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Table 4: Main MS-EI fragments of the identified compounds in Table 2 (odorants in glucuronidase-treated urine) and compilation of their odor
thresholds and CAS numbers.
No.a Odorant CAS
numberb
MS-EI
fragmentsc
Odor threshold in air
[µg//L]
Odor threshold in water
(orthonasal) [µg//L]
Frequently occurring odorants in solvent extracts of human urine after enzymatic hydrolysis
1 Dimethyl trisulphide 3658-80-8 126, 79 0.000077
(Blank et al. 1989)
0.0060 – 0.016
(R. G. Buttery et al. 1997;
Czerny et al. 2008; Hansen et
al. 1992; C. Milo 1995; C Milo
and Grosch 1996)
2 3-(Methylthio)-propanal (Methional) 3268-49-3 104, 76 0.0010 - 0.00014
(Blank et al. 1989; I.
Blank et al. 1992 a; P.
Schieberle and Grosch
1994)
0.20 – 1.8
(R. Buttery and Ling 1995;
Cerny and Grosch 1993;
Czerny et al. 2008; H. Guth and
Grosch 1994; Kerler and
Grosch 1996)
3 Butanoic acid 107-92-6 60, 73 0.0010 – 0.0028 204 – 7700
No.a Odorant CAS
numberb
MS-EI
fragmentsc
Odor threshold in air
[µg//L]
Odor threshold in water
(orthonasal) [µg//L]
(Christlbauer 2006;
Leonardos et al. 1969) (Czerny et al. 2008; Karagul-
Yuceer et al. 2003; J. A. Pino
and Mesa 2006; P Schieberle
1991; Schnabel et al. 1988)
4 2-/3-Methylbutanoic acid 116-53-0
or
503-74-2
60, 87 2-methylbutanoic acid
0.0069 -0.14
(Christlbauer 2006;
Steinhaus 2001)
2-methylbutanoic acid
0.32 – 6600
(Czerny et al. 2008; Keith and
Powers 1968; Larsen and Poll
1992; T. Pyysalo et al. 1977;
Schnabel et al. 1988)
3-methylbutanoic acid
0.00048 – 0.0042
(Amoore 1977;
Christlbauer 2006;
3-methylbutanoic acid
12 – 1600
(R. Buttery et al. 1990; Czerny
et al. 2008; Ong and Acree
No.a Odorant CAS
numberb
MS-EI
fragmentsc
Odor threshold in air
[µg//L]
Odor threshold in water
(orthonasal) [µg//L]
Steinhaus 2001) 1999; P Schieberle 1991;
Schnabel et al. 1988)
5 (E)-1-(2,6,6-Trimethyl-1,3-cyclohexadienyl)-but-2-en-1-
one ((E)--Damascenone)
23696-85-
7
69, 121, 105,
175, 190
0.0000028
(Blank et al. 1989; I.
Blank et al. 1992 a)
0.00075 – 10
(R. G. Buttery et al. 1989;
Czerny et al. 2008; J. A. Pino
and Mesa 2006; P Schieberle
1991; Semmelroch et al. 1995)
6 (E)-3,7-Dimethylocta-2,6-dien-1-ol (Geraniol) 106-24-1 69, 67, 93, 91,
121
- 1.1 – 75
(Czerny et al. 2008; Ong and
Acree 1999; J. Pino et al. 1986;
T. Pyysalo et al. 1977; Schuh
and Schieberle 2006)
7 2-Methoxyphenol (Guaiacol) 90-05-1 124, 109, 81 0.00028 – 0.0015
(H Guth and Grosch
1991; Yang et al.
0.84 – 21
(R. Buttery et al. 1971; Cerny
and Grosch 1993; Czerny et al.
