Appendix A Threshold Data

The following table is a collection of sensory threshold data, O for olfactory and T for taste, for a variety of relevant compounds, measured in a variety of solvents— water, beer, wine, and spirits. The data comes from literature over the past 50 years, from a number of different researchers using different methods of analysis. Some papers distinguish a recognition threshold from a detection threshold: those are indicated by rO and dO, respectively. For taste, which is generally broken down into sweetness, sourness, saltiness, bitterness, and umaminess, the appropriate taste characteristic is indicated when known. It is tempting to think that the olfactory threshold is determined strictly by the concentration of a chemical in the air being inhaled. If this is the case, then the identity of the solvent is relevant only in so far as it determines a relation between the concentration in solution and the concentration in air. We can test this hypothesis for some materials as follows. If species i were in vapor-liquid equilibrium, then (subject to approximations)

γ P ∗ y = x i i i i P (A.1) where γi is activity coefficient in the liquid (a strong function of the liquid ∗ composition, and a weaker function of temperature), Pi is the vapor pressure of pure i (a function of temperature only), and P is the experimental pressure (assumed constant). To estimate γi we can make reference to the partition coefficients of Ikari and Kubo [377], which permit the calculation

yi = Ki(x)xi,

© Springer Nature Switzerland AG 2019 421 G. H. Miller, Whisky Science, https://doi.org/10.1007/978-3-030-13732-8 422 A Threshold Data where the temperature is determined by water-ethanol equilibrium and the ethanol mole fraction x (no subscript). If the temperature dependence of (A.1) lies entirely ∗ with Pi , then

∗ Pi (T ) yi = Ki(x) ∗ xi, Pi (Teq(x)) where the ratio of vapor pressures corrects the partition coefficient for the effect of temperature. We explore this hypothesis for isoamyl alcohol (Fig. A.1) using a vapor pressure function tabulated by Yaws [912]. In this plot, where each point comes from a different literature source, often using different methods, the raw threshold data shows significant variability. There is, however, an apparent positive correlation: the threshold level generally increases with increasing ethanol mole fraction. The ∗ threshold data, multiplied by Ki and the Pi ratio, is also plotted. If the hypothesis were correct, and the approximations all valid, these corrected points would have constant amplitude. The diamond symbols in Fig. A.1 are approximately constant

literature threshold calculated headspace proof 0 40 80 60000 9000

8000 50000 7000

40000 6000

5000 30000 4000

20000 3000 headspace concentration olfactory threshold [ppb] 2000 10000 1000

0 0 00.05 0.10.15 0.2 x

Fig. A.1 Olfactory threshold data for isoamyl alcohol in a variety of solutions, and calculated proxy for headspace concentration A Threshold Data 423

