asbc methods of analysis hop flavor database€¦ · 86.13; nif nif; 0.026 52; 500 •oxidation...

Chemical Name Synonyms StrutureMolecular

Weight (g/mol)

Flavor DescriptorsConc.

Minimum (mg/l)

Conc. Maximum

(mg/l)

Conc. Mean (mg/l)

TH 1 (mg/l) TH 2 (mg/l) TH 3 (mg/l)TH Water

(mg/l)Formation/Description

Compound Classification

References CAS Number

1-(2,3,6-Trimethylphenyl)-1,3-butadiene

NIF NIF NIF leather, geranium NIF NIF NIF NIF NIF NIF NIF NIF Hydrocarbon [4] NIF

1,2-EpithiohumuleneHumulene-1,2-

episulfideC15H24S 236.42 musty, sulfury, cardboard NIF NIF NIF 0.2 NIF NIF NIF •derived from hop oil Sulfur compound

[4], [10], [18], [32], [35]

NIF

1,3(E),5(Z),9-undecatriene

NIF C11H18 150.26 fresh, balsamic NIF NIF NIF NIF NIF NIF NIF NIF Hydrocarbon [29] NIF

1,3(E),5(Z)-undecatriene NIF C11H18 150.26 fresh, balsamic NIF NIF NIF NIF NIF NIF NIF NIF Hydrocarbon [29], [60] 51447-08-6

1,3,5-Trimethylcyclohexane

NIF C9H18 126.24 NIF NIF NIF NIF NIF NIF NIF NIF NIF Hydrocarbon [43] 1839-63-0

11-Selinene-4-ol Selin-11-ene-4-ol C15H26O 222.37 NIF NIF NIF 0.025 NIF NIF NIF NIF NIF Sesquiterpene [4], [15], [56] 16641-47-71-Butanol NIF C4H10O 74.12 NIF NIF NIF NIF NIF NIF NIF NIF NIF Alcohol [54] 71-36-3

1-Heptanol NIF C7H10O 110.16 NIF NIF NIF NIF NIF NIF NIF NIF NIF Alcohol [54] 111-70-61-Hexanol NIF C6H10O 98.14 NIF NIF NIF NIF NIF NIF NIF NIF NIF Alcohol [54] 111-27-3

1-Hydroxy-3-methyl-2-butanone

NIF C5H10O2 102.13 NIF NIF NIF NIF NIF NIF NIF NIF NIF Ketone [43] 36960-22-2

1-Octen-3-ol NIF C8H16O 128.21 mushroom NIF NIF NIF NIF NIF NIF NIF NIF Alcohol [54], [59] 3391-86-41-Pentanol NIF C5H12O 88.15 NIF NIF NIF NIF NIF NIF NIF NIF NIF Alcohol [54] 71-41-0

2(E),4(E)-Nona-2,4-dienal NIF C9H14O 138.21 fatty NIF NIF NIF NIF NIF NIF NIF NIF Aldehyde [60] 5910-87-2

2,2,6-Trimethyl-1-crotonyl-1,3-

cyclohexadieneNIF NIF NIF NIF NIF NIF NIF NIF NIF NIF NIF NIF Hydrocarbon [4] NIF

2,2,7,7-Tetramethyl-1,6-dioxaspiro-(4,4)-non-3-

eneDihydrospiroacetal C11H18O2 182.26 NIF NIF NIF 0.005 NIF NIF NIF NIF NIF Hydrocarbon [4], [54], [56] 15031-05-7

2,2,7,7-Tetramethyl-1,6-dioxaspiro-(4,4)-nona-3,8-

dieneSpiroacetal NIF NIF NIF NIF NIF 0.01 NIF NIF NIF NIF NIF Hydrocarbon

[39], [41], [54], [56]

15129-55-2

2,2-Dimethylhexane NIF C8H18 114.23 NIF NIF NIF NIF NIF NIF NIF NIF NIF Hydrocarbon [4] 590-73-8

2,3,5-TrithiahexaneMethyl

methylthiomethyl disulfide

C3H8S3 140.29 burnt rubber NIF NIF NIF 0.004 NIF NIF NIF NIF Sulfide [10], [18], [32] 42474-44-2

2,4-Heptadienal NIF C7H10O 110.16 green NIF NIF NIF NIF NIF NIF NIF NIF Aldehyde [44] 5910-85-02,4-Hexadienal NIF C6H8O 96.13 NIF NIF NIF NIF NIF NIF NIF NIF NIF Aldehyde [39] 142-83-62,6,6-Trimethyl-

cyclohexylidene-1-acetic acid lactone

Dihydroactinidiolide C11H16O2 180.24 tea-like, astringent, oxidized

NIF NIF 0.03 0.5 NIF NIF NIF NIF Lactone [4] 17092-92-1

2,6-Dimethyl-2,4,6-octatriene

Allo-ocimene C10H16 136.23 NIF NIF NIF NIF NIF NIF NIF NIF NIF Hydrocarbon [59] 673-84-7

2-Acyl-4-alkenyltetronic acid

NIF NIF NIF NIF NIF NIF trace NIF NIF NIF NIF NIF Acid [4] NIF

2-Decanol NIF C10H22O 158.28 coconut, aniseed NIF NIF 0.005 0.015 NIF NIF NIF NIF Alcohol [17], [21] 1120-06-5

2-Decanone NIF C10H20O 156.27 ketone, flowery, sweet, citrus

NIF NIF NIF 0.25 NIF NIF NIF NIF Ketone[4], [7], [21],

[54], [59]693-54-9

2-Dodecanone NIF C12H24O 184.32ketone, varnish, green

plants, geranium, fruity, citrus, orange

NIF NIF 0.005 0.25 NIF NIF NIF NIF Ketone[21], [39], [54],

[59]6175-49-1

2-Heptadecanone NIF C17H34O 254.46 NIF NIF NIF NIF NIF NIF NIF NIF NIF Ketone [12] 2922-51-2

2-Heptanol NIF C7H16O 116.20 coconut, unpleasant, ketonic solvent

NIF NIF NIF 0.25 1 NIF NIF NIF Alcohol [21] 543-49-7

2-Heptanone NIF C7H14O 114.19 varnish, ketone, walnut, hops, stale

0.004 0.1 0.057 2 NIF NIF NIF NIF Ketone[4], [7], [21],

[54]110-43-0

2-Heptenoic acid NIF C7H12O2 128.17 NIF NIF NIF 0.01 NIF NIF NIF NIF NIF Acid [39] 18999-28-52-Hexadecanone NIF C16H32O 232.37 NIF NIF NIF 0.005 NIF NIF NIF NIF NIF Ketone [39], [54] 18787-63-8

2-Hexanone NIF C6H12O 100.16 ketone, roquefort cheese NIF NIF 0.025 4 NIF NIF NIF NIF Ketone [7], [21], [39] 591-78-6

2-Hexen-1-ol NIF C6H12O 100.16 NIF NIF NIF NIF NIF NIF NIF NIF NIF Alcohol [54] 2305-21-72-Hexenoic acid NIF C6H10O2 114.14 NIF NIF NIF NIF NIF NIF NIF NIF NIF Acid [54] 1191-04-4

2-Hexyl-5-methylfuran NIF C11H18O 166.26 NIF NIF NIF NIF NIF NIF NIF NIF NIF Other [59] 5312-82-32-Isopropyl-3-

methoxypyrazineNIF C8H12N2O 152.19 bell pepper NIF NIF NIF NIF NIF NIF NIF NIF Other [60] 25773-40-4

2-Ketohexanoic acid NIF C6H10O3 130.14 1 NIF NIF NIF NIF NIF Acid [4] 2492-75-32-Methyl-1-propanol NIF C4H10O 74.12 NIF NIF NIF NIF NIF NIF NIF NIF NIF Alcohol [54] 78-83-12-Methyl-2-butene NIF C5H10 70.14 NIF NIF NIF NIF NIF NIF NIF NIF NIF Hydrocarbon [4] 513-35-9

2-Methyl-3-buten-1-ol NIF C5H10O 86.13 kettle hop aroma NIF NIF NIF 10 NIF NIF NIF NIF Alcohol [4], [58] 4516-90-9

2-Methyl-3-buten-2-ol NIF C5H10O 86.13 NIF NIF NIF 0.026 52 500 NIF NIF

•oxidation product of iso-α-acid•formed by cleavage of the isoprenyl side chains of the α- and b-acid•created during the boil from colupulone

Alcohol[4], [29], [31],

[39]115-18-4

2-Methyl-3-furanethiol NIF C5H6OS 114.17 roasted meat NIF NIF NIF NIF NIF NIF NIF NIF Thiol [58] 28588-74-1

2-Methyl-5-thiahex-2-ene Isopentyl methyl sulfide C6H14S 118.24 garlic-like, rubbery, onion-like

NIF NIF NIF 0.0002 NIF NIF NIF NIF Sulphur-containing terpenoid

[32] 13286-90-3

2-Methyl-butanethiolate NIF NIF NIF NIF NIF NIF >30 ppm NIF NIF NIF NIF NIF Thioester [4] NIF

2-Methylbutanoic acid 2-Methylbutyric acid C5H10O2 102.13 sweaty, rancid, unpleasantly sour, cheesy

0.1 0.5 0.3 NIF NIF NIF 0.54

•can be formed by the degradation of thecarbonyl side-chain of α-acids and β-acids•also created by the cleavage of the acylside chains from adhumulone and adlupulone•cheesy aroma of aged hops

Acid[1], [4], [5], [29],

[31], [40]116-53-0

2-Methylbutyl 2-methylbutanoate

NIF C10H20O2 172.27 fruity, apple NIF NIF NIF NIF NIF NIF NIF NIF Ester [59] 2445-78-5

2-Methylbutyl 2-methylpropanoate

2-Methylbutyl isobutanoate, 2-

Methylbutyl isobutyrateC9H18O2 158.24 fruity NIF NIF 0.07 0.05 0.06 NIF NIF •can be derived from hops

•product of fermentationEster

[4], [17], [29], [59]

2445-69-4


2-Methylbutylisovalerate

C10H20O2 172.27 apple, fatty, minty, herbaceous

NIF NIF NIF NIF NIF NIF NIF NIF Ester [29], [59] 2445-77-4

2-Methylbutyl heptanoate

NIF C12H24O2 200.32 NIF NIF NIF NIF NIF NIF NIF NIF NIF Ester [59] 55195-33-0

2-Methylbutyl hexanoate NIF C11H22O2 186.29 ethereal NIF NIF NIF NIF NIF NIF NIF NIF Ester [59] 2601-13-0

2-Methylbutyl propanoate

NIF C8H16O2 144.21 sweet, fruit, apple, melon NIF NIF NIF NIF NIF NIF NIF NIF Ester [59] 2438-20-2

2-Methyl-propanethiolate NIF NIF NIF NIF NIF NIF >30 ppm NIF NIF NIF NIF NIF Thioester [4] NIF

2-Methylpropanoic acid2-Methylpropionic acid,

Isobutyric acidC4H8O2 88.11 sweaty, bitter, sour,

butyric0.1 2 1 30 NIF NIF NIF

•can be formed by the degradation of thecarbonyl side-chain of α-acids and β-acids•also created by the cleavage of the acylside chains from cohumulone and colupulone•cheesy aroma of aged hops

Acid[4], [21], [29], [31], [39], [54]

79-31-2

2-Methylpropyl 2-methylbutanoate

NIF C9H18O2 158.24 sweet, fruity NIF NIF NIF NIF NIF NIF NIF NIF Ester [59] 2445-67-2

2-Methylpropyl 2-methyl-propanoate

2-Methyl-propylisobutanoate, 2-

Methylpropyl isobutyrate

C8H16O2 144.21 NIF NIF NIF NIF NIF NIF NIF NIF NIF Ester [29] 97-85-8

2-Methylpropyl hexanoate

NIF C10H20O2 172.27 apple, pineapple, fruity NIF NIF NIF NIF NIF NIF NIF NIF Ester [59] 105-79-3

2-Nonanol NIF C9H20O 144.25 coconut NIF NIF 0.01 0.075 NIF NIF NIF NIF Alcohol [17], [21], [54] 628-99-9

2-Nonanone Nonan-2-one C9H18O 142.24 ketone, varnish, stale NIF NIF 0.03 0.02 0.2 20 NIF •located in hop oil fractions dervied from hops

Ketone[4], [7], [17],

[21], [54]821-55-6

2-Nonenic acid NIF C9H16O2 156.22 0.01 NIF NIF NIF NIF NIF Acid [39] 3760-11-0

2-Octanol NIF C8H18O 130.23 coconut, walnut, oily, rancid

NIF NIF 0.005 0.04 NIF NIF NIF •reduction of corresponding aldehyde in malt

Alcohol [17] 123-96-6

2-Octanone Octyl alcohol C8H16O 128.21 varnish, ketone, walnut, stale


[54]111-13-7

2-Pentadecanone NIF C15H30O 226.40 NIF NIF NIF NIF NIF NIF NIF NIF NIF Ketone [54] 2345-28-02-Pentanol NIF C5H12O 88.15 NIF NIF NIF NIF NIF NIF NIF NIF NIF Alcohol [54] 6032-29-7

ASBC Methods of AnalysisHop Flavor Database

2-Phenylethyl 3-methylbutanoate

NIF C13H18O2 206.28 floral, minty 0.00018 0.00056 0.00037 0.0885 NIF NIF NIF NIF Ester [51] 140-26-1

2-Tetradecanone NIF C14H28O 212.38 NIF NIF NIF NIF NIF NIF NIF NIF NIF Ketone [54] 2345-27-92-Tridecanone NIF C13H26O 198.34 fatty, herbal NIF NIF >30 ppm NIF NIF NIF NIF NIF Lactone [4], [54], [59] 593-08-82-Undecanol NIF C11H24O 172.31 NIF 0.016 0.027 0.022 NIF NIF NIF NIF NIF Alcohol [15] 113666-64-1

2-Undecanone Methyl nonyl ketone C11H22O 170.29ketone, varnish, bitter,

green plants, geranium, fruity, citrus


[54], [59]112-12-9

3-(4-methylpent-3-enyl)thiophene

Myrcene sulfide C10H14S 166.28 rubbery NIF NIF NIF 0.01 NIF NIF NIF NIF Sulphur-containing terpene

[32], [34], [39] 62429-57-6

3(E),5(Z),9(E)-Undeca-1,3,5,9-tetraene

NIF C11H18 150.26 fresh, pineapple NIF NIF NIF NIF NIF NIF NIF NIF Hydrocarbon [60] NIF

3,3-Dimethylallyl methyl sulfide

NIF C6H12S 117.09 garlic, rubbery, onion NIF NIF NIF 0.0002 NIF NIF NIF •derived from hop oil•increased content when wort is boiled

Sulfide [10], [18] NIF

3,3-Dimethylbutan-2-one NIF C6H12O 100.16 NIF NIF NIF NIF NIF NIF NIF NIF NIF Ketone [4] 75-97-8

3-Hepten-2-one NIF C7H12O 112.17 NIF NIF NIF NIF NIF NIF NIF NIF NIF Ketone [54] 1119-44-43-Hexenoic acid NIF C6H10O2 114.14 NIF NIF NIF NIF NIF NIF NIF NIF NIF Acid [54] 4219-24-3

3-Hydroxy-α-damascone NIF NIF NIF NIF NIF NIF NIF NIF NIF NIF NIF NIF Ketone [43] NIF

3-Mercapto-3-methylbutan-1-ol

3-Sulfanyl-3-methylbutan-1-ol

C5H12OS 120.21 sulfur, soup NIF NIF NIF NIF NIF NIF NIF NIF Thiol [36] 34300-94-2

3-Mercapto-4-methylpentan-1-ol

3S4MP, 3-Sulfanyl-4-methylpentan-1-ol

C6H14OS 134.24 rhubarb, grapefruit 0.00003 0.00055 0.0003 0.00007 NIF NIF NIF •concentration increases from wort to beer Thiol [6], [36], [38] NIF

3-Mercapto-4-methylpentan-2-ol

NIF C6H14OS 134.24 rhubarb, grapefruit NIF NIF NIF 0.00007 NIF NIF NIF NIF Thiol [5] NIF

3-Mercapto-4-methylpentanacetate

NIF NIF NIF NIF NIF NIF NIF NIF NIF NIF NIF NIF Thiol [6] NIF

3-Mercapto-4-methylpentyl acetate

3S4MPA, 3-sulfanyl-4-methylpentyl acetate

C8H16O2S 176.28 grapefruit 0.00003 0.0002 0.00012 0.00016 NIF NIF NIF •concentration increases from wort to beer Thiol [36], [38] NIF