No.a Odorant CAS
numberb
MS-EI
fragmentsc
Odor threshold in air
[µg//L]
Odor threshold in water
(orthonasal) [µg//L]
2008) 2008; Kerler and Grosch 1996;
Wassermann 1966)
8 2-Methoxy-5-methylphenol (5-Methylguaiacol) 1195-09-1 138, 123, 95, - -
9 3-Hydroxy-2-methylpyran-4-one (Maltol) 118-71-8 126, 71, 97, 127 - 210 – 35000
(R. G. Buttery et al. 1997;
Karagul-Yuceer et al. 2003;
Keith and Powers 1968; Pittet
et al. 1970)
10 4-Ethyl-2-methoxyphenol (4-Ethylguaiacol) 2785-89-9 137, 152 0.000017
(I. Blank et al. 1992 a)
4.4 – 50
(Czerny et al. 2008;
Semmelroch et al. 1995)
11 4-Hydroxy-2,5-dimethyl-3(2H)-furanone (Furaneol) 3658-77-3 128, 57, 85, 129 0.00087 – 0.0010
(I. Blank et al. 1992 a;
P. Schieberle and
Grosch 1994)
3.2 – 1700
(Czerny et al. 2008; Kerler and
Grosch 1996; Larsen and Poll
1992; Semmelroch et al. 1995;
No.a Odorant CAS
numberb
MS-EI
fragmentsc
Odor threshold in air
[µg//L]
Odor threshold in water
(orthonasal) [µg//L]
Wilson III et al. 1990)
12 -Nonalactone 104-61-0 85, 57 - 9.7 – 27
(Czerny et al. 2008)
13 2-Methoxy-4-methylphenol (4-Methylguaiacol) 93-51-6 138, 123, 95, 67 - 10 - 90
(Czerny et al. 2008; Kennison
et al. 2007; Wassermann 1966)
14 4-Methylphenol (p-Cresol) 106-44-5 107, 108, 77, 79 0.00055 – 0.0010
(Blank et al. 1989;
Leonardos et al. 1969)
1.0 - 55
(R. G. Buttery et al. 1988;
Czerny et al. 2008; Hoak 1957;
Karagul-Yuceer et al. 2003;
Kerscher 2000)
15 -Decalactone 706-14-9 85, 128 - 1.1 – 90
(Czerny et al. 2008; Engel et al.
1988; Keith and Powers 1968;
No.a Odorant CAS
numberb
MS-EI
fragmentsc
Odor threshold in air
[µg//L]
Odor threshold in water
(orthonasal) [µg//L]
Larsen and Poll 1992; J. A.
Pino and Mesa 2006)
16 -Decalactone 705-86-2 99, 71 - 2.5 - 410
(Czerny et al. 2008; Engel et al.
1988; Karagul-Yuceer et al.
2003; Ong and Acree 1999; J.
A. Pino and Mesa 2006)
17 4-Allyl-2-methoxyphenol (Eugenol) 97-53-0 164, 149 0.00024
(Blank et al. 1989)
0.71 – 150
(I Blank et al. 1992 b; R.
Buttery et al. 1971; Czerny et
al. 2008; J. A. Pino and Mesa
2006; T. Pyysalo et al. 1977)
18 3-Hydroxy-4,5-dimethyl-2(5H)furanone (Sotolone) 28664-35-
9
83, 55, 128, 129 0.000010 – 0.000014
(I. Blank et al. 1992 a;
0.30 - 20
(Czerny et al. 2008; Kerler and
No.a Odorant CAS
numberb
MS-EI
fragmentsc
Odor threshold in air
[µg//L]
Odor threshold in water
(orthonasal) [µg//L]
Christlbauer 2006) Grosch 1996; Semmelroch et
al. 1995; Zeller and Rychlik
2006)
19 2-Methoxy-4-vinylphenol (4-Vinylguaiacol) 7786-61-0 150, 135, 107,
77
0.00057 – 0.0028
(Blank et al. 1989; I.
Blank et al. 1992 a;
Yang et al. 2008)
3.0 – 100
(R. Buttery and Ling 1995; R.
G. Buttery et al. 1988; Czerny
et al. 2008; J. A. Pino and Mesa
2006; P Schieberle 1991)
20 2-Methoxy-5-vinylphenol (5-Vinylguaiacol) 621-58-9 - 0.15 – 0.35
(Scheidig et al. 2007)
21 -Undecalactone 104-67-6 85, 57 0.00012
(Christlbauer 2006)
2.1 - 410
(Czerny et al. 2008; Greger
2007; Keith and Powers 1968;
J. A. Pino and Mesa 2006)
22 Indole 120-72-9 117, 90, 89 0.0081 11 – 140
No.a Odorant CAS
numberb
MS-EI
fragmentsc
Odor threshold in air
[µg//L]
Odor threshold in water
(orthonasal) [µg//L]
(Yang et al. 2008)
(R. G. Buttery et al. 1988;
Czerny et al. 2008; Karagul-
Yuceer et al. 2003)
23 2H-Chromen-2-one (Coumarin) 91-64-5 118, 146, 89, 63 - 25 -250
(R. G. Buttery et al. 1978;
Cartwright and Kelley 1952;
Masanetz and Grosch 1998)
24 4-Hydroxy-3-methoxybenzaldehyde (Vanillin) 121-33-5 151, 152, 123,
81
0.00032 - 0.00085
(Blank et al. 1989; I.
