.5, 1.3
7.215.8, 6.5
8.316.016.0
15.8, 1.28.2, 2.0
2.0
16.0
Ac MeA3,4 OMeB3 OMe
βγ1γ2B γα
B ຶ
βA5D βCβB αA6A2B2B6
C,D 3,5D 2,6C ຶ
αC 2,6
Atom
(acetone)
S. QuideauNotes:
2062Compound Number
FPL/DFRC NMR Database -- April 2009
Methyl 7-hydroxy-5-methoxy-1-(4-hydroxy-3-methoxyphenyl)- trans-1,1-dihydronapthalene-3-carboxylic Acid 2-carboxylate
13CCDCl3
CS i
46.4648.06
52.2556.1856.36
112.01113.11
115.52116.75120.82
123.97
124.58132.08135.45
138.07
146.14147.51148.11149.34
168.80173.44
8764
969595
9587
7264100
24
646473
56
35484835
1263
Acetone
CS i CS i
DMSO
αβ
A g OMeA3 OMeB3 OMe
A2B2
A5B5A6
B β
B1B6A1
B α
A4B3A3B4
B γA γ
Atom
1HJMultH Shifts
3.553.743.87
3.964.51
6.436.6576.6616.777.06
7.66
sss
dd
dddsds
s
3.13.1
8.3, 1.98.3
2.0
A γ OMeA3 OMeB3 OMe
βα
A6A5B5A2B2
B α
Atom
(acetone)
S. QuideauNotes:
2063Compound Number
FPL/DFRC NMR Database -- April 2009
Dihydroconiferyl 4-hydroxydihydrocinnamate
13C
46424445
47
44
4847
9999
51
100100
2528252326
24
30.1130.4031.7536.17
55.87
63.85
110.96114.28
115.31115.31
120.93
129.37129.37
132.46133.09143.76146.40154.13
173.26
CDCl3
CS i
30.7531.3332.2436.69
56.16
64.03
112.73115.62
116.00116.00
121.55
130.05130.05
132.38133.55146.58148.16156.57
173.09
47474749
45
48
4945
8989
51
100100
2325221722
21
Acetone
CS i
29.4929.9530.9135.47
55.48
63.13
112.43115.28
115.03115.03
120.30
129.04129.04
130.50131.83144.53147.38155.55
172.32
37383639
47
35
4092
3939
43
100100
3033353133
34
CS i
DMSO
B αβα
B β
OMe
γ
A2A5
B3B5
A6
B2B6
B1A1A4A3B4
B γ
Atom
1HJMultH Shifts
1.862.552.562.82
3.80
4.036.616.736.756.797.06
7.868.10
mttt
s
tdddmdm
ss
7.47.67.6
6.58.0, 2.0
7.9
2.0
βα
B βB α
OMe
γA6A5
B 3,5A2
B 2,6
ArOHArOH
Atom
(acetone)
S. QuideauNotes:
2064Compound Number
FPL/DFRC NMR Database -- April 2009
Dihydrosinapyl dihydro-p-coumarate
13C
48444646
9696
48
9494
9595100100
312426
5050
28
29
30.1130.4132.2636.17
56.2756.27
63.82
105.03105.03
115.32115.32129.34129.34
132.28132.36132.93
146.93146.93
154.19
173.21
CDCl3
CS i
30.7731.3132.7136.71
56.5756.57
64.04
106.69106.69
116.01116.01130.07130.07
132.40132.59135.07
148.62148.62
156.61
173.08
49484749
9292
49
9090
9292100100
262723
4343
25
26
Acetone
CS i
29.4929.9031.4135.46
55.8755.87
63.15
105.63105.63
115.02115.02129.03129.03
130.50131.04133.55
147.85147.85
155.55
172.32
36373236
100100
33
6969
81819191
252725
5353
28
30
CS i
DMSO
B αβα
B β
OMeOMe
γ
A2A6
B3B5B2B6
B1A1A4
A3A5
B4
B γ
Atom
1HJMultH Shifts
1.872.552.562.82
3.79
4.03
6.486.74
6.897.068.08
mttt
s
t
sm
sms
7.67.57.6
6.5
βα
B βB α
OMe
γ
A 2,6B 3,5
A4 OHB 2,6
B4 OH
Atom
(acetone)
S. QuideauNotes:
2065Compound Number
FPL/DFRC NMR Database -- April 2009
Sinapyl p-coumarate
13C
100100
43
8989
45
9393
44
2827
9494
44
28
39
5959
32
26
56.2856.28
65.15
103.55103.55
115.15
115.92115.92
121.44
126.98127.84
129.98129.98
134.53
135.03
144.91
147.10147.10
158.06
167.32
CDCl3
CS i
56.6156.61
65.42
105.16105.16
115.52
116.70116.70
122.07
126.99128.22
130.95130.95
135.14
137.27
145.45
148.84148.84
160.62
167.22
9191
43
9191
45
100100
48
2425
9999
47
22
45
4949
27
23
Acetone
CS i
ຶ55.9755.97
64.50
104.20104.20
114.08
115.78115.78
121.06
125.08126.47
130.34130.34
134.03
135.80
144.88
148.04148.04
159.87
166.40
100100
23
6464
38
6464
28
2526
7373
30
26
36
6464
25
24
CS i
DMSO
OMeOMe
γ
A2A6
B β
B3B5
β
B1A1
B2B6
α
A4
B α
A3A5
B4
B γ
Atom
1HJMultH Shifts
3.84
4.786.28
6.38
6.64
6.796.897.55
7.63
s
dddt
d
dt
smm
d
6.5, 1.315.8, 6.5
15.9
15.8, 1.3
15.9
OMe
γβ
B β
α
A 2,6B 3,5B 2,6
B α
Atom
(acetone)
S. QuideauB5 and C β can be interchanged
Notes:
2066Compound Number
FPL/DFRC NMR Database -- April 2009
2-(4-Acetoxy-3,5-dimethoxybenzoyl)-2-(2-methoxyphenoxy)ethyl 4-acetoxycinnamate
13C
5251
529393
3141
7676
4943
48
47100100459696313020
42
3129636331
35
2929
33
20.4121.10
55.7156.3456.34
64.7080.76
105.93105.93
112.59117.42
118.35
121.03122.18122.18123.60129.32129.32131.84132.66133.39
144.59
146.72150.37152.28152.28152.36
166.62
168.05169.08
194.44
CDCl3
CS i
20.2120.94
56.1256.6856.68
65.0780.41
106.52106.52
113.82118.33
118.38
121.64123.24123.2412334130.27130.27132.66133.94134.24
145.13
147.84151.34153.40153.40153.59
166.84
168.13169.41
194.92
4545
498989
3644
8484
4750
51
471001008919182627
13
4224222249
23
2622
24
Acetone
CS i
20.0820.83
55.5556.2156.21
63.8278.23
105.47105.47
112.95116.01
117.39
120.63122.38122.38122.55129.69129.69131.49132.49132.55
144.28
146.32149.51151.95151.95152.13
165.85
167.63168.94
194.02
5650
63100100
2028
5252
3435
41
409090328787343430
36
3739767634
33
3742
35
CS i
DMSO
AcAc
B3 OMeOMeOMe
γ
β
A2A6
B2B5
C β
B6C3C5B1C2C6C1A1A4
C α
B4B3A3A5C4
C γ
Ac C=OAc C=O
α
Atom
1HJMultH Shifts
2.262.263.753.86
4.604.865.966.50
6.836.987.187.56
7.62
7.69
ssss
ddddddd
dddmms
d
m
12.0, 6.812.0, 3.66.8, 3.6
16.0
7.9, 8.8, 2.5
16.0
Ac MeAc Me
B3 OMeOMe
γ1γ2β
C α
B6B 1,2,5C 3,5A 2,6
C β
C 2,6
Atom
(acetone)
S. QuideauNotes:
2067Compound Number
FPL/DFRC NMR Database -- April 2009
1(4-acetoxy-3,5-dimethoxyphenyl)-3-hydroxy-2-(2-methoxyphenoxy)propanone
13CCDCl3
CS i
20.20
56.1156.6256.62
63.9084.04
106.56106.56
113.67117.03121.61123.24
133.99134.39148.26151.03
153.25153.25
168.15
196.77
46
489494
4750
100100
50465353
13252121
4848
24
26
Acetone
CS i CS i
DMSO
Ac Me
B3 OMeOMeOMe
γβ
A2A6
B2B5B6B1
A4A1B4B3
A3A5
Ac C=O
α
Atom
1HJMultH Shifts
3.773.85
4.104.285.56
7.496.806.416.96
ss
ddtt
smmm
6.2, 5.06.25.0
B3 OMeOMe
γγ OH
β
A 2,6B6
B 1,5B2
Atom
(acetone)
S. QuideauNotes:
2068Compound Number
FPL/DFRC NMR Database -- April 2009
13CCDCl3
CS i
20.2520.94
56.2156.3956.39
64.0173.4983.04
104.37104.37
113.66
118.84
119.77121.73123.18123.18123.67128.89130.15130.15132.86140.77
144.38
148.69152.04152.89152.89153.43
166.80
168.58169.43
5051
459494
314040
7575
46
42
4647100100431594942830
42
2525525224
28
2130
Acetone
CS i CS i
DMSO
AcAc
B3 OMeOMeOMe
γα
β
A2A6
B2
C β
B5B6C3C5B1A4C2C6C1A1
C α
B4B3A3A5C4
C γ
Ac C=OAc C=O
Atom
1HJMultH Shifts
2.202.263.783.814.474.524.734.785.076.41
6.846.886.957.047.17
7.517.66
ssss
ddddmd
br td
dddsm
br ddm
dm
11.9, 3.911.9, 6.1
4.54.816.0
7.9, 6.4, 2.7
1.4
16.0
AcAc
OMeB3 OMe
γ1γ2β
α OHα
C β
B6A 2,6B 1,2B5
C 3,5
C αC 2,6
Atom
(acetone)
erythro
S. QuideauDiaxial configuration on 6-membered ring --Trans 7,8Natural occuring isomer is (+), i.e. 7S.8R, 8R'
Notes:
2069Compound Number
FPL/DFRC NMR Database -- April 2009
Isotaxiresinol
13CCDCl3
CS i
20.3620.4520.5020.6020.72
33.5036.2744.3447.51
56.18
63.5766.69
112.97124.12124.36124.92127.98
131.84135.41139.26142.08143.41144.19150.55
168.52168.63168.92171.04171.05
85100888386
67828080
96
6572
7474827879
54554641425844
4646455855
Acetone
CS i CS i
DMSO
A3 Ac MeA4 Ac MeB4 Ac Me
Ac MeAc Me
B αB β
β
α
OMe
γB γ
B2B5A5A2A6
B6B1B4A4A3A1B3
A4 Ac C=OB4 Ac C=OA3 Ac C=O
Ac C=OAc C=O
Atom
1HJMultH Shifts
2.002.012.102.142.222.242.262.903.783.904.064.114.124.226.346.887.047.107.14
sssmssmms
ddbr dddddddd
br sdddd
11.7, 3.510.2
11.2, 6.011.7, 3.511.2, 4.4
0.9
2.18.3, 4.1
8.3
Ac MeAc MeAc Me
βAc MeAc Me
B βB α
A3 OMeγ1α
Bγ1γ2
B γ2B5B2A2A6A5
Atom
(acetone)
S. Quideaunatural occuring isomer (-), i.e. 8R, 8R'As this compound has a plane of symmetry the shifts for the other half areidentical.