3-Mercaptoheptan-1-ol 3-Sulfanylheptan-1-ol C7H16OS 148.26 lemon, hoppy NIF NIF NIF NIF NIF NIF NIF NIF Thiol [36] NIF3-Mercapto-hexan-1-ol 3-Sulfanylhexan-1-ol C6H14OS 134.24 grapefruit NIF NIF NIF 0.000055 NIF NIF NIF NIF Thiol [36], [51] 51755-83-03-Mercapto-octan-1-ol 3-Sulfanyloctan-1-ol C8H18OS 162.29 NIF NIF NIF NIF NIF NIF NIF NIF NIF Thiol [36] NIF

3-Mercapto-octanal 3-Sulfanyl-octanal C8H17OS 161.28 citrus, peach NIF NIF NIF NIF NIF NIF NIF NIF Thiol [36] NIF3-Mercapto-octanol 3-Sulfanyl-octanol C8H19OS 163.30 catty, grapefruit NIF NIF NIF NIF NIF NIF NIF NIF Thiol [36] NIF

3-Mercapto-pentan-1-ol 3-Sulfanylpentan-1-ol NIF NIF catty, citrus, grapefruit NIF NIF NIF NIF NIF NIF NIF NIF Thiol [36] NIF

3-Methyl-1-butanol Isoamyl alcohol C5H12O 88.15 NIF NIF NIF NIF NIF NIF NIF NIF NIF Alcohol [54] 123-51-3

3-Methyl-2-butanone 3-Methylbutan-2-one C5H10O 86.13 ketone, sweet, mint NIF NIF 0.005 0.005 10 60 NIF•oxidation product of iso-α-acids•derived from humulone and lupulone and created during the boil

Ketone[4], [7], [21],

[31], [39]563-80-4

3-Methyl-2-buten-1-ol NIF C5H10O 86.13 NIF 0.018 0.028 0.023 NIF NIF NIF NIF NIF Alcohol [15] 556-82-1

3-Methyl-2-buten-1-thiol MBT, Prenyl mercaptan C5H10S 102.20almond, roasted, sulfury, mercaptan, skunk, leek-

like, lightstruck0.000001 0.0001 0.00005 0.00000001 0.0000013 0.00001 0.0000002

•iso-alpha-acids are proposed to undergo photodegradation leading to 3-methyl-2-butenyl radicals and subsequently combine with thiol radicals derived from sulfur-containing components (e.g. amino acids, proteins, hydrogen sulfide)•the range of wavelengths effectively promoting sunstruck flavor is determined to be 350-500 nm•riboflavin (vitamin B2) acts as a photosensitizer•beer especially sensitive when packaged in clear, blue or green glass

Thiol

[1], [2], [3], [9], [11], [14], [16], [17], [18], [28],

[51]

5287-45-6

3-Methyl-2-buten-1-thiol NIF C5H10S 102.20 NIF 0.000001 0.0001 0.00005 0.000002 NIF NIF NIF NIF Thiol 5287-45-6

3-Methyl-3-mercaptobutyl

NIF C5H10OS 118.20 catty, ribes NIF NIF NIF NIF NIF NIF NIF NIF Sulfur compound [16] NIF

3-Methyl-3-mercaptobutyl formate

3-Mercapto-3-methylbutyl formate

C6H12O2S 148.22 catty, ribes NIF NIF NIF NIF NIF NIF NIF NIF Sulfur compound [16], [31] 50746-10-6

3-Methyl-3-pentenoic acid

NIF C6H10O2 114.14 NIF 0.05 0.1 0.075 1 NIF NIF NIF NIF Acid [4] NIF


NIF C10H20O2 172.27 fruity, citrus NIF NIF NIF NIF NIF NIF NIF NIF Ester [59] 27625-35-0

3-Methylbutyl 2-methylpropanoate

Isoamyl isobutyrate C9H18O2 158.24 spicy NIF NIF NIF >30 ppm NIF NIF 0.03 NIF Ester [4], [9], [59] 2050-01-3


Isoamyl isovalerate C10H20O2 172.27 NIF NIF NIF NIF NIF NIF NIF NIF NIF Ester [29] 659-70-1

3-Methylbutyl octanoate NIF C13H26O2 214.35 fruity, green, soapy, pineapple

NIF NIF NIF NIF NIF NIF NIF NIF Ester [59] 2035-99-6

3-Methylpentan-2-one NIF C6H12O 100.16 NIF NIF NIF 0.06 NIF NIF NIF NIF NIF Ketone [4], [54] 565-61-73-Methylpentanal NIF C6H12O 100.16 NIF NIF NIF NIF NIF NIF NIF NIF NIF Aldehyde [4] 15877-57-3

3-Methylthiophene NIF C5H6S 98.17 burnt, astringent 0 0.005 0.0025 0.5 NIF NIF NIF•derived from hop oil•created by sulfur heterocyclics and residual free sulfur

Sulphur-containing terpenoid

[4], [10], [18], [32]

616-44-4

3-Nopinenone NIF C10H14O 150.22 minty, medium NIF NIF NIF NIF NIF NIF NIF NIF Ketone [43] 547-62-6

4-(4-methylpent-3-enyl)-3,6-dihydro-1,2-dithiine

Myrcene disulfide C10H16S2 200.36 fragrant, grassy NIF NIF NIF 0.01 NIF NIF NIF NIF Sulphur-containing terpenoid

[32], [34] NIF

4,4-Dimethyl-but-2-en-1,4-olide

NIF NIF NIF NIF NIF NIF 0.4 NIF NIF NIF NIF NIF Lactone [39] NIF

4,4-Dimethylbutan-4-olide

4,4-Dimethylbutyrolactone

C6H10O2 114.14 NIF 0.036 0.16 0.1 NIF NIF NIF NIF NIF Lactone[4], [15], [39],

[41]13861-97-7

4,5-EpithiocaryophylleneCaryophyllene-4,5-

episulfideNIF NIF musty, sulphury NIF NIF >30 ppm 1.8 NIF NIF NIF •created by sulfur heterocyclics and residual

free sulfurSulphur-containing

terpenoid[4], [10], [32],

[35], [39]NIF

4,5-EpithiohumuleneHumulene-4,5-

episulfideNIF NIF musty, sulphury NIF NIF >30 ppm 1.5 NIF NIF NIF •created by sulfur heterocyclics and residual

free sulfurSulphur-containing

terpenoid[4], [10], [32],

[35], [39]NIF

4,8-Decadienoic acid NIF NIF NIF NIF NIF NIF NIF NIF NIF NIF NIF NIF Acid [54] NIF4-Butanolide NIF C4H6O2 86.09 0.08 0.1 0.09 NIF NIF NIF NIF NIF Other [42] 96-48-0

4-Decenoic acid NIF C10H18O2 170.25 NIF NIF NIF 0.23 NIF NIF NIF NIF NIF Acid [12], [39], [54] 57602-94-5

4-Mercapto-4-methyl-pentan-2-one

4-MMP, 4-Methyl-4-mercapto-pentan-2-one,

4-Methyl-4-sulfanyl-2-pentanone, 4-Sulfanyl-4-

methylpentan-2-one

C6H12OS 132.23 ribes, black current, muscat-like, fruity

0.00001 0.0002 0.0001 0.000002 0.00005 0.0015 NIF •found at different concentrations in hops depending on where hops were cultivated

Thiol[5], [6], [9], [14], [16], [31], [36],

[37]19872-52-7

4-Methyl-2-hexanoic acid NIF C7H12O2 128.17 NIF NIF NIF NIF NIF NIF NIF NIF NIF Acid [54] NIF

4-Methyl-2-pentanoneMethyl isobutyl ketone, 4-Methyl-pentan-2-one

C6H12O 100.16 varnish, ketone, melon, apricot

0.005 0.12 0.063 1.5 5 NIF NIF •oxidation product of iso-α-acids•hop degradation product

Ketone[4], [15], [21],

[26], [31], [39], [54]

108-10-1

4-Methyl-3-buten-2-one NIF NIF NIF NIF NIF NIF NIF NIF NIF NIF NIF •derived from humulone and lupulone during the boil

Ketone [39] NIF

4-Methyl-3-penten-2-one NIF C6H10O 98.14 NIF NIF NIF NIF NIF NIF NIF NIF NIF Ketone [54] 141-79-7

4-Methyl-3-pentenoic acid

NIF C6H10O2 114.14 NIF NIF NIF 0.032 1.0 NIF NIF NIF •created from the photooxidation of the ring structure of the α- and β-acids

Acid [29], [39], [54] 504-85-8

4-Methylhexenoic acid NIF NIF NIF NIF NIF NIF NIF NIF NIF NIF NIF NIF Acid [54] 68062-14-64-Methylvaleric acid NIF C6H12O2 116.16 fatty, smelly NIF NIF NIF NIF NIF NIF NIF •located in the polar fraction of hops Acid [44] 646-07-1

5-(4-methylpent-3-enyl)-1,2,3-trithiacyclohept-5-

eneNIF NIF NIF NIF NIF NIF NIF NIF NIF NIF NIF NIF Sulphur-containing

terpenoid[32] NIF

5,5-Dimethyl-2(5H)-furanone

4,4-Dimethyl-2-buten-4-olide, 4,4-

DimethylcrotonolactoneC6H8O2 112.13 grassy, minty, earthy,

gentian0.005 1.8 0.9 40 200 NIF NIF •smells similar to tetrahydrofuran and not

like hops in pure formLactone

[4], [39], [54], [55], [56]

20019-64-1

5-Methylhexanoic acid NIF C7H14O2 130.19 smelly, fishy NIF NIF NIF NIF NIF NIF NIF •located in the polar fraction of hops Acid [44] 628-46-65-Undecen-2-one NIF C11H20O2 168.28 NIF NIF NIF NIF NIF NIF NIF NIF NIF Ketone [59] 40657-56-5

6-(4-methylpent-3-enyl)-1,2,3,4-tetrathiacylooct-6-

eneNIF NIF NIF NIF NIF NIF NIF NIF NIF NIF NIF NIF Sulphur-containing

terpenoid[32] NIF

6-Methyheptanoic acid NIF NIF NIF NIF NIF NIF NIF NIF NIF NIF NIF NIF Acid [54] NIF

6-Methyl-5-hepten-2-one NIF C8H14O 126.20 NIF 0.006 0.05 0.028 NIF NIF NIF NIF NIF Ketone[4], [15], [54],

[56]110-93-0

6-Methylhept-2-en-1-ol NIF C8H16O 128.21 NIF NIF NIF 0.008 NIF NIF NIF NIF NIF Alcohol [15] NIF7,7-Dimethyl-6,8-

dioxabicyclo-(3,2,1)-octane

NIF NIF NIF NIF NIF NIF 0.05 NIF NIF NIF NIF NIF Hydrocarbon [4], [39], [41] NIF

7-Hydroxy-a-terpineol p-Menth-1-ene-7,8-diol NIF NIF intense fruity, floral (rose), slightly citrus

NIF NIF NIF NIF NIF NIF NIF NIF Alcohol [43] NIF

7-Methyloctan-2-one NIF C9H18O 142.24 NIF NIF NIF NIF NIF NIF NIF NIF NIF Ketone [54] 1482-13-9

8-Acetoxylinalool NIF NIF NIF warm, fruity, woody, floral

NIF NIF NIF NIF NIF NIF NIF •located in the polar fraction of hops Alcohol [43], [44] NIF

8-Hydroxylinalool NIF C10H18O2 170.25 honey, citrus, dill NIF NIF NIF NIF NIF NIF NIF NIF Alcohol [43] 64142-78-58-Methylnonanoic acid NIF C10H20O2 172.27 NIF NIF NIF NIF NIF NIF NIF NIF NIF Acid [54] 5963-14-49-Methyldecan-2-one NIF C11H22O 170.30 NIF NIF NIF NIF NIF NIF NIF NIF NIF Ketone [54] 68067-35-6

a-Amorphene NIF C15H24 204.36 NIF NIF NIF NIF NIF NIF NIF NIF •located in the non-polar fraction from oxidized hops

Sesquiterpene [44] 483-75-0

a-Cadinene NIF C15H24 204.36 thyme, herbal, woody NIF NIF NIF NIF NIF NIF NIF NIF Sesquiterpene [54], [59] 24406-05-1a-Cadinol NIF C15H26O 222.37 NIF NIF NIF >30 ppm NIF NIF NIF NIF NIF Sesquiterpene [4], [54] 481-34-5

a-Calacorene NIF C15H20 200.32 woody NIF NIF NIF NIF NIF NIF NIF NIF Sesquiterpene [43] 21391-99-1Acetic acid NIF C2H4O2 60.05 NIF NIF NIF NIF NIF NIF NIF NIF NIF Acid [39] 64-19-7

Acetone NIF C3H6O 58.08 acetone, fruity 0.0037 0.017 0.01 200 NIF NIF NIF •oxidation product of iso-α-acids Ketone [7], [21], [31] 67-64-1a-Copaene NIF C15H24 204.35 NIF NIF NIF >30 ppm NIF NIF NIF NIF NIF Sesquiterpene [4] 3856-25-5

a-Eudesmol NIF C15H26O 222.37 NIF 0.001 0.15 0.076 NIF NIF NIF NIF NIF Sesquiterpene[4], [6], [12],

[29], [55]473-16-5

a-Gurjunene NIF C15H24 204.35 NIF NIF NIF NIF NIF NIF NIF NIF •located in the non-polar fraction from oxidized hops


a-Ionone4-(2,6,6-Trimethyl-1-

cyclohexenyl)-3-buten-2-one

C13H20O 192.30 artificial raspberry, cedarwood, violets

0.001 0.003 0.002 0.0026 0.1 NIF NIF NIF Terpene [4], [21], [54] 127-41-3

a-Muurolene NIF C15H24 204.35 NIF NIF NIF >30 ppm NIF NIF NIF NIF NIF Sesquiterpene [4] 31983-22-9

Anethole NIF C10H12O 148.21 aniseed, sweet NIF NIF NIF NIF NIF NIF NIF NIF Ether [60] 4180-23-8

a-Pinene NIF C10H16 136.23 rosmary, pine, fruity, green, resinous

NIF NIF NIF NIF NIF NIF 0.14 •transformation product of both b-pinene and limonene

Monoterpene[4], [39], [46],

[59]80-56-8

Aromadendiene Aromadendrene C15H24 204.35 NIF NIF NIF >30 ppm NIF NIF NIF NIF•only found in certain hop varieties•located in the non-polar fraction from oxidized hops

Sesquiterpene [4], [5], [44] 11026-29-2

a-Selinene NIF C15H24 204.35 NIF NIF NIF >30 ppm NIF NIF NIF NIF NIF Sesquiterpene [4], [5] 473-13-2

a-Terpinene NIF C10H16 136.23 herbaceous, citrus, woody, spicy

NIF NIF NIF NIF NIF NIF NIF NIF Monoterpene [29], [59] 99-86-5

a-Terpineol NIF C10H18O 154.25

pine, terpenoid, floral (lilac, rose), conifer-like, resinous, fresh, clean,

woody, lime

0.001 0.190 0.096 0.33 1 2 0.04

•can be formed from linalool and nerol by yeast•usually low concentrations in beer•no direct contribution in the hop aroma

Monoterpene alcohol

[4], [5], [9], [11], [12], [19], [21], [43], [54], [55]

98-55-5

b-Caryophyllene Caryophyllene C15H24 204.35woody (cedar), spicy,

flower, turpentine, clove, lime, dry, green, terpene

0.0002 0.08 0.04 0.16 0.23 0.45 0.064

•found in dry-hopped beers•located in the non-polar fraction from oxidized hops•transformation product of farnesene

Sesquiterpene

[4], [5], [9], [13], [17], [19], [29], [39], [44], [46],

[59]