(i.e., show less variability than the raw square symbols do), especially if the data at x = 0.04 were considered an outlier. Thus, this plot lends some qualitative support to the hypothesis that the solvent only acts to regulate headspace concentration. However, a quantitative evaluation of the hypothesis is not possible given the paucity and variability of the data (Table A.1). 424 A Threshold Data ] ] ] ] ] ] ] ] ] ] ] ] ] ] ] ] ] ] ] ] ] ] ] 198 198 528 198 528 528 528 528 198 131 528 198 528 723 198 723 723 528 528 723 722 321 207 [ [ [ [ [ [ [ [ [ [ [ [ [ [ [ [ [ [ References [ [ [ [ [ Water 34% Spirit 9.4% (w/w) Spirit 10% (w/w) Ethanol 34% Spirit White wine at 10% 34% Spirit Water 34% Spirit Beer Beer Water Water Beer Beer Beer Beer Water Water In Beer Water Beer Beer O O O O O O O O dO T T dO dO T T T T rO rO By T rO T T 000 000 500 100 550 000 590 000 000 000 000 000 000 000 000 000 000 000 000 000 , , , , , , , , , , , , , , , , , 4300 2300 >5000 75 40 75 16 306 450 200 990 800 500 000 000 000 600 500 >10 , , , , , , >720 1 2 1 4 14 10 Threshold [ppb] Ethanol-like Alcohol, strong Malty, solvent-like Alcohol Malty Alcohol Alcohol, solvent Ethanol-like Descriptor Alcohol Alcohol Malty, solvent-like Alcohol Rubber, sweetish, warming, diacetyl Malty Alcohol A compilation of aroma threshold data Compound Alcohols Methanol Ethanol 1-Propanol 2-Propanol 1-Butanol 2-Methylpropan-1-ol (aka isobutyl alcohol) 2-Butanol 2-Methylpropan-2-ol (aka tert-butyl alcohol) Butane-2,3-diol Table A.1 A Threshold Data 425 ] ] ] ] ] 681 681 681 681 658 ] ] ] ] ] ] ] , ] ] ] ] ] ] ] ] , , , ] ] , ] (continued) 321 198 528 198 528 528 131 680 528 198 790 723 723 528 528 198 680 680 680 207 722 656 131 [ [ [ [ [ [ [ [ [ [ [ [ [ [ [ [ [ [ [ [ [ [ [ Water Water 9.4% (w/w) Spirit 10% Ethanol 34% Spirit Whitewineat10% 10% (w/w) Ethanol 34% Spirit Water 12% Ethanol Dry Riesling Ugni Blanc 40% Ethanol Water Water Beer Beer Beer Beer Water Water Beer Beer O T O O O O dO T T T O O O O dO T T T rO T rO T T 250 220 430 000 000 400 100 350 000 000 000 000 980 000 000 000 000 , , , , , , , , , , , , 4000 7000 7000 6500 1200 3700 64 30 32 56 80 70 65 45 50 310 330 300 Malty Alcohol, banana, sweetish, aromatic Malty Malty, solvent-like Alcohol, banana, medicinal, solvent Pungent, alcoholic, solvent Alcohol, medicinal Alcohol, fruity, raspberry, nutty, ether Alcohol, medicinal, ether, nutty, fruity Malty, solvent-like Malty 1-Pentanol 3-Methylbutanol (aka isoamyl alcohol) 2-Methyl-1-butanol 2-Pentanol 3-Pentanol 1-Penten-3-ol 426 A Threshold Data ] ] ] ] ] ] ] ] ] ] ] ] ] ] ] ] ] ] ] ] ] ] ] ] ] 528 528 528 198 528 528 528 131 723 723 528 790 528 528 528 131 722 321 207 207 198 321 207 207 528 [ [ [ [ [ [ [ [ [ [ [ [ [ [ [ [ [ [ [ References [ [ [ [ [ [ 9.4% (w/w) Spirit 10% Ethanol 10% (w/w) Ethanol 34% Spirit White wine at 10% White wine at 10% Water 10% (w/w) Ethanol White wine at 10% White wine at 10% 34% Spirit Water Water Beer Beer Beer Beer Water Beer In Beer Beer Beer Beer Beer Beer O O O O O O O O O O O O dO T T T rO T By T T T T T T T 9 . 3 70 13 40 400 820 400 250 000 150 000 900 200 000 000 000 , , , , , 5200 5200 8000 5200 5280 1080 2450 1100 1000 13 15 400 400 900 Threshold [ppb] Coconut, green leaves, unpleasant Lettuce-like Green leaves, banana, sweetish Coconut, walnut, oily Descriptor Coconut Coconut Coconut Green leaves, perfumed, sweetish Bitter, green leaves Lettuce-like Green leaves Coconut, walnut, oily Almonds, bitter (continued) )-2-Octanol + Compound 1-Hexanol 2-Hexanol (E)-2-Hexen-1-ol (Z)-3-Hexen-1-ol 1-Heptanol 2-Heptanol 1-Hepten-3-ol Phenylmethanol (aka benzyl alcohol) 1-Octanol (S)-( 1-Octen-3-ol Table A.1 A Threshold Data 427 ] ] ] ] ] ] ] ] ] ] ] ] ] ] ] ] ] ] ] ] ] ] ] ] ] ] 321 447 658 528 528 528 198 207 528 528 447 528 528 198 131 528 723 198 790 723 198 528 722 207 321 131 (continued) [ [ [ [ [ [ [ [ [ [ [ [ [ [ [ [ [ [ [ [ [ [ [ [ [ [ 9.4% (w/w) Spirit 10% Ethanol 34% Spirit Deflavored white wine at 10% White wine at 10% 34% Spirit 10% (w/w) Ethanol Water 10% (w/w) Ethanol 23% (v/v) Grain whisky 23% (v/v) Grain whisky 40% Ethanol Beer Beer Water Beer Beer Beer Beer Beer Water Water Beer Water Beer Water O O O dO O O O O O O rO O T T dO T T T dO T T rO T O T rO 087 17 . . 0 6 0 15 75 80 15 80 310 360 210 350 000 000 000 140 000 500 390 180 000 , , , , , 7500 7500 2000 7500 2600 10 80 414 125 200 Flowery, honey-like Roses, sweetish, perfumed Floral Flowery Lime, flowery (hyacinth, rose) Aniseed, terpenoid Citrus-like, bergamot-like Almonds, solvent Coconut, walnut, oily Coconut Coconut, walnut, oily, rancid Coconut, aniseed Flowery, honey-like Citrus-like, bergamot-like Bitter, chemical -terpineol) α 2-Phenylethanol 4-(2-Hydroxyethyl)phenol (aka tyrosol) 1-Nonanol 2-Nonanol 1-Decanol 2-Decanol (Z)-3,7-Dimethyl-2,6-octadien-1-ol (aka nerol) 2,7-Dimethylocta-1,6-dien-3-ol (aka linalool) (R)-2,7-Dimethylocta-1,6-dien-3-ol 2-(4-Methyl-1-cyclohex-3-enyl)propan-2-ol (aka 428 A Threshold Data ] ] ] ] ] ] ] ] ] ] ] ] ] ] ] ] ] ] ] ] 321 654 723 723 447 777 447 654 777 198 447 528 447 528 723 583 723 528 207 198 [ [ [ [ [ [ [ [ [ [ [ [ [ [ [ [ [ References [ [ [ Beer White wine at 10% 34% Spirit 23% (v/v) Grain whisky 34% Spirit Water 10% (w/w) Ethanol 23% (v/v) Grain whisky 23% (v/v) Grain whisky 23% (v/v) Grain whisky Water 34% Spirit 34% Spirit White wine White wine Water Water In Beer Beer Water T O O dO O O dO O rO rO dO O O O O rO T By T T O 70 300 000 000 000 000 000 400 000 500 000 400 000 000 , , , , , , , , , , 1001 1000 8000 5000 1100 3100 24 26 36 99 11 13 35 200 233 180 Threshold [ppb] Fruity, cotton candy, sour Caramel, fragrant Sweet Maple Caramel, maple Vinegar Sour Descriptor Fatty acids, coconut Perfumed, sweetish, coconut, varnish, musty Fatty acids, coconut, banana Vinegar Sweet, cotton candy, burnt sugar (continued) Compound 1-Undecanol 2-Undecanol 1-Dodecanol 1-Tetradecanol 1-Hexadecanol Maltol (aka 3-hydroxy-2-methylpyran-4-one) Cyclotene (aka 2-hydroxy-3-methyl-2- cyclopentenone) Acids Acetic acid Table A.1 A Threshold Data 429 ] ] ] ] ] ] ] ] ] ] ] ] ] ] ] ] ] ] ] ] ] ] ] ] ] ] ] (continued) 722 447 321 198 528 321 528 528 447 528 198 528 723 198 198 790 790 723 790 723 723 198 790 198 722 722 722 [ [ [ [ [ [ [ [ [ [ [ [ [ [ [ [ [ [ [ [ [ [ [ [ [ [ [ 9.4% (w/w) Spirit 10% Ethanol 34% Spirit 9.4% (w/w) Spirit 10% Ethanol 34% Spirit 9.4% (w/w) Spirit 10% Ethanol 34% Spirit 23% (v/v) Grain whisky 10% (w/w) Ethanol 9.4% (w/w) Spirit 10% Ethanol 34% Spirit 10% (w/w) Ethanol Water 23% (v/v) Grain whisky Water Water Beer Beer Beer Water Beer Water Beer Water O O dO O O O O O O O O O O O O dO rO dO dO T T T rO rO T T rO 000 000 000 000 700 700 100 750 000 490 300 000 000 000 000 000 , , , , , , , , , , 4000 4000 3400 8000 8100 8200 2400 1500 2200 7700 1200 10 20 20 20 16 30 29 200 400 150 Sweaty Cheese, old hops, sweaty Sweaty Sweaty Buttery, cheesy, sweaty Sweaty, cheesy Sweaty, bitter, sour Sweaty Vinegar, milky Sweaty Acid Sweaty, cheesy 3-Methylbutanoic acid (aka isovaleric acid) Butanoic acid (aka butyric acid) (E)-But-2-enedioic acid (aka fumaric acid) 2-Methylpropanoic acid (aka isobutyric acid) Propanoic acid (aka propionic acid) 430 A Threshold Data ] ] ] ] ] ] ] ] ] ] ] ] ] ] ] ] ] ] ] ] ] ] 198 198 723 723 790 723 723 790 723 723 528 722 790 722 528 528 321 722 528 723 528 321 [ [ [ [ [ [ [ [ [ [ [ [ [ [ [ References [ [ [ [ [ [ [ 34% Spirit 9.4% (w/w) Spirit 10% Ethanol 10% (w/w) Ethanol 34% Spirit 9.4% (w/w) Spirit 10% Ethanol 34% Spirit 9.4% (w/w) Spirit 10% Ethanol 10% (w/w) Ethanol 34% Spirit 34% Spirit Water Beer In 34% Spirit 34% Spirit Water Beer Beer Beer Beer O O O O O O O O O O O O dO T O By O O rO T T T T 000 000 000 000 000 000 000 000 , , , , , , , , 8800 8300 3000 8600 8200 8200 9400 8000 1300 8000 >500 >500 >500 >1100 15 15 15 15 11 17 10 13 Threshold [ppb] Sweaty, fruity Sweaty, body odor Descriptor Dry leaves, goaty, fatty acids Sweaty, fruity Waxy, tallowy, caprylic, rancid, soapy Goaty, fatty acid, vegetable oil, sweaty Goaty, fatty acid, vegetable oil, Wet dog (continued) Compound Pentanoic acid (aka valeric acid) Hexanoic acid (aka caproic acid) Hex-3-enoic acid Heptanoic acid (aka enanthic acid) Octanoic acid (aka caprylic acid) Nonanoic acid (aka pelargonic acid) Decanoic acid (aka capric acid) Undecanoic acid Table A.1 A Threshold Data 431 ] ] ] ] ] ] ] ] ] ] ] ] ] ] ] ] ] ] ] (continued) 723 723 528 198 528 723 723 528 198 528 723 723 528 723 723 528 528 723 528 [ [ [ [ [ [ [ [ [ [ [ [ [ [ [ [ [ [ [ 34% Spirit 34% Spirit 34% Spirit Beer Beer Beer 34% Spirit 34% Spirit Beer Water 34% Spirit 34% Spirit 34% Spirit 34% Spirit Beer Beer Water Beer Beer O O O T T O T O T dO O O O O T rO T T T 000 000 000 000 000 000 000 000 000 000 , , , , , , , , , , 7200 2500 6100 6100 >500 >500 >1200 >1600 >2200 12 17 400 175 000 300 >11 >12 >10 , >200 2 Phenolic, sour, grainy Honey-like, beeswax-like Honey, sweet Astringent Acid Honey-like, beeswax-like Harsh, astringent, papery Soapy, waxy Acid Acid, salty, forage Dodecanoic acid (aka lauric acid) Tridecanoic acid Tetradecanoic acid (aka myristic acid) Pentadecanoic acid Hexadecanoic acid (aka palmitic acid) (9Z)-Hexadec-9-enoic acid (aka palmitoleic acid) Octadecanoic acid (aka stearic acid) (9Z)-Octadec-9-enoic acid (aka oleic acid) (9Z,12Z)-9,12-Octadecadienoic acid (aka linoleic acid) 2-Oxopropanoic acid (aka pyruvic acid) Oxaldehydic acid (aka glyoxylic acid) 2-Oxo-3-phenylpropanoic acid (aka phenylpyruvic acid) 2-Phenylacetic acid 2-Hydroxy-2-phenylacetic acid (aka mandelic acid) (E)-Non-2-enoic acid DL-2-Hydroxypropanoic acid (aka DL-lactic acid) 432 A Threshold Data ] ] ] ] ] ] ] ] ] ] ] ] ] ] ] ] ] ] ] ] 207 528 131 528 723 528 528 723 198 723 723 528 321 658 790 198 528 658 722 370 [ [ [ [ [ [ [ [ [ [ [ [ [ [ References [ [ [ [ [ [ Water 10% (w/w) Ethanol 34% Spirit 34% Spirit 9.4% (w/w) Spirit 10% Ethanol 34% Spirit 34% Spirit 40% Ethanol Water 40% Ethanol Beer Beer Beer In Whitewineat10% Water Beer Water Beer Beer O O O O O O O O O O dO T T T By T T O rO T T 76 5 4 . . . 0 9 2 40 20 150 000 000 000 000 000 000 400 100 000 , , , , , , , 3452 1840 2500 >4000 >5700 14 14 14 370 500 600 250 Threshold [ppb] Acid, salty Acid Acid Fruity Fruity Papaya, butter, sweetish, apple, perfumed Fruity Descriptor Puckering astringency Fruity Fatty acids Artificial strawberry, raspberry, perfumed (continued) Compound 2,3-Dihydroxybutanedioic acid (aka DL-tartaric acid) (2S,3S)-2,3-Dihydroxybutanedioic acid (aka D-tartaric acid) (2R,3R)-2,3-Dihydroxybutanedioic acid (aka L-tartaric acid) (Z)/(E)-Aconitic acid Esters Methyl 2-hydroxybenzoate (aka methyl salicylate) Ethyl propionate (aka ethyl propanoate) Ethyl butanoate (aka ethyl butyrate) Ethyl 2-hydroxypropanoate (aka ethyl lactate) Ethyl tetradecanoate (aka ethyl myristate) Table A.1 A Threshold Data 433 ] ] ] ] ] ] ] ] ] ] ] ] ] ] ] ] ] ] ] ] (continued) 528 528 528 723 723 723 723 723 723 723 723 723 723 723 528 528 528 723 528 528 [ [ [ [ [ [ [ [ [ [ [ [ [ [ [ [ [ [ [ [ 34% Spirit 34% Spirit 34% Spirit 34% Spirit 34% Spirit 34% Spirit 34% Spirit 34% Spirit 34% Spirit 34% Spirit 34% Spirit 34% Spirit Beer Beer Beer Beer Beer Beer Beer Beer T O O O O O O O O O O O T T T T T T T T 000 500 870 450 250 600 000 900 , , 3400 1400 4000 2000 2000 1600 3000 5000 3500 >100 >1000 >5000 10 >14 Fatty acids, vegetable oil, rancid Fatty acids, fruity, solvent, perfumed Fruity, hot (spicy), orange, pear, melon Fatty acids, fruity, sweetish, rancid Fatty acids Fatty acids, vegetable oil, rancid Banana, sweet, fruity Fatty acids, tropical fruits Ethyl hexadecanoate (ethyl palmitate) Ethyl (E)-hexadec-9-enoate (aka ethyl palmitoleate) Ethyl octadecanoate (aka ethyl stearate) Ethyl (E)-octadec-9-enoate (aka ethyl oleate) Ethyl (9Z,12Z)-octadeca-9,12-dienoate (aka ethyl linoleate) 2-Methylpropyl acetate (aka isobutyl acetate) 3-Methylbutyl 2-methylpropanoate (aka isoamyl isobutyrate) 3-Methylbutyl 3-methylbutanoate (aka isoamyl isovalerate) Pentyl 3-methylbutanoate (aka isoamyl n-valerate) 3-Methylbutyl hexanoate (aka isoamyl caproate) 3-Methylbutyl octanoate (aka isoamyl capyrlate) 3-Methylbutyl decanoate (aka isoamyl caprate) 434 A Threshold Data ] ] ] ] ] ] ] ] ] ] ] ] ] ] ] ] ] ] ] ] ] ] 723 528 528 447 790 723 723 528 528 722 790 636 207 321 658 207 321 207 722 745 321 658 [ [ [ [ [ [ [ [ [ [ [ [ [ [ [ [ [ [ References [ [ [ [ 10% (w/w) Ethanol 9.4% (w/w) Spirit 10% Ethanol 10% (w/w) Ethanol 34% Spirit White wine at 10% 34% Spirit Whitewineat10% Whitewineat10% 9.4% (w/w) Spirit 10% Ethanol Model wine at 10% 10% (w/w) Ethanol 20% Ethanol 34% Spirit 40% Ethanol 40% Ethanol 23% (v/v) Grain whisky Beer Mexican beer In Beer US beer O O O O O O O O O O O O O O O O O rO T By T T T 5 80 76 30 270 000 000 000 000 000 650 650 250 700 108 400 230 000 210 , , , , , , , 1510 7500 3800 12 17 17 18 74 17 30 Threshold [ppb] Roses, honey, apple, sweetish Flowery Apple, fruity, sweetish, aniseed Fruity-appley Fruity Descriptor Solvent, fruity, sweetish Apple, estery, aniseed -phenylethyl β (continued) Compound 2-Phenylethyl acetate (aka Ethyl acetate Ethyl hexanoate (aka ethyl caproate) acetate) Table A.1 A Threshold Data 435 ] ] ] ] ] ] ] ] ] ] ] ] ] ] ] ] ] ] ] ] ] ] ] ] (continued) 447 447 528 447 528 447 528 723 723 723 790 723 790 636 528 207 722 321 658 207 722 321 658 528 [ [ [ [ [ [ [ [ [ [ [ [ [ [ [ [ [ [ [ [ [ [ [ [ 10% (w/w) Ethanol White wine at 10% 9.4% (w/w) Spirit 10% Ethanol 34% Spirit White wine at 10% 34% Spirit 23% (v/v) Grain whisky 34% Spirit 9.4% (w/w) Spirit 10% Ethanol 10% (w/w) Ethanol 20% Ethanol 23% (v/v) Grain whisky 34% Spirit 40% Ethanol 40% Ethanol 23% (v/v) Grain whisky 23% (v/v) Grain whisky US beer Mexican beer Beer Beer Beer O O O O O O O O dO O O O O dO O O O rO rO T T T T T 2 30 580 250 250 240 510 800 640 200 200 300 230 147 245 900 1100 1000 1000 3000 1200 1600 3500 1500 Fruity Soapy Banana, estery Banana, apple, solvent Fruity Fruity Fatty acids, fruity, apple, solvent Apple, sweetish, fruity Soapy, estery Ethyl octanoate (aka ethyl caprylate) Ethyl decanoate (aka ethyl caprate) Ethyl dodecanoate (aka ethyl laurate) 3-Methylbut-1-yl-ethanoate (aka isoamyl acetate, 3-methylbutyl acetate) 436 A Threshold Data ] ] ] ] ] ] ] ] ] ] ] ] ] ] ] ] ] ] ] ] ] ] ] ] ] 207 528 207 528 528 528 207 528 528 207 207 207 207 207 207 207 528 528 528 528 528 528 528 207 528 [ [ [ [ [ [ [ [ [ [ References [ [ [ [ [ [ [ [ [ [ [ [ [ [ [ Whitewineat10% Deflavored white wine at 10% Whitewineat10% Whitewineat10% Whitewineat10% Whitewineat10% Whitewineat10% Whitewineat10% Deflavored white wine at 10% Whitewineat10% Beer White wine at 10% In Beer Beer Beer Beer Beer Beer Beer Beer Beer Beer Beer Beer Beer O O O O O O O O O O T O By T T T T T T T T T T T T T 10 220 850 670 830 800 200 000 000 180 400 000 500 900 000 000 000 000 , , , , , , , , 4740 1830 3500 1400 1200 7500 5000 30 30 85 155 470 150 550 000 , 5 Threshold [ppb] Fruity, solvent Descriptor Light estery, fruity, solvent Light solvent, fruity, pleasant Coconut, vegetable, oil, aromatic Fruity, perfumed, fatty Fruity, fatty acids, perfumed, sweetish Solvent, sweetish, perfumed Solvent, banana, acetone, sweetish Sweetish, aromatic, perfumed Pear, fruity, aromatic, sweetish Papaya, fruity, apple, sweetish Ethereal, light, flowery, pleasant Grassy, oil paint, forage Plum, solvent, unpleasant (continued) Compound Ethyl formate Ethyl pentanoate (aka ethyl valerate) Ethyl heptanoate Ethyl nonanoate Methyl acetate n-Propyl acetate n-Butyl acetate Pentyl acetate (aka amyl acetate) n-Hexyl acetate n-Heptyl acetate n-Octyl acetate Methyl methanoate (aka methyl formate) 2-Methylpropyl formate (aka isobutyl formate) Ethyl 2-oxopropanoate (aka ethyl pyruvate) 3-Methylbutyl formate (aka isoamyl formate) Table A.1 A Threshold Data 437 ] ] ] ] ] ] ] ] ] ] ] ] ] ] ] ] ] ] ] ] ] ] 528 528 528 198 198 528 528 528 528 198 198 528 528 528 528 528 528 528 321 658 658 528 (continued) [ [ [ [ [ [ [ [ [ [ [ [ [ [ [ [ [ [ [ [ [ [ 10% (w/w) Ethanol 40% Ethanol 40% Ethanol Water Water Beer Beer Beer Beer Water Water Beer Beer Beer Beer Beer Beer Beer Beer Beer Beer Beer O O O rO dO T T T T rO dO T T T T T T T T T T T 22 089 5 6 110 023 ...... 