Notes:
2070Compound Number
FPL/DFRC NMR Database -- April 2009
Seco-isolariciresinol
13CCDCl3
CS i
20.4720.83
35.5140.8164.67
114.00121.67123.32139.14140.00152.01
169.04171.04
10084
647768
79808045150
4652
Acetone
CS i CS i
DMSO
4 Ac Meγ AcMe
αβ
γ
265413
4 Ac C=OγAc C=O
Atom
1HJMultH Shifts
2.002.21
2.222.702.83
3.74
4.034.25
6.706.876.92
ss
mdddd
s
dddd
dddd
13.9, 7.913.8, 6.7
11.4, 5.511.4, 6.1
8.0, 1.951.928.0
γ Ac Me4 Ac Me
βα1α2
A3 OMe
γ1γ2
A6A2A5
Atom
(acetone)
S. QuideauNotes:
2071Compound Number
FPL/DFRC NMR Database -- April 2009
13C
54545656
233529
78789898
38
96964432100100413833
44
7979717137
23
56.0156.0156.2556.25
63.9274.6687.07
103.75103.75105.16105.16
114.87
115.97115.97124.30126.83129.98129.98130.58134.50136.62
144.86
146.99146.99152.93152.93158.23
167.12
CDCl3
CS i
56.4456.4456.5956.59
64.7874.8186.87
105.39105.39106.35106.35
115.52
116.68116.68124.72126.97130.92130.92132.00136.27137.85
145.28
148.38148.38154.03154.03160.58
167.12
81814949
283538
7272100100
42
959540449191302420
41
5353515132
27
Acetone
CS i
55.7855.7855.9355.93
64.0972.1783.84
104.32104.32105.58105.58
114.12
115.82115.82123.62125.07130.21130.21131.16134.63136.12
144.38
147.49147.49152.97152.97159.80
166.25
2626100100
81717
36365151
36
747422255454263228
13
4040636324
32
CS i
DMSO
B OMeB OMeA OMeA OMe
γα
β
A2A6B2B6
C β
C3C5B1C1C2C6A1A4B4
C α
A3A5B3B5C4
C γ
Atom
1HJMultH Shifts
3.763.83
4.064.274.455.004.606.33
6.686.676.897.01
7.48
7.53
ss
ddddddd
br ddd
ddmdd
d
m
11.9, 4.27.3, 4.2, 3.112.0, 3.2
7.13.216.0
8.40.3
8.7, 8.1
16.0
A 3,5 OMeB 3,5 OMe
γ1βγ2α
α OHC β
B 2,6A 2,1C 3,5B1
C α
C 2,6
Atom
(acetone)
threo
S. QuideauNotes:
2072Compound Number
FPL/DFRC NMR Database -- April 2009
13C
92928989
303641
85859292
46
97974436100100322930
44
6969707035
37
56.2056.2056.3356.33
62.5971.9083.18
102.78102.78105.36105.36
115.19
115.91115.91124.44126.85129.88129.88129.75133.91134.69
144.58
147.00147.00153.69153.69158.15
167.29
CDCl3
CS i
56.4856.4856.6056.60
63.5773.1984.40
104.59104.59106.34106.34
115.73
116.65116.65124.75127.03130.82130.82131.66135.91136.59
144.99
148.49148.49154.53154.53160.43
167.16
78787676
314042
88889696
46
45453732100100282424
47
5757575734
32
Acetone
CS i
55.7755.7755.9255.92
63.3872.6283.51
103.77103.77105.32105.32
114.12
115.81115.81123.40125.03130.11130.11132.10134.45135.92
144.16
147.63147.63152.89152.89159.74
166.27
7676100100
192728
62626969
42
878731378383293236
37
6767848432
38
CS i
DMSO
B OMeB OMeA OMeA OMe
γα
β
A2A6B2B6
C β
C3C5B1C1C2C6A1A4B4
C α
A3A5B3B5C4
C γ
Atom
1HJMultH Shifts
3.793.82
4.234.454.584.6974.966.15
6.686.716.847.01
7.33
7.46
ss
ddddmd
br md
ddmdd
d
m
11.8, 3.411.8, 7.3
3.9
16.0
8.40.7
8.6, 8.2
16.0
A 3,5 OMeB 3,5 OMe
γ1γ2β
α OHα
C β
B 2,6A 2,6C 3,5B1
C α
C 2,6
Atom
(acetone)
erythro
S. QuideauNotes:
2073Compound Number
FPL/DFRC NMR Database -- April 2009
13C
498383
1001007878
223029
51516969
34
797931189696263024
33
5555245353
27
254127
20.3621.0221.02
55.8955.8956.1356.13
64.0175.6380.86
104.10104.10105.09105.09
117.75
122.09122.09123.74128.57129.19129.19131.92135.42136.56
143.86
151.94151.94152.10153.14153.14
166.24
168.45169.05169.68
CDCl3
CS i
20.2320.9520.95
56.3556.3556.4956.49
64.6676.7981.83
104.92104.92106.22106.22
118.88
123.20123.20124.47129.54130.22130.22132.90136.76137.85
144.48
153.07153.07153.46154.19154.19
166.62
168.46169.45169.93
477373
72727373
253432
61617777
38
10010037148888243620
39
5353245353
26
212927
Acetone
CS i
20.1520.7520.88
55.8055.8056.0156.01
63.7275.9780.62
103.89103.89105.29105.29
117.82
122.43122.43123.68127.74129.68129.68131.66135.61136.15
143.76
151.55151.55152.09152.69152.69
165.86
168.06169.06169.44
544752
77775656
101618
34347070
27
10010022256767312731
29
7474306666
32
283830
CS i
DMSO
Ac Me Ac Me
α Ac Me
OMe OMe OMe OMe
γα
β
A2A6B2B6
C β
C3C5B1A4C2C6C1B4A1
C α
A3A5C4B3B5
C γ
Ac C=OAc C=OAc C=O
Atom
1HJMultH Shifts
1.972.022.27
3.783.79
4.074.414.686.186.56
6.666.866.997.197.55
7.72
sss
ss
ddddddddd
dbr s
tmd
m
11.9, 4.711.9, 3.8
6.8, 4.7, 3.86.816.0
8.4
8.4
16.0
α Ac Me Ac MeAc Me
OMeOMe
γ1γ2βα
C β
B 2,6A 2,6
B1C 3,5C α
C 2,6
Atom
(acetone)
threo
S. QuideauB3,5 OMe and A3,5 OMe can be interchanged
Notes:
2074Compound Number
FPL/DFRC NMR Database -- April 2009
13C
578686
100100100100
253435
65657575
41
87873219494312733
39
6262296666
32
303530
20.3621.0221.02
55.8755.8756.0756.07
63.1374.5080.92
103.93103.93105.05105.05
117.84
122.03122.03124.00128.37129.19129.19131.98135.39135.73
143.73
151.84151.84152.04153.32153.32
166.42
168.49169.04169.43
CDCl3
CS i
20.2420.9520.95
56.3256.3256.4756.47
63.7375.5881.67
104.60104.60106.12106.12
118.80
123.19123.19124.72129.35130.15130.15132.85136.69136.77
144.29
153.06153.06153.44154.34154.34
166.52
168.51169.44170.00
427171
80807979
283738
84848383
42
10010043159090263421
41
5555235656
27
252726
Acetone
CS i
20.1520.7620.87
55.7855.7855.9755.97
62.6474.2380.19
103.45103.45105.27105.27
117.70
122.43122.43124.00127.59129.57129.57131.56134.77135.43
143.54
151.58151.58152.06152.85152.85
165.70
168.10169.05169.49
615453
1001008888
152626
55556969
36
999929318282333934
36
8585369494
36
404539
CS i
DMSO
Ac Meα Ac MeAc Me
B OMeB OMeA OMeA OMe
γα
β
A2A6B2B6
C ֤β
C3C5B1A4C2C6C1B4A1
C α
A3A5C4B3B5
C γ
Ac C=OAc C=OAc C=O
Atom
1HJMultH Shifts
2.152.212.263.793.81
4.364.534.806.146.35
6.656.836.997.18
7.44
7.66
sssss
dddddtdd
dbr st(dd)
m
d
m
11.9, 4.011.9, 6.26.2, 4.0
4.216.0
8.4
8.4
16.0
α Ac Me Ac MeAc Me
B 3,5 OMeA 3,5 OMe
γ1γ2βα
C β
B 2,6A 2,6
B1C 3,5
C α
C 2,6
Atom
(acetone)
erythro
S. QuideauNot run in DMSO
Notes:
2075Compound Number
FPL/DFRC NMR Database -- April 2009
γ-p-coumaroylated syringylglycerol-β04-guaiacol ether (Ac'd)
13C
20.4221.1021.10
35.7756.2056.20
63.3974.8880.50
104.09104.09112.45
117.52
118.85121.00122.14122.14123.34128.81129.31129.31131.91134.81
144.25
147.99150.86152.01152.01152.20
166.32
168.47169.09169.71
CDCl3
CS i
20.2320.9420.94
56.2156.5156.51
63.9775.9280.89
105.00105.00113.74
118.62
119.25121.70123.22123.22123.75129.70130.26130.26132.83136.23
144.78
149.16151.87153.21153.21153.53
166.64
168.43169.43170.03
254040
305151
142019
414131
24
262710010024756561517
25
1313292918
19
142214
Acetone
CS i CS i
DMSO
Ac MeAc Me
αAc Me
B3 OMeOMeOMe
γα
β
A2A6B2
C β
B5B6C3C5B1A4C2C6C1A1
C α
B4B3A3A5C4
C γ
Ac C=OAc C=OAc C=O
Atom
1HJMultH Shifts
2.042.202.273.793.814.194.394.886.156.54
6.876.88
6.93 - 7.007.08 - 7.10
7.19
7.58
7.71
sssss
ddddddddd
mbr smmm
d
m
12.0, 5.511.9, 3.96.6, 5.5
6.616.0
16.0
α Ac Me Ac MeAc MeB OMe
A 3,5 OMeγ1γ2βα
C β
B6A 2,6B 1,2B5
C 3,5
C α
C 2,6
Atom
(acetone)
threo
S. QuideauNotes:
2076Compound Number
FPL/DFRC NMR Database -- April 2009
γ-p-coumaroylated syringylglycerol-β04-guaiacyl ether
13C
509191
293936
808050
44
9999495052331001003436
44
6868323236
36
55.8256.3156.31
63.1974.7086.09
103.82103.82112.19
114.66
115.95115.95120.53121.45124.12126.89130.04130.04130.29134.73
145.18
147.11147.11147.91150.91158.08
166.86
CDCl3
CS i
56.2756.5956.59
64.2374.1184.42
105.41105.41113.60
115.30
116.68116.68119.33121.82123.52126.96130.97130.97132.11136.36
145.57
148.47148.47149.37151.80160.60
167.15
387474
313241
858548
46
9999505147301001002518
46
4545242330
29
Acetone
CS i
55.6055.8855.88
63.4771.5381.02
104.24104.24112.70
113.86
115.78116.25116.25120.71121.71125.00130.30131.30131.22134.67
144.84
147.58147.58147.86149.91159.87
166.38
549595
153129
686846
43
1001005447354895953653
35
9999465541
52
CS i
DMSO
B3 OMeOMeOMe
γα
β
A2A6B2
C β
C3C5B5B6B1C1C2C6A1A4
C α
A3A5B4B3C4
C γ
Atom
1HJMultH Shifts
3.793.84
4.114.364.574.966.31
6.826.85-6.90
6.886.94-7.01
7.15
7.48
7.51
ss
ddddtd
(br)dd
dmmmdd
d
m
12.0, 6.212.0, 3.46.1, 3.4
5.916.0
0.4
7.9, 1.5
16.0
A OMeB3 OMe
γ1γ2βα
C β
A 2,6B6
C 3,5B 1,2B5
C α
C 2,6
Atom
(acetone)
threo
S. QuideauNotes:
2077Compound Number
FPL/DFRC NMR Database -- April 2009
γ-p-coumaroylated syringylglycerol-β04-guiacol ether (Ac'd)
13C
514758
529393
273536
737343
43
4345959541201001003031
41
3132616129
30
283327
20.4021.0121.06
55.7356.1456.14
62.9874.1780.31
104.43104.43112.51
117.59
119.50120.95122.09122.09123.58128.67129.28129.28131.93134.92
144.23
147.24151.07151.98151.98152.16
166.44
168.49169.06169.48
CDCl3
CS i
20.2420.9020.94
56.2056.5056.50
63.4174.9980.38
105.14105.14113.75
118.57
119.79121.65123.21123.21124.02129.57130.22130.22132.79136.25
144.74
148.36152.03153.07153.07153.51
166.63
168.48169.43169.95
433747
478282
273534
707043
40
4142100100381383832426
38
2221454521
26
212521
Acetone
CS i
20.1220.7020.84
55.6155.9755.97
62.3573.5378.34
104.10104.10112.88
117.53
117.81120.69122.38122.38122.81127.73129.63129.63131.51134.99
143.94
146.75150.27151.48151.48152.08
165.76
168.01168.97169.34
505154
589999
182924
535343
40
4245100100342786863332
39
3641707036
33
333730
CS i
DMSO
Ac Meα Ac MeAc Me
B3 OMeA OMeA OMe
γα
β
A2A6B2
C β
B5B6C3C5B1A4C2C6C1A1
C α
B4B3A3A5C4
C γ
Ac C=OAc C=O
α Ac C=O
Atom
1HJMultH Shifts
2.092.212.263.813.814.434.494.946.126.45
6.856.89
6.95-7.007.03-7.06
7.19
7.57
7.69
sssss
ddddmdd
mdmmm
d
m
11.9, 4.311.9, 5.8
5.116.0
0.4
16.0
α Ac MeAc MeAc Me
B3 OMeA OMe
γ1γ2βα
C β
B6A 2,6B 1,2B5
C 3,5
C α
C 2,6
Atom
(acetone)
erythro
S. QuideauNotes:
2078Compound Number
FPL/DFRC NMR Database -- April 2009
γ-p-coumaroylated syringylglycerol-β04-guaiacyl ether
13C
53100100
303340
848449
46
99994954463699993737
44
6060393538
39
55.8356.2956.29
62.7072.3984.23
103.13103.13112.22
114.40
115.95115.95120.53121.46124.03126.44129.98129.98130.16134.15
145.25
147.00147.00147.02151.42158.68
167.39
CDCl3
CS i
56.2356.6056.60
64.0473.5183.41
105.23105.23113.63
115.37
116.67116.67119.55121.72123.46126.92130.90130.90132.59136.12
145.42
148.42148.42148.91152.00160.58
167.28
488989
333542
848447
45
1001004848452894943126
43
5151242231
28
Acetone
CS i
55.5455.9055.90
63.2971.7780.92
104.38104.38112.74
113.93
115.75115.75116.89120.62121.83124.99130.24130.24132.05134.61