87-44-5

b-Cyclocitral NIF C10H16O 152.24 floral NIF NIF NIF NIF NIF NIF NIF •located in the polar fraction of hops Aldehyde [44] 432-25-7b-Damascenone NIF C13H18O 190.28 0.001 0.2 0.1 0.15 NIF NIF NIF NIF Ketone 23696-85-7

b-Damascenonetrans-2,6,6-Trimethyl-1-crotonyl-cyclohexa-1,3-

dieneC13H18O 190.28

stewed (cooked) apple, honey-like, rhubarb, strawberry, red fruit,

cooked fruit, kettle hop aroma, peach, fruity,

tobacco, coconut, blackcurrant, raspberry,

menthol, prunes

0.002 0.2 0.1 0.000004 0.00002 0.010,000001, 0,000004, 0,000009

•from hop oil fractions dervied from hops•degraded during fermentation to low concentrations•component in aged beer

Ketone

[2], [3], [4], [5], [8], [13], [16],

[17], [26], [27], [29], [31], [40],

[58]

23696-85-7

Benzaldehyde NIF C7H6O 106.12 bitter almond, cherry stone, almond

0.0008 0.025 0.013 0.5 0.6 2 NIF

•increased formation with high oxygen concentrations during brewing and packaging as well as inappropriate storage of the finished beer•component in aged beer•mostly lost during hop kilning

Aldehyde[1], [17], [21], [22], [26], [29]

100-52-7

Benzenemethanol Benzyl alcohol C7H8O 108.14 sweet, floral, fruity with chemical nuances

NIF NIF NIF NIF NIF NIF NIF NIF Alcohol [43] 100-51-6

Benzoic acid NIF C7H6O2 122.12 NIF NIF NIF NIF NIF NIF NIF NIF NIF Acid [54] 65-85-0

b-Eudesmol NIF C15H26O 222.37 spicy, wood, green, okay, plastic

0.0004 0.15 0.075 10 NIF NIF NIF •located in the polar fraction of hops Sesquiterpene[4], [13], [15], [19], [43], [44]

473-15-4

b-Farnesene NIF C15H24 204.35 woody, citrus, sweet 0.00036 0.00054 0.00045 0.55 NIF NIF NIF •only b-Farnesene isomer is found in hops of the Farnesene compound

Sesquiterpene [4], [13], [44] 18794-84-8

b-Fenchyl alcohol Fenchyl alcohol, Fenchol C10H18O 154.25 NIF 0.006 0.04 0.023 NIF NIF NIF NIF NIF Monoterpene alcohol

[4], [15], [29], [39], [54]

1632-73-1

b-Guaiene NIF C15H24 204.35 NIF NIF NIF NIF NIF NIF NIF NIF •non-polar fraction from oxidized hops Sesquiterpene [44] 88-84-6Bicyclogermacrene NIF C15H24 204.35 NIF NIF NIF >30 ppm NIF NIF NIF NIF NIF Sesquiterpene [4] 24703-35-3

b-Ionone NIF C14H22O 206.32

raspberry, citrus, woodlands, violet, kettle

hop aroma, artificial raspberry, strawberry,

floral, berry

0.001 0.003 0.002 0.00001 0.0006 0.001 0.000007

•from hop oil fractions•1/3 of population have anosmia and cannot detect this compound•located in the polar fraction of hops

Terpenoid[5], [14], [17],

[21], [29], [46], [58]

14901-07-6

b-Ionone epoxide NIF C13H20O2 208.30 fruity, sweet, berry, woody, violet, orris

NIF NIF NIF NIF NIF NIF NIF NIF Epoxide [43] 23267-57-4

Borneol NIF C10H18O 154.25 NIF NIF NIF 0.01 NIF NIF NIF NIF NIF Monoterpene alcohol

[15], [29] 507-70-0

b-Phellanderene NIF C10H16 136.23 pine, terpentine, fruity, spicy

NIF NIF NIF NIF NIF NIF NIF NIF Monoterpene [44], [59] 555-10-2

b-Pinene NIF C10H16 136.23 pine, woody, green, resinous, dry

NIF NIF >30 ppm NIF NIF NIF 0.006 •transformation product of both a-pinene and limonene


[46], [59]129-91-3

b-Selinene NIF C15H24 204.35 NIF NIF NIF >30 ppm NIF NIF NIF NIF •only found in certain hop varieties Sesquiterpene [4], [5] 17066-67-0Butyric acid Butanoic acid C4H8O2 88.11 rancid, cheesy NIF NIF NIF NIF NIF NIF NIF NIF Acid [54], [60] 107-92-6

Cadalene NIF C15H18 198.30 NIF NIF NIF NIF NIF NIF NIF NIF NIF Hydrocarbon [54] 483-78-3Calamenene NIF C15H22 202.34 NIF NIF NIF NIF NIF NIF NIF NIF NIF Sesquiterpene [54] 72937-55-4

Calarene NIF C15H24 204.35 NIF NIF NIF NIF NIF NIF NIF NIF •located in the non-polar fraction from oxidized hops


Calarene oxide NIF NIF NIF chinese herd NIF NIF NIF NIF NIF NIF NIF •located in the polar fraction of hops Oxide [44] NIFCamphene NIF C10H16 136.23 camphoraceous, oily NIF NIF NIF NIF NIF NIF NIF NIF Monoterpene [29], [59] 79-92-5 Camphor NIF C10H16O 152.24 NIF NIF NIF 0.01 NIF NIF NIF NIF NIF Terpenoid [4] 76-22-2Carvacrol NIF C10H14O 150.22 NIF 0.01 2 1 NIF NIF NIF NIF NIF Terpenoid [4], [55] 499-75-2Carvone D-Carvone C10H14O 150.22 caraway seed, mint NIF NIF NIF 0.4 NIF NIF NIF •oxidation product of limonene Terpene [21], [46] 2244-16-8

Caryophylla-3,8(13)-dien-5-b-ol

NIF C15H24O 220.35 cedarwood NIF NIF NIF NIF NIF NIF NIF NIF Alcohol [52] NIF

Caryophyllene alcoholCaryolan-1-ol, β-

Caryophyllene alcoholC15H26O 222.37 NIF 0 0.025 0.013 NIF NIF NIF NIF NIF Sesquiterpene

[4], [19], [29], [41], [54]

472-97-9

Caryophyllene epoxide Caryophyllene oxide C15H24O 220.35musty, floral, spicy, cedar, sweet, fresh, dry, woody,

cosmetic, lime0.01 0.018 0.014 NIF NIF NIF NIF

•oxidation product that increases over storage of raw hops•located in the polar fraction of hops

oxygenated Sesquiterpenoxide

[4], [12], [29], [43], [54], [59]

1139-30-6

Caryophyllenol NIF C15H24O 220.35 NIF NIF NIF NIF NIF NIF NIF NIF NIF Sesquiterpene [29] 32214-89-4cis-5-Tridecen-2-one NIF NIF NIF NIF NIF NIF NIF NIF NIF NIF NIF NIF Ketone [59] NIF

cis-b-Ocimene NIF C10H16 136.23 citrus, terpene, woody, green

NIF NIF NIF NIF NIF NIF NIF NIF Monoterpene [59] 3338-55-4

cis-Dihydroocimene NIF C10H18 138.25 NIF NIF NIF NIF NIF NIF NIF NIF NIF Monoterpene [59] NIFcis-Geranic acid NIF C10H16O2 168.24 woody, flowery NIF NIF NIF NIF NIF NIF NIF •oxidation product of geranial Acid [46] NIF

cis-Jasmone NIF C11H16O 164.24 NIF 0.01 0.02 0.015 NIF NIF NIF NIF •contribution to beer flavor is not significant

Ketone [4], (12], [39] 488-10-8

cis-Linalool oxide Linalool oxide 1 NIF NIF NIF 0.0 0.025 0.013 NIF NIF NIF NIF •transferred to wort during boiling of hops Oxide [12], [19], [54] NIF

Citral NIF C10H16O 152.24 lemon, bitter, sweet floral

NIF NIF NIF 0.15 NIF NIF NIF •mixture of two isomers - neral and geranial•located in the polar fraction of hops

Terpene [21], [29] 5392-40-5

Citronellol β-Citronellol C10H20O 156.27floral, citrus, rose-like,

apple, fruity, lime, lychee, leather, waxy

0.001 0.09 0.05 0.009 0.04 NIF 0.01

•hop-derived compound in beer not found in hop essential oil•Geraniol is isomerized to Citronellol•Nerol reduces to Citronellol

Monoterpene alcohol

[5], [11], [13], [17], [29], [43]

106-22-9

Citronellyl acetate NIF C12H22O2 198.31 floral, rose, fruity, sweet 0 0.02 0.01 NIF NIF NIF NIF NIF Monoterpene [4], [15], [43] 150-84-5

d-3-Carene NIF C10H16 136.23 NIF NIF NIF NIF NIF NIF NIF NIF NIF Monoterpene [29] 13466-78-9d-Cadinene NIF C15H24 204.35 NIF NIF NIF >30 ppm NIF NIF NIF NIF NIF Sesquiterpene [4] 60305-17-1

d-Cadinol d-Cadinol C15H26O 222.37 NIF 0.005 0.2 0.103 NIF NIF NIF NIF NIF Sesquiterpene[4], [19], [29],

[54], [55]36564-42-8

Decanal NIF C10H20O 156.27 green, wax, floral, fruity NIF NIF NIF NIF NIF NIF NIF NIF Aldehyde [59] 112-31-2

Decanoic acid NIF C10H20O2 172.27 NIF NIF NIF NIF NIF NIF NIF NIF NIF Acid [12], [29], [54] 334-48-5Decen-2-one NIF NIF NIF NIF NIF NIF NIF NIF NIF NIF NIF NIF Ketone [54] NIF

Diallyl sulphide NIF C6H10S2 190.28 garlic-like NIF NIF NIF NIF NIF NIF NIF NIF Sulfide [32] 2179-57-9

Diethyl disulphide S-Methylthioisovalerate C4H10S2 122.25rotting vegetable, onion-

like, rubbery, sewage-like, sweat

NIF NIF NIF 0.0004 0.025 NIF NIF NIF Sulfide [32], [40], [58] 110-81-6

Diethyl sulphide NIF C4H10S 90.19 rotting vegetable, onion-like, rubbery, sewage-like

NIF NIF NIF 0.0003 0.0012 0.03 NIF NIF Sulfide [32], [39] 352-93-2

Dihydrojasmone NIF C11H18O 166.26Fruity, sweet, floral,

woody with a powdery nuance

NIF NIF NIF NIF NIF NIF NIF NIF Ketone [43] 1128-08-1

Dimethyl disulfide DMDS C2H6S2 94.20cooked vegetable, onion,

rubbery, rotten vegetables, cheesy, glue

0.0001 0.003 0.0016 0.003 0.0075 0.05 NIF •derived from hop oil Sulfide[10], [11], [17], [18], [29], [32],

[39], [40]624-92-0

Dimethyl sulfide DMS, Methyl sulfide C2H6S 62.13

cooked vegetable (corn, onion), garlic, sween

corn, tin, black currant, sulfury, cooked cabbage,

tinned tomato, baked beans

0.005 0.1 0.053 0.001 0.008 0.03 0.00033 NIF Sulfide

[1], [2], [3], [4], [5], [8], [9], [11], [16], [17], [19], [21], [22], [23], [28], [32], [39]

75-18-3

Dimethyl sulfide NIF C2H6S 62.13 0.005 0.1 0.053 0.05 0.13 NIF NIF NIF Sulfide 75-18-3

Dimethyl tetrasulfide NIF C2H6S4 158.33 sulfury, cooked vegetable, onion-like

NIF NIF NIF 0.2 NIF NIF NIF NIF Sulfide [32], [39] 5756-24-1

Dimethyl trisulfideDMTS, 2,3,4-

Trithiapentane, Dimethyltrisulfane

C2H6S3 126.26

onion (soup), rotting fruit, red cabbage,

sulfury, rotten vegetables, fresh onion,

cooked vegetables

0.00001 0.0008 0.0004 0.000027 0.00005 0.0001 NIF

•formed from S-methylcysteine sulfoxide during steam distillation•reaction between methanesulfenic acid and hydrogen sulfide leads to DMTS during beer storage•methanesulfenic acid is introduced to beer from hops•derived from hop oil

Sulfide

[10], [11], [17], [18], [25], [26], [31], [32], [34], [39], [40], [60]

3658-80-8

Dimethylallyl methyl sulfide

NIF C6H12S 117.09 garlic, rubbery, onion NIF NIF NIF 0.0002 NIF NIF NIF •derived from hop oil Sulfide [10], [18] NIF

Dodecanal NIF C12H24O 184.32 NIF NIF NIF NIF NIF NIF NIF NIF NIF Aldehyde [59] 112-54-9Dodecanoic acid NIF C12H24O2 200.32 0.01 NIF NIF NIF NIF NIF Acid [39] 26303-90-2

E,Z-2,6-Nonadienal trans,cis-2,6-Nonadienal C9H14O 138.21 green, cucumber, green leaves

0.00002 0.0007 0.0004 0.00005 0.0005 NIF NIF NIF Aldehyde[5], [7], [14],

[17], [21], [60]557-48-2

E-2-Hexenal trans-2-Hexenal C6H10O 98.14 bitter, astringent, green leaves, green

0 0.046 0.023 0.6 NIF NIF NIF •lost during the kilning of hops•located in the polar fraction of hops

Aldehyde [7], [21], [29] 6728-26-3

E-2-Methyl 2-pentenoic acid

NIF C6H10O2 114.14sour, acidic, sweaty and

fruity with a jammy, woody nuance

NIF NIF NIF NIF NIF NIF NIF NIF Acid [43] 16957-70-3

Epicubenol epi-Cubenol C15H26O 222.37 NIF 0.0 0.025 0.013 NIF NIF NIF NIF NIF Sesquiterpene [4], [19] 19912-67-5

Epoxydecenaltrans-4,5-Epoxy-(E)-2-

decenalC10H20O2 172.27 metallic NIF NIF NIF NIF NIF NIF NIF

•increases during the kilning of hops•can react with degraded fatty acids in stored beer to a taint•product of lipid oxidation during the storage of hops

Aldehyde [6], [29], [46] 123932-68-3

Ethenyl ester cyclohexanecarboxylic

acidNIF C9H16O2 156.22 fruity, cheese, winey NIF NIF NIF NIF NIF NIF NIF NIF Acid [43] 3289-28-9

Ethyl 2-methylbutanoate Ethyl 2-methylbutyrate C7H14O2 130.19 NIF 0.0003 0.00077 0.0005 0.001 NIF NIF NIF NIF Ester [51] 7452-79-1

Ethyl 2-methylpropanoate

Ethyl Isobutyrate C6H12O2 116.16 apple, sweet, citrus, fruity, pineapple

0.002 0.01 0.007 0.0011 0.0063 0.045 0.00003 NIF Ester[2], [5], [14],

[16], [21]97-62-1

Ethyl 2-methylpropanoate

NIF C6H12O2 116.16 NIF 0.002 0.01 0.007 0.164 5 NIF NIF NIF Ester 97-62-1

Ethyl 3-methylbutanoateEthyl 3-methylbutyrate,

Ethyl IsovalerateC7H14O2 130.19

fruity, apple, sweet, valeric, citrus, wine-like,

artificial strawberry, candy, violet

0.0006 0.007 0.004 0.002 0.09 1.3 0.00003

•possible creation by degredation of side chains of iso-α-acids•more precisely by 3-Methylbutyric acid by the oxidation of α- and β-acids•component in aged beer

Ester[5], [14], [16], [21], [26], [31]

108-64-5

Ethyl 4,8-decadienoate NIF C12H20O2 196.29 NIF 0.008 0.02 NIF NIF NIF NIF NIF •derived from Methyl 4,8-decadienoate in hop oil

Ester [4], [12], [39] 60388-64-9

Ethyl 4-decenoate NIF C12H22O2 198.31 NIF 0.018 0.1 NIF NIF NIF NIF NIF NIF Ester [4] 6142-44-5

Ethyl 4-methylpentanoate

NIF C8H16O2 144.21 fruity, citrus, pineapple 0.0001 0.0003 0.0002 0.001 0.018 NIF NIF NIF Ester [2], [5], [14] 25415-67-2

Ethyl caproate NIF C8H16O2 144.21 fruity, rum NIF NIF NIF NIF NIF NIF NIF NIF Ester [40] 123-66-0

Ethyl cinnamateEthyl 3-phenyl-2-

propenoateC11H12O2 176.21

fruity, sweet, cinnamon-like, honey-like,

strawberryNIF NIF 0.005 NIF NIF NIF 0.00006

•component in aged beer•hop-derived compound in beer not found in hop essential oil