0 0 4 1 0 0 15 700 000 000 000 600 000 , , , , 5000 6000 1300 1000 2000 1000 1200 1200 5000 24 12 200 300 , 1 Fruity Fruity Sweetish, apple Fruity Sour, bitter, fruity Fruity, blueberry-like Fruity, blueberry-like Fruit, apple, sweetish, valeric Fruity Pineapple, aniseed Medicinal, tincture Fruity (peach), coconut, sweet, fatty acids Paint thinner, medicinal, menthol Fatty acids, pear, grassy Cider, apple, sweets, papaya, fatty acids Coconut, fatty acids, fruity Fatty acids, coconut, tropical fruits Orange peel, fruity, coconut, fatty acids Paint thinner, glue Estery, burnt, unpleasant, sweetish Fruity, papaya, red currant Butan-2-yl acetate (aka sec-butyl acetate) tert-Butyl acetate Ethyl 2-methylpropanoate (aka ethyl isobutyrate) 4-Ethoxy-4-oxobutanoic acid (aka ethyl hydrogen succinate) Ethyl-3-methylbutanoate (aka ethyl isovalerate) Ethyl 4-oxopentanoate (aka ethyl levulinate) 3-Methylbutyl propanoate (aka isoamyl propionate) Ethyl pyridine-3-carboxylate (aka ethyl nicotinate) Pentyl butanoate (aka n-amyl butyrate) Heptyl butanoate (aka sec-heptyl butyrate) Methyl decanoate (aka methyl caprate) Octyl butanoate (aka n-octyl butyrate) Ethyl undecanoate Octyl hexanoate (aka octyl caproate) 3-Methylbutyl nonanoate (aka isoamyl nonanoate) 438 A Threshold Data ] ] ] ] ] ] ] ] ] ] ] ] ] ] ] ] ] ] ] ] ] ] ] 370 528 656 656 528 198 370 370 370 370 370 321 198 370 658 658 370 370 370 370 370 370 370 [ [ [ [ [ [ [ [ [ [ [ References [ [ [ [ [ [ [ [ [ [ [ [ 10% (w/w) Ethanol 40% Ethanol 40% Ethanol Water Water Water Water Water Water Water Water In Beer Water Water Water Water Water Water 40% Ethanol Water 40% Ethanol Water Beer O O O dO T T T T T T T By T T rO T T T T O O T T T 7 013 2 063 0 5 ...... 1 9 0 0 0 8 30 000 000 000 000 000 000 000 000 000 000 000 000 000 000 , , , , , , , , , , , , , , 5000 3000 4 9 37 58 25 15 27 229 438 137 294 158 182 130 Threshold [ppb] Fruity Fruity Fruity Bitterness Astringency Bitterness Bitterness Bitterness Bitterness Bitterness Descriptor Fatty acids, soapy, hot (spicy) Astringency Fatty acids Astringency Astringency Astringency Astringency Astringency Fruity Astringency (continued) Compound Ethyl tridecanoate Ethyl pentadecanoate Ethyl 3-phenylprop-2-enoate (aka trans ethyl cinnamate) (S)-Ethyl-2-methylbutanoate (2S,3S)-Ethyl-hydroxy-3-methylpentanoate (S)-Ethyl-2-hydroxy-3-methylbutanoate Caffeic acid ethyl ester Gallic acid ethyl ester p-Coumaric acid ethyl ester Vanillic acid ethyl ester Ferulic acid ethyl ester Protocatechuic acid ethyl ester Syringic acid ethyl ester Table A.1 A Threshold Data 439 ] ] ] ] ] ] ] ] ] ] ] ] ] ] ] ] ] ] ] ] ] ] ] (continued) 528 447 528 528 528 198 528 656 447 528 198 723 131 528 528 723 314 723 723 528 198 321 198 [ [ [ [ [ [ [ [ [ [ [ [ [ [ [ [ [ [ [ [ [ [ [ 34% Spirit 10% (w/w) Ethanol Water 23% (v/v) Grain whisky 34% Spirit 34% Spirit 34% Spirit Water 23% (v/v) Grain whisky Water Water 40% Ethanol Beer Mexican beer Water Beer Water US beer Beer Beer Beer Beer Beer O O O O O dO O O rO dO dO O T T rO T rO T T T T T T 5 4 . . 4 2 28 12 25 10 63 500 100 110 700 350 000 000 000 500 000 , , , , 1200 2000 2000 6000 1000 8000 , 25 30 10 19 400 Fresh, green Green leaves, fruity, sharp Green leaves, fruity Solvent-like Green grass, fruity Green, grassy Bitter, vinous, aldehyde Grassy Green, grassy Fresh, green Astringent, fruity, later burning Fruity, varnish, bitter, aldehyde Melon, green leaves, varnish Grass, banana, aldehyde Apple, green leaves, almond Aldehydes Formaldehyde Acetaldehyde Propanal Butanal (aka butyraldehyde) 2-Ethylbutanal (E)-But-2-enal (aka crotonaldehyde) Pentanal (aka valeraldehyde) Hexanal 440 A Threshold Data ] ] ] ] ] ] ] ] ] ] ] ] ] ] ] ] ] ] ] ] ] ] ] ] ] 198 528 198 528 198 131 131 657 314 528 528 198 198 131 198 198 528 131 314 314 528 198 657 198 198 [ [ [ [ [ [ [ [ [ [ [ [ [ [ [ [ [ [ References [ [ [ [ [ [ [ Water Water Water Water Water Water Water Water Water Beer Water Beer Beer Water Water Beer In Beer Water Water Beer Water Water Water O O O O O O O dO dO dO dO O T rO rO T T T O By dO T T rO rO rO 7 , 25 12 008 4 2 8 9 0 4 21 025 ...... 0 0 0 3 0 2 6 8 3 0 0 0 17 13 98 16 20 18 20 40 600 110 190 Threshold [ppb] Green, grassy Green leaves, freshly cut grass Green apple-like, bitter almond-like Bitter, astringent, green leaves Fishy, fish oil-like Aldehyde, bitter, papery, vinous, unpleasant Citrus-like, green Orange peel, bitter, aldehyde, vinous Bitter, aldehyde, stale Citrus-like, soapy Soapy Astringent, bitter, aldehyde Citrus-like, green Citrus-like, soapy Descriptor Fatty, green Green, grassy Fishy, fish oil-like Green apple-like, bitter almond-like (continued) Compound (Z)-Hex-3-enal (aka cis-3-hexenal) (E)-Hex-2-enal (aka trans-2-hexenal) 1-Heptanal 2-Heptanal (Z)-Hept-4-enal (aka cis-4-heptenal) (E)-2-Heptenal Octanal (E)-2-Octenal (aka trans-2-octenal) Nonanal Table A.1 A Threshold Data 441 ] ] ] ] ] ] ] ] ] ] ] ] ] ] ] ] ] ] ] ] (continued) 198 198 528 314 131 131 131 528 636 658 198 198 723 314 658 528 658 198 528 198 [ [ [ [ [ [ [ [ [ [ [ [ [ [ [ [ [ [ [ [ Water Water 20% Ethanol 40% Ethanol Water Water 34% Spirit 40% Ethanol Water Water 40% Ethanol Water Water Beer Water Beer Beer Water Beer Water O O O O O O O O rO dO O dO O T dO T T rO T rO 08 6 6 07 1 9 49 9 19 5 027 3 11 077 69 ...... 0 0 0 0 5 1 1 0 5 0 0 0 0 0 0 32 12 150 1300 1000 Fatty, green Papery (cardboard), oxidized, stale Fatty, deep-fried Oily, aldehyde, deep-fried Fatty Lemon, bitter Malty Malty Banana, melon, vanish, green leaves, bitter Malty Fatty, deep-fried Fatty, green (E)-2-Nonenal (aka trans-2-nonenal) Undecanal (E,E)-2,4-Decadienal (E)-3,7-Dimethylocta-2,6-dienal (aka geranial, citral) 2-Methylpropanal (aka isobutanal, isobutyraldehyde) 442 A Threshold Data ] ] ] ] ] ] ] ] ] ] ] ] ] ] ] ] ] ] ] ] ] 198 528 528 131 528 198 528 528 314 636 723 198 198 528 528 528 528 528 658 131 528 [ [ [ [ [ [ [ [ [ [ [ [ References [ [ [ [ [ [ [ [ [ Water 20% Ethanol 34% Spirit Water 40% Ethanol Water Water Beer Water Water Beer Beer In Beer Beer Beer Beer Beer Water Beer Beer Beer O O O dO O dO O rO T O T T By T t T T T rO T T T 5 8 5 4 2 . . . . . 0 2 1 4 4 1 12 50 120 350 600 300 800 000 200 000 , , 2000 1600 1250 8000 1000 15 125 Threshold [ppb] Malty Unripe banana, apple, cherry, cheese Malty Malty Green grass, fruity, sour/medicinal Walnut, sherry, fruity Cinnamon, sweetish, green leaves, bitter Almond, cherry stone Fruity, aromatic, sweetish, astringent Hyacinth, lilac, aldehyde Descriptor Orange, grass, aldehyde, astringent Malty Sweet honey, sherry Varnish, banana Aldehyde, bitter, rancid, fruity, flowery Malty (continued) Compound 3-Methylbutanal (aka isovaleraldehyde) 2-Methylbutanal Prop-2-enal (aka acrolein) 2,3-Dihydroxypropanal (aka D- glyceraldehyde) 3-Hydroxybutanal (aka aldol) (2E,4Z)-Hexa-2,4-dienal (aka trans-2-cis- 4-hexadienal) Benzaldehyde Cyclohex-3-ene-1-carbaldehyde (aka 1,2,3,6-tetrahydrobenzaldehyde) 2-Ethylhexanal 2-Ethylhex-2-enal (trans+cis) 2-Phenylacetaldehyde Table A.1 A Threshold Data 443 ] ] ] ] ] ] ] ] ] ] ] ] ] ] ] ] ] ] ] (continued) 658 528 528 528 198 198 528 528 528 528 528 528 528 528 198 658 198 658 528 [ [ [ [ [ [ [ [ [ [ [ [ [ [ [ [ [ [ [ Beer 40% Ethanol 40% Ethanol Water Beer Beer Water Water Beer Beer Water Beer 40% Ethanol Beer Beer Beer Beer Beer Beer T O O dO T T rO dO T T T rO O T T T T T T 1 5 , , 6 3 062 009 004 5 05 19 2 ...... 2 0 0 0 0 1 0 0 0 6 5 350 300 400 6000 1000 4000 5000 1000 Fatty, green Oily, rancid, aldehyde Fatty Cucumber-like Cucumber-like Cucumber, green leaves Green Bitter, rancid, stale unpleasant Bitter, aldehyde, orange peel Hyacinth, shoewax Fatty, green Aldehyde, bitter, astringent, orange, Mint, bitter, aldehyde Cinnamon, sweet, cider Fatty Orange peel, bitter, burning Cinnamon Sweetish, flowery, astringent Cinnamon, sweetish, aldehyde (2E,4E)-Nona-2,4-dienal (2E,6Z)-Nona-2,6-dienal (aka violet leaf aldehyde) (E)-2,2-Dimethylhept-4-enal Cyclooctanecarbox-aldehyde 3,4-Dimethyl-1,3-cyclohexane-carboxaldehyde (E)-3-Phenylprop-2-enal (aka cinnamaldehyde) 2-Phenylprop-2-enal (aka 2-phenylacrolein) (Z)-3-Hydroxy-2-phenylprop-2-enal 2-Phenylpropanal Decanal (E)-2-Decenal (aka trans-2-decenal) 3,7-Dimethyloct-6-enal (aka citronellal) 444 A Threshold Data ] ] ] ] ] ] ] ] ] ] ] ] ] ] ] ] ] ] ] ] 528 528 447 528 723 528 528 528 198 658 528 528 528 528 198 722 745 321 790 447 [ [ [ [ [ [ [ [ [ [ [ References [ [ [ [ [ [ [ [ [ 9.4% (w/w) Grain spirit 9.4% (w/w) Spirit Model wine at 10% 10% (w/w) Ethanol 23% (v/v) Grain whisky 34% Spirit 40% Ethanol 23% (v/v) Grain whisky Water Beer Beer In Beer Beer Beer Beer Water Beer Beer Beer Beer O dO O O O O O rO dO T T By T T rO T T T T T T 5 5 8 0 5 5 9 5 ...... 2 2 2 2 1 6 4 3 1 2 3 50 20 100 150 400 000 000 000 , , , 1500 000 500 000 , , 2 7 Threshold [ppb] Cumin seed, almond, cinnamon, varnish Buttery Diacetyl, butterscotch Buttery Descriptor Bitter, orange, aldehyde, vinous Fatty acids, aldehyde Aldehyde, orange peel, bitter Aldehyde, bitter, orange peel Burning, astringent, dishcloth Astringent, flowery, aldehyde Buttery Acid Acid, salty, oxidized (continued) Compound 7-Hydroxy-3,7-dimethyloctanal 4-Propan-2-ylbenzaldehyde (aka cuminaldehyde) Undecanal Undec-9-enal Undec-10-enal Dodecanal Oxaldehyde (aka glyoxal) 2-Oxobutanedioic acid (aka oxalacetic acid) Oxaldehydic acid (aka glyoxylic acid) Ketones Butane-2,3-dione (aka diacetyl) Table A.1 A Threshold Data 445 ] ] ] ] ] ] ] ] ] ] ] ] ] ] ] ] ] ] ] ] ] ] ] ] (continued) 528 528 528 528 131 131 528 528 528 528 528 528 528 528 528 528 528 723 528 528 528 528 528 528 [ [ [ [ [ [ [ [ [ [ [ [ [ [ [ [ [ [ [ [ [ [ [ [ 34% Spirit Water Water Beer Beer Beer Beer Beer Beer Beer Beer Beer Beer Beer Beer Beer Beer Beer Beer Beer Beer Beer Beer Beer O O O T T T T T T T T T T T T T T T T T T T T T 25 9 . . 1 0 30 700 000 000 000 000 000 000 000 000 900 000 000 000 000 , , , , , , , , , , , , 4000 4000 3000 7000 2000 8000 4000 5 80 40 30 60 15 30 50 25 200 200 400 Acetone, varnish Jasmine, geranium, ketone, varnish Ethyl ether, ketone, sweetish Almond, sweetish, ethyl ether Ketone, Roquefort cheese Almond, ketone, bitter Varnish, ketone, walnut, hops Ketone, varnish, sweetish Ketone, varnish, mint Strawberry, diacetyl, pleasant Ketone, sweetish, mint Varnish, ketone, melon, apricot Ketone, sweetish Acetone, fruity Ethyl ether, varnish, sweetish Sweetish, ketone, bitter, caramel, unpleasant Fruity, moldy, woody Trainy butter (fishy, metallic, oily) Diacetyl, fruity Varnish, ethyl ether, ketone, sweetish Sweet, peach, strawberry, varnish 1-Penten-3-one (E)-Non-2-en-4-one Propan-2-one (aka acetone) Butan-2-one 3-Hydroxybutan-2-one (aka acetoin) Pentan-2-one Pentan-3-one 3-Methylbutan-2-one 1-Penten-3-one (aka ethyl vinyl ketone) Cyclopentanone Pentane-2,3-dione (aka acetylpropionyl) 3-Hydroxy-3-methylbutan-2-one Hexan-2-one 4-Methylpentan-2-one 3,3-Dimethylbutan-2-one (aka pinacolone) 4-Methyl-3-penten-2-one (aka mesityl oxide) Cyclohexanone Hexane-2,3-dione Heptan-2-one Heptan-3-one Heptan-4-one 5-Methylhexan-2-one 2,4-Dimethylpentan-3-one 446 A Threshold Data ] ] ] ] ] ] ] ] ] ] ] ] ] ] ] ] ] ] ] ] ] ] 528 198 131 528 528 528 528 528 528 131 528 528 528 198 528 528 528 131 528 528 528 528 [ [ [ [ [ [ [ References [ [ [ [ [ [ [ [ [ [ [ [ [ [ [ Beer Water Water Beer Water Beer Beer In Beer Water Beer Beer Beer Water Beer Beer Beer Beer Beer Beer Beer Beer Beer O T dO T O T T rO T By T T T O T T T T T T T T T 016 025 036 . . . 0 0 0 5 60 50 400 400 200 100 500 375 250 300 250 000 250 , 1200 8000 3000 2500 1000 25 Threshold [ppb] Mushroom-like Mushroom, metallic, bitter Caraway seed, mint Descriptor Varnish,ketone, walnut, octyl alcohol Ketone, varnish, spicy Ketone, varnish Ketone, flowery, sweetish Ketone, sweetish, varnish Mushroom-like Ketone, varnish, bitter, green plants, geranium Ketone, varnish, green plants, geranium Ketone, varnish Ketone, varnish Ketone, banana Mint, coconut Grape seeds, sweet, astringent Almond, marzipan, earthy Banana, mango, sweetish Ketone, cake topping aerosol, varnish (continued) Compound 4-Methylcyclohexan-1-one Octan-2-one Octan-3-one 6-Methylheptan-3-one 1-Octen-3-one 1-Phenylethanone (aka acetophenone) 1-(2-Aminophenyl)ethanone 2-Nonanone 2,6-Dimethylheptan-4-one Decan-2-one Decan-3-one (5S)-2-Methyl-5-prop-1-en-2-ylcyclohex-2-en- 1-one (aka D-carvone) 4-Phenylbutan-2-one (aka benzylacetone) (E)-4-Phenylbut-3-en-2-one (aka benzalacetone) Undecan-2-one Dodecan-2-one Tridecan-2-one 2-Methylhept-2-en-6-one 2-Methylhepta-2-trans-4-dien-6-one (5E)-6,10-Dimethylundeca-5,9-dien-2-one (aka geranylacetone) Table A.1 A Threshold Data 447 ] ] ] ] ] ] ] ] ] ] ] ] ] ] ] ] ] ] ] ] (continued) 198 198 658 152 198 528 528 528 198 131 133 131 152 152 198 303 321 198 321 511 [ [ [ [ [ [ [ [ [ [ [ [ [ [ [ [ [ [ [ [ Beer White wine Red wine 10% (w/w) Ethanol Water Water 10% (w/w) Ethanol Water 40% Ethanol 40% Ethanol Model wine Water Water Water White wine 12.5% Beer Beer Water Water Water O O T O O O O O O O O rO dO dO O T T dO rO rO 007 002 05 33 1 4 5 84 6 3 013 1 056 ...... 0 0 0 0 0 8 3 5 0 2 1 0 1 0 50 10 10 25 160 100 S 2 Artificial raspberry, cedarwood Flowery, violet-like Flowery, violet-like Artificial raspberry, strawberry Baked apple-like, grape juice-like Flowery Cooked apple Asparagus-like, putrid Cooked vegetable (corn, onion), garlic, H Quince, asparagine Asparagus, corn, molasses Asparagus-like, putrid Baked apple-like, grape juice-like -ionone) α -ionone) β -Damascenone β (E)-4-(2,6,6-Trimethylcyclohex-2-en-1-yl)but- 3-en-2-one (aka (E)-4-(2,6,6-Trimethylcyclohexen-1-yl)but-3- en-2-one (aka (E)- Sulfides and related compounds Dimethyl sulfide 448 A Threshold Data ] ] ] ] ] ] ] ] ] ] ] ] ] ] ] ] ] ] ] ] ] ] ] ] ] 447 198 447 152 528 152 528 152 152 147 152 636 455 152 152 147 198 303 321 152 152 303 455 455 303 [ [ [ [ [ [ [ [ [ [ [ [ [ [ [ [ [ [ [ [ [ [ References [ [ [ Light blended whisky Heavy blended whisky Malt whisky White wine White wine 12.5% Red wine 10% (w/w) Ethanol 20% Ethanol 34% (v/v) Grain whisky White wine Red wine Beer White wine White wine 12.5% Red wine Beer Model wine White wine 12.5% Grain spirit 23% (v/v) Grain whisky Model wine Water Model wine In Water Rectified spirit O O O O O dO O O O O O O O O T O T O O O rO dO O By rO O 9 , 2 1 93 3 10 2 4 009 5 016 005 ...... 0 0 4 3 5 6 0 4 0 1 0 6 0 2 0 0 45 29 30 15 18 40 25 20 20 Threshold [ppb] S 2 S 2 Cabbage-like Surfury Garlic Onion Descriptor Cooked vegetable (onion, garlic), H Garlic, burnt rubber, H Cabbage Cabbage-like Burnt, meaty (continued) Compound Dimethyl disulfide Dimethyl trisulfide Diethyl sulfide Diethyl disulfide Methyl-(2-methyl-3-furyl) disulfide Table A.1 A Threshold Data 449 ] ] ] ] ] ] ] ] ] ] ] ] ] ] ] ] ] (continued) 528 528 131 528 303 528 528 528 131 528 528 528 528 528 528 131 528 [ [ [ [ [ [ [ [ [ [ [ [ [ [ [ [ [ Beer Beer Beer Beer White wine 12.5% Water Water Beer Beer Beer Beer Water Beer Beer Beer Beer Beer T T T T O O O T T T T O T T T T T 07 , 6 000 1 5 08 2 20 7 7 002 15 ...... 2 0 0 1 2 0 0 0 1 0 0 0 20 16 120 250 000 , 23 S 2 Mashed potato, warm, soup-like Onion, rubber Putrefaction (of onion, garlic, egg) Putrefaction (of onion, garlic, egg) Putrefaction (of onion, garlic, egg) Putrefaction (of fruit (guava, peach),sunstruck, fish), Cat urine Cooked vegetable (garlic, onion, leek), ethereal, H estery egg) Sulfury, grainy, carbon disulfide Putrefaction (of leek, onion, garlic, egg) Putrefaction (of egg, cabbage), drains, Putrefaction (of onion, garlic, egg) Putrefaction (of onion, garlic, cheese, fish, Putrefaction (of onion, garlic, egg) Rubber, rotten onion, sulfury 3-Methylsulfanylpropanal (aka methional) 2-Methylthio acetaldehyde 2-Methylthio ethanol Methanethiol (aka methyl mercaptan) Ethanethiol (aka ethyl mercaptan) Propane-1-thiol (aka n-propyl mercaptan) Butane-1-thiol (aka n-butyl mercaptan) Butane-2-thiol (aka sec-butyl mercaptan) 1,3-Thiazole 2-Methylpropane-1-thiol (aka isobutyl mercaptan) 2-Methylpropane-2-thiol (aka tert-butyl mercaptan) 3-Methyl-1-butanethiol (aka isoamyl mercaptan) 2-Methylbutane-2-thiol (aka tert-amyl mercaptan) 2-Propan-2-ylsulfanylpropane (aka di-isopropyl sulfide) 1-Butylsulfanylbutane (aka di-n-butyl sulfide) 450 A Threshold Data ] ] ] ] ] ] ] ] ] ] ] ] ] ] ] ] ] ] 152 152 152 152 131 152 152 152 152 152 152 152 152 152 152 152 151 152 [ [ [ [ [ [ [ [ [ [ [ [ [ References [ [ [ [ [ White wine Red wine White wine Red wine White wine Red wine White wine Red wine Water Model wine White wine Red wine Model wine Model wine Model wine In Model wine, whitewine, red wine Model wine Model wine O O O O O O O O O O O O O O O By O O O 5 . 