144.71
147.52147.52147.52150.03159.82
166.41
CS i
DMSO
B3 OMeOMeOMe
γα
β
A2A6B2
C β
C3C5B5B6B1C1C2C6A1A4
C α
A3A5B4B3C4
C γ
Atom
1HJMultH Shifts
3.803.814.414.474.684.986.25
6.816.836.87
6.91-6.967.05
7.44
7.48
ss
dddddddbr d
d
brsmmm
br dd
d
m
11.8, 3.811.8, 6.4
6.4, 5.0, 3.84.916.0
7.8, 1.5
16.0
OMeB3 OMe
γ1γ2βα
C β
A 2,6B6
C 3,5B 1,2B5
C α
C 2,6
Atom
(acetone)
erythro
S. QuideauNotes:
2079Compound Number
FPL/DFRC NMR Database -- April 2009
13CCDCl3
CS i
20.2521.06
56.3656.3656.4556.45
64.9374.5685.88
104.48104.48106.35106.35
118.98
123.19123.19124.80128.98130.17130.17132.93137.65140.28
144.26
152.82152.82153.43154.07154.07
166.65
168.54169.45
5353
83838181
302337
69698888
40
10010043149191392121
40
5353245454
26
2536
Acetone
CS i CS i
DMSO
Ac MeAc Me
A OMeA OMeB OMeB OMe
γα
β
A2A6B2B6
C β
C3C5B1A4C2C6C1B4A1
C α
A3A5C4B3B5
C γ
Ac C=OAc C=O
Atom
1HJMultH Shifts
2.192.273.753.82
4.164.384.505.076.47
6.686.877.017.19
7.63
7.70
ssss
ddddddd
br dd
dbr s
tm
d
m
11.9, 4.66.3, 4.5, 3.6
11.9, 3.66.416.0
8.4
8.4
16.0
Ac MeAc MeA OMeB OMe
γ1βγ2α
C β
B 2,6A 2,6
B1C 3,5
C α
C 2,6
Atom
(acetone)
threo
S. QuideauNotes:
2080Compound Number
FPL/DFRC NMR Database -- April 2009
13CCDCl3
CS i
20.2620.94
56.3856.3856.4856.48
63.6773.3084.07
103.76103.76106.31106.31
119.10
123.16123.16124.83128.69130.11130.11132.93136.57140.05
144.00
152.94152.94153.36154.51154.51
166.71
168.59169.45
4754
86869797
313739
82828888
44
10010043148989292125
42
4848215252
28
2327
Acetone
CS i CS i
DMSO
Ac MeAc Me
A OMeA OMeB OMeB OMe
γα
β
A2A6B2B6
C β
C3C5B1A4C2C6C1B4A1
C α
A3A5C4B3B5
C γ
Ac C=OAc C=O
Atom
1HJMultH Shifts
2.192.263.783.83
4.304.514.625.056.34
6.096.827.037.17
7.44
7.66
ssss
ddddm
br td
dbr s
tm
d
m
11.7, 3.811.7, 6.9
3.716.0
8.4
8.4
16.0
Ac MeAc MeA OMeB OMe
γ1γ2βα
C β
B 2,6A 2,6
B1C 3,5
C α
C 2,6
Atom
(acetone)
erythro
S. QuideauNotes:
2081Compound Number
FPL/DFRC NMR Database -- April 2009
13C
4240
85858282
2738
91918282
43
10010046979733193524
44
6969286565
33
2929
33
20.4021.08
55.8855.8856.2856.28
64.4981.85
105.11105.11106.37106.37
117.67
122.15122.15124.23129.21129.21131.90133.05133.49135.68
144.02
152.08152.08152.16153.03153.03
166.34
168.06169.08
194.81
CDCl3
CS i
20.2320.95
56.3156.3156.6756.67
64.9081.50
106.18106.18106.93106.93
118.55
123.25123.25124.99130.19130.19132.72133.96134.72136.63
144.62
153.20153.20153.52154.07154.07
166.55
168.19169.43
195.26
Acetone
CS i
20.1220.85
55.8055.8056.2056.20
63.7779.82
105.39105.39105.86105.86
117.57
122.45122.45124.07129.61129.61131.48132.28133.31135.12
143.83
151.80151.80152.11152.53152.53
165.73
167.72169.02
184.38
4740
1001009292
1726
63634949
33
767628717132263332
32
6969317070
32
3332
31
CS i
DMSO
Ac MeAc Me
B OMeB OMeA OMeA OMe
γ
β
B2B6A2A6
C β
C3C5B1C2C6C1A4A1B4
C α
A3A5C4B3B5
C γ
Ac C=OAc C=O
α
Atom
1HJMultH Shifts
2.262.283.723.85
4.634.745.696.39
6.646.497.17
7.50
7.587.64
ssss
ddddddd
dtm
d
br sm
11.7, 6.211.7, 4.66.2, 4.6
16.0
8.48.4
16.0
Ac MeAc MeB OMeA OMe
γ1γ2β
C β
B 2,6B1
C 3,5
C α
A 2,6C 2,6
Atom
(acetone)
S.QuideauNotes:
2082Compound Number
FPL/DFRC NMR Database -- April 2009
13CCDCl3
CS i
20.21
56.2856.2856.6156.61
63.3586.41
106.22106.22106.51106.51
124.92133.59135.01137.01
153.06153.06153.77153.77
168.18
196.25
51
1001009797
4248
97979191
47142920
51515050
22
27
Acetone
CS i CS i
DMSO
Ac Me
B OMeB OMeA OMeA OMe
γβ
B2B6A2A6
B1A4A1B4
A3A5B3B5
Ac C=O
α
Atom
1HJMultH Shifts
2.27
3.733.86
3.90-3.985.22
6.677.027.48
s
ss
mdd
ddd t
s
5.7, 4.5
8.48.6, 8.2, 8.4
Ac Me
B OMeA OMe
γ + γ OHβ
B 2,6B1
A 2,6
Atom
(acetone)
jrf107.P1 /1 (H1), /2 (C13), /3 (Dept135)Notes:
3001Compound Number
FPL/DFRC NMR Database -- April 2009
4-O-5 dehydrodiethylferulate3-{3-[4-(2-ethoxycarbonyl-vinyl)-2-methoxy-phenoxy]-4-hydroxy-5-
methoxy-phenyl}acrylic acid ethyl ester
13CCDCl3
CS i
14.6014.60
56.4156.77
60.5360.64
107.99112.66114.45
116.99117.93
118.36122.84126.67131.04141.41144.45
144.81144.94
149.35150.12151.41
167.15167.16
10092
8982
7172
697873
7680
697856531940
7573
393443
5356
Acetone
CS i CS i
DMSO
A CH3B CH3
B3 OMeA3 OMe
A CH2B CH2
A2B2A6
A βB β
B5B6A1B1A4A5
B α A α
B4A3B3
B γ A γ
Atom
1HJMultH Shifts
1.241.27
3.933.96
4.164.19
6.366.486.816.897.177.227.467.537.62
tt
ss
dddddddddd
7.17.1
7.17.1
15.915.958.31.9
8.7, 2.01.92.015.915.95
A CH3B CH3
B3 OMeA3 OMe
A CH2B CH2
A βB βB5A6B6A2B2
A αB α
Atom
(acetone)
FLJ144As this dimer contains a plane of symmetry the CS's are reported for one unit.
Notes:
3002Compound Number
FPL/DFRC NMR Database -- April 2009
13CCDCl3
CS i
49.06
56.7756.77
83.39
104.31104.31
129.87
137.51
149.04149.04
176.05
Acetone
CS i CS i
DMSO
β
OMeOMe
α
26
4
1
35
g
Atom
1HJMultH Shifts
3.83
4.11
5.95
6.73
7.42
s
s
s
s
s
OMe
β
α
2,6
OH
Atom
(acetone)
Acetone: jrf117 /2 (C13) and /1 (H1) DMSO: jrf127.c7/2 Not soluble in chloroform1H NMR (DMSO-d6) d: 3.85 (B3-OMe), 3.86 (A3-OMe),6.35 (A8), 6.47 (B8),6.59 (B5), 6.85 (A6), 7.12 (B6), 7.20 (A2), 7.43 (B2), 7.42 (A7), 7.51 (B7)JCS Perkin 1, 3485-98 (1994) Cmpd 17
Notes:
3003Compound Number
FPL/DFRC NMR Database -- April 2009
4-O-5 dehydrodiferulic acid
13CCDCl3
CS i
56.4056.76
108.03112.7114.46
117.00117.95
118.33122.80
126.71131.06
141.38144.44
145.23145.38
149.34150.12151.38
168.02168.05
94100
707579
7576
7979
6363
4654
7673
565658
6266
Acetone
CS i
55.8556.24
107.58111.86114.05
116.96118.00
116.34121.91
125.22129.43
140.35142.94
143.81143.63
148.05149.28149.56
167.82167.82
10093
323946
2521
4346
6154
6464
3629
647179
6161
CS i
DMSO
B3 OMeA3 OMe
A2B2A6
A βB β
B5B6
A1B1
A4A5
A αB α
B4A3B3
B γA γ
Atom
1HJMultH Shifts
3.583.886.366.476.826.907.227.227.457.547.63
3.853.866.356.476.596.857.127.207.437.427.517.51
ssdddddddddd
15.915.958.31.9
8.3, 2.01.92.015.915.95
B3 OMeA3 OMe
A βB βB5A6B6A2B2
A αB α
DMSOB3 OMeA3 OMe
A βB βB5A6B6A2B2
A αB α
Atom
(acetone)
jrlz 15Liming Zhang, isolate from mild acidolysis
Notes:
3004Compound Number
FPL/DFRC NMR Database -- April 2009
1,2-diguaiacylpropane-1,3-diol
13CCDCl3
CS i
55.8555.95
56.3164.2174.66
111.01114.00114.81115.00119.95123.05
132.24136.67145.96146.17147.56147.63
100100
453857
999935369595
643816161816
Acetone
CS i CS i
DMSO
OMeOMe
βγ
α
A2B2A5B5A6B6
B1A1B4A4B3A3
Atom
1HJMultH Shifts
2.933.723.875.02
6.606.666.686.686.716.74
mmmbd
bddddmmd
8.1
1.9
βγ1γ2α
B6B5A5A6A2B2
Atom
(acetone)
erythro
jrlz9.1Liming Zhang, isolate from mild acidolysis
Notes:
3005Compound Number
FPL/DFRC NMR Database -- April 2009
Acetic acid3-acetoxy-2,3-bis-(4-acetoxy-3-methoxyphenyl)propyl ester
13CCDCl3
CS i
20.4120.4420.7221.01
50.7156.1856.21
64.7176.50
112.51114.33119.77121.85123.14123.22
137.82138.39139.96140.35151.76151.85
168.84168.88170.01170.81
96938192
7891100
6875
807680848284
605436384145
45404743
Acetone
CS i CS i
DMSO
Ac MeAc MeAc MeAc Me
βOMeOMe
γα
A2B2A6B6A5B5
B1A1B4A4B3A3
Ac C=OAc C=O
α Ac C=Oγ Ac C=O
Atom
1HJMultH Shifts
1.932.092.182.193.56
3.673.71
4.384.546.02
6.776.796.826.856.906.91
ssssm
ss
ddddd
dddbddddbddd
11.2, 5.2 11.2, 7.2
8.2
8.1, 2.0, 0.31.9
8.1, 1.9, 0.51.98.18.1
γ Ac Meα Ac MeAc MeAc Me
β
OMeOMe
γ1γ2α
B6A2A6B2B5A5
Atom
(acetone)
threo
jrlz11.1Liming Zhang, isolate from mild acidolysis1H data at 600 MHz
Notes:
3006Compound Number
FPL/DFRC NMR Database -- April 2009
Acetic acid3-acetoxy-2,3-bis-(4-acetoxy-3-methoxyphenyl)propyl ester
13CCDCl3
CS i
20.4320.4620.6520.83
50.9856.2056.22
64.8675.56
112.09114.52119.73121.93123.13123.30
137.43138.72140.05140.51151.80152.00
168.89168.95169.94170.74
981008385
769792
6575
747576757884
505040394649
41384646
Acetone
CS i CS i
DMSO
Ac MeAc MeAc MeAc Me
βOMeOMe
γα
A2B2A6B6B5A5
B1A1B4A4B3A3
Ac C=OAc C=O
α Ac C=Oγ Ac C=O
Atom
1HJMultH Shifts
1.921.972.202.21
3.50
3.693.73
4.204.376.16
6.846.846.876.926.966.98
ssss
m
ss
ddddd
dddbddddbddd
6.7
11.2, 6.711.2, 6.8
6.6
8.1, 1.9, 0.31.8
8.1, 1.8, 0.51.98.18.1
γ Ac Meα Ac MeAc MeAc Me
β
OMeOMe
γ1γ2α
B6A2A6B2B5A5
Atom
(acetone)
erythro
jrlz 13Liming Zhang, isolate from mild acidolysis
Notes:
3007Compound Number
FPL/DFRC NMR Database -- April 2009
Acetic acid 3-acetoxy-2,3-bis-(4-acetoxy-3-methoxyphenyl)propyl ester
13C
1148067
61
120120
496851
735865656879
515843436868
60
295265
93
20.6020.7920.96
50.13
55.8555.85
63.9674.76107.76
111.65113.15119.35121.12121.61122.45
135.71136.32139.10142.55150.75150.75
157.84
168.79169.70170.69
186.74
CDCl3
CS i
20.4320.6620.83
51.07
56.1256.22
64.8275.38108.01
122.68114.44120.17122.12122.14123.16
137.41138.17140.07143.24151.76151.81
159.33
168.91169.94170.71
187.55
585154
41
6666
424034
404143483152
272919182527
25
212324
45
Acetone
CS i CS i
DMSO
Ac MeAc MeAc Me
β
OMeOMe
γαγ'
A2B2A6B6A5B5
B1A1B4A4B3A3
β'
B4 Ac C=Oα Ac C=OγAc C=O
α'
Atom
1HJMultH Shifts
1.942.002.07 3.50
3.693.76
4.224.385.005.386.19
6.816.886.89
6.946.976.99
9.45
sss
m
ss
ddddddd
ddbddd
d
11.2, 6.811.2, 6.8
2.82.86.4
8.1, 1.6
7.3, 1.5
8.1
γ Ac Meα Ac MeAr Ac Me
β
OMeOMe
γ1γ2γ1'γ2'α
B6A2A6
B5A5A2
a'
Atom
(acetone)
erythro
jrlz 35Liming Zhang, isolate from mild acidolysis
Notes:
3008Compound Number
FPL/DFRC NMR Database -- April 2009
Acetic acid 3-acetoxy-3-(4-acetoxy-3-methoxyphenyl)-2-[4-(3-acetoxypropenyl)-2-methoxyyphenoxy]propyl ester
13CCDCl3
CS i
20.4120.5520.7520.89
56.2356.27
63.5465.3375.2980.62
111.30112.63118.73120.28120.52123.25123.54
132.34
134.14
136359140.90149.08151.74152.21
168.85169.95170.64170.64
56584550
5656
44575657
58475744445751
32
54
3122262322
26302323
Acetone
CS i CS i
DMSO
Ac MeAc MeAc MeAc Me
OMeOMe
γ
B γαβ
B2A2B5A6B6B βA5
B1
B α
A1A4B4B3A3
A4 Ac C=Oα Ac C=Oγ Ac C=O
B γ Ac C=O
Atom
1HJMultH Shifts
1.952.012.022.213.823.854.024.254.664.816.106.266.63
6.957.007.037.097.147.22
ssssss
ddddddmddtbdt
dddddddd
11.9, 5.711.9, 4.16.4, 1.3
6.415.9, 6.4
15.9
8.3, 2.08.38.2
8.2, 1.71.91.6
γ Ac MeB γ Ac Meα Ac Me
A4 Ac MeOMeOMe
γ1γ2B γβα
B βB α
B6B5A5A6B2A2
Atom
(acetone)
threo
J.Ralph jrf79.5As this dimer contains a plane of symmetry the CS's are reported for one unit.