Ester[16], [29], [31],

[40]103-36-6

Ethyl cis-4-decenoate NIF C12H22O2 198.31 green, fruity, waxy, leathery


Ethyl ester benzoic acid NIF C9H10O2 150.17 fruity, dry musty, sweet, wintergreen


Ethyl ester pentanoic acid NIF C7H14O2 130.19 sweet, fruity, apple, pineapple, green, tropical


Ethyl nonanoate NIF C11H22O2 186.29 fruity, rose, nutty, oily NIF NIF NIF NIF NIF NIF NIF NIF Ester [59] 123-29-5Ethyl nonenoate NIF C11H20O2 184.28 NIF NIF NIF 0.023 NIF NIF NIF NIF NIF Ester [4] 17463-01-3

E-α-Bergamotene a-trans-bergamotene C15H24 204.35 NIF NIF NIF NIF NIF NIF NIF NIF •located in the non-polar fraction from oxidized hops

Sesquiterpene [29], [54] 13474-59-4

Farnesene NIF C15H24 204.35 woody, green apple, lavender, sweet

0.001 0.005 0.003 0.16 0.55 0.63 NIF NIF Sesquiterpene [4], [5], [9], [46] 502-61-4

Farnesol NIF C15H26O 222.37 lily NIF NIF >30 ppm NIF NIF NIF NIF •transformation from farnesene Sesquiterpene [4], [12], [46] 4602-84-0g-Cadinene NIF C15H24 204.35 NIF NIF NIF >30 ppm NIF NIF NIF NIF NIF Sesquiterpene [4] 39029-41-9

g-Caryophyllene NIF C15H24 204.35 NIF NIF NIF 0.027 0.48 NIF NIF NIF NIF Sesquiterpene [4] 118-65-0

Geranial a-citral C10H16O 152.24 citrus, lemon, floral NIF NIF NIF NIF NIF NIF NIF

•isomer of citral•rapidly reduced to its alcohol (Geraniol) during storage or fermentation•located in the polar fraction of hops•oxidation product of geraniol

Monoterpene [29], [44], [46] 141-27-5

Geranic acid cis/trans-Geranic acid C10H16O2 168.24 woody, flowery NIF NIF 0.001 NIF NIF NIF NIF NIF Acid [42], [46] 459-80-3

Geraniol NIF C10H18O 154.25floral, citrus, rose-like, flowery, lime, lemon, hyacinth, geranium

0.001 0.2 0.1 0.004 0.01 0.036 NIF

•will be partly hydrogenated to citronellol and nerol by yeast•concentration varies by time and amount of hops added and the type of hops•usually at a low concentration in beer•no direct contribution to the hop aroma•biosynthetic product from myrcene

Monoterpene alcohol

[1], [4], [9], [11], [12], [13], [14], [17], [19], [21], [22], [29], [54]

106-24-1

Geraniol NIF C10H18O 154.25 NIF 0.001 0.2 0.1 0.07 0.3 0.5 NIF NIF Monoterpene alcohol

106-24-1

Geranyl acetate NIF C12H20O2 196.29 floral (lavender), perfumed pine

NIF NIF 0.035 NIF NIF NIF NIF •found in dry-hopped beers Monoterpene[11], [12], [15],

[29], [40]105-87-3

Geranyl isobutyrateGeranyl 2-

methylpropanoate, Geranyl isobutanoate

C14H24O2 224.34 floral (rose) 0.025 0.15 0.088 0.45 NIF NIF NIF

•derived from Methyl 4,8-decadienoate in hop oil•found at elevated levels in American Cascade hops•hydrolysed to free geraniol contributing to a floral hop aroma in beer•ester of terpene alcohols

Ester [12], [17], [29] 2345-26-8

Geranyl propanoate NIF C13H22O2 210.32 NIF NIF NIF NIF NIF NIF NIF NIF •ester of terpene alcohols Ester [29] 105-90-8Geranylic acid NIF NIF NIF NIF NIF NIF NIF NIF NIF NIF NIF NIF Acid [54] NIFGermacrene B NIF C15H24O 220.35 mushroom, balsamic NIF NIF NIF NIF NIF NIF NIF NIF Sesquiterpene [60] 15423-57-1

Germacrene D NIF C15H24O 220.35 NIF NIF NIF >30 ppm NIF NIF NIF NIF NIF Sesquiterpene [4] 37839-63-7g-Eudesmol NIF C15H26O 222.37 NIF NIF NIF NIF NIF NIF NIF NIF NIF Sesquiterpene [54] 1209-71-8

g-Nonalactone NIF C9H16O2 156.22coconut, vanilla, glue, rancid, peach, fruity,

sweet0.02 0.5 0.3 0.03 NIF NIF NIF

•concentration increases in aged beer•hop-derived compound in beer not found in hop essential oil•an indicator for thermal load in the brewing process•component in aged beer

Lactone[1], [5], [16],

[26], [29], [31], [40]

104-61-0

g-Selinene NIF C15H24 204.35 NIF NIF NIF NIF NIF NIF NIF NIF •located in the non-polar fraction from oxidized hops


g-Terpinene NIF C10H16 136.23 citrus, terpene, spicy NIF NIF NIF NIF NIF NIF NIF NIF Monoterpene [29], [59] 99-85-4Heptanoic acid NIF C7H14O2 130.19 NIF NIF NIF NIF NIF NIF NIF NIF NIF Acid [54] 111-14-8

Heptyl 2-methylbutanoate

NIF C13H26O2 214.35 apple NIF NIF NIF NIF NIF NIF NIF NIF Ester [59] 29811-50-5

Heptyl 2-methylpropanoate

NIF C11H22O2 186.29 apricot, cherry, apple, green


Heptyl butanoate Heptyl butyrate C11H22O2 186.29 fruity, herbaceous NIF NIF NIF NIF NIF NIF NIF NIF Ester [59] 5870-93-9

Heptyl ester acetic acid NIF C9H18O2 158.24 woody, citrus, pear, apricot


Heptyl propanoate NIF C10H20O2 172.27 rose, apricot NIF NIF NIF NIF NIF NIF NIF NIF Ester [59] 2216-81-1

Hexanal n-Hexanal, 1-Hexanal C6H12O 100.16bitter, winey, vinous,

green, leafy, aldehyde, grassy

0 0.07 0.035 0.09 0.35 NIF NIF

•created by the degredation (enzymatic, auto- or photooxidative) of the fatty acid linoleic acid during ageing•located in the polar fraction of hops

Aldehyde[1], [5], [7], [14], [17], [21], [26],

[44]66-25-1

Hexanethiolate NIF C6H12OS 132.23 NIF NIF NIF >30 ppm NIF NIF NIF NIF NIF Thioester [4] NIF

Hexanoic acid Caproic acid C6H12O2 116.16goaty, fatty acid,

vegetable oil, sweaty, caprylic

0.5 8 4.3 8 10.7 NIF NIF NIF Acid[1], [3], [17],

[20], [21], [54]142-62-1

Hexyl 2-methylbutanoate NIF C11H22O2 186.29 fresh, green fruity NIF NIF NIF NIF NIF NIF NIF NIF Ester [59] 10032-15-2

Hexyl 2-methyl-propanoate

NIF C10H20O2 172.27 green, fruity, apple, pear NIF NIF NIF NIF NIF NIF NIF NIF Ester [29], [59] 2349-07-7

Hexyl 3-methylbutanoate NIF C11H22O2 186.29 unripe fruit, apple, strawberry


Hop ether NIF C10H16O 152.24 NIF 0.01 0.035 0.023 0.1 NIF NIF 0.005 •transferred to the wort during boiling Monoterpene[4], [12], [15],

[19], [54], [56], [58]

19901-95-2

Hop furanone X NIF NIF NIF NIF NIF NIF NIF NIF NIF NIF NIF NIF Other [56] NIFHop furanone Z NIF NIF NIF NIF NIF NIF NIF NIF NIF NIF NIF NIF Other [56] NIF

Hop oils NIF NIF NIF NIF NIF NIF NIF 0.0008 0.005 0.5 0.012 NIF NIF [39] NIF

Humuladienone NIF C15H22O 218.33 spicy, grassy, flowery, fresh

0.01 0.7 0.36 0.1 NIF NIF NIF

•from hop oil fractions dervied from hops•result from the oxidation reaction of humulene•hop-derived compound in beer but not found in hop essential oil

Terpenoid[4], [17], [19], [29], [34], [40]

144614-66-4

Humulene α-Humulene C15H24 204.35balsamic, flowery, grassy,

herbal, spicy, woody, clove oil

0.0002 0.063 0.032 0.05 0.45 0.63 0.12 •transformation product of farnesen Sesquiterpene[4], [5], [9], [13], [29], [44], [46],

[59]6753-98-6

Humulene diepoxide NIF C15H24O2 236.36 NIF NIF NIF NIF NIF NIF NIF NIF NIF Sesquiterpene [29] 11066-50-5

Humulene diepoxide A NIF NIF NIF NIF NIF NIF 0.169 NIF NIF NIF NIF •predominates in hop oil and beer over Humulene diepoxides B-E

Oxygenated Sesquiterpenoids

[29], [42] NIF

Humulene diepoxide B NIF NIF NIF NIF NIF NIF NIF NIF NIF NIF NIF •derived from the oxidation of a-HumuleneOxygenated

Sesquiterpenoids[29] NIF

Humulene diepoxide C NIF NIF NIF NIF NIF NIF NIF NIF NIF NIF NIF •derived from the oxidation of a-HumuleneOxygenated


Humulene diepoxide D, E NIF NIF NIF NIF NIF NIF NIF NIF NIF NIF NIF •derived from the oxidation of a-HumuleneOxygenated


Humulene diepoxide II NIF NIF NIF NIF 0.017 0.033 0.025 NIF NIF NIF NIF NIF Oxygenated sesquiterpene

[15] NIF

Humulene diepoxide IIIHumulene-1,2,4,5-

diepoxideC15H24O 220.35 NIF NIF NIF NIF NIF NIF NIF NIF NIF Oxygenated

sesquiterpene[15] 21624-36-2

Humulene diepoxide V NIF NIF NIF NIF 0.011 0.03 0.021 NIF NIF NIF NIF NIF Oxygenated sesquiterpene

[15] NIF

Humulene epoxide IHumulene oxide I,

Humulene-8,9-epoxideC15H24O 220.35 hay-like, grassy, herbal,

spicy, kettle hop aroma0.0001 0.125 0.06 0.01 0.45 NIF 0.01

•formed by the storage of hops in the presence of oxygen•resists hydrolysis during storage•found at greater concentrations in beer than Humulene epoxide II, III•derived from the oxidation of a-Humulene

Oxygenated sesquiterpene

[4], [5], [6], [11], [12], [13], [15], [17], [29], [54],

[55], [58]

19888-33-6

Humulene epoxide I, II, III NIF NIF NIF musty, floral, spicy NIF NIF NIF NIF NIF NIF NIF •combination of humulene epoxides I, II, IIIOxygenated

sesquiterpene[29] NIF

Humulene epoxide IIHumulene oxide II,

Humulene-1,2-epoxideC15H24O 220.35 moldy, cedar, lime,

herbal0.002 0.27 0.14 0.45 NIF NIF NIF

•formed by the storage of hops in the presence of oxygen•hydrolyzed during storage•derived from the oxidation of a-Humulene


[4], [5], [6], [11], [17], [29], [43],

[54]19888-34-7

Humulene epoxide IIIHumulene oxide III,

Humulene-4,5-epoxideC15H24O 220.35 cedar NIF NIF 0.02 NIF NIF NIF NIF

•formed by the storage of hops in the presence of oxygen•hydrolyzed during storage•derived from the oxidation of a-Humulene


[6], [12], [19], [29], [58]

NIF

Humulenol Humulenol I C15H24O 220.35 sagebrush-like, pineapple 0.001 1.15 0.58 0.15 0.5 2.5 NIF •formed by the storage of hops in the presence of oxygen

Sesquiterpene[4], [5], [6], [11], [12], [13], [17]

19888-01-8

Humulenol II NIF C15H24O 220.35 NIF NIF NIF NIF 2.5 NIF NIF NIF NIF Sesquiterpene 19888-00-7

Humulenol II b-Humulen-1-ol C15H24O 220.35sagebrush, pineapple, herbal, spicy, noble,

hoppy, kettle hop aroma0.013 1.05 0.532 0.15 0.5 1.05 NIF

•precursor Humulene-1,2-epoxide that is rearranged to b-Humulen-1-ol during the boil•oxidation product•will increase over time of storage

Sesquiterpene[12], [15], [19], [29], [55], [57],

[58]19888-00-7

Humulenone NIF C15H22O 218.33 NIF NIF NIF NIF NIF NIF NIF NIF •result from the oxidation reactions of humulene

Terpenoid [4], [29], [54] 19888-05-2

Humulol NIF C15H26O 222.37 hay-like, kettle hop aroma

0.05 0.22 0.135 1.05 2.0 NIF NIF NIF Sesquiterpene[4], [19], [29],

[54], [55], [57], [58]

24405-58-1

Hydrogen sulfide NIF H2S 34.08 NIF NIF NIF NIF NIF NIF NIF NIF NIF Sulfide [34] 7783-06-4Isoamyl 4-decenoate NIF NIF NIF NIF 0.01 0.02 0.015 NIF NIF NIF NIF NIF Ester [4] NIF

Isoprene 2-Methyl-1,3-butadiene C5H8 68.12 NIF NIF NIF NIF NIF NIF NIF NIF NIF Hydrocarbon [4] 78-79-5

Isovaleric acid3-Methylbutanoic acid, 3-Methylbutryric acid

C5H10O2 102.13sweat, cheese, rancid, old hops, floral, minty, sweet,

smelly socks0.1 3.5 1.8 0.325 0.4 0.85 NIF

•can be formed during early fermentation and amino acid metabolism•degradation of the carbonyl side chains of α-acids and β-acids•cheesy aroma of aged hops•yeast autolysis•also created by the cleavage of the acyl side chains from humulone and lupulone•located in the polar fraction of hops

Acid

[1], [2], [3], [4], [9], [14], [17],

[20], [21], [22], [23], [27], [28], [31], [40], [44],

[54], [60]

503-74-2

Isovaleric acid NIF C5H10O2 102.13 NIF 0.1 3.5 1.8 1.5 NIF NIF NIF NIF Acid 503-74-2Junenol NIF C15H26O 222.37 NIF 0.005 0.01 0.008 NIF NIF NIF NIF NIF Sesquiterpene [4], [39] 472-07-1

Juniper camphor NIF C15H26O 222.37 NIF NIF NIF >30 ppm NIF NIF NIF NIF NIF Sesquiterpene [4], [39] 473-04-1

Karahana ether Karahana C10H16O 152.24 NIF 0.04 0.08 0.06 0.10 NIF NIF 0.005 •transferred to the wort during boiling Terpene[4], [12], [19],

[39], [54], [56], [58]

19901-96-3

Karahanaenone2,2,5-

Trimethylcyclohept-4-enone

C10H16O 152.24 NIF 0.003 0.06 0.03 NIF NIF NIF NIF NIF Ketone [4] 19822-67-4

Ledene oxide NIF C15H24O 220.35 minty NIF NIF NIF NIF NIF NIF NIF •located in the polar fraction of hops Oxide [44] NIF

Limonene NIF C10H16 136.23 citrus, orange, green, fruity

0.75 0.10 0.43 0.1 1.493 NIF NIF •found in dry-hopped beers•transformation product of myrcene


[29], [46], [59]138-86-3

Limonene dioxide NIF C10H16O2 168.24 citrus NIF NIF NIF NIF NIF NIF NIF •located in the polar fraction of hops Oxide [44] 96-08-2

Limonene-10-ol NIF C10H16O 152.24 NIF NIF NIF NIF NIF NIF NIF NIF NIF Monoterpene alcohol

[29] 3269-90-7

Linalool R/S-Linalool C10H18O 154.25

flowery, fruity, floral, citrus, rosewood-like,

aniseed, terpenic, rose-like, hoppy, coriander

seed

0.001 0.5 0.2 0.001 0.008 0.009 0,00014-0,006

•can be formed by geraniol decomposition by yeast•amount affected by time and amount of hops added during boil•correlation between linalool concentration and flowery-fruity hop aroma•biosynthetic product from myrcene•ratio for most hops is ~93% R-Linalool and ~7% L-Linalool

Monoterpene alcohol

[1], [2], [3], [4], [5], [9], [11],

[13], [14], [16], [17], [21], [28], [29], [40], [55]