3 50 50 100 115 350 200 440 300 1500 1000 Nil Nil Nil Nil Threshold [ppb] Nil Nil Metallic, sulfury Mushroom, alliaceous Descriptor Rubber Alliaceous, muddy Odorless Chive (continued) Compound Ethyl 2-amino-4-(methylsulfanyl) butanoate (aka ethyl methionate) 3-Methylmethylsulfanylmethylpropyl acetate (aka methionyl acetate) 1,3-Benzothiazole 2-Methylthiophene-3-ol (cis) 2-Methylthiophene-3-ol (trans) 4-Methylthiobutan-2-ol 2-(2-Methylpropyl)-1,3-thiazole (aka 2-isobutylthiazole) Table A.1 A Threshold Data 451 ] ] ] ] ] ] ] ] ] ] ] ] ] ] ] ] ] ] ] ] 198 201 201 447 131 150 818 150 150 401 636 201 150 122 201 321 201 198 447 658 [ [ [ [ [ [ [ [ [ [ [ [ [ [ [ [ [ [ [ [ (continued) 100 g/L sucrose + Water Model wine White wine Red wine 10% Spirit 10% (w/w) Ethanol 20% Ethanol 23% (v/v) Grain whisky White wine Red wine Water 23% (v/v) Grain whisky 40% Ethanol Water Water 10% Ethanol 12% (v/v) Ethanol 10% Ethanol Water Water O O O O O O O dO O O O rO O O O O dO O O rO 0033 0033 0001 5 2 84 0008 6 ...... 0 0 3 3 0 5 9 0 0 1 20 95 75 10 60 30 700 0.000,066, 0.000,165 0.000,990, 0.001,18 0.000,792, 0.001,98 Cat urine Box tree, broom Smoky, sweet Smoke Smoky Phenolic Smoky, sweet 4-Mercapto-4-methyl-2-pentanoneone (aka cat urine ketone) Phenolics 2-Methoxyphenol (aka guaiacol) 452 A Threshold Data ] ] ] ] ] ] ] ] ] ] ] ] ] ] ] ] ] ] ] ] 198 149 198 656 658 151 198 198 150 150 150 150 150 150 149 151 401 150 150 528 [ [ [ [ [ [ [ [ [ [ [ [ [ [ [ [ References [ [ [ [ Model wine White wine Red wine Model wine White wine Red wine Model wine Water Model wine 10% Spirit Water Water Beer 40% Ethanol Water 40% Ethanol Water Water In Water Water O O O O O O O O O O O O O T O dO rO dO By rO O 6.9 30 65 65 47 70 150 47 25 47 33 25 10 231 130 Threshold [ppb] 4.4 30 21 16 25 Vanilla-like, clove-like, smoky Vanilla-like, clove-like, smoky Burned, hearth Smoky, phenolic Smoky, gammon-like Spicy, smoke Phenolic, sweet Phenolic, clove-like Descriptor Smoky, gammon-like Woody, spicy, smoky, phenolic (continued) Compound 2-Methoxy-4-methylphenol (aka 4- methylguaiacol, p-methoxyguaiacol, creosol) 4-Ethyl-2-methoxy-phenol 4-Ethyl-2-methoxyphenol (aka 4-ethylguaiacol) Table A.1 A Threshold Data 453 ] ] ] ] ] ] ] ] ] ] ] ] ] ] ] ] ] ] ] ] ] (continued) 198 447 198 447 131 150 150 150 150 150 150 401 791 150 321 321 150 528 198 198 658 [ [ [ [ [ [ [ [ [ [ [ [ [ [ [ [ [ [ [ [ [ Water 10% (w/w) Ethanol Model wine White wine Red wine 10% (w/w) Ethanol Model wine White wine Red wine 10% Spirit 20% Spirit 23% (v/v) Grain whisky Water 23% (v/v) Grain whisky 40% Ethanol Beer Water Water Water Water Water O O O O O O O O O dO O O O rO dO O rO O T dO rO 0.71 7.1 2.5 5 50 5.1 40 15 11 32 19 130 440 380 200 6 100 500 2000 7 300 Clove-like, smoky Clove-like, smoky Carnation pepper Phenolic, bitter Spicy Clove-like Clove Clove-like Clove-like 4-Ethenyl-2-methoxyphenol (aka 4-vinylguaiacol) 4-Allyl-2-methoxyphenol (aka eugenol) 454 A Threshold Data ] ] ] ] ] ] ] ] ] ] ] ] ] ] ] ] ] ] ] ] ] ] ] ] 198 198 198 401 150 150 401 791 150 401 401 150 150 150 791 150 656 150 150 656 150 150 150 198 [ [ [ [ [ [ [ [ [ [ [ [ [ [ [ [ [ [ [ [ [ References [ [ [ 10% Spirit Model wine White wine Red wine 10% Spirit 20% Spirit 40% Ethanol Model wine White wine Red wine 10% Spirit 10% Spirit Model wine White wine Red wine 20% Spirit 40% Ethanol Water Water Water Water In Water Water Water O O O O O O O O O O O O O O O O O dO O dO By O rO rO 5 9 . . 3 60 31 90 68 10 28 15 85 45 31 10 000 000 000 000 120 800 300 200 380 180 , , , , 7100 5500 15 35 25 40 Threshold [ppb] Smoky, phenolic Pharmaceutical Fecal, horse stable-like Ink Descriptor Bitumen Fecal, horse stable-like Smoky, phenolic (continued) Compound Phenol 2-Methylphenol (aka o-cresol) 3-Methylphenol (aka m-cresol) 4-Methylphenol (aka p-cresol) Table A.1 A Threshold Data 455 ] ] ] ] ] ] ] ] ] ] ] ] ] ] ] ] ] ] ] ] ] (continued) 149 528 151 150 150 401 791 150 150 150 149 150 150 150 150 150 198 150 656 150 198 [ [ [ [ [ [ [ [ [ [ [ [ [ [ [ [ [ [ [ [ [ Water Model wine Model wine 10% Spirit 20% Spirit Model wine White wine White wine Red wine Red wine Model wine White wine Red wine Water 40% Ethanol Water Water Water Beer Water Water O O O O O O O O O O O O O dO O O O O T rO O 13 85 21 140 230 440 140 600 180 770 173 130 130 300 400 1100 1200 1500 1700 1500 2000 Phenolic Stable, horse Phenolic, animal Phenolic, astringent Phenolic Datura, gouache Phenolic Smoke 4-Ethylphenol (aka p-ethylphenol) 4-Ethenylphenol (aka 4-vinylphenol, p-vinylphenol) 1,3-Dimethoxy-2-hydroxybenzene (aka syringol) 456 A Threshold Data ] ] ] ] ] ] ] ] ] ] ] ] ] ] ] ] ] ] ] ] 150 370 488 488 150 150 150 150 150 150 150 488 488 488 488 150 150 150 150 150 [ [ [ [ [ [ [ [ [ [ [ [ [ [ [ [ [ [ [ [ References 10% Ethanol 40% Ethanol Water 10% Ethanol 40% Ethanol Model wine White wine Red wine Model wine White wine Red wine Model wine White wine Red wine Water Water Water Water Water Water In O O O O O O O O O O O O O O O O O O O T By 000 000 000 000 000 000 000 000 000 000 000 000 , , , , , , , , , , , , 3000 9000 2500 8500 8000 1300 1200 3000 15 10 30 15 15 12 15 25 25 52 210 >50 Threshold [ppb] Puckering astringency Spicy, smoke Woody, vanilla Vanilla Descriptor (continued) Compound 4-Hydroxy-3,5-dimethoxybenzoic acid (aka syringic acid) 4-Hydroxy-3,5-dimethoxybenzaldehyde (aka syringaldehyde) 4-Allyl-2,6-dimethoxyphenol (aka 4- allylsyringol) 1-(4-Hydroxy-3-methoxyphenyl)ethanone (aka acetovanillone) Ethyl 4-hydroxy-3-methoxybenzoate (aka ethyl vanillate) Table A.1 A Threshold Data 457 ] ] ] ] ] ] ] ] ] ] ] ] ] ] ] ] ] ] ] ] ] ] 198 447 658 198 370 488 447 150 150 488 150 488 488 636 150 321 488 488 656 528 528 656 (continued) [ [ [ [ [ [ [ [ [ [ [ [ [ [ [ [ [ [ [ [ [ [ Water Model wine White wine Red wine 10% Ethanol 10% (w/w) Ethanol 40% Ethanol 20% Ethanol 23% (v/v) Grain whisky Water 10% Ethanol 40% Ethanol Model wine 23% (v/v) Grain whisky 40% Ethanol 40% Ethanol 40% Ethanol Beer Beer Water Water Water O O O O O O O O dO O O O O rO O O O T T rO dO T 32 89 . . 0 1 65 22 53 000 000 000 400 320 500 200 100 100 600 105 000 000 210 000 , , , , , , 2000 3000 85 45 30 13 690 660 Vanilla-like, sweet Vanilla-like, sweet Vanilla Vanilla Vanilla-like Smoky Phenolic Astringent Puckering astringency Astringent 4-Hydroxy-3-methoxybenzaldehyde (aka vanillin) 5-Methyl-2-methoxyphenol (aka 6-methoxy-m-cresol) 4-Propyl-2-methoxyphenol (aka 4-propylguaiacol) (E)-3-(3,4-Dihydroxyphenyl)prop-2-enoic acid (aka caffeic acid) (E)-3-(4-Hydroxy-3-methoxyphenyl)prop-2- enoic acid (aka ferulic acid) 458 A Threshold Data ] ] ] ] ] ] ] ] ] ] ] ] ] ] ] ] ] ] ] ] ] ] 370 370 528 370 528 370 885 885 885 885 297 488 885 488 488 488 488 488 488 528 791 370 [ [ [ [ [ [ [ [ [ [ [ [ [ [ [ References [ [ [ [ [ [ [ Water 10% Ethanol 40% Ethanol 10% Ethanol 40% Ethanol 10% Ethanol 40% Ethanol Beer Beer Water Water Beer Water Water Water Water In Water Water 20% Spirit Water Water Water O O O O O O O T T T T T T T T By T T O T T T T 5 , 000 003 6 . . . 4 0 0 0 23 000 000 000 000 000 000 000 000 000 000 000 500 000 000 000 970 , , , , , , , , , , , , , , , 5000 25 25 25 80 50 23 50 80 32 44 140 100 360 520 533 Threshold [ppb] Puckering astringency Vanilla, sweet, astringent Puckering astringency Astringent, phenolic Puckering astringency Astringent Descriptor Puckering astringency Phenolic/iodine Phenolic Puckering astringency Phenolic Iodoform Iodoform Astringency (continued) Compound 4-Hydroxy-3-methoxybenzoic acid (aka vanillic acid) (E)-3-(4-Hydroxy-3,5-dimethoxyphenyl)prop- 2-enoic acid (aka sinapic acid) 3-(4-Hydroxy-3,5-dimethoxyphenol)prop-2- enal (aka sinapaldehyde) (E)-3-(4-Hydroxyphenyl)prop-2-enoic acid (aka para-coumaric acid) 3,4,5-Trihydroxybenzoic acid (aka gallic acid) 2,3-Dimethylphenol (aka 2,3-xylenol) Protocatechuic acid (E)-Caftaric acid 2-Bromophenol 4-Bromophenol 2,4-Dibromophenol 2,6-Dibromophenol 2,4,6-Tribromophenol Table A.1 A Threshold Data 459 ] ] ] ] ] ] ] ] ] ] ] ] ] ] ] ] ] ] ] ] ] (continued) 317 658 198 198 198 198 247 247 131 247 247 198 131 247 198 198 198 528 658 317 317 [ [ [ [ [ [ [ [ [ [ [ [ [ [ [ [ [ [ [ [ [ Water Water Water Water Water Not specified 40% Ethanol Not specified Water Water Water 40% Ethanol Beer Not specified Water Water Water Water Water Water Water O O O O O O dO O dO O O O dO T dO O O rO rO rO rO 5 7 5 1 6 . . . . . 7 7 6 9 1 1 7 1 2 11 21 21 24 27 400 200 400 400 420 1600 1600 Coconut-like Fruity, strawberry Fruity, coconut Coconut-like Coconut-like Coconut-like Peach-like, coconut-like Apricot, peach Peach-like Fruity, peach Coconut-like Coconut-like Coconut-like Peach-like, coconut-like -heptalactone) -nonalactone) -decalactone) -octalactone) -hexalactone) γ γ γ -octalactone) γ γ δ -octalactone) -decalactone) -octalactone) γ γ γ Lactones 5-Ethyloxolan-2-one (aka 5-Propyloxolan-2-one (aka 5-Butyloxolan-2-one (aka (5R)-5-Butyloxolan-2-one (aka (R)- (5S)-5-Butyloxolan-2-one (aka (S)- 6-Propyloxan-2-one (aka 5-Pentyloxolan-2-one (aka 5-Hexyloxolan-2-one (aka (5R)-5-Hexyloxolan-2-one (aka (R)- 460 A Threshold Data ] ] ] ] ] ] ] ] ] ] ] ] ] ] ] ] ] ] ] ] ] ] ] ] 317 447 198 247 2 320 198 149 447 320 247 149 723 150 150 150 118 118 610 641 198 198 528 150 [ [ [ [ [ [ [ [ [ [ [ [ [ [ [ [ [ [ [ [ [ References [ [ [ Water Water Model wine 34% Spirit Model wine 9% White wine White wine 14.5% Red wine Red wine 30% Ethanol Gas 23% (v/v) Grain whisky Not specified 23% (v/v) Grain whisky Water Water Model wine Beer 10 ppm Sucrose 10% Ethanol Water In Water Water O O O O O O O O O O dO O dO O dO dO O T T O O By O rO rO 43 6 0 . . . 7 1 0 5 2 15 51 25 24 92 57 74 31 28 20 51 100 300 790 400 7000 Threshold [ppb] Fruity, peach Coconut-like Peach, apricot, dull Peach-like Coconut, woody, polish, resin Coconut Light coconut, musty, hay Spicy, coconut-like Coconut, oak Descriptor Sweet woody Coconut-like Peach-like -dodecalactone) -decalactone) γ δ -octalactone γ -Methyl- -octalactone, whisky lactone) β (continued) γ -decalactone) γ -methyl- Compound (5S)-5-Hexyloxolan-2-one (aka (S)- 6-Pentyloxan-2-one (aka 5-Octyloxolan-2-one (aka 5-Butyl-4-methyloxolan-2-one (aka β (4S,5S) cis- (cis/trans mixture) Table A.1 A Threshold Data 461 ] ] ] ] ] ] ] ] ] ] ] ] ] ] ] ] ] ] ] (continued) 150 320 320 320 2 150 150 150 118 610 118 118 641 320 118 118 320 118 320 [ [ [ [ [ [ [ [ [ [ [ [ [ [ [ [ [ [ [ Model wine 9% White wine White wine 14.5% Red wine Red wine 30% Ethanol Gas 9% White wine 14.5% Red wine 9% White wine 14.5% Red wine 10% Ethanol Model wine 10 ppm Sucrose 10 ppm Sucrose 10% Ethanol 10 ppm Sucrose 10% Ethanol O O O O O O O O O T O O O T O O T O O 67 20 64 110 172 460 380 320 132 175 305 285 Spicy, celery, slight coconut, green walnut Coconut-like, sweet, creamy, fatty Coconut, oak Sweet, woody, coconut Creamy, coconut Coconut, celery Spicy Coconut -octalactone -octalactone (not γ γ -octalactone (not γ -Methyl- -Methyl- β β -Methyl- β naturally occurring) (4S,5R) trans- (4R,5R) cis- (4R,5S) trans- naturally occurring) 462 A Threshold Data ] ] ] ] ] ] ] ] ] ] ] ] ] ] ] 660 660 660 660 247 660 507 198 198 785 660 247 321 513 424 [ [ [ [ [ [ [ [ [ [ [ References [ [ [ [ White wine Wine 10% (w/w) Ethanol Water Water 12% Ethanol 12% Ethanol 12% Ethanol Water Water Water 12% Alcohol solution Water In White wine White wine O O O O O O O O rO dO O O O By O O 001 8 1 49 5 . . . . . 8 5 0 2 0 1 0 2 5 15 89 150 121 2000 Threshold [ppb] 1–50 Seasoning-like, spicy Seasoning-like, spicy Bouillon-seasoning, walnut Caramel Sugar-like, caramel-like Curry, walnut Walnut, rancid Curry, walnut Descriptor (continued) Compound 3-Hydroxy-4,5-dimethylfuran-2(5H)-one (aka sotolon) (R)-3-Hydroxy-4,5-dimethylfuran-2(5H)-one (S)-3-Hydroxy-4,5-dimethylfuran-2(5H)-one 6-[(Z)-Pent-2-enyl]oxan-2-one (aka (Z)-dec-7-en-5-olide, jasmine lactone) 6-Pentylpyran-2-one Table A.1 A Threshold Data 463 ] ] ] ] ] ] ] ] ] ] ] ] ] ] ] ] ] ] ] ] ] ] 150 447 528 150 447 528 723 131 528 528 150 150 150 150 150 150 150 150 150 150 528 131 (continued) [ [ [ [ [ [ [ [ [ [ [ [ [ [ [ [ [ [ [ [ [ [ 34% Spirit Model wine White wine Red wine Model wine White wine Red wine Model wine White wine Red wine 23% (v/v) Grain whisky Water Water 23% (v/v) Grain whisky Beer Water Beer Beer Water Beer Water Beer O O O O dO O O O O O O O rO O T O T O T T O T 6 000 000 000 000 000 000 000 000 000 000 000 000 000 000 000 000 , , , , , , , , , , , , , , , , 5800 8000 6000 3000 1000 15 65 20 39 16 52 45 15 35 45 20 80 000 210 150 000 , , 1 >3 Almond Paper, husk Grainy Grilled almonds Almonds, burnt/phenolic, pyrazole Sugar cane, woody Aldehyde, stale, vegetable oil Hay, verbena Almonds, rubber, burnt/phenolic, pyrazole Furans Furan-2-carbaldehyde (aka furfural) 5-Methylfuran-2-carbaldehyde (aka 5-methylfurfural) 2-Furanmethanol (aka furfuryl alcohol) 2-Pentylfuran 5-(Hydroxymethyl)furan-2-carbaldehyde (aka 5-(hydroxymethyl)furfural) 1-(Furan-2-yl)ethanone (aka 2-acetylfuran) 464 A Threshold Data ] ] ] ] ] ] ] ] ] ] ] ] ] ] ] ] ] ] ] 528 131 370 370 370 528 216 370 370 370 370 528 370 636 216 321 658 370 370 [ [ [ [ [ [ [ [ [ [ References [ [ [ [ [ [ [ [ [ Water 10% (w/w) Ethanol 20% Ethanol Water 40% Ethanol Beer Water Water Water Beer Water In Water Beer Water Water Water Water Water Water O O O T T O T T T T By T T T T T T T T T 10 50 10 100 719 000 000 000 000 000 000 200 100 , , , , , , , 1000 8900 1000 1700 1100 2100 46 10 270 290 250 119 270 Threshold [ppb] Vanilla, cinnamon, bitter, perfume Astringent, bitter Fruity Musty Bitterness Bitterness Descriptor Astringency Astringency Velvety astringency Velvety astringency Velvety astringency Velvety astringency Velvety astringency Velvety astringency -L-rhamnoside α -L-rhamnoside α -D-glucopyranoside β -D-glucopyranoside -D-glucuropyranoside -D-galactopyranoside β β β (continued) )-Epicatechin )-Catechin − + Compound (E)-3-(Furan-2-yl)prop-2-enal (aka furylacrolein) Terpenes 1-Methyl-4-(1-methylethenyl)-cyclohexene (aka limonene) Glycosides Quercitrin Ethers 1,1-Diethoxyethane (aka acetal, acetaldehyde diethyl acetal) 1,2,4-Trichloro-3-methoxybenzene (aka 2,3,6-trichloroanisole) Flavonols Quercetin-3-O- Quercetin-3-O- Dihydrokaempferol-3-O- Dihydroquercetin-3-O- Isorhamnetin-3-O- Syringetin-3-O- ( ( Table A.1 A Threshold Data 465 ] ] ] ] ] ] ] ] ] ] ] ] ] ] ] ] ] ] ] ] ] ] ] (continued) 297 297 297 297 297 297 297 297 297 297 297 297 297 297 297 297 297 370 216 297 297 297 370 [ [ [ [ [ [ [ [ [ [ [ [ [ [ [ [ [ [ [ [ [ [ [ Water Water Water Water Water Water Water Water Water Water Water Water Water Water Water Water Water Water Water Water Water Water Water T T T T T T T T T T T T T T T T T T T T T T T 600 100 100 000 100 210 210 090 490 500 500 100 700 500 500 000 , , , , , , , , , , , , , , 5370 5550 1030 1030 1990 2500 1690 14 12 12 655 460 437 231 535 159 199 372 578 578 139 , , , , , , 1 1 1 1 1 1 Bitterness Bitterness Bitterness Bitterness Bitterness Bitterness Bitterness Bitterness Bitterness Bitterness Astringency Astringency Astringency Astringency Astringency Astringency Astringency Astringency Astringency Astringency Astringency Astringency -d-glucose β Tannins, Ellagitannins Tannic acid Grandinin 33-Deoxy-33-carboxyvescalagin 1,2,3,4,6-Pentagalloyl- Ellagic acid Roburin A Roburin B Roburin C Roburin D Roburin E Vescalagin Castalagin Procyanidin B1 466 A Threshold Data ] ] ] ] ] ] ] ] ] ] ] ] ] ] ] ] ] ] ] ] 140 370 426 192 426 316 316 370 370 370 216 316 19 140 370 370 370 140 140 140 [ [ [ [ [ [ [ [ [ [ [ [ References [ [ [ [ [ [ [ [ Water Water Water Water Water Water Water Water White wine Water Water Water Water Water Water In Water Water Water Water Water O O T O O T T T T T O O By T T T O O O O O 950 300 000 000 000 000 460 000 000 400 000 400 000 000 000 000 , , , , , , , , , , , , 2500 1800 9000 1000 17 60 22 35 280 289 347 110 116 260 500 100 Threshold [ppb] Bitterness Bitterness Bitterness Puckering astringency Descriptor Strong sweet, slightly ammonical Astringency Astringency Astringency Bitter Chocolate character Pungent, chocolate Pungent, chocolate Pungent, chocolate (continued) 5kDa) > )-Lyoniresinol + Compound Procyanidin B2 Procyanidin B3 Procyanidin C1 Polymeric tannin fraction ( Lignans ( N-cyclic Pyridine Pyrazine 2-Methylpyrazine 2,3-Dimethylpyrazine 2,5-Dimethylpyrazine 2,3,4-Trimethylpyrazine 2,3,5-Trimethylpyrazine 2,3,5,6-Tetramethylpyrazine Table A.1 A Threshold Data 467 ] ] ] ] ] ] ] ] 426 921 172 140 316 132 316 444 [ [ [ [ [ [ [ [ Water Water Water 20% Ethanol Water Water Water Water O O T O T O O O 1 067 . . 0 0 40 10 000 120 , 6000 22 2.4–3.8 Popcorn, cooked oatmeal, cooked rice, sweet Popcorn, cereal Iodine Copper Strong galbanum note 2-Ethylpyrazine 2-Ethyl-3-methylpyrazine 2-Isopropyl-3-methoxypyrazine 1-(3,4-Dihydro-2H-pyrrol-5-yl)ethan-1- one,(aka 2-acetyl-1-pyrroline) Miscellaneous Iodine Copper II References