Notes:
3009Compound Number
FPL/DFRC NMR Database -- April 2009
13CCDCl3
CS i
20.2620.6120.93
56.1756.52
63.5175.3180.70
111.90113.72119.41121.64121.68123.87
131.91135.93138.48148.99151.87152.58
168.88170.09170.71
62.95
74.59
80344
120.09
124.19
131.70
138.36
148.19
152.11
6911277
8678
563452
41654210110155
254518463532
113936
Acetone
CS i CS i
DMSO
Ac MeAc MeAc Me
OMeOMe
γα
β
A2B2B5A6B6B1
A5A1A4B4B3A3
4 Ac C=Oα Ac C=Oγ Ac C=O
erythro isomerγ
α
β
B5
B1
A5
A4
B4
B3
Atom
1HJMultH Shifts
3.773.85
4.094.294.786.08
6.80-6.906.966.997.027.26
ss
mmmd
mmmmm
OMeOMe
γ1γ2βα
A6,B6B1B2B5A2
Atom
(acetone)
threo
jrlz 29 1mgLiming Zhang, isolate from mild acidolysissee 3011 some shifts taken from isomer mix
Notes:
3010Compound Number
FPL/DFRC NMR Database -- April 2009
Acetic acid 3-acetoxy-3-(4-acetoxy-3-methoxyphenyl)-2-[2-methoxy-4-(3-oxopropenyl)phenoxy]propyl ester
13C
804560
7185
252830
313531383232
34
222419
242423
45
232424
58
20.6020.6820.94
55.9055.98
62.8174.1479.67
111.28111.58117.36119.48122.71122.89
127.40
128.88134.87140.01
150.72150.68151.16
152.26
168.72169.41170.48
193.43
CDCl3
CS i
20.4320.5720.88
56.3056.41
63.4575.1980.26
112.56112.66117.85120.34123.61123.76
128.23
129.89136.40140.99
151.73151.73152.26
153.29
168.87169.85170.66
193.61
392420
3925
252524
273132282431
27
141815
222216
26
171515
32
Acetone
CS i CS i
DMSO
g Ac Mea Ac Me
A4 Ac Me
OMeOMe
γαβ
B2A2B5A6A5B6
B β
B1A1A4
B4B3A3
B α
A4 Ac C=Oα Ac C=Oγ Ac C=O
B γ
Atom
1HJMultH Shifts
2.012.082.213.823.914.074.284.966.11
6.70
7.037.087.157.247.257.40
7.599.66
sssss
ddddmd
dd
ddddbdddd
dd
12.0, 5.812.0, 4.1
6.4
15.9, 7.7
8.18.5, 1.4
8.4
8.8, 1.71.8
16.07.6
Ac MeAc MeAc MeOMeOMe
γ 1γ 2βα
Bβ
A5A6B5A2B6B2
B αB γ
Atom
(acetone)
threo
jrlz41Liming Zhang, isolate from mild acidolysisCS's taken from isomer mix spectrum
Notes:
3011Compound Number
FPL/DFRC NMR Database -- April 2009
Acetic acid 3-acetoxy-3-(4-acetoxy-3-methoxyphenyl)-2-[2-methoxy-4-(3-oxopropenyl)phenoxy]propyl ester
13C
804560
7185
252827
322829292929
34
222217
182222
45
232222
58
20.6020.6820.94
55.8755.90
62.4473.5579.56
111.38112.00117.93119.76122.61122.81
127.47
129.10134.80139.90
150.02150.95151.00
152.26
168.74169.57170.65
193.43
CDCl3
CS i
20.6520.7921.10
56.5156.65
63.1974.5780.02
112.85113.08118.49120.75123.50123.91
128.53
130.22136.48141.11
151.22152.12152.35
153.45
169.09170.07170.88
194.10
734538
5339
302731
323332333736
33
192115
162016
32
232020
66
Acetone
CS i CS i
DMSO
γ Ac Meα Ac MeA4 Ac Me
OMeOMe
γα
β
B2A2B5A6A5B6
B β
B1A1A4
B4B3A3
B α
A4 Ac C=Oα Ac C=Oγ Ac C=O
B γ
Atom
1HJMultH Shifts
3.823.90
4.274.374.996.07
6.797.027.077.117.237.277.38
7.589.65
ss
mmmd
dddmdmdd
dd
5.2
15.9, 7.78.1
8.3
1.82.0
15.9 7.7
Ac MeAc MeAc MeOMeOMe
γ 1γ 2βα
B βA5A6B5A2B6B2
B αB γ
Atom
(acetone)
erythro
jrlz 19 15mg Liming Zhang, isolate from mild acidolysis. Due to the complexityof the model and the number of isomers present only the side chains chemical shiftshave been assigned. The A side chain is a single isomer and the B chain is botherythro and threo giving 4 isomers.
Notes:
3012Compound Number
FPL/DFRC NMR Database -- April 2009
13CCDCl3
CS i
50.6450.67
50.9050.95
50.9551.2351.26
64.74
64.8564.89
65.5565.6365.85
75.7575.76
76.5676.62
87.9188.0388.04
Acetone
CS i CS i
DMSO
B β tB β t
B β eB β e
A βA βA β
B γ t
B γ eB γ e
A γA γA γ
B α eB α e
B α tB α t
ααα
Atom
1HJMultH ShiftsAtom
(acetone)
jrlz 7 and jrlz 17 Liming Zhang - isolate from mild acidolysis.threo β-O-4/threo+erythro β-1Due to the complexity of the model and the number of isomers present only theside chains chemical shifts have been assigned.
Notes:
3013Compound Number
FPL/DFRC NMR Database -- April 2009
Acetic acid 3-acetoxy-3-(4-acetoxy-3-methoxyphenyl)-2-{4-[1,3-diacetoxy-2-(4-acetoxy-3-methoxyphenyl)propyl]-2-methoxyphenoxy}
propyl ester
13CCDCl3
CS i
50.3750.46
50.7150.75
63.37
64.7464.75
64.8464.86
75.1375.3575.19
75.4775.53
76.3076.35
80.3480.3680.42
Acetone
CS i CS i
DMSO
B β tB β t
B β eB β e
γ
B γ tB γ t
B γ eB γ e
ααα
B α eB α e
B α tB α t
βββ
Atom
1HJMultH ShiftsAtom
(acetone)
threo
jrlz5, mixture of 2 isomers in ca. 2:1 ratio.Data for major isomerLiming Zhang, isolate from mild acidolysis
Notes:
3014Compound Number
FPL/DFRC NMR Database -- April 2009
4-(4-hydroxy-3-methoxyphenyl)-7-methoxy-1,3,3a,4,9,9a-hexahydronaphtho[2,3-c]furan-1,6-diol
13CCDCl3
CS i
29.8446.2447.0051.09
55.9656.05
72.0698.75
112.38112.84115.51116.17121.75128.34133.42137.28
145.11145.93146.61148.24
55563062
7986
5734
2957323542443938
19172120
Acetone
CS i CS i
DMSO
α
B ββ
B α
OMeOMe
B γγ
B2A2B5A5B6A1A6B1
A4B4A3B3
Atom
1HJMultH Shifts
1.982.542.843.003.473.643.77
3.773.80
4.995.406.226.636.726.746.777.177.39
mmmmdddm
ss
dddddsddss
10.0, 8.012.2
4.34.30.9
8.0, 2.0
2.08.0
A βB β
A α1A α2B γ1B αB γ2
OMeOMe
A γ OHA γA5B6A2B2B5
A4 OHB4 OH
Atom
(acetone)
jrlz5, mixture of 2 isomers in ca. 2:1 ratio.Data for minor isomerLiming Zhang, isolate from mild acidolysis
Notes:
3015Compound Number
FPL/DFRC NMR Database -- April 2009
4-(4-hydroxy-3-methoxyphenyl)-7-methoxy-1,3,3a,4,9,9a-hexahydronaphtho[2,3-c]furan-1,6-diol
13CCDCl3
CS i
31.9849.8849.8850.12
55.9656.05
70.96104.08
112.28112.79115.51116.28121.75127.93133.38136.75
145.31145.95146.63148.20
22484818
7986
2314
2927321442181714
911119
Acetone
CS i CS i
DMSO
α
Bββ
B α
OMeOMe
Bγγ
B2A2B5A5B6A1A6B1
A4B4A3B3
Atom
1HJMultH Shifts
1.982.282.803.003.643.72
3.773.80
5.185.286.556.626.726.746.777.177.39
mmmmmbd
ss
dddddsddss
11.4
6.2
10.1, 2.0
2.08.0
A βB β
A α1A α2
B γ 1,2B α
OMeOMe
A γA γOH
A5B6A2B2B5
A4 OHB4 OH
Atom
(acetone)
jrlz25Liming Zhang, isolate from mild acidolysis
Notes:
3016Compound Number
FPL/DFRC NMR Database -- April 2009
Acetic acid 4-(4-acetoxy-3-methoxyphenyl)-7-methoxy-1-oxo-1,3,3a,4,9,9a-hexahydroanphtho[2,3-c]furan-6-yl ester
13C
8286
49837471
92103
63
228036507857484530565434
5336
60
20.5320.63
29.5741.6647.4449.93
55.8755.93
71.60
111.77112.98120.61123.20123.70130.39133.59138.36139.08140.74149.92151.59
168.90169.03
176.43
CDCl3
CS i
20.3620.48
30.1241.8747.6550.09
56.2056.20
71.85
113.40114.00121.45123.86124.12132.09134.97139.27140.00142.52150.80152.59
168.75168.75
176.77
4850
23484745
8484
44
174219455027272321352519
2121
26
Acetone
CS i CS i
DMSO
Ac MeAc Me
αβ
B βBα
OMeOMe
B γ
B2A2B6B5A5A6A1A4B4B1A3B3
Ac C=OAc C=O
γ
Atom
1HJMultH Shifts
2.132.23
2.752.782.983.18
3.753.81
4.164.16
6.446.836.966.987.03
ss
mmmdd
ss
mm
sdddsd
16.0, 5.0
8.1, 1.91.9
8.1
Ac MeAc Me
B βA β
A α1A α2
OMeOMe
B αB γ
A5B6B2A2B5
Atom
(acetone)
jrlz33Liming Zhang, isolate from mild acidolysis
Notes:
3017Compound Number
FPL/DFRC NMR Database -- April 2009
6-Hydroxy-4-(4-hydroxy-3-methoxyphenyl)-7-methoxy-3a,4,9,9a-tetrahydro-3H-naphtho[2,3-c]furan-1-one
13CCDCl3
CS i
29.7341.9847.6149.95
55.9956.03
71.78
112.25112.93115.61116.23121.92
126.77132.87135.09
145.61146.29146.89148.42
177.15
66807570
8085
66
1867232630
514245
14121917
42
Acetone
CS i CS i
DMSO
αβ
B βB α
OMeOMe
B γ
B2A2B5A5B6
A1A6B1
A4B4A3B3
γ
Atom
1HJMultH Shifts
2.672.673.07
3.783.82
3.954.10
6.266.696.796.806.80
mmdd
ss
bdm
dddsdd
16.2, 4.5
9.5
0.98.0, 2.0
2.08.0
B βA βA α
OMeOMe
B αB γ
A5B6A2B2B5
Atom
(acetone)
jrlz27Liming Zhang, isolate from mild acidolysis
Notes:
3018Compound Number
FPL/DFRC NMR Database -- April 2009
Acetic acid 8-(4-acetoxy-3-methoxyphenyl)-6,7-bis-acetoxymethyl-3-methoxy-5,6,7,8-tetrahydronaphthalen-2-yl ester
13C
67676793
45585650
6577
4846
6542555353
46383434
46
4341
26254149
20.5620.6520.7720.82
33.0235.1343.4447.22
55.8355.91
63.0466.20
111.81113.17121.52122.81123.71
131.13134.05138.03138.03
142.77
149.35151.16
168.91169.11170.80170.97
CDCl3
CS i
20.3620.4720.6920.72
33.5336.2944.2547.98
56.1756.19
63.5766.74
112.90114.53121.11123.64124.16
132.26135.25139.17139.63
144.24
150.46152.28
168.93168.96171.06171.06
54515151
33444339
4545
3740
5046574440
26311926
23
2022
23233131
Acetone
CS i CS i
DMSO
Ac MeAc MeAc MeAc Me
αβ
B βB α
OMeOMe
B γγ
A2B2B6B5A5
A6A1A4B4
B1
A3B3
Ac C=OAc C=OAc C=OAc C=O
Atom
1HJMultH Shifts
2.012.022.112.222.162.292.92
3.743.78
3.924.024.094.114.236.346.746.876.926.99
ssssmmm
ss
dddmmddbsddsdd
11.7, 3.610.5
11.1, 5.3
8.1, 2.0
2.08.1
Ac MeAc MeAc MeAc Me
Bββα
OMeOMe
B γ1B αB γ2A γ1A γ2A5B6A2B2B5
Atom
(acetone)
jrf101.C9-12Authenticated assignments in acetone.