78-70-6

Linalool NIF C10H18O 154.25 NIF 0.001 0.5 0.2 0.027 0.08 NIF NIF NIF Monoterpene alcohol

78-70-6

Linalool NIF C10H18O 154.25 NIF 0.001 0.5 0.2 0.1 NIF NIF NIF NIF Monoterpene alcohol

78-70-6

Linalool oxide I NIF NIF NIF NIF NIF NIF NIF NIF NIF NIF NIF NIF Oxide [56] NIFLinalool oxide II NIF NIF NIF NIF NIF NIF NIF NIF NIF NIF NIF NIF Oxide [56] NIF

Linalool oxides NIF NIF NIF citrus, green, woody 0 0.05 0.025 200 NIF NIF NIF •includes furan and pyran structure Oxide[11], [12], [39],

[46]NIF

Linalyl acetate NIF C12H20O2 196.29 NIF NIF NIF trace NIF NIF NIF NIF •ester of the terpene alcohols Ester [4], [29] 115-95-7m-Camphorene NIF C20H32 272.47 NIF NIF NIF NIF NIF NIF NIF NIF •derived from hop oil Terpene [12] NIFMethanethiol NIF CH4S 48.11 NIF NIF NIF NIF NIF NIF NIF NIF NIF Sulfur compound [34] 74-93-1

Methional NIF C4H8OS 104.17 NIF 0.001 1 0.5 0.25 NIF NIF NIF NIF Aldehyde 3268-49-3

Methional

3-Methylthiopropanal, 4-Thiapentanal, 3-(Methylsulfanyl)-

propanal

C4H8OS 104.17cooked/boiled potatoes,

soup-like, warm, raw potato, mashed potato

0.001 1 0.5 0.004 0.008 0.04 0.00004

•found in hop oil•mainly originates from the oxidative degredation of methionine in the presence of light and riboflavin•also created by the Strecker degradation of methionine•component in aged beer•inappropriate storage of the finished beer

Sulfide[1], [5], [7], [11], [16], [17], [21], [26], [32], [60]

3268-49-3

Methyl 10-undecenoate NIF C12H22O2 198.31 banana, honey, rose, earthy


Methyl 2,6-dimethylheptanoate

NIF C10H20O2 172.27 NIF NIF NIF NIF NIF NIF NIF NIF NIF Ester [59] 33315-72-9

Methyl 2-methylbutanoate

NIF C6H12O2 116.16 sweet, fruity, apple-like NIF NIF NIF NIF NIF NIF NIF NIF Ester [29] 868-57-5

Methyl 2-methylheptanoate

NIF C9H18O2 158.24 pineapple NIF NIF NIF NIF NIF NIF NIF NIF Ester [59] 51209-78-0

Methyl 2-methylpropanoate

NIF C5H10O2 102.13 pineapple NIF NIF NIF NIF NIF NIF NIF NIF Ester [59] 547-63-7

Methyl 3,6-dodecadienoate

NIF C13H22O2 210.32 floral NIF NIF NIF NIF NIF NIF NIF NIF Ester [59] 16106-01-7

Methyl 3-nonenoate NIF C10H18O2 170.25 fruity, green, pear-like, melon


Methyl 4,6-dimethyloctanoate

NIF C11H22O2 186.29 NIF NIF NIF NIF NIF NIF NIF NIF NIF Ester [59] NIF

Methyl 4,8-decadienoate NIF C11H18O2 182.26 NIF 0.0001 0.01 0.005 0.2 0.3 NIF NIF •appears as Ethyl 4,8-decadienoate in beer Ester [4], [12], [54] 1191-03-3

Methyl 4-decenoate NIF NIF NIF NIF 0.0001 0.012 0.006 0.2 0.3 NIF NIF NIF Ester [4], [54] NIFMethyl 4-methyl-2-

hexenoateMethyl 4-methyl-hex-2-

enoateC8H14O2 142.20 NIF 0.013 0.03 0.022 NIF NIF NIF NIF NIF Ester [4], [15], [54] 54378-97-1

Methyl 4-methyloctanoate

NIF NIF NIF NIF NIF NIF NIF NIF NIF NIF NIF NIF Ester [59] NIF

Methyl 6-methylheptanoate

NIF C9H18O2 158.24 NIF NIF NIF NIF NIF NIF NIF NIF NIF Ester [29], [54], [59] 2519-37-1

Methyl 7-methyl nonanoate


Methyl 8-methyl nonanoate


Methyl cis-4-decenoate Methyl Z-4-decenoate C11H20O2 184.28 NIF NIF NIF NIF NIF NIF NIF NIF NIF Ester [29], [59] 7367-83-1

Methyl decanoate Methyl caprate C11H22O2 186.29 coconut, fatty acids, fruity, oily

NIF NIF trace 1 NIF NIF NIF NIF Ester[4], [21], [54],

[59]110-42-9

Methyl dithioacetate NIF C3H6S2 106.21 NIF NIF NIF NIF NIF NIF NIF NIF NIF Sulfur compound [34] 2168-84-5Methyl dodecadienoate NIF NIF NIF NIF NIF NIF NIF NIF NIF NIF NIF NIF Ester [54] NIF

Methyl dodecenoate Methyl laurate C13H26O2 214.35 NIF NIF NIF NIF NIF NIF NIF NIF NIF Ester [54] 111-82-0Methyl E-2-decenoate NIF C11H20O2 184.28 NIF NIF NIF NIF NIF NIF NIF NIF NIF Ester [29] 7367-85-3

Methyl geranate Methyl (E)-geranate C11H18O2 182.26 waxy, green, fruity, floral NIF NIF 0.022 NIF NIF NIF NIF•Ester from a conjugated acid resist hydrolysis and can be found in beer•ester of terpene alcohol


[29], [43], [54], [59]

1189-09-9

Methyl heptanoate NIF C8H16O2 144.21 fruity NIF NIF NIF NIF NIF NIF NIF NIF Ester [54], [59] 106-73-0Methyl hexanoate NIF C7H14O2 130.19 NIF NIF NIF NIF NIF NIF NIF NIF NIF Ester [54] 106-70-7Methyl hexenoate NIF C7H12O2 128.17 NIF NIF NIF NIF NIF NIF NIF NIF NIF Ester [4] 13894-63-8Methyl nerolate NIF C11H18O2 182.26 NIF NIF NIF NIF NIF NIF NIF NIF •ester of the terpene alcohols Ester [29] 1862-61-9

Methyl nonanoate NIF C10H20O2 172.27 citrus NIF NIF NIF NIF NIF NIF NIF NIF Ester [54], [59] 1731-84-6Methyl nonenoate NIF C10H18O2 170.25 NIF NIF NIF NIF NIF NIF NIF NIF NIF Ester [54] 37822-76-7

Methyl octanoate NIF C9H18O2 158.24 waxy, orange, fruity, green

NIF NIF 8 NIF NIF NIF NIF NIF Ester [4], [54], [59] 111-11-5

Methyl trans-3-dedecenoate

NIF C11H20O2 184.28 NIF NIF NIF NIF NIF NIF NIF NIF NIF Ester [59] NIF

Methyl trans-4-decenoate NIF C11H20O2 184.28 fruity NIF NIF NIF NIF NIF NIF NIF NIF Ester [59] 93979-14-7

Methyl undecenoate NIF C12H22O2 198.31 NIF NIF NIF NIF NIF NIF NIF NIF NIF Ester [54] 25339-67-7

Methyl-2-Methylpropanethiolate

S-Methyl-2-methylthiopropionate

C5H10O2S 134.20 chessy, estery, cooked vegetable

NIF NIF NIF 0.005 NIF NIF NIF •derived from hop oil•almost all removed through fermentation

Thioester [10], [18] 42075-45-6

Methylbutyl hexanoate NIF NIF NIF NIF NIF NIF NIF NIF NIF NIF NIF NIF Ester [59] NIF

Myrceneβ-Myrcene, 7-Methyl-3-

methylene-1,6-octadiene

C10H16 136.23

herbs, metallic, resinous, spicy, balsamic, geranium-

like, green, peppery, terpene, balsam, plastic,

sweet carrot, slight piney, celery, lemon, woody

0.0001 1 0.5 0.009 0.01 0.03 0,013-0,042

•biosynthetic product during hop growth, and therefore degrades to geraniol and linalool

Monoterpene[4], [5], [9], [13], [17], [29], [43],

[44], [59]123-35-3

Myrcene NIF C10H16 136.23 NIF 0.0001 1 0.5 0.2 0.5 1.0 NIF NIF Monoterpene 123-35-3

Myrcene disulfide4-(4-methylpent-3-enyl)-3,6-dihydro-1,2-dithiine

C10H16S2 200.36 fragrant, grassy NIF NIF NIF 0.01 NIF NIF NIF

•created by the reaction of sulfur and myrcene•could be present in late-hopped beers or by steam distillation of hops

Sulphur-containing terpenoid

[10], [18], [32], [34]

73188-23-5

Myrcenol NIF C10H18O 154.25 NIF NIF NIF 0.01 NIF NIF NIF NIF NIF Terpenoid [4] 543-39-5

Myrtenol NIF C10H16O 152.24 NIF NIF NIF NIF NIF NIF NIF NIF NIF Monoterpene alcohol

[29] 515-00-4

N-(methyl)mercaptoacetam

ideNIF C3H7NOS 105.16 sweat, fruity NIF NIF NIF NIF NIF NIF NIF NIF Other [40] 20938-74-3

Neral Z-Citral C10H16O 152.24 citrus, spicy, lemon, green

NIF NIF NIF NIF NIF NIF NIF

•isomer of citral•rapidly reduced to their alcohol during storage or fermentation•oxidation product of nerol

Monoterpene [29], [46] 106-26-3

Nerol NIF C10H18O 154.25 flowery (hyacinth, rose), lime, lemon, fresh

NIF NIF NIF 0.08 0.5 NIF NIF •usually at a low concentration in beer•no direct contribution to the hop aroma

Monoterpene alcohol

[5], [9], [21], [43]

106-25-2

Nerolidol NIF C15H26O 222.37 0.02 0.075 0.048 NIF NIF NIF NIF NIF Sesquiterpene[4], [12], [29],

[54], [55]7212-44-4

Neryl acetate NIF C12H20O2 196.29 NIF 0 0.01 0.005 NIF NIF NIF NIF NIF Ester [4] 141-12-8Neryl isobutanoate NIF C14H24O2 224.34 NIF NIF NIF NIF NIF NIF NIF NIF NIF Ester [29] 2345-24-6Neryl propanoate NIF C13H22O2 210.32 NIF NIF NIF NIF NIF NIF NIF NIF NIF Ester [29] 105-91-9

Nonanal n-Nonanal C9H18O 142.24

bitter, astringent, cardboard, aldehydic,

citrus, soapy, fatty, green, fruity, floral, wax

0 0.014 0.007 0.018 NIF NIF NIF •in hop oil but mainly lost during kiln of hops

Aldehyde[7], [17], [21], [29], [59], [60]

124-19-6

Nonanoic acid NIF C9H18O2 158.24 NIF NIF NIF NIF NIF NIF NIF NIF NIF Acid [54] 112-05-0Nonenoic acid NIF C9H16O2 156.22 NIF NIF NIF NIF NIF NIF NIF NIF NIF Acid [54] 29830-11-3

Ocimene NIF C10H16 136.23 NIF NIF NIF NIF NIF NIF NIF NIF •includes (Z)- and (E)-b-Ocimene Monoterpene [4], [29], [39] 13877-91-3Octanal NIF C8H16O 128.21 citrus NIF NIF NIF NIF NIF NIF NIF NIF Aldehyde [60] 124-13-0

Octanoic acid Caprylic acid C8H16O2 144.21 rancid NIF NIF NIF NIF NIF NIF NIF NIF Acid [44], [54] 124-07-2Octenyl acetate NIF C10H18O2 170.25 NIF NIF NIF NIF NIF NIF NIF NIF NIF Ester [29] 32717-31-0

Octyl 2-methylpropanoate

NIF C12H24O2 200.32 earthy, fatty, green, woody


Octyl propanoate NIF C11H22O2 186.29 waxy, myrtle berries, pineapple


p-Camphorene NIF C20H32 272.47 NIF NIF NIF NIF NIF NIF NIF NIF •derived from hop oil Terpene [12] 532-87-6

p-Cymene NIF C10H14 134.22 citrus, pine, fruity, sweet, lemon, spicy

NIF NIF NIF NIF NIF NIF NIF •oxidation product of limonene, with p-Methadiene as by product of reaction

Monoterpene [29], [46], [59] 99-87-6

Pentadecadiene-2-one NIF NIF NIF NIF NIF NIF >30 ppm NIF NIF NIF NIF NIF Lactone [4], [54] 68062-16-8Pentadecene-2-one NIF NIF NIF NIF NIF NIF >30 ppm NIF NIF NIF NIF NIF Lactone [4], [54] 68062-15-7

Pentanethiolate NIF NIF NIF NIF NIF NIF >30 ppm NIF NIF NIF NIF NIF Thioester [4] NIFPentanoic acid NIF C5H10O2 102.13 cheesy NIF NIF NIF NIF NIF NIF NIF NIF Acid [54], [60] 109-52-4

Pentyl 2-methylpropanoate

NIF C9H18O2 158.24 apricot NIF NIF NIF NIF NIF NIF NIF NIF Ester [59] 2445-72-9

Pentyl ester 2-methyl 2-propenoic acid

NIF C9H16O2 156.22 NIF NIF NIF NIF NIF NIF NIF NIF NIF Acid [43] 2849-98-1

Pentyl propanoate NIF C8H16O2 144.21 NIF NIF NIF NIF NIF NIF NIF NIF NIF Ester [29] 624-54-4Perillene NIF C10H14O 150.22 woody, citrus NIF NIF NIF NIF NIF NIF NIF NIF Monoterpene [59] 539-52-6

Phenylacetaldehyde NIF C8H8O 120.15 green, floral, honey NIF NIF NIF NIF NIF NIF NIF •located in the polar fraction of hops Aldehyde [44], [60] 122-78-1Phenylacetic acid NIF C8H8O2 136.15 honey NIF NIF NIF NIF NIF NIF NIF NIF Acid [60] 103-82-2

p-Methane-8-thiol-3-one p-Mentha-8-thiol-3-one C10H18OS 186.31 ribes, cat piss, black currants

NIF NIF NIF NIF NIF NIF NIF

•increased production by oxygen pick-up in brewing and bottling and inappropriate storage of the finished beer•component in aged beer

Ketone [1] 38462-22-5

Propl 2-methylbutanoate NIF C8H16O2 144.21 sweet, fruity NIF NIF NIF NIF NIF NIF NIF NIF Ester [29] 37064-20-3

Propyl ester propanoic acid

NIF C6H12O2 116.16 sharp, chemical, pungent with sweet fruity notes


Raspberry ketone4-(4-Hydroxyphenyl)-2-

butanoneC10H12O2 164.20 citrus, raspberry 0.0034 0.025 0.014 0.0212 NIF NIF NIF NIF Ketone [5], [14], [51] 5471-51-2

R-Linalool NIF C10H18O 154.25woody, lavender, flowery,

citrus-like, coriander, fruity

0.0033 0.11 0.055 0.0008 0.0022 0.027 0.00014

•ratio for most raw hops is ~93% R-Linalool and ~7% S-Linalool•racemization during wort boiling causes a reduction of hoppy flavor•early addition of hops into beer results in a more balanced ratio: R: ~55%, S: 45%•late additions: R: ~80%, S: 20%

Monoterpene alcohol

[44], [45], [58] 126-91-0

Rose oxide cis-Rose oxide C10H18O 154.25 rose, fresh, fruity, herbal NIF NIF NIF NIF NIF NIF NIF NIF Oxide [29], [46], [52] 16409-43-1

Sabinene NIF C10H16 136.23 NIF NIF NIF NIF NIF NIF NIF NIF NIF Monoterpene [29] 3387-41-5sec-Amyl acetate NIF C7H14O2 130.19 ripe, fruity, apple NIF NIF NIF NIF NIF NIF NIF NIF Ester [43] 626-38-0Selina-3,7-diene NIF C15H24 204.35 NIF NIF NIF >30 ppm NIF NIF NIF NIF NIF Sesquiterpene [4] 6813-21-4Selina-4,7-diene NIF C15H24 204.35 NIF NIF NIF >30 ppm NIF NIF NIF NIF NIF Sesquiterpene [4] NIF