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A Barrel Acrospire, 85, 116 anatomy, 280 Adam, Jean-Édouard, 13 capacity, 367–371, 415 Adams-Bashforth, 385 char, 28, 259, 307 Aerometer, 390 charred vs. uncharred, 262 Agonists, 47 entering proof, 39 Alcohol and Tobacco Tax and Trade Bureau standard size, 39 (TTB), 41, 333, 395, 396, 399 surface to volume ratio, 313 Allen, Alfred Henry, 260 ullage, 368, 372–373, 418 Allen-Marquardt, 261, 270 variety, 368–370 Allt A’Bhainee, 110 Bear, 5 Animal feed, 122 Beer, 24, 26, 31, 32, 241, 246, 247, 250, 251 Antagonists, 47 Benriach, 106 Antoine’s equation, 201 Benrinnes, 110 ethanol, 201 Bere, 5 water, 201 Bilge, 280 Aqua vitae, 2, 4 Biological oxygen demand, 86 Ardbeg, 106, 109, 110, 165 Birefringence, 123 Aroma, 46 Black Bush, 106 Aroma extract dilution analysis (AEDA), 64, Bluing, see haze 65, 310 Boll, 2, 9 Aroma standards, 70 Bonaparte, Charles Joseph, 37 Association of Official Analytical Chemists Bond number, 403–405, 407, 408, 411 (AOAC), 385 Bottled in bond, 33, 34, 42 Auchentoshan, 110 Bourbon, 40, 65–78, 262–264, 266, 268, 285, Auchriosk, 110 292, 293, 295, 296, 301, 307, 314, Aultmore, 110 315 Azeotrope, 194 barrel, 260, 274, 281, 307 compared to rye, 81 special status, vii B Bowmore, 107, 110 Bacon, 104 Box, George Edward Pelham, 323 Bain Marie, vi, 24 Boyle, Robert, 387 Ballentines, 107 Braeval, 110 Barnard, Alfred, 15 Brewer’s points, 90