Notes:
3019Compound Number
FPL/DFRC NMR Database -- April 2009
3-(4-{3-hydroxy-1-(4-hydroxy-3-methoxyphenyl)-2[4-(2-methoxycarbonylvinyl)phenoxy]propoxy}phenyl)acrylic acid methyl ester
13C
5450
65
273535
3335414587879393333838458484100100
4338494541424448
51.5551.59
55.92
61.4378.7081.89
109.26114.48115.68115.86116.24116.24116.54116.54120.21127.73128.00128.67129.57129.57129.61129.61
144.12144.23145.72146.78159.14159.81167.62167.63
CDCl3
CS i
51.5251.53
56.26
61.4279.3282.67
112.00115.55116.15116.25117.23117.23117.34117.34121.43128.19128.22129.37130.46130.46130.48130.48
144.87144.94147.35148.23160.49161.67167.67167.72
5151
58
243432
3524454286869292344243388686100100
3943222545444039
Acetone
CS i
51.2755.63
55.80
59.7977.7581.24
111.78115.29115.13115.13116.20116.20116.24116.24120.28126.74126.86127.73129.93129.93129.93129.93
144.16144.26146.29147.31159.17160.5166.86166.92
5966
22
151818
172737375050646419444340100100100100
2429415243535556
CS i
DMSO
C γ OMeB γ OMe
A3 OMe
γ
αβ
A2A5B βC βC2C6B2B6A6C1B1A1B3B5C3C5
C αB αA4A3C4B4C γB γ
Atom
1HJMultH Shifts
3.703.71
3.78
3.954.164.885.60
6.346.376.797.006.977.027.127.507.547.557.59
ss
s
mtmd
dddmmmdmmdd
5.85.8
5.5
16.016.08.1
8.88.81.98.68.616.016.0
B γ OMeC γ OMe
A3 OMe
γ 'sγ OH
βα
C βB βA5A6
C2,6B2,6A2
C3,5B3,5C αB α
Atom
(acetone)
erythro
jrf119.C2assignments not authenticated - from #3019
Notes:
3020Compound Number
FPL/DFRC NMR Database -- April 2009
3-(4-{1-(3,4-dimethoxyphenyl)-3-hydroxy-2[4-(2-methoxy-carbonylvinyl)phenoxy]propoxy}phenyl)acrylic acid methyl ester
13CCDCl3
CS i
51.5251.52
55.9756.12
61.3879.2182.64
112.38112.47116.21116.33117.26117.26117.38117.38121.02128.26128.32130.51130.51130.52130.52130.56
144.87144.96150.25150.26160.50161.69
167.66167.72
3838
4040
203434
3228403486869898383032100100949432
384032283032
3028
Acetone
CS i CS i
DMSO
C γ OMeB γ OMe
A4 OMeA3 OMe
γ
αβ
A2A5B βC βC2C6B2B6A6C1B1B3B5C3C5A1
C αB αA4A3C4B4
C γB γ
Atom
1HJMultH Shifts
3.6933.7113.7323.752
3.9544.1574.8815.603
6.3356.3636.8766.9737.0157.0477.1267.5157.5507.5437.582
ssss
mtmd
dddmmdddmmdd
5.9, *5.9
5.5, 4.95.5
16.016.08.28.88.7
8.2, 1.91.98.88.716.016.0
B γ OMeC γ OMeA4 OMeA3 OMe
γ 'sγ OH
βα
C βB βA5
C2,6B2,6A6A2
C3,5B3,5C αB α
Atom
(acetone)
erythro
jrf137assignments not authenticated - from #3019/3020A4 vs A3 OMe may be switched
Notes:
3021Compound Number
FPL/DFRC NMR Database -- April 2009
3-(4-{3-carboxyoxy-1-(3,4-dimethoxyphenyl)-2-[4-(2-methoxycarbonylvinyl)phenoxy]propoxy}phenyl)acrylic acid methyl ester
13CCDCl3
CS i
20.58
51.5451.57
55.9756.14
63.4979.3279.81
112.17112.47116.49116.55117.27117.27117.41117.41120.88128.55128.74130.09130.53130.53130.61130.61
144.81144.81150.38150.43160.24161.18167.66167.69
170.79
53
5347
5355
343939
4242454795959797392424341001009797
8282262426262926
24
Acetone
CS i CS i
DMSO
γ Ac Me
C γ OMeB γ OMe
A4 OMeA3 OMe
γ
αβ
A2A5B βC βC2C6B2B6A6C1B1A1B3B5C3C5
C αB αA4A3C4B4C γB γ
γ Ac C=O
Atom
1HJMultH Shifts
1.9203.6943.7123.7363.7594.4604.5075.0845.629
6.3436.3786.8886.9927.0187.0737.1617.5277.5707.5487.584
sssss
ddddmd
dddmmdddmmdd
11.9, 6.211.9, 3.8
6.2, 5.8, 3.85.8
16.016.08.38.78.7
8.3, 2.02.08.78.716.016.0
γ Ac MeB γ OMeC γ OMeA4 OMeA3 OMe
γ 1γ 2βα
C βB βA5
C2,6B2,6A6A2
C3,5B3,5CαBα
Atom
(acetone)
erythro
jrf103.C12-25fully authenticated in acetone
Notes:
3022Compound Number
FPL/DFRC NMR Database -- April 2009
3-(4-{3-hydroxy-1-(4-hydroxy-3-methoxyphenyl)-2-[2-methoxy-4-(2-methoxycarbonylvinyl)phenoxy]propoxy}phenyl)acrylic acid methyl
ester
13C
5756
6969
314242
46424447481001004347483939439797
4647
4642424643
4544
51.5551.66
55.8355.96
61.2978.4686.25
110.87109.37114.49115.62116.77116.28116.28120.21119.50122.14127.67129.92129.32129.57129.57
144.21144.28
145.68146.78149.40151.14159.30
167.39167.64
CDCl3
CS i
51.5251.56
56.2256.32
61.3179.4484.21
112.14112.21115.38116.16116.59117.23117.23117.54121.53123.04128.13129.21129.39130.42130.42
144.89145.23
147.29148.17151.24151.54160.57
167.68167.71
5956
6966
304142
49413852519898484149414446100100
4848
3738434643
4446
Acetone
CS i
51.2751.28
55.4855.79
59.6677.9581.84
111.43112.01114.89115.16115.24116.22116.22115.45120.44122.48126.79127.27127.54129.91129.91
144.18144.61
146.27147.24149.76150.11159.25
166.86166.95
8982
99100
283434
403436444992924734446265609090
4644
6574796963
7671
CS i
DMSO
B γ OMeC γ OMe
A3 OMeB3 OMe
γ
αβ
B2A2A5C βB βC2C6B5A6B6C1B1A1C3C5
C αB α
A4A3B4B3C4
C γB γ
Atom
1HJMultH Shifts
3.6963.7203.8043.8533.954.7915.6216.3306.417
6.7986.9787.0137.0657.1237.2057.2837.493
7.5547.584
ssssmmddd
dmdddddddd
dd
-5.316.016.0
8.28.8
8.2, 1.98.3
8.3, 1.91.91.98.8
16.016.0
B γ OMeC γ OMeA3 OMeB3 OMe
γ 'sβα
C βB β
A5C2,6A6B5B6A2B2
C3,5
C αB α
Atom
(acetone)
erythro
jrf121.C5-7assignments not authenticated - from #3022 and 3020A4 vs A3 OMe may be switched*γ and γ-OH protons buried, C-H correlations not run.
Notes:
3023Compound Number
FPL/DFRC NMR Database -- April 2009
3-(4-{1-(3,4-dimethoxyphenyl)-3-hydroxy-2-[2-methoxy-4-(2-methoxycarbonylvinyl)phenoxy]propoxy}phenyl)acrylic acid methyl
ester
13CCDCl3
CS i
51.5251.55
55.9856.0756.37
61.2979.3784.19
112.19112.24112.70116.27116.67117.29117.29117.60121.14123.10128.25129.30130.49130.49130.59
144.91145.25
150.20150.23151.31151.65160.63
167.68167.71
5345
505050
233732
42403742429797423942273110010031
4240
2627242727
2726
Acetone
CS i CS i
DMSO
B γ OMeC γ OMe
A4 OMeA3 OMeB3 OMe
γ
αβ
B2B5A2C βB βC2C6B5A6B6C1B1C3C5A1
C αB α
A4A3B4B3C4
C γB γ
Atom
1HJMultH Shifts
3.6933.7153.7413.7733.865
*4.7875.6406.3376.4166.8716.9817.0677.0687.1347.2007.3027.5177.5377.573
sssss*mddddmdddddddddd
--
5.316.016.08.38.8
8.3, 1.98.3
8.3, 1.91.91.98.816.016.0
B γ OMeC γ OMeA3 OMeA4 OMeB3 OMe
γ *βα
C βB βA5
C2,6A6B5B6A2B2
C3,5C αB α
Atom
(acetone)
erythro
jrf139assignments not authenticated - from #3023 and 3021A4 vs A3 OMe may be switchedNote γ's, J's switch from #3021!!
Notes:
3024Compound Number
FPL/DFRC NMR Database -- April 2009
3-(4-{3-carboxyoxy-1-(3,4-dimethoxyphenyl)-2-[2-methoxy-4-(2-methoxycarbonylvinyl)phenoxy]propoxy}phenyl)acrylic acid methyl
ester
13CCDCl3
CS i
20.61
51.5451.58
55.9956.0956.35
63.4979.6281.21
112.24112.38112.38116.42116.98117.28117.28118.21120.82122.93128.46129.89130.14130.52130.52
144.85145.14
150.33150.37150.72151.80160.44
167.67167.67
170.79
46
5446
505250
303735
33767637399191393539302630100100
4141
2828263028
3535
30
Acetone
CS i CS i
DMSO
g Ac Me
B γ OMeC γOMe
A4 OMeA3 OMeB3 OMe
γαβ
A2B5B2C βB βC2C6B5A6B6C1B1A1C3C5
C αB α
A4A3B4B3C4
C γB γ
γ OAc C=O
Atom
1HJMultH Shifts
1.9203.6953.7163.7453.7753.8774.4284.4874.9885.6596.3456.4316.8886.9957.0517.0667.1437.1907.3237.5277.5537.576
ssssss
ddddmddddmmddddddmdd
11.9, 3.811.9, 6.2
6.2, 5.3, 3.85.316.016.0 8.3 8.88.3
8.3, 2.0, 0.48.3, 2.0, 0.4
2.02.08.816.016.0
γ Ac MeB γ OMeC γ OMeA3 OMeA4 OMeB3 OMe
γ1γ2βα
C βB βA5
C2,6B5A6B6A2B2
C3,5C αB α
Atom
(acetone)
erythro
jrbha69Notes:
3025Compound Number
FPL/DFRC NMR Database -- April 2009
3-(4-hydroxy-3-methoxyphenyl)-2-(2-methoxy-4-propylphenoxy)propan-1-ol
13C
801006166
4242
6760
938698868894
625861525454
13.7724.5837.3737.76
55.7655.89
63.4185.32
112.16112.32114.34119.95121.00122.08
129.75138.23144.20145.33146.44150.88
CDCl3
0.9151.5942.5042.8663.0403.5743.656
3.8233.8414.160
5.611
CDCl3
CS i
14.0125.3937.7438.22
56.1556.20
63.3883.67
113.85113.99115.49118.72121.37122.83
130.58137.46145.88146.82148.05151.63
79896669
3334
4454
8773718010091
525339413442
Acetone
CS i
13.7524.2936.5236.97
55.4955.58
61.8280.83
112.89113.64115.19115.70120.21121.63
129.16135.30144.79145.45147.26149.69
DMSO
0.8561.5312.462.7332.831
4.761
3.6803.7034.265
8.70
86966189
10086
5750
616164796457
827571687171
CS i
DMSO
B γB βα
B α
OMeOMe
γβ
B2A2A5B5B6A6
A1B1A4B4A3B3
1H
B γB βB αα1α2γ1γ2
γ OH
OMeOMe
β
Ar-OH
Atom
1HJMultH Shifts
0.8951.5852.4922.912.943.593.731
3.7863.802
4.308
6.6466.726.726.8166.8276.918
7.333
tmmmmmt
ss
m
ddtmmddm
s
7.3
6.1
8.1, 2.1, 0.6
2.18.1
B ຶ
γB βB αα1α2γ
γ OH
OMeOMe
β
B6A5A6B2B5A2
Ar OH
Atom
(acetone)
jrbha61Hγ's are perfect dd's after adding D2O to acetone - otherwise complex multiplets;J's are from D2O exchanged spectra. All spectra ref'd to solvent, Acetone 2.04, 29.8CDCl3 7.24, 77.0, DMSO 2.49, 39.5
Notes:
3026Compound Number
FPL/DFRC NMR Database -- April 2009
2-(2,6-dimethoxy-4-propylphenoxy)-3-(4-hydroxy-3-methoxyphenyl)propan-1-ol
13C
64864850
3562
4548
9292
796874
4939554740100100
13.7624.5137.2838.39
55.8155.97
62.1784.36
105.42105.42
112.20114.15122.03
130.19133.40138.77143.99146.31152.99152.99
CDCl3
0.9281.6142.5132.9663.1923.4183.543.563.8053.8314.150
6.3926.7456.8096.796
5.698
CDCl3
CS i
14.0625.3038.0038.91
56.1756.41
62.7785.24
106.55106.55
113.87115.50122.78
130.81134.92139.25145.78148.03154.09154.09
44473838
1935
2832
100100
444750
35223328245656
Acetone
CS i
13.7324.1036.8637.64
55.5155.81
61.6583.39
105.58105.58
113.58115.06121.64
129.36133.46137.62144.60147.11152.76152.76
DMSO
0.8861.5732.7532.871~3.35?~3.35?~3.35?~3.35?3.6973.7084.068
6.4656.5836.6416.763
8.634
55572737
50100
2928
5555
383635
42334143388282
CS i
DMSO
B γB βα
B α
A OMeB OMe
γβ
B2B6
A2A5A6
A1B4B1A4A3B3B5
1H
B γB βB αα1α2γ1γ2
γ OHA OMeB OMe
β
B2,6A6A5A2
Ar OH
Atom
1HJMultH Shifts
0.9171.6192.5232.9413.0773.3923.4833.5
3.8093.8174.128
6.5406.7116.7406.892
7.349
tmddddddmmmssm
sddddd
s
7.3
13.6, 8.213.6, 5.412.0, 4.112.0, 3.4
8.0, 1.88.0, 0.4
1.8
B γB βB αα1α2γ1γ2
γ OHA OMeB OMe
β
B2,6A6A5A2
Ar OH
Atom
(acetone)
jrbha67Notes:
3027Compound Number
FPL/DFRC NMR Database -- April 2009
3-(4-hydroxy-3,5-dimethoxyphenyl)-2-(2-methoxy-4-propylphenoxy)propan-1-ol
13C
63845348
3153
5348
100100
677069605252
51959552
13.7724.5737.7637.94
55.7756.28
63.4785.35
106.13106.13
112.30120.04121.03128.98133.32138.31
145.32146.97146.97150.89
CDCl3
0.9101.5892.4992.8563.0323.5783.655
3.8313.8414.160
6.4786.6286.6976.651
8.03
CDCl3
CS i
14.0125.4038.2138.23
56.1956.56
63.4683.47
107.93107.93
113.81118.54121.36129.59135.34137.38
146.85148.48148.48151.57
45494145
1933
2231
100100
504558272028
22353522
Acetone
CS i
13.6724.2236.9036.90
55.4755.82
61.8480.56
106.83106.83
112.74115.44120.11128.24133.78135.09
145.41147.64147.64149.53
DMSO
0.861.542.452.742.84
4.75
3.683.714.30
6.496.626.766.83
8.03
66755959
6297
2838
5050
414741475644
4410010047
CS i
DMSO
B γB βA αB α
B OMeA OMe
γβ
A2A6
B2B5B6A1A4B1
B4A3A5B3
1H
B γB βB αα1α2γ1γ2
γ OH
A OMeB OMe
β
A2,6B6B2B5
Ar OH
Atom
1HJMultH Shifts
0.8941.5852.4912.852.9223.6023.734
3.7703.8064.335
6.5966.6466.8176.833
6.940
tmmddddmt
ssm
sddtdd
7.4
13.9, 6.213.9, 6.1
8.2, 2.1, 0.62.18.2
B γB βB αα1α2γ
γ OH
A OMeB OMe
β
A2,6B6B2B5
Ar OH
Atom
(acetone)
jrbha63 Hγ's are dd's after adding D2O to acetone - otherwise complexmultiplets; J's are from D2O exchanged spectra. In acetone: Many peakswere split with a 2:1 ratio. Aα 38.38 & 38.50, Bα 38.80 & 38.93, A1 129.69 &129.86, B4 134.94 & 134.97, A4 135.24 & 135.28, B1 139.10 & 139.26 , A3/5148.44 & 148.49, B3/5 154.07 & 154.12
Notes:
3028Compound Number
FPL/DFRC NMR Database -- April 2009
3-(4-hydroxy-3,5-dimethoxyphenyl)-2-(2,5-dimethoxy-4-propylphenoxy)propan-1-ol
13C
371003947
9086
5149
3737
3535
4929284355557979
13.7024.4737.6538.24
55.9656.19
62.1984.19
105.42105.42
106.12106.12
129.21133.07133.28138.64146.75146.75152.92152.92
CDCl3
0.9171.5922.4892.9503.1753.4083.5423.47
3.7983.829
4.152
6.3866.498
5.493
CDCl3
CS i
14.0625.3038.3838.80
56.4356.58
62.9385.20
106.57106.57
107.83107.83
129.69134.94135.24139.10148.44148.44154.07154.07
100824545
7276
4956
5959
5555
3814163845455454
Acetone
CS i
13.8224.1837.3537.60
55.9155.97
61.8883.32
105.67105.67
106.89106.89
128.54133.46133.70137.61147.65147.65152.79152.79
DMSO
0.8791.5622.452.7562.868
4.334?