Selinadienes NIF NIF NIF NIF NIF NIF NIF NIF NIF NIF NIF NIF Sesquiterpene [29] NIF

Sesquiterpene epoxide 1 NIF NIF NIF NIF NIF NIF NIF NIF NIF NIF NIF NIF Sesquiterpene [54] NIF






S-Linalool NIF C10H18O 154.25 sweet, floral 0.0023 0.025 0.014 0.02 0.08 NIF NIF

•ratio for most raw hops is ~93% R-Linalool and ~7% S-Linalool•racemization during wort boiling causes a reduction of hoppy flavor•early addition of hops into beer results in a more balanced ratio: ~55% R: 45% S•late additions: ~80% R: 20% S

Monoterpene alcohol

[44], [45] 126-90-9

S-Methyl 2-methylpropanethioate

NIF C5H10OS 118.20 cheesy, estery, cooked vegetable

NIF NIF NIF 0.005 0.04 NIF NIF NIF Thioester [32] 42075-42-3

S-Methyl 4-methylpentanethioate

S-Methylthio-4-methylpentanoate

C7H14OS 146.25sulfury, soapy/fatty,

cabbagy, musty, cooked vegetable

NIF NIF NIF 0.015 NIF NIF NIF NIF Thioester [4], [25], [32] 61122-71-2

S-Methyl pentanethioate NIF C6H12OS 132.23 NIF NIF NIF NIF 0.01 NIF NIF NIF NIF Thioester [32] 42075-43-4

S-Methyl-2-methylthiobutanoate

S-Methyl 2-methylbutanethioate

C6H12OS2 164.29truffle, cabbagy,

sulphury, soapy/fatty, cooked vegetable

0.0002 0.001 0.00065 0.001 NIF NIF NIF NIF Thioester [4], [18], [32] 51534-66-8

S-Methyl-3-methylthiobutanoate

S-Methyl 3-methylbutanethioate

C6H12OS2 164.29 cheesy, hop, cooked vegetable, estery

NIF NIF NIF 0.05 NIF NIF NIF•derived from hop oil•almost completely removed through fermentation

Thioester [10], [18], [32] 207983-28-6

S-Methylcysteine oxide NIF C4H9NO3S 151.19 NIF NIF NIF >30 ppm NIF NIF NIF NIF •in hop oil Sulfide [4], [10] 6853-87-8

S-MethylthiohexanoateS-Methyl

hexanethioate, Methylhexanethiolate

C7H14OS 146.25cooked vegetable,

sulfury, soapy/fatty, cabbagy

0.0003 0.0025 0.001 0.0003 0.001 NIF NIF•derived from hop oil•almost completely removed through fermentation

Thioester[4], [10], [18],

[25], [32]2432-77-1

S-Methylthiomethyl 2-methylbutanethioate

NIF C7H14OS 146.25 onion-like, garlic-like NIF NIF NIF NIF NIF NIF NIF NIF Thioester [32] NIF

S-methylthiomethyl 2-methylpropanethioate

NIF C6H12OS2 164.29 NIF NIF NIF NIF NIF NIF NIF NIF NIF Thioester [32] 77974-85-7

S-Methylthiomethyl 3-methylbutanethioate

NIF C7H14OS 146.25 NIF NIF NIF NIF NIF NIF NIF NIF NIF Thioester [32] NIF

S-methylthiomethyl 4-methylpropanethioate

NIF C6H12OS2 164.29 NIF NIF NIF NIF NIF NIF NIF NIF NIF Thioester [32] NIF

S-methylthiomethyl hexanethioate

NIF NIF NIF NIF NIF NIF NIF NIF NIF NIF NIF NIF Thioester [32] 77974-88-0

S-Methylthiomethyl-2-methylbutanethiolate

Methylthiomethyl-2-methylbutanethiolate

NIF NIF onion, garlic, astringent NIF NIF NIF 0.008 NIF NIF NIF•derived from hop oil•almost completely removed through fermentation

Thioester [10], [18] 74416-64-1

Sorelone NIF NIF NIF sherry aroma, pleasant wine-like odor

NIF NIF NIF NIF NIF NIF NIF NIF Ketone [43] NIF

Sotolon3-Hydroxy-4,5-dimethyl-

2(5H)-furanoneC6H8O3 128.13 soup seasoning NIF NIF NIF NIF NIF NIF NIF NIF Lactone [60] 28664-35-9

Spathulenol NIF C15H24O 220.35 NIF NIF NIF 0.005 NIF NIF NIF NIF NIF Sesquiterpene [15] 6750-60-3

t-Cadinol NIF C15H26O 222.37 NIF 0.02 0.2 0.11 NIF NIF NIF NIF NIF Sesquiterpene[4], [12], [15],

[54], [55]5937-11-1

Terpene-methyl-sulphideS

2-Methyl-5-thiahex-2-ene and 2-Methyl-5-

thiahex-1-eneNIF NIF NIF NIF NIF >30 ppm NIF NIF NIF NIF NIF Sulfide [4] NIF

Terpinen-4-ol NIF C10H18O 154.25Woody, ceding,

mentholic, citrus terpy, spicy

0.006 0.015 0.011 NIF NIF NIF NIF NIF Monoterpene alcohol

[4], [15], [43], [54]

562-74-3

Terpinolene a-Terpinolene C10H16 136.23 woody, fruity, piney NIF NIF 0.015 NIF NIF NIF NIF •found in dry-hopped beers Monoterpene [19], [29], [59] 586-62-9Tetradecadien-2-one NIF C14H22O 206.32 NIF NIF NIF NIF NIF NIF NIF NIF NIF Ketone [54] 85416-33-7

Tetradecen-2-one NIF C14H26O 210.36 NIF NIF NIF NIF NIF NIF NIF NIF NIF Ketone [54] 68062-19-1

Thioperillene NIF NIF NIF NIF NIF NIF >30 ppm NIF NIF NIF NIF •Created by sulfur heterocyclics and residual free sulfur

Sulfur compound [4], [10] NIF

Thymol NIF C10H14O 150.22 thyme, spicy 0.00024 0.00035 0.0003 0.23 NIF NIF NIF NIF Terpene [30] 89-83-8T-Muurolol NIF C15H26O 222.37 NIF NIF NIF 0.005 NIF NIF NIF NIF NIF Sesquiterpene [4], [39] 19912-62-0

Toluene NIF C7H8 92.14 sweet NIF NIF NIF NIF NIF NIF NIF NIF Hydrocarbon [43] 108-88-3trans-b-Ocimene E-b-Ocimene C10H16 136.23 citrus, terpene NIF NIF >30 ppm NIF NIF NIF NIF NIF Monoterpene [4], [59] 3779-61-1

trans-Cinnamaldehyde NIF C9H8O 132.16 sweet, honey NIF NIF NIF NIF NIF NIF NIF NIF Aldehyde [60] 14371-10-9trans-Geranic acid NIF C10H16O2 168.24 woody, flowery NIF NIF NIF NIF NIF NIF NIF •oxidation product of neral Acid [46] NIF

trans-Linalool oxide Linalool oxide 2 C10H18O2 170.25 NIF 0.020 0.025 0.023 NIF NIF NIF NIF •transferred to the wort during boiling Oxide[4], [12], [19], [41], [54], [55]

NIF

trans-Shisool NIF C10H18O 154.25 NIF NIF NIF NIF NIF NIF NIF NIF NIF Monoterpene alcohol

[43] 22451-48-5

trans-Z-a-Bisabolene epoxide

a-Bisabolene C15H24O 220.35 NIF NIF NIF NIF NIF NIF NIF NIF NIF Epoxide [43] NIF

Tricyclohumene NIF NIF NIF NIF NIF NIF 0.5 NIF NIF NIF NIF NIF Sesquiterpene [5] NIFTridecen-2-one NIF C13H24O 196.33 NIF NIF NIF NIF NIF NIF NIF NIF NIF Ketone [54] 67881-14-5

Undecanal NIF C11H20O 170.29 fruity, green, wax NIF NIF NIF NIF NIF NIF NIF NIF Ketone [59] 112-44-7Undecen-2-one NIF C11H20O 170.29 NIF NIF NIF NIF NIF NIF NIF NIF NIF Ketone [54] 27936-14-7Undecenoic acid NIF C11H20O2 184.28 NIF NIF NIF NIF NIF NIF NIF NIF NIF Acid [54] 1333-28-4

Valencene NIF C15H24 204.35 NIF NIF NIF NIF NIF NIF NIF NIF •located in the non-polar fraction from oxidized hops


Vanillin NIF C8H8O3 152.15 vanilla NIF NIF NIF NIF NIF NIF NIF •located in the polar fraction of hops Aldehyde [44], [60] 121-33-5

Viridiflorene Ledene C15H24 204.35 NIF NIF NIF >30 ppm NIF NIF NIF NIF •located in the non-polar fraction from oxidized hops


Ylangene a-Ylangene C15H24 204.35 NIF NIF NIF NIF NIF NIF NIF NIF•derived from hop oil•located in the non-polar fraction from oxidized hops

Sesquiterpene [12], [29] 14912-44-8

Z-1,5-Octadien-3-onecis-1,5-Octadien-3-one,

Octadienone, (5Z9-Octa-1,5-dien-3-one

C8H12O 124.18 green, metallic, geranium-like (leaf)

NIF NIF NIF 0.0000034 NIF NIF NIF NIF Ketone [6], [14], [60] 50306-18-8

Z-3-Hexen-1-ol NIF C6H12O 100.16 green 0.0015 0.013 NIF 0.884 NIF NIF NIF NIF Alcohol [51] 928-96-1

Z-3-Hexenal cis-3-Hexenal C6H10O 98.14 green, leafy, green leaves, freshly cut grass

NIF NIF NIF 0.02 NIF NIF NIF

•created by the degredation (enzymatic, auto- or photooxidative) of the fatty acid linolenic acid during ageing•present in freshly picked hops•lost during the kilning of hops

Aldehyde[1], [5], [6], [14],

[21]6789-80-6

Z-3-Hexenoic acid NIF C6H10O2 114.14 rancid, sweaty NIF NIF NIF 1.3 NIF NIF NIF NIF Acid [51] 1775-43-5Z-4-Decanoic acid NIF NIF NIF NIF NIF NIF NIF NIF NIF NIF NIF NIF Acid [29] NIFZ-a-Bergomotene NIF NIF NIF NIF NIF NIF NIF NIF NIF NIF NIF NIF Sesquiterpene [29] NIF

Chemical Name Synonyms StrutureMolecular

Weight (g/mol)

Flavor Descriptors

Bitterness compared to

Isohumulone at 100% (%)

Conc. Minimum

(mg/l)

Conc. Maximum

(mg/l)

Conc. Mean (mg/l)

TH 1 (mg/l) TH 2 (mg/l)TH Water

(mg/l)Formation/Description

Compound Classification

References CAS Number

(-)-Epicatechin NIF C15H14O6 290.26 NIF NIF 0.01 1.1 0.56 NIF NIF NIF NIF Phenol [6], [33], [49] 490-46-0

(+)-Catechin NIF C15H14O6 290.26 NIF NIF 0 12.6 6.31 NIF NIF NIF NIF Phenol [6], [33], [49] 154-23-4

2-Perhydroxylupulone NIF NIF NIF pleasantly strong bitter

NIF NIF NIF NIF NIF NIF NIF •can be synthetically produced b-acid derivative

Acid [39] NIF

4-Acetylhumulinic acid Weichharz B C17H24O5 308.37 NIF NIF NIF NIF NIF NIF NIF NIF NIF Acid [4] NIF4-Desoxyadhumulone NIF C21H30O4 346.46 NIF NIF NIF NIF NIF NIF NIF NIF NIF Acid [39] NIF4-Desoxycohumulone NIF C20H28O4 332.43 NIF NIF NIF NIF NIF NIF NIF NIF NIF Acid [39], [53] NIF

4-Desoxyhumulone NIF

C21H30O4

346.46 NIF NIF NIF NIF NIF NIF NIF NIF

•precursor of humulone and lupulone•suspected to cause bittering with ist homologes 4-Desoxyadhumulon and 4-Desoxycohumulone

Acid [39] NIF

6-Prenylnaringenin 6-PN C20H20O5 340.37 NIF NIF 0.001 0.56 0.28 NIF NIF NIF •found in hops Phenol [6], [49] 68236-13-5 8-Prenylnaringenin 8-PN C20H20O5 340.37 NIF NIF 0.001 0.24 0.12 NIF NIF NIF •found in hops Phenol [6], [49] 53846-50-7

a-Acids NIF NIF NIF NIF NIF NIF 4.000 NIF NIF NIF NIF

•no bitter taste up to 100mg/l•improve foam stability•suppress gushing•contribute to bacteriological stability•sum of all a-acids

Acid [61] NIF

Abeo-isohumulones Abeo-iso-a-acids C21H28O6 376.44 not bitter/tasteless

10-20 6.0 175.0 91 100.00 NIF NIF

•low bitterness•positive for head retention•series of seven oxidation products derived from isohumulones•0.5-1.15% in hops

Acid[4], [39], [53], [61]

NIF

Adhulupone NIF C21H30O4 346.46 NIF NIF 0.35 0.43 0.4 NIF NIF NIF NIF Acid [47] NIFAdhumulinone NIF C21H30O5 362.46 NIF NIF 0.61 0.93 0.8 NIF NIF NIF •oxidation product of adhumulone Acid [47], [61] NIF

Adhumulone NIF C21H30O5 362.46 NIF NIF 0.06 0.35 0.2 NIF NIF NIF•10-15% content of the hop alpha acids, relatively stable between hop varieties

Acid [47], [61] 31769-65-0

Adlupulone NIF C26H38O4 414.58 NIF NIF 0.11 0.15 0.1 NIF NIF NIF •10-15% content of b-acids Acid [47] 31769-60-5Allo-isohumulone A NIF C21H30O5 362.46 NIF NIF NIF NIF NIF NIF NIF NIF NIF Acid [53] NIFAllo-isohumulone B NIF C21H30O5 362.46 NIF NIF NIF NIF NIF NIF NIF NIF NIF Acid [53] NIFAllo-isohumulones Allo-iso-a-acids C21H30O7 394.46 bitter 120-150 0.1 5.0 2.6 2.75 NIF NIF NIF Acid [4], [5], [39] NIF

Allo-isohumulonhydroperoxide NIF NIF NIF NIF NIF NIF NIF 0.1 NIF NIF NIF NIF Other [5] NIFAllo-isohumulonhydroxide NIF NIF NIF NIF NIF NIF NIF 0.1 NIF NIF NIF NIF Other [5] NIF

Anti-isohumulones NIF C21H30O5 362.46 bitter 200 NIF NIF trace NIF NIF NIF •bitterest of all hop acids•only in trace amounts in beer

Acid [4], [39], [61] NIF

Ashurst's compound NIF NIF NIF astringent 20 0.4 3.0 1.7 NIF NIF NIF NIF Acid [4], [48] NIFcis-Adhumulinic acid NIF C15H21O4 265.32 NIF NIF 0.007 0.010 0.008 NIF NIF NIF NIF Other [47] NIF

cis-Alloisoadhumulonehydroperoxide

NIF NIF NIF NIF NIF 0.008 0.020 0.014 NIF NIF NIF NIF Other [47] NIF

cis-Alloisoadhumulonehydroxide NIF NIF NIF NIF NIF 0.017 0.028 0.023 NIF NIF NIF NIF Other [47] NIFcis-Alloisocohumulonehydroxide NIF NIF NIF NIF NIF 0.023 0.033 0.028 NIF NIF NIF NIF Other [47] NIF

cis-Alloisohumulonehydroperoxide NIF NIF NIF NIF NIF 0.023 0.047 0.035 NIF NIF NIF NIF Other [47] NIFcis-Alloisohumulonehydroxide NIF NIF NIF NIF NIF 0.039 0.052 0.046 NIF NIF NIF NIF Other [47] NIF

cis-Antiisohumulones cis-antiiso-a-acids C21H30O5 362.46 bitter NIF 0.8 4.0 2.4 NIF NIF NIF 5 types Acid [4] NIFcis-Cohumulinic acid NIF C14H20O4 252.31 NIF NIF 0.009 0.016 0.013 NIF NIF NIF NIF Acid [47] NIF

cis-Humulinic acid NIF C15H22O4 266.33 NIF NIF 0.019 0.025 0.022 NIF NIF NIF NIF Acid [47] NIFcis-Iso-a-acids NIF NIF NIF bitter NIF 5.0 23.0 14.0 4.0 NIF NIF 5 types Acid [4] NIF

cis-Isoadhumulone NIF C21H30O5 362.46 NIF NIF 3.66 4.35 4.0 NIF NIF NIF NIF Acid [47] NIFcis-Isocohumulone NIF C20H28O5 348.43 NIF NIF 7.81 8.55 8.2 NIF NIF NIF NIF Acid [47] NIF

cis-Isohumulone NIF C21H30O5 362.46 NIF NIF 4.4 10.28 7.3 NIF NIF NIF NIF Acid [47], [53] 1534-03-8Cohulupone NIF C19H20O4 312.36 NIF NIF 1.07 1.50 1.3 NIF NIF NIF NIF Acid [47] 1891-34-5