© Springer Nature Switzerland AG 2019 507 G. H. Miller, Whisky Science, https://doi.org/10.1007/978-3-030-13732-8 508 Subject Index

Briggs, Henry, 371 Crow, James, 29 Bruichladdich, 106, 107 Cucumber, 98, 443 Brunswig, Heironymous, 2 Bubble curve, 193 Bung, 280 D Bunnahabhain, 106, 110 Dailuaine, 112 Burns, Robert, 367 Darcy’s law, 132, 133 Debye, Peter Joseph William, 134 Densitometer C hydrometer, 7, 376, 387, 391 Cabin Still, 106 vibrating tube, 174, 412 Cachaça, 116 Dephlegmator, 116, 117, 165 Cake, 132 Dew curve, 193 Cambus, 15 Diageo, 166 Cameron Bridge, 15 Diagonal rod, 368 Cameron Brig, 106 Differential scanning calorimeter (DSC), 124, Cannon Mills, 9, 12 126, 332 Caol Ila, 106, 109, 110 Dip rod, 368 Caprice, legislative, 393 Dissolved solids, 264, 272, 315 Caramel, 22, 24, 41, 84, 109, 301, 307, Distillers Company Limited (DCL), 22, 42, 318–321, 428, 445, 462 143, 166, 174 Carlisle, John Griffin, 34 Dog Cat urine, 170, 449, 451 panting, 189 Cellulose, 135 wet, 430 Char, 28, 259, 307 Doig, Charles Chree, 112 Charles Mackinlay & Co., 178 Doubler, 25, 26, 31, 32, 168, 224, 226, 228, CHARM, 64 229, 246, 248–250 Chaucer, Geoffrey, 3 Douglas, Sylvester, 10 Chime, 280 Draper, Norman Richard, 323 Chugging, 189 Civil War English, 5, 117 E US, 26–29, 39, 42, 393, 394 Earlywood, 277 Coffee, 101, 176 Edradour, 165 Coffey still, 29 Ehrlich pathway, 144, 146, 147, 151 Coffey, Aeneas, 15 Elijah Craig, 106 Cologne spirits, 29, 31, 33, 34, 42 Enthalpy, 339, 351, 352 Color, 259, 263, 264, 272, 315 excess, 202, 327–329 effect of entry proof, 315 partial molar, 327, 328 Condenser formation, 202 shell and tube, 22, 172, 189 gelatinization, 126 worm, 6, 22, 25, 172 hydration, 129 Constant molar overflow, 198, 244 phase diagram, 197 Control volume, 230–232, 234, 236, 237, 250, vaporization, 202, 327 383 Entropy, 202, 324, 327, 339, Copper 351, 352 catalysis, 116, 174 excess, 329 mineralization, 170 Equilibrium constant, 178 sulfur removal, 170 Ergun equation, 134 tinned, 169 Ester hydrolysis, 173, 251 Craigend, 10 Everard, Thomas, 371, 373, 414 Critical micelle concentration (CMC), 339, Eötvös number, 403 343, 353 Subject Index 509