3.6923.696
4.103
6.4496.462
8.044
49482527
10096
2723
1111
1010
3024282548485252
CS i
DMSO
B γB βα
B α
A OMeB OMe
γβ
B2B6
A2A6
A1B4A4B1A3A5B3B5
1H
B γB βB αα1α2γ1γ2
γ OH
A OMeB OMe
β
B2,6A2,6
Ar OH
Atom
1HJMultH Shifts
0.9171.6202.5252.9253.0743.4023.4863.47
3.7933.825
4.142
6.5446.573
6.949
tmmddddmmm
ss
m
ss
s
7.4
13.6, 8.113.6, 5.312.0, 4.112.0, 3.6
B γB βB αα1α2γ1γ2
γ OH
A OMeB OMe
β
B2,6A2,6
Ar OH
Atom
(acetone)
JRHKC25Notes:
3029Compound Number
FPL/DFRC NMR Database -- April 2009
1-(4-benzyloxy-3-methoxyphenyl)-propane-1,3-diol
13CCDCl3
CS i
20.7021.0135.78
56.16
61.20
71.26
73.17
111.49114.64119.58128.28128.28129.09129.09
128.45134.19138.33149.02150.68
170.17170.80
Acetone
CS i CS i
DMSO
γ Ac Meα Ac Me
β
OMe
γ
B α
α
A2A5A6B3B5B2B6
B4A1B1A4A3
α Ac C=Oγ Ac C=O
Atom
1HJMultH Shifts
1.992.032.183.834.085.095.856.916.997.04
7.28-7.51
ssmsms
dddddd
m
8.2, 5.78.3, 2.0
8.32.0
γ Ac Meα Ac Me
βOMe
γB α
αA6A5A2
Bz H's
Atom
(acetone)
JRHKB117 (Higuchi)13mg
Notes:
3030Compound Number
FPL/DFRC NMR Database -- April 2009
beta-[5-(2-formylvinyl)-2-hydroxy-3-methoxyphenyl]coniferyl aldehyde
13CCDCl3
CS i
55.5556.63
110.61113.56115.95
123.15
126.36126.92127.29127.38127.44
136.33
148.13148.59149.30150.16
151.36
153.79
193.43193.96
Acetone
CS i CS i
DMSO
A3 OMeB3 OMe
B2A2A5
A β
B6A6B βA1B1
B5
A3B4A3B4
A α
B α
A γB γ
Atom
1HJMultH Shifts
3.473.96
6.66
6.776.876.987.017.447.577.578.439.619.69
ss
dd
ddddddsdsds
15.8, 7.8
8.32.0
8.3, 2.02.02.0
15.8
7.8
A3 OMeB3 OMe
B β
A5A2A6B6B2A αB αOHB γA γ
Atom
(acetone)
JRHKB119 (Higuchi)4 mg
Notes:
3031Compound Number
FPL/DFRC NMR Database -- April 2009
beta-[4-(2-formylvinyl)-2-methoxyphenoxy] coniferyl aldehyde
13CCDCl3
CS i
56.0156.52
112.55113.98115.25116.25
123.63125.31126.80128.32130.20
138.21147.70148.48148.90150.37150.56
153.15
197.48193.85
Acetone
CS i CS i
DMSO
B3 OMeA3 OMe
B2A2B5A5
B6A1A6B βB1
A αA βB3B4A3A4
B α
A γB γ
Atom
1HJMultH ShiftsAtom
(acetone)
JRHKb121 11mgHiguchiAs this dimer contains a plane of symmetry the CSs are reported for one unit.
Notes:
3032Compound Number
FPL/DFRC NMR Database -- April 2009
2,3-diformyl-1,4-bis(4-hydroxy-3-methoxyphenyl)buta-1,3-diene
13CCDCl3
CS i
56.11
113.71
116.24
126.25
127.47
134.42
148.41
150.51
152.83
192.74
Acetone
CS i CS i
DMSO
OMe
2
5
6
1
β
3
4
α
γ
Atom
1HJMultH Shifts
3.70
6.82
7.21
7.28
7.78
8.29
9.66
s
d
dd
d
s
s
s
8.31
8.31, 2.15
2.15
OMe
5
6
2
α
OH
γ
Atom
(acetone)
JRHKb123 37mgHiguchiAs this dimer contains a plane of symmetry the CSs are reported for one unit.
Notes:
3033Compound Number
FPL/DFRC NMR Database -- April 2009
5,5'-bis-coniferyl aldehyde
13CCDCl3
CS i
56.52
110.00
126.05
126.13
126.81
127.10
149.42
149.63
154.40
193.92
Acetone
CS i CS i
DMSO
OMe
2
1
5
β
6
3
4
α
γ
Atom
1HJMultH Shifts
3.95
6.68
7.27
7.36
7.59
9.65
s
dd
s
s
s
s
15.84, 7.84
2.0
2.0
15.84
7.84
OMe
β
6
2
α
γ
Atom
(acetone)
HKc63.4Notes:
3034Compound Number
FPL/DFRC NMR Database -- April 2009
13CCDCl3
CS i
55.8456.17
113.51113.82
114.85116.07
121.34
123.35
125.49
126.57
137.82
146.22
148.09
148.30149.89
150.20
187.90
Acetone
CS i CS i
DMSO
A3 OMeB3 OMe
B2A2
B5A5
B6
B1
A1
A6
α
B4
β
A3B3
A4
γ
Atom
1HJMultH Shifts
3.733.88
6.726.766.876.957.05
7.26
7.337.59
9.50
ss
dddddd
ddddd
s
ddd
s
8.0, 2.08.2, 7.1, 2.0
8.38.2, 7.1, 2.0
8.2, 2.0
8.3, 2.02.0
A4 OMeB3 OMe
B5B6A5B1B2
α
A6A2
γ
Atom
(acetone)
HKc 63.4AcNotes:
3035Compound Number
FPL/DFRC NMR Database -- April 2009
13CCDCl3
CS i
20.41
55.97
56.20113.62114.66115.56121.39
123.83
124.06124.53
132.33
135.40
142.47146.01
149.94
150.01152.27
168.73
188.21
Acetone
CS i CS i
DMSO
Ac Me
A3 OMeB3 OMe
B2A2B5B6
B1
A5A6
A1
α
A4B4
β
B3A3
Ac C=O
γ
Atom
1HJMultH Shifts
2.23
3.733.87
6.796.796.977.067.11
7.30
7.457.68
9.55
s
ss
mmmbdd
s
ddd
s
7.88.3
8.3, 2.02.0
Ac Me
A3 OMeB3 OMe
B5B6B1B2A5
α
A6A2
γ
Atom
(acetone)
HKd 59.1Notes:
3036Compound Number
FPL/DFRC NMR Database -- April 2009
13CCDCl3
CS i
56.1156.3156.31
109.27109.27113.39114.53121.32
123.27124.05
138.23
139.74146.16
148.15
148.57148.57149.76
187.91
Acetone
CS i CS i
DMSO
B3 OMeA3 OMeA5 OMe
A2A6B2B5B6
B1A1
α
A4B4
β
A3A5B3
γ
Atom
1HJMultH Shifts
3.743.88
6.706.766.947.05
7.24
7.269.51
ss
dddddddddd
s
ss
8.2, 1.78.2, 7.2, 1.58.2, 7.2, 1.7
8.2, 1.5
A3,5 OMeB3 OMe
B5B6B1B2
A2,6
αγ
Atom
(acetone)
HKd 59.1 AcNotes:
3037Compound Number
FPL/DFRC NMR Database -- April 2009
13CCDCl3
CS i
20.17
56.1456.2956.29
108.10108.10113.48115.07121.37
123.68131.35131.53
136.12
145.97
149.81
149.84153.20153.20
168.30
188.26
Acetone
CS i CS i
DMSO
Ac Me
B3 OMeA3 OMeA5 OMe
A2A6B2B5B6
B1A1A4
α
B4
b
B3A3A5
Ac C=O
γ
Atom
1HJMultH Shifts
2.21
3.733.88
6.766.776.977.067.29
7.31
9.57
s
ss
dddddddddds
s
s
8.2, 2.48.2, 6.5, 1.48.2, 6.5, 2.4
8.2, 1.4
Ac Me
A3,5 OMeB3 OMe
B5B6B1B2
A2,6
α
γ
Atom
(acetone)
HKd 23.3Notes:
3038Compound Number
FPL/DFRC NMR Database -- April 2009
13CCDCl3
CS i
56.0756.5356.53
106.40106.40114.55115.95
124.17125.77126.72
129.06
135.22148.04149.05
150.82
152.47152.47
186.64
Acetone
CS i CS i
DMSO
A3 OMeB3 OMeB5 OMe
B2B6A2A5
B1A6A1
α
B4A3A4
β
B3B5
γ
Atom
1HJMultH Shifts
3.743.81
6.64
6.656.886.997.457.60
9.25
ss
s
ddddddd
s
8.28.3
8.2, 7.68.3, 2.0
2.0
B3,5 OMeA3 OMe
α
B2,6A5B1A6A2
γ
Atom
(acetone)
HKd 23.3 AcNotes:
3039Compound Number
FPL/DFRC NMR Database -- April 2009
13CCDCl3
CS i
20.45
56.0956.5256.52
106.29106.29115.15123.78124.04
124.53
126.73
133.43134.81141.52152.04
152.11
152.41152.41
168.85
187.00
Acetone
CS i CS i
DMSO
Ac Me
A3 OMeB3 OMeB5 OMe
B2B6A2A5A6
B1
α
A1B4A4A3
β
B3B5
Ac C=O
γ
Atom
1HJMultH Shifts
2.24
3.753.80
6.67
6.71
7.017.117.547.68
9.32
s
ss
d
s
dddddd
s
8.3
8.3, 7.98.2
8.2, 1.91.9
Ac Me
B3,5 OMeA3 OMe
B2,6
α
B1A5A6A2
γ
Atom
(acetone)
HKd 63.1Notes:
3040Compound Number
FPL/DFRC NMR Database -- April 2009
13CCDCl3
CS i
56.5156.5156.5956.59
106.50106.50109.41109.41
124.18125.37
129.08
135.21138.72148.44148.44
150.91
152.46152.46
186.60
Acetone
CS i CS i
DMSO
A3 OMeA5 OMeB3 OMeB5 OMe
B2B6A2A6
B1A1
α
B4A4A3A5
β
B3B5
γ
Atom
1HJMultH Shifts
3.753.80
6.63
6.666.997.31
9.25
ss
s
dts
s
8.38.3
B3,5 OMeA3,5 OMe
α
B2,6B1
A2,6
γ
Atom
(acetone)
HKd 63.1 AcNotes:
3041Compound Number
FPL/DFRC NMR Database -- April 2009
13CCDCl3
CS i
20.22
56.3556.3556.5656.56
106.37106.37108.07108.07124.51
126.81
130.47132.69134.76
152.09
152.35152.35153.01153.01
168.43
186.95
Acetone
CS i CS i
DMSO
Ac Me
B3 OMeB5 OMeA3 OMeA5 OMe
B2B6A2A6B1
α
A4A1B4
β
B3B5A3A5
Ac C=O
γ
Atom
1HJMultH Shifts
2.23
3.773.78
6.67
6.69
7.01
7.34
9.32
s
ss
d
s
dd
s
s
8.3
8.6, 8.2
Ac Me
A3,5 OMeB3,5 OMe
B2,6
α
B1
A2,6
γ
Atom
(acetone)
FLj 144As this dimer contains a plane of symmetry the CS's are reported for one unit.