Blank et al. 1992 a;
Christlbauer 2006)
25 – 1200
(R. G. Buttery et al. 1997;
Czerny et al. 2008; Ong and
Acree 1999; Schuh and
Schieberle 2006; Semmelroch
et al. 1995; Zeller and Rychlik
No.a Odorant CAS
numberb
MS-EI
fragmentsc
Odor threshold in air
[µg//L]
Odor threshold in water
(orthonasal) [µg//L]
2007)
25 5-Androst-16-en-3-one (Androstenone) 18339-16-
7
- 0.0021
(Amoore 1977)
0.18
(Amoore 1977)
26 Androsta-4,16-dien-3-one (Androstadienone) 794-58-9 - - -
Odorants that were only present in the minority of solvent extracts of human urine after enzymatic hydrolysis
1 Butan-2,3-dione (Diacetyl) 431-03-8 - 0.00026 – 0.014
(Christlbauer 2006; I.
Blank et al. 1992 a;
Hall and Andersson
1983)
1.0 – 6.5
(Czerny et al. 2008; R. G.
Buttery et al. 1997; R. Buttery
and Ling 1995; C. Milo 1995;
Mulders 1973)
2 Oct-1-en-3-one 4312-99-6 - 0.000020 - 0.00010
(Christlbauer 2006;
Koszinowski and
Piringer 1986)
0.0050 – 4.0
(R. G. Buttery et al. 1978;
Czerny et al. 2008; R. G.
Buttery et al. 1997; C. Milo
No.a Odorant CAS
numberb
MS-EI
fragmentsc
Odor threshold in air
[µg//L]
Odor threshold in water
(orthonasal) [µg//L]
1995; H. Pyysalo and Suihko
1976)
3 2-Acetyl-1-pyrroline 85213-22-
5
83, 111 0.000020 – 0.000028
(Blank et al. 1989;
Hofmann et al. 1995;
P. Schieberle and
Grosch 1991, 1994)
0.053 - 0.12
(R. G. Buttery et al. 1983; R.
G. Buttery et al. 1988; Czerny
et al. 2008; R. Buttery and Ling
1995)
4 Phenol 108-95-2 94, 66, 65 0.047
(Leonardos et al. 1969)
31 - 10000
(Hoak 1957; Young et al. 1996)
5 -Nonalactone 3301-94-8 71, 99, 114, 128 - -
6 3-Ethylphenol 620-17-7 107, 122, 77 - 0.85 – 1.7
(Czerny et al. 2008)
7 5-ethyl-3-hydroxy-4-methyl-2(5H)-furanone (Abhexone) 698-10-2 - 0.0000028
(I. Blank et al. 1992 a)
7.5 – 500
(Semmelroch et al. 1995; Pittet
No.a Odorant CAS
numberb
MS-EI
fragmentsc
Odor threshold in air
[µg//L]
Odor threshold in water
(orthonasal) [µg//L]
et al. 1970)
8 3-Methylindole (Skatol) 83-34-1 130, 131, 103,
77
0.000020
(Christlbauer 2006)
0.13 – 3.0
(Audouin et al. 2001; R. G.
Buttery et al. 1997; Czerny et
al. 2008; Heiler and Schieberle
1997; Karagul-Yuceer et al.
2003)
9 7-Methoxychromen-2-one (7-Methoxycoumarin) 531-59-9 - - -
Footnotes to Table 4a
a) Numbering refers to Figure 3a and 3b (supplementary material and Table 2.
b) Chemical abstracts service number.
c) Main MS-EI fragments as obtained in our experiments. Fragments are listed according to their relative height.
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