F Gravity Federal Alcohol Administration, 38 degrees, 90 Feed, 122 Grist, 132 Feints, 5, 24, 208, 218, 222, 224, 225, 229, 251 Grist box, 121 Fischer-Speier mechanism, 174 Grist-water ratio, 127, 128, 136 Fitzgeralds, 106 Grog, 260, 310 Flame ionization detector (FID), 65, 362 Gunter, Edmund, 371, 414 Flavor, 46 Guymon, James, 179, 244, 265, 268 Flavor dilution index (FD), 65 Flavor wheel, 58, 60 H Fluorescence, 296 Hall, Harrison, 122 Ford, Henry, 176 Hamilton, Alexander, 390, 392 Fordham, Edward Snow, 20 Hangovers, 175, 260 Franklin, Benjamin, 23 Hastie, Stuart Henderson, 166–168, 173, 176, Free amino nitrogen (FAN), 87, 88, 150, 151 250 French, John, 3, 24 Haze, 22, 42, 138, 297, 361 Fresh weight basis, 85 Hazelburn, 18, 165, 174 Fungus, 143, 306 Heat capacity Fusel oil, 19, 264, 271 ethanol, 202 excess, 203 water, 202 G Heaven Hill, 106 Gall, 5 Helix, double, 123 Galletti, Antoni, 376 Hemicellulose, 265 Gas chromatograph (GC), 362 High wines, 24 Gas chromatograph olfactometer (GCO), 64, High-performance liquid chromatography 65 (HPLC), 282, 303, 304, 313, 318 Gas chromatography mass spectroscopy High-resolution gas chromatograph (HRGC), (GCMS), 81, 104, 304, 305, 312, 65 318 Highland line, 7 Gas liquid chromatography (GLC), 316 Highland Park, 110 Gauge points, 415 Hiram Walker, 38, 314 line of, 416, 417 Hohenheimer, 107 Gauging tables, 333, 395–399 Holdup, 196, 220, 221, 252 Gelatinization, 122, 125, 126, 137 Hoop, 280 enthalpy, 125, 126 Hough, Warwick Massey, 23, 34, 36, 38 kinetics, 125 Husk, 121, 122, 132, 136, 138, 139 temperature, 123, 125 Hydrometer malting and, 125 Boyle, 387 Gibbs, 198 Clarke, 7, 375, 387, 388 Gillespie, Robert, 26 Dicas, 391, 392, 419 Glen Elgin, 110 force balance, 378 Glen Garioch, 107 how to read, 377 Glen Scotia, 107 jar, 382 Glenfarclas, 110 sensitivity, 379 Glenfiddich, 69, 71, 73 Sikes, 375, 388, 419 Glengoyne, 110 Glenlivet, 12, 17 The Glenlivet, 107 I Glenlossie, 110 Iceberg model, 326 Glenochil, 15 Inoculation level, 146 β-Glucanase, 110 Internal Revenue Service (IRS), 333 Glycolysis, 144 The Invergordon, 106 Granules, starch, 123 Islington, 20, 37, 42 510 Subject Index