Notes:
3042Compound Number
FPL/DFRC NMR Database -- April 2009
13CCDCl3
CS i
20.18
48.7655.5655.56
82.61
103.05103.05
129.76137.84
153.54153.54
168.50
175.77
Acetone
CS i CS i
DMSO
Ac Me
β
3 OMe5 OMe
α
26
41
35
Ac C=O
γ
Atom
1HJMultH Shifts
2.23
3.81
4.205.86
6.81
s
s
ss
s
Ac Me
OMe
βα
2,6
Atom
(acetone)
F. Luflm11
Notes:
3043Compound Number
FPL/DFRC NMR Database -- April 2009
13CCDCl3
CS i
56.2656.32
61.8364.6176.9779.30
104.10108.55111.90115.70121.49
129.50133.24135.46145.19147.92148.44149.84
98105
53639391
8497895298
54254039262449
Acetone
CS i CS i
DMSO
B3 OMeA3 OMe
γBααβ
B2B6A2A5A6
A1B4B1B5A4A3B3
Atom
1HJMultH Shifts
3.473.76
3.813.85
3.994.494.95
6.536.606.866.947.09
7.80
mm
ss
dddmd
ddddd
dddd
s
7.9, 3.9, 2.5
7.9
1.8, 0.75, 0.751.88.1
8.1, 1.9, 0.51.9
γ1γ2
B3 OMeA3 OMe
βBαα
B6B2A5A6A2
A4 OH
Atom
(acetone)
F. Luflm11Ac
Notes:
3044Compound Number
FPL/DFRC NMR Database -- April 2009
13CCDCl3
CS i
20.4520.4920.81
56.3656.44
63.3666.3675.9777.01
106.08110.41112.77120.75123.88
129.92133.65136.00141.45144.92149.98152.57
168.86170.62170.83
181812
1818
14171616
1415151616
98107989
985
Acetone
CS i CS i
DMSO
A4 Ac Meγ Ac Me
Bα Ac Me
A3 OMeB3 OMe
γBαβα
B2B6A2A6A5
B1B4A1A4B5B3A3
A4 Ac C=Oγ Ac C=O
Bα Ac C=O
Atom
1HJMultH Shifts
1.992.032.24
3.833.84
4.024.284.404.985.04
6.616.667.087.117.26
sss
ss
ddddddd
sd
dddddd
12.4, 4.312.4, 3.4
7.7, 4.3, 3.4
7.7
1.91.9
8.1, 1.78.11.7
Bα Ac Meγ Ac Me
A4 Ac Me
B3 OMeA3 OMe
γ1γ2β
Bαα
B6B2A6A5A2
Atom
(acetone)
HKE-11Raney nickel reaction of hke5.5
Notes:
3045Compound Number
FPL/DFRC NMR Database -- April 2009
13CCDCl3
CS i
26.11
30.33
33.51
56.73
59.83
104.24
128.60
134.89
138.17
144.71
148.47
Acetone
CS i CS i
DMSO
β
γ
α
5 OMe
3 OMe
6
2
1
4
3
5
Atom
1HJMultH Shifts
1.982.782.83
3.773.79
6.58
1.862.712.86
3.283.75
6.32
quintbr tbr t
ss
s
quintdt
ss
s
7.27.27.2
7.377.37, 0.66
7.37
βαγ
5 OMe3 OMe
6
Benzene
βαγ
5 OMe3 OMe
6
Atom
(acetone)
hke 5.4.1Thioacidolysis product of β-O-4 (S-G) aldehyde dimer
Notes:
3046Compound Number
FPL/DFRC NMR Database -- April 2009
13CCDCl3
CS i
15.1115.4126.3329.12
41.68
56.91
62.30
105.00
126.93
131.50
133.78
104.04
141.58
147.06
148.43
Acetone
CS i CS i
DMSO
γ S-CH3β S-CH3β S-CH2γ S-CH2
α
5 OMe
3 OMe
6
γ
2
1
3
4
5
β
Atom
1HJMultH Shifts
1.151.302.892.95
3.58
3.82
3.85
6.87
ttqq
d
s
s
br t
7.377.377.377.37
0.92
0.92
γ S-CH3β S-CH3γ S-CH2β S-CH2
α
5 OMe
3 OMe
6
Atom
(acetone)
hke 5.5Thioacidolysis product of γ-O-4 (S-G) aldehyde dimer
Notes:
3047Compound Number
FPL/DFRC NMR Database -- April 2009
13CCDCl3
CS i
14.3914.4522.2326.80
52.56
56.71
60.09
100.11
124.89
128.89
135.82
137.70
145.14
145.23
149.46
Acetone
CS i CS i
DMSO
γ S-CH3β S-CH3γ S-CH2β S-CH2
γ
5 OMe
3 OMe
6
α
2
1
4
β
3
5
Atom
1HJMultH Shifts
1.001.33
2.22,2.042.94
3.82
3.96
4.39
6.38
6.63
tt
dq, dqq
s
s
d
d
s
7.57.37
12.1, 7.57.37
1.18
1.18
γ S-CH3β S-CH3γ S-CH2β S-CH2
5 OMe
3 OMe
γ
α
6
Atom
(acetone)
hke87Desulfurized (Raney-nickle Rxn)thioacidolysis product of β-O-4 (G-S) aldehyde model compound
Notes:
3048Compound Number
FPL/DFRC NMR Database -- April 2009
6-methoxy-indan-5-ol
13CCDCl3
CS i
26.45
33.13
33.25
56.48
108.74
111.56
135.00
136.73
146.11
147.01
Acetone
CS i CS i
DMSO
β
α
γ
OMe
6
3
1
2
4
5
Atom
1HJMultH Shifts
1.99
2.74
2.76
3.79
6.66
6.78
quint
t
t
s
s
s
7.63
7.63
7.63
β
α
γ
OMe
3
6
Atom
(acetone)
hke83.3Thioacidolysis product of β-O-4 (G-S) aldehyde dimer model.
Notes:
3049Compound Number
FPL/DFRC NMR Database -- April 2009
2,3-bis-ethylsulfanyl-6-methoxy-1H-inden-5-ol
13CCDCl3
CS i
15.4715.74
23.6527.70
41.57
56.83
106.37
109.01
128.64
133.31
140.13
146.09
146.91
148.16
Acetone
CS i CS i
DMSO
β S CH3γ S CH3
β S CH2γ S CH2
α
OMe
4
6
γ
1
2
5
4
β
Atom
1HJMultH Shifts
1.671.31
2.812.99
3.58
3.83
6.87
7.06
tt
d
s
s
br t
7.377.37
7.377.37
0.79
0.79
γ S CH3β S CH3
γ S CH2β S CH2
α
OMe
3
6
Atom
(acetone)
hkd79.2Cpossibly erythro
Notes:
3050Compound Number
FPL/DFRC NMR Database -- April 2009
13CCDCl3
CS i
14.41
56.1356.4456.4460.69
71.3774.3186.14
106.37106.37112.31114.41120.34124.73
128.31128.31128.41
129.09129.09134.57137.19138.62148.71150.33
153.64153.64169.44
Acetone
CS i CS i
DMSO
CH3
A OMeB OMeB OMe
CH2
C ααβ
B2B6A2A5A6B1
C2C6C4
C3C5A1B4C1A4A3
B3B5γ
Atom
1HJMultH Shifts
1.093.753.824.044.684.965.096.646.926.966.997.17
7.27-7.407.37
tssmddsddddtdm
br d
7.10
5.395.39
8.168.29, 1.71
8.298.161.71
7.37
CH3B OMeA OMe
CH2βα
C αB 2,6A6A5B1A2
C 3,4,5C 2,6
Atom
(acetone)
hkd79.2Expossibly threo
Notes:
3051Compound Number
FPL/DFRC NMR Database -- April 2009
13CCDCl3
CS i
14.30
56.1556.4256.42
60.68
71.3876.0490.35
106.26106.26
112.09114.61120.46125.18
128.33128.33
128.44
129.11129.11
132.51138.07138.56149.17150.62
153.39153.39
169.49
Acetone
CS i CS i
DMSO
CH3
A OMeB OMeB OMe
CH2
C ααβ
B2B6
A2A5A6B1
C2C6
C4
C3C5
A1B4C1A4A3
B3B5
γ
Atom
1HJMultH Shifts
0.993.793.823.954.024.845.096.716.816.946.997.05
7.29-7.397.46
tssmddsdddddtm
br d
7.23
8.428.42
8.58.29, 1.97
8.291.978.55
7.37
CH3A OMeB OMe
CH2βα
C αB 2,6A6A5A2B1
C 3,4,5C 2,6
Atom
(acetone)
hkd 17.2.1.3Notes:
3052Compound Number
FPL/DFRC NMR Database -- April 2009
13CCDCl3
CS i
14.35
56.0956.7956.79
61.05
107.08107.08
114.38115.74
119.07
123.37125.09126.76136.27
143.08
148.01148.10
152.01152.01
163.74
Acetone
CS i CS i
DMSO
CH3
A OMeB OMeB OMe
CH2
B2B6
A2A5
α
B1A6A1B4
β
A3A4
B3B5
γ
Atom
1HJMultH Shifts
1.113.743.764.066.67
6.79
6.826.947.297.52
tssqd
s
dt
ddd
7.10
7.108.68
8.298.68
8.29, 1.841.84
CH3B OMeA OMe
CH2B 2,6
α
A5B1A6A2
Atom
(acetone)
hkd87Notes:
3053Compound Number
FPL/DFRC NMR Database -- April 2009
13CCDCl3
CS i
Acetone
CS i CS i
DMSO
1H dataonly
Atom
1HJMultH Shifts
3.76
3.77
3.97
5.75
6.68
6.79
7.07
7.18
7.46
s
s
br s
br s
d
d
t
dd
d
8.42
8.29
8.42
8.29, 1.84
1.84
A OMe
B OMe
γ
α
B 2,6
A5
B1
A6
A2
Atom
(acetone)
hkd35.2.1.2possibly erythro (see 3055)separated by cyclohexane:EtOAc:Acetic Acid (100:50:1)
Notes:
3054Compound Number
FPL/DFRC NMR Database -- April 2009
13CCDCl3
CS i
14.35
56.3656.4456.44
61.29
75.0675.5984.38
105.44105.44113.87117.25121.61123.44128.31128.76128.76128.82128.82
136.70137.61139.47148.70151.03154.17154.17
169.85
Acetone
CS i CS i
DMSO
CH3
B OMeA OMeA OMe
CH2
C ααβ
A2A6B2B5B6B1C4C3C5C2C6
A1A4C1B4B3A3A5
γ
Atom
1HJMultH Shifts
1.083.803.824.044.724.935.086.83
6.77-6.856.90-7.007.24-7.38
7.50
tssmdsdsmmm
br d
7.1
7.15.52
5.52
7.37
CH3B OMeA OMe
CH2β
Cαα
A 2,6B 5,6B 1,2
C 3,4,5C 2,6
Atom
(acetone)
hkd35.2.1.1Possible threo (see 3054)separated by cyclohexane:EtOAc:Acetic Acid (100:50:1)
Notes:
3055Compound Number
FPL/DFRC NMR Database -- April 2009
13CCDCl3
CS i
14.16
56.2856.4056.40
61.28
74.8475.0483.40
105.51105.51113.77116.96121.52123.43128.28128.73128.73128.80128.80
137.51137.79139.50148.35151.08154.04154.04
170.25
Acetone
CS i CS i
DMSO
CH3
B OMeA OMeA OMe
CH2
αC α
β
A2A6B2B5B6B1C4C3C5C2C6
A4A1C1B4B3A3A5
γ
Atom
1HJMultH Shifts
1.193.773.834.164.704.945.076.796.90
6.90-6.977.24-7.37
7.5
tssqdsdmsmm
br d
7.10
7.106.71
6.71
7.37
CH3B OMeA OMe
CH2β
C αα
B 5,6A 2,6B 1,2
C 3,4,5C 2,6
Atom
(acetone)
hkd91.1.2Notes:
3056Compound Number
FPL/DFRC NMR Database -- April 2009
13CCDCl3
CS i
14.19
56.3056.3756.37
61.58
109.09109.09113.72114.15121.49123.24
124.12
127.99138.78
138.94146.94148.50148.50149.87
164.06
Acetone
CS i CS i
DMSO
CH3
B OMeA OMeA OMe
CH2
A2A6B2B5B6B1
A1
αβ
A4B4A3A5B3
γ
Atom
1HJMultH Shifts
1.213.733.904.206.726.796.947.067.167.33
tssqddddddddddss
7.10
7.108.02, 1.58
8.02, 7.37, 1.588.02, 7.37, 1.58
8.02, 1.58
CH3A OMeB OMe
CH2B5B6B1B2
A 2,6α
Atom
(acetone)
hkd57.41H Data only
Notes:
3057Compound Number
FPL/DFRC NMR Database -- April 2009
13CCDCl3
CS i
Acetone
CS i CS i
DMSO
1H dataonly
Atom
1HJMultH Shifts
3.673.90
4.156.21
6.906.75-7.05
8.00
ss
br sbr s
sms
A OMeB OMe
γ
α
A 2,6B 1,2,5,6A4 OH
Atom
(acetone)
hkc43.4.1Notes:
3058Compound Number
FPL/DFRC NMR Database -- April 2009
13CCDCl3
CS i
55.9356.1456.50
112.55113.95114.87115.18115.42116.26123.59
125.21
125.59126.78
128.03
128.38
130.35
137.15138.31147.52
148.46148.47
148.51
148.72149.91150.35150.58
153.13
187.43187.65193.91
Acetone
CS i CS i
DMSO
A OMeB OMeC OMe
C2A2B2B5C5A5C6
A1
B6A6
B1
Cβ
C1
BαAαAβ
A3B4
Bβ
C4B3C3A4
Cα
AγBγCγ
Atom
1HJMultH Shifts
3.693.833.986.706.796.826.857.157.287.307.307.337.487.527.587.678.379.489.539.65
sss
dddddddddddssddddbsssd
15.92, 7.658.298.298.29
8.29, 1.978.29, 1.978.29, 1.97
1.971.9715.921.97
7.65
A OMeB OMeC OMe
C βB5C5A5C6B6A6A αB αC2A2C αB2
A OHAγBγCγ
Atom
(acetone)
hkf69.2.2Fll73.12
Notes:
3059Compound Number
FPL/DFRC NMR Database -- April 2009
13CCDCl3
CS i
56.3156.54
62.9185.24
110.66114.27115.93119.49119.81125.79
127.69
129.66132.18146.01147.91148.57151.77
153.45
193.83197.57
Acetone
CS i CS i
DMSO
A OMeB OMe
β
α
A2B2A5B6A6B5
Bβ
B1A1B3A3A4B4
Bα
Bγγ
Atom
1HJMultH Shifts
3.823.92
4.506.206.70
6.846.907.067.387.43
7.618.299.649.94
ss
dddd
ddddss
dsds
6.56.5
15.78, 7.76
8.168.16, 1.84
1.84
15.78
7.76
A OMeB OMe
βα
B β
A5A6A2B2B6
B αA OH
B γA γ
Atom
(acetone)
hkf7-1This compound has a plane of symmetry and so the signals are reported for onlyone half.