Cohumulinone NIF C20H28O5 348.43 NIF NIF 0.91 1.23 1.1 NIF NIF NIF •oxidation product of cohumulone Acid [47], [61] NIF

Cohumulone NIF C20H28O5 348.43 NIF NIF 0.75 2.55 1.7 NIF NIF NIF •20-65% content of the hop alpha acids, depending on hop variety

Acid [47], [61] 511-25-1

Colupox a NIF C25H36O5 416.55 NIF NIF NIF NIF trace NIF NIF NIF •formed by the oxidation of colupulone Acid [61] NIF

Colupox b NIF C25H36O5 416.55 NIF NIF NIF NIF trace NIF NIF NIF NIF Acid [61] NIF

Colupox c NIF C25H36O5 416.55 NIF NIF NIF NIF trace NIF NIF NIF •formed by the oxidation of colupulone Acid [61] NIF

Colupulone NIF C25H36O4 400.55 tasteless NIF 0.11 0.30 0.2 NIF NIF NIF •20-55% content of b-acids Acid [47], [61] 468-27-9Connet's compound NIF NIF NIF bitter, astringent 0.2 1.5 0.85 NIF NIF NIF NIF NIF NIF [4], [48] NIF

Deacylated acetylhumulinic acid NIF C12H16O4 224.25 NIF NIF NIF NIF trace NIF NIF NIF 4 types Acid [4] NIFDeacylated anti-humulone NIF NIF NIF slightly bitter 50 NIF NIF NIF NIF NIF NIF NIF Acid [39] NIFDeacylated humulinic acid NIF NIF NIF NIF NIF NIF NIF trace NIF NIF NIF 2 types Acid [4] NIF

Deacylated iso-a-acids NIF NIF NIF NIF NIF NIF NIF NIF NIF NIF NIF NIF Acid [4] NIFDehydrated

hydroxyalloisohumulones (spiro)Spiro-isohumulone C21H30O5 362.46 bitter low NIF NIF trace NIF NIF NIF NIF Acid [4], [39] 31319-12-7

Dehydroisohumulinic acid NIF NIF NIF NIF NIF NIF NIF NIF NIF NIF NIF •oxidation product of humulone Acid [39] NIFDesmethylxanthohumol NIF C20H20O5 340.37 NIF NIF NIF NIF NIF NIF NIF NIF •found in hops Phenol [6] 115063-39-3

Dihydrohumulone NIF C21H32O5 364.47 NIF NIF NIF NIF NIF NIF NIF NIF NIF Acid [39] NIF

Dihydroisohumulone Dihydro-iso-a-acid C21H32O5 364.47 NIF NIF NIF NIF NIF NIF NIF NIF •improves foam stability similar to iso-a-acids

Acid [50] 24149-26-6

Dihydrooxyhumulinic acid NIF C15H23O5 283.34 NIF NIF NIF NIF NIF NIF NIF NIF •oxidation product of humulone Acid [39] NIFFerulic acid NIF C10H10O4 194.18 NIF NIF 1.420 1.980 1.70 NIF NIF NIF NIF Acid [49] 1135-24-6

Hexahydrocolupulone NIF C25H42O4 406.60 NIF NIF NIF NIF NIF NIF NIF NIF •can be synthetically produced b-acid derivative

Acid [39] 52755-22-3

Hexahydrohumulone NIF NIF NIF NIF NIF NIF NIF NIF NIF NIF NIF •could cause gushing Acid [39] NIFHexahydroisohumulones NIF NIF NIF bitter 100-120 5.0 20.0 12.5 NIF NIF NIF NIF Acid [4] NIF

Hexahydrolupulenol NIF C20H36O3 324.50 NIF NIF NIF NIF NIF NIF NIF NIF •synthetically produced b-acid derivative

[39] NIF

Homovanillic acid3-Methoxy-4-

hydroxy-phenylacetic acid

C9H10O4 182.17 NIF NIF 0.02 0.7 0.36 NIF NIF NIF NIF Phenol [6], [24] 306-08-1

Hulupinic acid NIF C15H20O4 264.32 NIF NIF 0.023 0.1 0.06 NIF NIF NIF •found in all hops Acid[4], [5], [39],

[47]1891-42-5

Hulupone d-acids C20H28O4 332.43 NIF NIF 1 6.0 4 8 10 NIF

•contributes to bitterness•roughly half as bitter as isohumulones•created by the auto-oxidation (contact with oxygen) of the b-acids•formed during wort boiling

Acid

[4], [28], [34], [39], [47], [53],

[61]

468-62-2

Humulinic acid NIF C15H22O4 266.33 not bitter, slight harsh bitterness

NIF 0.0 3.0 1.5 15 NIF NIF

•can cause gushing•created by hydrolysis of humulones•one-third as bitter as isohumulones•causes disturbances for spectrophotometric measurement of bitterness

Acid[4], [39], [53], [61]

520-40-1

Humulinone NIF C21H30O5 362.46 bitter, astringent 30 0.3 2.2 1.25 NIF NIF NIF

•one-third as bitter as iso-α-acids (not established in beer)•cis-Humulinone created from humulinone during wort boiling•oxidation product of humulone

Ketone[4], [39],

[47], [53], [61]

981-03-3

Humulone a-acids C21H30O5 362.46 bitter 40-50 0.0 4.0 2.0 8 10 NIF•helps prevent gushing•35-70% content of the hop alpha acids, depending on hop variety

Acid[4], [39], [47], [61]

26472-41-3

Hupulinic acid NIF NIF NIF not bitter NIF NIF NIF trace NIF NIF NIF •found in old hop samples•created by hydrolysis of hulupones

Acid [4], [39], [53] NIF

Hydrated isohumulone NIF NIF NIF NIF NIF 0.0 2.0 1.0 NIF NIF NIF NIF Acid [4], [39] NIFHydroxyalloisohumulones NIF NIF NIF bitter NIF NIF NIF trace NIF NIF NIF NIF Acid [4] NIF

Hydroxyepoxy alloishumulones NIF NIF NIF bitter NIF NIF NIF trace NIF NIF NIF NIF Acid [4] NIF

http://chem.sis.nlm.nih.gov/chemidplus/ProxyServlet?objectHandle=DBMaint&actionHandle=default&nextPage=jsp/chemidlite/ResultScreen.jsp&TXTSUPERLISTID=0000490460

Hydroxy-isohumulone NIF NIF NIF NIF NIF NIF NIF NIF NIF NIF NIF NIF Acid [39] NIFHydroxytricycloadlupone epimer 1 NIF NIF NIF NIF NIF nd nd NIF NIF NIF NIF NIF Other [47] NIFHydroxytricycloadlupone epimer 2 NIF NIF NIF NIF NIF nd nd NIF NIF NIF NIF NIF Other [47] NIF

Hydroxytricyclocolupone 1 NIF NIF NIF NIF NIF 0.14 0.28 0.2 NIF NIF NIF NIF Acid [47] NIFHydroxytricyclocolupone 2 NIF NIF NIF NIF NIF 0.27 0.45 0.4 NIF NIF NIF NIF Acid [47] NIF

Hydroxytricyclolupone epimer 1 NIF NIF NIF NIF NIF nd nd NIF NIF NIF NIF NIF Other [47] NIFHydroxytricyclolupone epimer 2 NIF NIF NIF NIF NIF nd nd NIF NIF NIF NIF NIF Other [47] NIF

Hydroxytricyclolupulone NIF NIF NIF NIF NIF NIF NIF 0.1 NIF NIF NIF NIF Other [5] NIF

Iso-adprehumulone NIF C22H32O5 376.49 NIF NIF NIF NIF NIF NIF NIF NIF •improves foam stability similar to iso-a-acids

Acid [50] NIF

Isobutylbenzene NIF C10H14 134.22 NIF NIF NIF NIF NIF NIF NIF NIF NIF Hydrocarbon [4] 538-92-2Isohumulinones NIF C21H30O6 378.46 bitter NIF 0.0 0.2 0.1 6.0 NIF NIF •bacteriostatic Acid [4], [53] NIF

Isohumulone NIF C21H30O5 362.46 bitter 100 10.0 80 45 4.0 5.7 1.2

•main bitterness component in beer•concentration depends on type,amount and addtion of hops•bacteriostatic against gram-positive bacteria

Hydrocarbon[1], [4], [5], [22], [39]

25522-96-7

Isohumulone oxidation products NIF NIF NIF NIF NIF 100 200 150 NIF NIF NIF NIF Other [4] NIF

Isoxanthohumol NIF C21H22O5 354.40 NIF NIF 0.03 0.06 0.045 NIF NIF NIF NIF Phenol [5], [47], [49] 70872-29-6

Iso-α-acids NIF NIF NIF NIF NIF 15.0 80 47.50 NIF NIF NIF •the sum of all isomerised a-acids Acid [61] NIFKaempferol NIF C15H10O6 286.24 NIF NIF 0.96 16 8.7 NIF NIF NIF NIF Phenol [6], [49] 520-18-3

Law's Compound NIF NIF NIF astringent 30 NIF NIF NIF NIF NIF NIF NIF Acid [48] NIFLupdeps NIF NIF NIF bitter 50 0.4 1.8 1.1 NIF NIF NIF NIF Acid [4], [39] NIFLupdols NIF NIF NIF astringent 50 0.3 1.0 0.65 10.0 12.0 NIF NIF Acid [4], [39] NIF

Lupdoxes a NIF C25H36O6 432.55 astringent 40-50 0.2 1.2 0.7 8.0 10.0 NIF •created by the autoxidation of b-acids Acid [4], [39], [53] NIF

Lupdoxes b NIF C25H36O6 432.55 astringent 30-40 0.2 1.2 0.7 10.0 12.0 NIF •created by the autoxidation of b-acids Acid [4], [39], [53] NIF

Lupone NIF C35H46O4 530.74 NIF NIF NIF NIF NIF NIF NIF NIF •can be synthetically produced b-acid derivative

Acid [39] NIF

Lupoxes a NIF NIF NIF harsh bitter 40-50 0.5 2.0 1.25 8.0 10.0 NIF •created by the autoxidation of b-acids•formed during wort boiling

Acid [4], [39], [53] NIF

Lupoxes b NIF NIF NIF astringent 40-50 0.2 0.8 0.5 8.0 10.0 NIF •created by the autoxidation of b-acids•formed during wort boiling

Acid [4], [39], [53] NIF

Lupoxes c NIF NIF NIF astringent 30-40 0.2 0.8 0.5 10.0 12.0 NIF •created by the autoxidation of b-acids•formed during wort boiling

Acid [4], [39], [53] NIF

Lupulenol NIF C19H30O3 306.44 NIF NIF NIF NIF NIF NIF NIF NIF •can be synthetically produced b-acid derivative

Acid [39] NIF

Lupulone NIF C26H38O4 414.58 bitter 20 0.0 1.0 0.5 20.0 NIF NIF •4-10% hops (dry matter)•30-55% content of b-acids

Acid[4], [39], [47], [61]

468-28-0

Lupuloxinic acid NIF C20H30O5 350.45 NIF NIF NIF NIF NIF NIF NIF NIF •can be synthetically produced b-acid derivative

Acid [39] NIF

Luputriones NIF NIF NIF bitter NIF NIF NIF trace NIF NIF NIF

•can be synthetically produced b-acid derivative•can be created by pyrolysis and hydrolysis of b-acids

Acid [4], [39], [53] NIF

Oxycohumulinic acid NIF NIF NIF NIF NIF NIF NIF NIF NIF NIF NIF •oxidation product of humulone Acid [39] NIFOxyhumulinic acid NIF C15H21O5 281.32 NIF NIF NIF NIF NIF NIF NIF NIF •oxidation product of humulone Acid [39] 469-30-7

p-Coumaric acid NIF C9H8O3 164.16 NIF NIF 0.67 1.13 0.90 NIF NIF NIF NIF Acid [49] 501-98-4

Posthumulone NIF C19H26O6 350.41 NIF NIF NIF NIF NIF NIF NIF NIF•1-3% content of the hop alpha acids,•higher levels when hops are harvested late

Acid [61] NIF

Postlupulone NIF C19H26O5 334.41 NIF NIF NIF NIF NIF NIF NIF NIF NIF Acid [39] NIF

Prehumulone NIF C22H32O5 376.49 NIF NIF NIF NIF NIF NIF NIF NIF•1-10% content of the hop alpha acids•higher levels when hops are harvested late

Acid [61] NIF

Prelupulone NIF C27H40O4 428.60 NIF NIF NIF NIF NIF NIF NIF NIF •1-3% of all β-acids Acid [39], [61] NIFProcyanidin B3 NIF C30H26O12 578.52 NIF NIF 3.76 13.02 NIF NIF NIF NIF NIF Phenol [49] 23567-23-9

Procyanidin trimer NIF NIF NIF NIF NIF 1.09 3.52 NIF NIF NIF NIF NIF Phenol [49] NIFProdelphinidin B3 NIF C30H26O13 594.52 NIF NIF 2.69 7.32 NIF NIF NIF NIF NIF Phenol [49] 78362-05-7

Prodelphinidin trimer NIF NIF NIF NIF NIF 0.54 1.39 NIF NIF NIF NIF NIF Phenol [49] NIFQuercetin derivative NIF NIF NIF NIF NIF 0.94 2.16 1.6 NIF NIF NIF NIF Phenol [49] NIF

Quercetinglycose NIF NIF NIF NIF NIF NIF NIF 1 NIF NIF NIF NIF Flavonoide [5] NIFQuercetinglycoside NIF NIF NIF NIF NIF NIF NIF 1 NIF NIF NIF NIF Flavonoide [5] NIF

Resveratrol NIF C14H12O3 228.25 NIF NIF NIF NIF < 0,1 NIF NIF NIF NIF Phenol [5] 501-36-0

Rho-Iso-a-acidsRHIA,

DihydroishumuloneC21H32O5 NIF hoppy, tea taste,

medicinal70 NIF NIF NIF 11.2 NIF 6 •pleasant taste (up to 10mg/l), bitter

that faded quicklyNIF

[28], [39], [61]

NIF

Rutin NIF C27H30O16 610.52 NIF NIF 2.61 6.41 4.51 NIF NIF NIF NIF Phenol [49] 153-18-4Shaw's compound NIF NIF NIF sharp bitter 0.15 0.30 0.23 NIF NIF NIF NIF NIF Acid [4] NIF

Tetcyclodehydroisohumulones NIF NIF NIF NIF NIF 1.0 4.0 2.5 NIF NIF NIF NIF Acid [4] NIFTetracyclohumol NIF NIF NIF NIF NIF NIF NIF 0.5 NIF NIF NIF Alcohol [5] NIF

Tetrahydrohulupone NIF C19H26O4 318.41 NIF NIF NIF NIF NIF NIF NIF NIF •can be synthetically produced b-acid derivative

Acid [39] NIF

Tetrahydrohumulinone NIF C21H34O6 382.49 NIF NIF NIF NIF NIF NIF NIF NIF •oxidation product of humulone•precursor tetrahydrohumulone

Acid [39] NIF

Tetrahydrohumulones NIF C21H34O5 366.49 NIF 200 NIF NIF NIF NIF NIF NIF•can be synthetically produced b-acid derivative•could cause gushing

Acid [39], [61] NIF

Tetrahydro-iso-a-acidsTHIA,

Tetrahydroisohumulones

NIF NIF dry bitter, chamomile tea

100-110 NIF NIF NIF 2.8 8.5 1.6•pleasant taste (up to 5mg/l), delayed bitter intensity•sum of all tetrahydro-iso-a-acids