Notes:
3060Compound Number
FPL/DFRC NMR Database -- April 2009
13CCDCl3
CS i
56.54
109.07
109.07
126.05
134.78
140.10
148.71
148.71
152.98
192.70
Acetone
CS i CS i
DMSO
OMe
2
6
1
β
4
3
5
α
γ
Atom
1HJMultH Shifts
3.72
7.02
7.79
7.94
9.67
s
s
s
bs
s
OMe
2,6
α
OH
γ
Atom
(acetone)
hkf75.322Notes:
3061Compound Number
FPL/DFRC NMR Database -- April 2009
13CCDCl3
CS i
53.84
56.3056.37
64.2289.87
110.65113.44115.79119.82121.43131.19
132.40133.42
145.81147.67148.49154.87
190.90
Acetone
CS i CS i
DMSO
β
A OMeB OMe
γ
α
A2B2A5A6B6B5
B1A1
B3A4A3B4
B α
Atom
1HJMultH Shifts
3.673.823.923.925.696.816.887.057.427.537.659.82
bqssmddddddddbss
6.848.16
8.16, 1.971.971.45
1.45. 0.92
βA OMeB OMe
γα
A5A6A2B2B6
A OHB α
Atom
(acetone)
hkf83.2.1 (6 mg)Notes:
3062Compound Number
FPL/DFRC NMR Database -- April 2009
13CCDCl3
CS i
56.3256.3756.62
62.2985.1187.48
111.71111.88112.08115.64121.57125.15125.32
130.25
133.27133.72
134.42134.56
147.73148.23152.46152.81154.23154.39
191.66191.71
Acetone
CS i CS i
DMSO
C OMeA OMeB OMe
γα
β
B2C2A2A5A6C6B6
A1
B5C5
B1C1
A4A3B4C4B3C3
CαBα
Atom
1HJMultH Shifts
3.483.953.823.914.034.185.056.846.937.057.567.657.707.7410.0210.06
mmsssmdddddddddss
10.148.16
8.16, 1.971.971.841.841.841.84
γ1γ2
A OMeC OMeB OMe
βα
A5A6A2C2B2C6B6C αB α
Atom
(acetone)
hkh 99.14 Morreel #6Morreel, K., Ralph, J., Kim, H., Lu, F., Goeminne, G., Ralph, S.A., Messens, E.,Boerjan, W.Profiling of oligolignols reveals monolignol coupling conditions inlignifying poplar xylem. Plant Physiol. November 2004, Vol.136, pp.3537-3549
Notes:
3063Compound Number
FPL/DFRC NMR Database -- April 2009
Simulanol, S-(8-5)-G4-[3-hydroxy-5-(3-hydroxy-propenyl)-7-methoxy-2,3-
dihydrobenzofuran-2-yl]-2,6-dimethoxy-phenol
13CCDCl3
CS i
54.78
56.4456.4456.67
63.3964.5288.74
104.55104.55111.80116.07
128.38
130.47
130.52
131.95133.30136.68145.16148.74148.74148.95
Acetone
CS i CS i
DMSO
Aβ
B OMeB OMeA OMe
BγAγAα
A2A6B2B6
Bβ
B5
Bα
B1A1A4B3A3A5B4
Atom
1HJMultH Shifts
3.793.86
3.544.195.546.236.526.746.846.977.19
ss
mtdddtdtssss
J = 5.52, 1.58J = 6.71
J = 15.92, 5.52J = 15.92, 1.58
A OMeB OMe
AβBγAαBβBα
A 2,6B2B6
A4-OH
Atom
(acetone)
hkh 99.6 Morreel #22Morreel, K., Ralph, J., Kim, H., Lu, F., Goeminne, G., Ralph, S.A., Messens, E.,Boerjan, W. Profiling of oligolignols reveals monolignol coupling conditions inlignifying poplar xylem. Plant Physiol. November 2004, Vol.136, pp.3537-3549
Notes:
3064Compound Number
FPL/DFRC NMR Database -- April 2009
buddlenol E, G-(8-O-4)-S-(8-8)-G1-(4-hydroxy-3-methoxy-phenyl)-2-{4-[4-(4-hydroxy-3-methoxy-
phenyl)-tetrahydro-furo[3,4c]furan-1-yl]-2,6-dimethoxy-phenoxy}-propane-1,3-diol
13CCDCl3
CS i
55.1555.46
56.2456.5956.5956.70
60.9872.3072.5473.3886.5786.6087.86
104.12104.12110.62110.92115.20115.54119.60120.04
133.77133.80134.10135.72139.10146.47146.90147.98154.20154.20
Acetone
CS i CS i
DMSO
CβBβ
OMeB OMeB OMeOMe
AγCγBγAαBαCαAβ
B2B6C2A2A5C5C6A6
C1B1A1C4B4A3C3A4B3B5
Atom
1HJMultH Shifts
3.103.433.843.864.154.244.684.734.976.766.987.037.377.49
mmmmmmddmsddss
J = 4.34J = 4.34
J = 1.84J = 1.84
Cβ +BβAγ1Aγ2
Cγ2 + Bγ2Aβ
Cγ1 + Bγ1CαBαAα
B 2,6C2A2
A4-OHC4-OH
Atom
(acetone)
threo
hkh 19.1t Morreel #23Morreel, K., Ralph, J., Kim, H., Lu, F., Goeminne, G., Ralph, S.A., Messens, E.,Boerjan, W.Profiling of oligolignols reveals monolignol coupling conditions inlignifying poplar xylem. Plant Physiol. November 2004, Vol.136, pp.3537-3549
Notes:
3065Compound Number
FPL/DFRC NMR Database -- April 2009
buddlenol A, G-(t8-O-4)-S-(8-5)-G’3-(2-{4-[2-hydroxy-3-methoxy-phenyl)1-hydroxymethyl-ethoxy]-3.5-
dimethoxy-phenyl}-3-hydroxymethyl-7-methoxy-2,3-dihydrobenzofuran-5-yl-propenal
13CCDCl3
CS i
Acetone
CS i CS i
DMSO
PROTONdataonly
Atom
1HJMultH Shifts
3.823.843.94
4.975.706.666.766.836.837.037.599.64
sss
tddddddsddd
J = 4.47J = 6.45
J = 15.78, 7.63J = 8.02
J = 8.02, 1.84
J =1.84J = 15.78J = 7.63
OMeB OMeOMe
AαBαCβA5A6
B 2,6A2CαCγ
Atom
(acetone)
threo
Fln 117 Morreel #19Morreel, K., Ralph, J., Kim, H., Lu, F., Goeminne, G., Ralph, S.A., Messens, E.,Boerjan, W Profiling of oligolignols reveals monolignol coupling conditions inlignifying poplar xylem. Plant Physiol. November 2004, Vol.136, pp.3537-3549
Notes:
3066Compound Number
FPL/DFRC NMR Database -- April 2009
SP-(8,8)-Stetrahydro-α4,2-bis-(4-hydroxy-3,5-dimethoxyphenyl) α-3O-(4-
hydroxybenzoyl)-3,4-furandimethanol
13CCDCl3
CS i
48.3749.80
56.5056.5056.5056.50
63.9969.9572.5985.34
104.45104.45104.53104.53115.98115.98
122.40
132.45132.45
134.49134.91136.01136.01
148.54148.54148.54148.54
162.56
166.43
Acetone
CS i CS i
DMSO
BβAβ
OMeOMeOMeOMe
AγBγBαAα
A2A6B2B6C3C5
C1
C2C6
A1B1A4B4
A3A5B3B5
C4
Cα
Atom
1HJMultH Shifts
2.553.743.783.994.144.414.684.904.966.666.726.877.77
mssmmmmddssmm
J = 6.3J = 5.0
AβOMeOMeBβBγ
Aγ1Aγ2AαBα
A2,6B2,6C3,5C2,6
Atom
(acetone)
HKh83.5, FLl112 Compound #8, Morreel, K., Ralph, J., Kim, H., Lu, F.,Goeminne, G., Ralph, S.A., Messens, E., Boerjan, W. Profiling of oligolignolsreveals monolignol coupling conditions in lignifying poplar xylem. Plant Physiol.November 2004, Vol.136, pp.3537-3549 See compound #118 for peracetate
Notes:
3067Compound Number
FPL/DFRC NMR Database -- April 2009
G-(8-O-4)-Sthreo-1-(4-hydroxy-3-methoxy-phenyl)-2-[2,6 dimethoxy-phenoxy-4-(3-
hydroxy-propenyl)]-propane-1,3-diol
13CCDCl3
CS i
Acetone
CS i CS i
DMSO
PROTONdataonly
Atom
1HJMultH Shifts
3.39
3.833.87
4.214.334.96
6.376.54
6.766.796.827.03
7.33
m
ss
mddd
dtd
ds
ddd
br s
-
-J = 3.8
J = 6.8, 8.4
J = 15.8, 5.1J = 15.8
J = 8.2
J = 8.2, 1.3J = 1.3
Aγ
A3 OMeB3 OMe
BγAα−ΟΗ
Aα
BβBα
A5B2/6A6A2
A4-OH
Atom
(acetone)
threo
FLm08 Cmpd 1a:Phenolic profiling of caffeic acid O-methyltransferase-deficientpoplar reveals novel benzodioxane oligolignols. K. Morreel, J. Ralph, F. Lu, G.Goeminne, R. Busson, P. Herdewijn, J.L. Goeman, J. Van der Eycken, W. Boerjanand E. Messens. Plant Physiology, 136(4), 4023-4036 (2004).
Notes:
3068Compound Number
FPL/DFRC NMR Database -- April 2009
G-(8-O-4)-5H [nocomtol]4-[3-hydroxymethyl-7-(E)-(3-hydroxypropenyl)-5-methoxy-2,3-
dihydro-benzo[1,4]dioxin-2-yl]-2-methoxyphenol
13CCDCl3
CS i56.256.2
61.963.676.779.3
103.2108.5111.7115.7121.4129.0129.1130.1130.3
133.7145.2147.8148.3149.8
Acetone
CS i CS i
DMSO
B3-OMeA3-OMe
AγBγAαAβ
B2B6A2A5A6BβA1BαB1
B4B5A4A3B3
Atom
1HJMultH Shifts
3.503.76
3.853.85
4.054.204.966.266.47
6.686.876.957.10
mm
ss
mddddtdt
ddddd
--
-J = 5.4, 1.6
J = 7.9J = 15.9, 5.4J = 15.9, 1.6
J = 1.8J = 8.1
J = 8.1, 1.8J = 1.8
Aγ1Aγ2
B3 OMeA3 OMe
AβBγAαBαBβ
B6A5A6A2
Atom
(acetone)
trans
FLn55 Cmpd 3:Phenolic profiling of caffeic acid O-methyltransferase-deficientpoplar reveals novel benzodioxane oligolignols. K. Morreel, J. Ralph, F. Lu, G.Goeminne, R. Busson, P. Herdewijn, J.L. Goeman, J. Van der Eycken, W. Boerjanand E. Messens. Plant Physiology, 136(4), 4023-4036 (2004).
Notes:
3069Compound Number
FPL/DFRC NMR Database -- April 2009
G-(8-O-4)-5H′ [nocomtal](2E)-3-[3-(4-hydroxy-3-methoxy-phenyl)-2(hydroxymethyl)-8-
methoxy-2,3-dihydro-1,4-benzodioxin-6-yl]acrylaldehyde
13CCDCl3
CS i56.456.5
61.677.079.8
105.5111.9112.0115.8121.6
127.5128.0128.9137.4
145.6148.1148.5150.4153.7
193.8
Acetone
CS i CS i
DMSO
A3-OMeB3-OMe
AγAαAβ
B2B6A2A5A6
B1BβA1Bα
B5A3A4B3B4
Bγ
Atom
1HJMultH Shifts
3.533.82
3.863.91
4.145.016.67
6.886.926.977.027.12
7.537.59
9.64
mm
ss
dddddd
dddddddd
dbs
d
--
J = 8.0, 3.8, 2.6J = 8.0
J = 15.8, 7.6
J = 8.0J = 2.0, 0.4
J = 8.0, 2.0, 0.4J = 2.0J = 2.0
J = 15.8-
7.6
Aγ1Aγ2
A3 OMeB3 OMe
AβAαBβ
A5B6A6B2A2
BαA4-OH
Bγ
Atom
(acetone)
trans
FLl111 Cmpd c:Phenolic profiling of caffeic acid O-methyltransferase-deficientpoplar reveals novel benzodioxane oligolignols. K. Morreel, J. Ralph, F. Lu, G.Goeminne, R. Busson, P. Herdewijn, J.L. Goeman, J. Van der Eycken, W. Boerjanand E. Messens. Plant Physiology, 136(4), 4023-4036 (2004).
Notes:
3070Compound Number
FPL/DFRC NMR Database -- April 2009
G-(8-O-4)-5H′′
3-[3-(4-hydroxy-4-methoxyphenyl)-2-hydroxymethyl-8-methoxy-2,3-dihydrobenzo[1,4] dioxin-6-yl]-acrylic acid ethyl ester
13CCDCl3
CS i14.656.256.3
61.661.676.979.5
104.7111.1111.7115.7117.0121.4127.4128.8136.4
145.2145.3147.8148.3150.1
167.2
Acetone
CS i CS i
DMSO
MeB3-OMeA3-OMe
AγCH2AαAβ
B2B6A2A5BβA6B1A1B4
BαB5A4B3A3
Bγ
Atom
1HJMultH Shifts
1.253.503.83
3.853.92
4.094.174.986.40
6.856.886.956.967.10
7.54
tmm
ss
mqdd
dddddd
d
J = 7.1--
-J = 7.1J = 8.0J = 15.9
J = 1.5J = 8.1J = 1.5
J = 8.1, 1.8J = 1.8
J = 15.9
MeAγ1Aγ2
B3 OMeA3 OMe
AβCH2AαBβ
B6A5B2A6A2
Bα
Atom
(acetone)
trans
HKj51T6.7 Cmpd #9, Morreel, K., Ralph, J., Kim, H., Lu, F., Goeminne, G.,Ralph, S.A., Messens, E., Boerjan, W. Profiling of oligolignols reveals monolignolcoupling conditions in lignifying poplar xylem. Plant Physiol. November 2004,Vol.136, pp.3537-3549 Note the single γ-acetate!
Notes:
3071Compound Number
FPL/DFRC NMR Database -- April 2009
13CCDCl3
CS i20.66
56.6256.73
63.5973.3184.56
104.65106.94
129.11131.09131.65136.04139.26
148.51153.45154.57
167.76
193.90
Acetone
CS i CS i
DMSO
γ Ac Me
A3 OMeB3 OMe
γαβ
A2/6B2/6
BβB1A1A4B4
A3/5Bα
B3/5
γ Ac C=O
Bγ
Atom
1HJMultH Shifts
1.84
3.803.94
4.124.394.624.94
6.706.777.12
7.61
9.67
s
ss
ddddmdd
sdds
d
d
-
--
J = 11.9, 3.2J - 11.9, 7.4
-J = 6.7, 4.0
-J = 15.8, 7.6
-
J = 15.8
J = 7.6
γ Ac Me
A3/5 OMeB3/5 OMe
γ1γ2βα
A2/6Bβ
B2/6
Bα
Bγ
Atom
(acetone)
HKf145, mixture of isomers Morreel #39 Morreel, K., Ralph, J., Kim, H., Lu, F.,Goeminne, G., Ralph, S.A., Messens, E., Boerjan, W. Profiling of oligolignolsreveals monolignol coupling conditions in lignifying poplar xylem. Plant Physiol.November 2004, Vol.136, pp.3537-3549
Notes:
3072Compound Number
FPL/DFRC NMR Database -- April 2009
S-(8-O-4)-G-(8-5)-G
13CCDCl3
CS i
54.8
56.3556.3956.58
61.8663.2664.58
73.84
86.3288.03
88.24
105.36111.14119.33
128.42130.48
Acetone
CS i CS i
DMSO
Bβ
OMeOMeOMe
AγCγBγ
Aα
AβeAβt
Bα
A2/6C2/6
B2/5/6
CβCα
Atom
1HJMultH Shifts
3.513.513.713.85
3.773.863.94
4.194.244.324.86
5.596.236.51
6.76
mmmm
sss
ddmmd
ddtd
s
J = 5.5, 1.3
J = 5.9
J = 6.5J = 15.9, 5.5
J = 15.9
BβAγ1Aγ2Bγ
ΟΜεΟΜεΟΜε
CγAβtAβeAα
BαCβCα
A 2,6
Atom
(acetone)