NIF [5], [28] NIF

Tetrahydroisohumulone NIF C21H34O5 366.49 bitter NIF 5.0 20.0 12.5 NIF NIF NIF NIF Acid [4] 28815-20-5trans-Adhumulinic acid NIF C15H21O4 265.32 NIF NIF 0.0008 0.0017 0.001 NIF NIF NIF NIF Acid [47] NIF

trans-Alloisoadhumulonehydroperoxide


trans-Alloisocohumulonehydroperoxide


trans-Alloisocohumulonehydroxide NIF NIF NIF NIF NIF 0.009 0.015 0.012 NIF NIF NIF NIF Other [47] NIF

trans-Alloisohumulonehydroperoxide


trans-Alloisohumulonehydroxide NIF NIF NIF NIF NIF 0.028 0.036 0.032 NIF NIF NIF NIF Other [47] NIF

trans-Antiisohumulones trans-antiiso-a-acids C21H30O5 362.46 bitter NIF 0.4 2.0 1.2 NIF NIF NIF NIF Acid [4] NIF

trans-Cohumulinic acid NIF C14H20O4 252.31 NIF NIF 0.0017 0.0025 0.002 NIF NIF NIF NIF Acid [47] NIFtrans-Humulinic acid NIF C15H22O4 266.33 NIF NIF 0.0017 0.0034 0.003 NIF NIF NIF NIF Acid [47] NIFtrans-Isoadhumulone NIF C21H30O5 362.46 NIF NIF 3.99 4.66 4.3 NIF NIF NIF NIF Acid [47] NIFtrans-Isocohumulone NIF C20H28O5 348.43 NIF NIF 4.43 5.03 4.7 NIF NIF NIF NIF Acid [47] NIF

trans-Isohumulone trans-iso-a-acids C21H30O5 362.46 bitter NIF 2.0 13.2 7.6 4.0 7 NIF NIF Acid [4], [47], [53] NIF

Tricycloadhumol NIF NIF NIF NIF NIF 0.35 0.66 0.5 NIF NIF NIF NIF Alcohol [47] NIFTricyclocohumol NIF NIF NIF NIF NIF 0.62 1.02 0.8 NIF NIF NIF NIF Alcohol [47] NIF

Tricyclodehydroisohumulones TCD C21H28O5 360.44 bitter 70 1.0 4.0 2.5 NIF NIF NIF

•amounts between 0.01-0.3% found in hops•increases over storage of hops•75% utilization rate during the brewing process•quality of bitterness high

Acid [4], [39], [61] 56143-68-1

Tricyclohumol NIF NIF NIF NIF NIF 1.19 1.74 1.5 NIF NIF NIF NIF Alcohol [47] NIfTricylclohumol NIF NIF NIF NIF NIF NIF NIF 1.0 NIF NIF NIF Alcohol [5] NIF

Vanillic acid4-Hydroxy-3-

methoxybenzoicacid

C8H8O4 168.15 vanilla, sweet, astringent

NIF 0.06 10 5 80 NIF NIF•predominantly found in malt, with asmall amount coming from hops•not significant for flavor in beer

Phenol[6], [17],

[21], [24], [33]

121-34-6

Xanthohumol NIF C21H22O5 354.40 slightly sour NIF 0.002 0.002 3.4 1.7 NIF 3.3 •less sour than Isoxanthohumol Phenol[4], [6], [28],

[47]6754-58-1

β-acids NIF NIF NIF NIF NIF NIF NIF NIF NIF NIF NIF •the sum of all b-acids Acid [61] NIF

ρ-Isohumulones reduced iso-a-acids C21H32O5 364.47 bitter NIF 5.0 20.0 12.5 NIF NIF NIF NIF Acid [4], [39] NIF

[1] W Back, et. al. (2005) Ausgewählte Kapitel der Brauereitechnologie. 2 edn. Fachverlag Hans Carl, Nuremberg.

[2] HD Belitz, Schieberle, P. (2009) Food Chemistry. 4 edn. Springer, Berlin.

[3] H Fritsch, Schieberle, P. (2005) Identification Based on Quantitative Measurements and Aroma Recombination of the Character Impact Odorants in a Bavarian Pilsner-type Beer. J. Agric. Food Chem. 53:7544-7551.

[4] M Moll, De Blauwe, J.J. (1994) Beer and Coolers. Lavoisier.

[5] M Biendl, et. al. (2012) Hopfen - Vom Anbau bis zum Bier. 1 edn. Fachverlag Hans Carl, Nuremberg.

[6] C Gerhäuser, Becker, H. (2009) Phenolic Compounds in Beer. Beer in Health and Disease Prevention, 1 edn. Academic Press, London.

[7] H Graf (1984) Carbonyle und Alterung des Bieres. Technische Universität München, Munich

[8] L Guido, Rajendram, R., Barros, A. (2009) Pitching Yeast and Beer Flavor. In: V Preedy (ed) Beer in Health and Disease Prevention. 1 edn. Academic Press, London, pp 22-32.

[9] S Hanke (2009) Untersuchungen zum Einfluss der Hopfungstechnologie auf die Geschmacksstabilität und Harmonie untergäriger Biere. Technische Universität München, Munich

[10] JC Seaton, Moir, M. (1987) Suphur compounds and their impact on beer flavour. EBC Symposium Hops:130-145.

[11] P Hughes (2009) Beer Flavor. In: Beer A Quality Perspective. Academic Press, London, pp 61-83.

[12] M Moir (1994) Hop Aromatic Compounds. EBC Symposium Hops:165-180.

[13] T Kishimoto, et al. (2005) Analysis of hop-derived terpenoids in beer and evaluation of their behavior using the stir bar-sorptive extraction method with GC-MS. Journal of agricultural and food chemistry 53 (12):4701-4707.

[14] T Kishimoto, et al. (2006) Comparison of the odor-active compounds in unhopped beer and beers hopped with different hop varieties. Journal of agricultural and food chemistry 54 (23):8855-8861.

[15] AJ Irwin (1989) Varietal Dependence of Hop Flavor Volatiles in Lager. J. Inst. Brew. (95):185-194.

[16] D Komarek (2001) Key odorants in beer - Influence of storage on the flavor stability. Technische Universität München, Munich

[17] R Kratky, Buiatti, S. (2009) The Chemical Nature of Flavor in Beer. Beer in Health and Disease Prevention. Academic Press, London.

[18] G Lermusieau and S Collin (2003) Volatile sulfur compounds in hops and residual concentrations in beer-A review. American Society of Brewing Chemists 61 (3):109-113.

[19] KJ Siebert Sensory Analysis of Hop Oil-Derived Compounds in Beer; Flavor Effects of Individual Compounds. In: EBC Symposium Hops, Netherlands, 1994. Hans Carl, pp 198-224.

[20] M Meilgaard (1975a) Flavor chemistry of beer I. Flavor Interaction Between Principal Volatiles. Master Brewers Association of the Americas Technical Quarterly 12 (3):107-117.

[21] M Meilgaard (1975) Flavor chemistry of beer. II. Flavor and threshold of 239 aroma volatiles. Master Brewers Association of the Americas Technical Quarterly 12 (3):151-168.

[22] M Meilgaard (1993) Individual Differences in Sensory Threshold for Aroma Chemicals Added to Beer. Food Quality and Preference 4:153-167.

[23] M Meilgaard (1982) Prediction of Flavor Differences between Beers from their Chemical Composition. J. Agric. Food Chem. 30:1009-1017.

[24] L Montanari, Perretti, G., Natella, F., Guidi, A., Fantozzi, P. (1999) Organic and Phenolic Acids in Beer. Lebensmittel-Wissenschaft und -Technologie 31:535-539.

[25] T Peppard, Douse, J. (1979) Simple and sensitive technique for detecting trace flavour components in beer. Journal of Chromatography 176:444-447.

[26] D Saison, De Schutter, D., Uyttenhove, B., Delvaux, F. (2009) Contribution of staling compounds to the aged flavour of lager beer by studying their flavour thresholds. Food Chemistry 114:1206-1215.

[27] P Schieberle (1991) Primary odorants of pale lager beer: Differences to other beers and changes during storage. Lebensm. Unters. Forsch. 193:558-565.

[28] C Schönberger (2003) Beurteilung nicht-flüchtiger Geschmacksstoffe in Bier. Technische Universität München, Munich

[29] G Eyres, Dufour, J.P. (2009) Hop Essential Oil: Analysis, Chemical Composition and Odor Characteristics. In: V Preedy (ed) Beer in Health and Disease Prevention. Academic Press, London, pp 239-254.

[30] F Sterckx, Missiaen, J., Saison, D., Delvaux, F. (2011) Contribution of monophenols to beer flavour based on flavour thresholds, interactinos and recombination experiments. Food Chemistry 126:1679-1685.

[31] B Vanderhaegen, Neven, H., Verachtert, H., Derdelinckx, G. (2006) The chemistry of beer ageing - a critical review. Food Chemistry 95:357-381.

[32] TL Peppard (1981) Volatile organosulphur compounds in hops and hop oils: a review. J Inst Brew 87:376-385

[33] H Zhao, Chen, W., Lu, J., Zaho, M. (2010) Phenolic profiles and antioxidant activities of commercial beers. Food Chemistry 119:1150-1158.

[34] FR Sharpe and DRJ Laws (1981) Essential oil of hops: a review. Journal of the Institute of Brewing 87:96-107.

[35] A Suggett, Moir, M., Seaton, J.C. The Role of Sulphur Compounds in Hop Flavour. In: European Brewery Convention, Amsterdam, 1979. pp 79-89.

[36] J Gros, Peeters, F., Collin, S. (2012) Occurence of Odorant Polyfuntional Thiols in Beers Hopped with Different Cultivars. First evidence of an S-Cysteine Conjugate in Hop (Humulus lupulus L.). Journal of Agricultural and Food Chemistry 60:7805-7816.

[37] T Kishimoto, et al. (2008) Comparison of 4-mercapto-4-methylpentan-2-one contents in hop cultivars from different growing regions. Journal of agricultural and food chemistry 56 (3):1051-1057.

[38] K Takoi, et al. (2009) Specific flavour compounds derived from Nelson Sauvin hop and synergy of these compounds. Brewing Science 62:108-118.

[39] P Demmelmeier (1981) Vorkommen und Bedeutung der Hopfeninhaltsstoffe des Bieres. Technical University of Munich, Weihenstephan

[40] G Lermusieau, Bulens, M., Collin, S. (2001) Use of GC-Olfactometry to Identify the Hop Aromatic Compounds in Beer. J. Agric. Food Chem. 49:3867-3874.

[41] JS Hough, Briggs, D.E., Stevens, R., Young, T.W. (1999) Malting and Brewing Science: Hopped Wort and Beer, vol 2. Aspen Publishers, New York.

[42] V Peacock, Deinzer, M. (1988) Fate of Hop Oil Components in Beer. Am. Soc. of Brew. Chem.

[43] T Inui, Ishimaru, M., Tsuchiya, F., Oka, K., Fukui, N. The detection of hop-derived aroma compounds in beer using high speed GCxGC TOF-MS and comarison of hop varieties in beer. In: Am. Soc. Brew. Chem. Annual Meeting, Sanibel Island, Florida, USA, 2011.

[44] MC Qian Flavor Chemistry of Hop. In: Am. Soc. Brew. Chem. Annual Meeting, Tuscon, Arizona, USA, 2013.

[45] M Steinhaus, Fritsch, H.T., Schieberle, P. (2003) Quantitation of (R)- and (S)-Linalool in Beer Using Solid Phase Microextraction (SPME) in Combination with a Stable Isotope Dilution Assay (SIDA). Journal of Agricultural and Food Chemistry 51:7100-7105.

[46] L-A Garbe, Rettberg, N., Thörner, S. Hopfenöl - Zusammensetzung, Aroma und analytische Herausforderungen. In: VLB Oktobertagung, Berlin, 2012.

[47] G Haseleu, Lagemann, A., Stephan, A., Intelmann, D., Dunkel, A., Hofmann, T. (2010) Quantitative Sensomics Profiling of Hop-Derived Bitter Compounds Throughout a Full-Scale Beer Manufacturing Process. Journal of Agricultural and Food Chemistry 58:7930-7939.

[48] M Kowaka, Kokubo, E. (1976) Composition of Bitter Substances of Hops and Characteristics of Beer Bitterness. Am. Soc. of Brew. Chem.:16-21.

[49] B Jaskula, et al. (2009) Hopping technology in relation to α-acids isomerization yield, final utilization, and stability of beer bitterness. Journal of the American Society of Brewing Chemists 67 (1):44-57.

[50] RJ Smith, et al. (1998) Natural foam stabilizing and bittering compounds derived from hops. Journal of the American Society of Brewing Chemists 56 (2):52-57.

[51] T Kishimoto Investigations of Hop-Derived Odor-Active Components in Beer. In: 1st International Brewers Symposium, Oregon, USA, 2009. Hop Flavor and Aroma. Master Brewers Association of the Americas, pp 49-58.

[52] TP Nielsen (2009) Character-Impact Hop Aroma Compounds in Ale. In: TH Shellhammer (ed) Hop Flavor and Aroma. Master Brewers Association of the Americas, Oregon, USA, pp 59-78.

[53] JS Hough, Briggs, D.E., Stevens, R., Young, T.W. (1999) Malting and Brewing Science: Hopped Wort and Beer, vol 2. Aspen Publishers, New York.

[54] R Tressl, Friese, L., Fendesack, F., Köppler, H. (1978) Studies of the Volatile Composition of Hops during Storage. Journal of the American Society of Brewing Chemists 26 (6):1426-1430.

[55] VE Peacock, et al. (1980) Hop aroma in American beer. Journal of agricultural and food chemistry 28 (4):774-777.

[56] T Peppard, Ramus, S., Witt, C., Siebert, K.J. (1988) Correlation of Sensory and Instrumental Data in Elucidating the Effect of Varietal Differences on Hop Flavor in Beer. Am. Soc. of Brew. Chem. 47 (1):18-26.

[57] K Goiris, De Ridder, M., De Rouck, G., Boeykens, A., Van Opstaele, F., Aerts, G., De Cooman, L., De Keukeleire, D. (2002) The Oxygenated Sesquiterpenoid Fraction of Hops in Relation to the Spicy Hop Character of Beer. J. Inst. Brew. 108 (1):86-93.

[58] F Van Opstaele, Goiris, K., Syryn, E., De Rouck, G., Jaskula, B., De Clippeleer, J. Aerts, G., De Cooman, L. (2007) Hop: Aroma and Bitterness Perception. Cerevisia (31):167-188.

[59] F Van Opstaele, De Causmaecker, B., Aerts, G., De Cooman, L. (2012) Characterization of Novel Varietal Floral Hop Aromas by Headspace Solid Phase Microextraction and Gas Chromatography-Mass Spectrometry/Olfactometry. J. Agric. Food Chem. 60:12270-12281.

[60] M Steinhaus, et al. (2007) Comparison of the most odour-active volatiles in different hop varieties by application of a comparative aroma extract dilution analysis. European Food Research and Technology 226 (1):45-55.

[61] M Verzele, De Keukeleiere, D. (1991) Chemistry and Analysis of Hop and Beer Bitter Acids, vol 27. Developments in Food Science. Elsevier, Amsterdam.

Chemical Name

Synonyms StrutureMolecular

Weight (g/mol)

Flavor DescriptorsConc.

Minimum (mg/l)

Conc. Maximum

(mg/l)

Conc. Mean (mg/l)

TH 1 (mg/l) TH 2 (mg/l) TH 3 (mg/l)TH Water

(mg/l)Formation/De

scriptionCompound

ClassificationReferences CAS Number

Myrcene

β-Myrcene, 7-Methyl-3-

methylene-1,6-octadiene

C10H16 136.23

herbs, metallic, resinous, spicy,

balsamic, geranium-like, green, peppery,

terpene, balsam, plastic, sweet carrot, slight piney, celery,

lemon, woody

0.0001 1 0.5 0.009 0.01 0.03 0,013-0,042

•biosynthetic product during hop growth, and therefore degrades to geraniol and linalool

Monoterpene alcohol

[4], [5], [9], [13], [17], [29], [43], [44], [59]

123-35-3

Myrcene NIF C10H16 136.23 NIF 0.0001 1 0.5 0.2 0.5 1.0 NIF NIF Monoterpene alcohol

123-35-3

asbc methods of analysis hop flavor database€¦ · 86.13; nif nif; 0.026 52; 500 •oxidation...

Documents