J Maillard, 22, 101, 107, 176, 178, 190, 307 Jack Daniels, 107 Maize, 21, 23, 28, 38, 40, 70, 90, 119, 122, 125, Jackson, Andrew, 186 126, 137, 141, 161 Jameson, 106, 107 Malt, 2, 83–119 Jefferson, Thomas, 26, 392 green, 98 Jim Beam, 67, 70, 72, 76, 77, 80, 107 slack, 130 Johnnie Walker, 107 Maple, 309, 428 Johnston, Donald, 131, 162, 198 Marriage, 321 Joule, James Prescott, 131 Martin, Martin, 4 Juggler, 393 Martyrdom, 260 Jura, 107 Mash, 9, 21, 23, 24, 40, 43, 83, 86, 89, 91–93, 95, 97, 109, 110, 112, 119, 121–141, 150, 151, 153, 158, 159, 161–163, K 261, 300 Kelvin, 385 sour, 158, 262, 263 Kepler, Johannes, 367, 419 sweet, 262, 263 Keto acid overflow theory, 150 Mashing-in temperature, 136 Kirliston, 13 Maturation Knockando, 106 in glass, 262 McCabe-Thiele, 198 McCulloh, Richard Sears, 393 L Mealy, barley, 84, 86 Lactobacilli, 158 Medullary ray, 278, 280 Lagavulin, 105–107, 109, 110 Mendeleev, Dmitri, 324, 397 Landseer, Sir Edwin, 11 Mill, 121 Laphroaig, 69, 71, 75, 105–107, 109, 110 Mist transfer, 180 Lautering, 132 Misting test, 185 Le Châtelier’s principle, 269 Modification, 83 Lee, Robert Edward, 394 Molar overflow, 198 Lever rule, 195 Moor’s head, 116, 117 Light whisky, 39–41 Morewood, Samuel, 3, 15 Lignin, 137 Mortlach, 106 Lincoln, Abraham, 393, 394 Mucus, 49, 50 Lipids, 98, 150 Multivariate curve resolution – alternating least Liter absolute alcohol (LAA), 374 squares (MCR-ALS), 348, 350 Lobry de Bruyn—Alberda van Ekenstein transformation, 319 Loftus, William Robert, 17 N Longmorn, 106, 312 Napier, John, 414 Lord Rayleigh, 205 Navier-Stokes equation, 405–407, 409 Lovibond Nettleton, Joseph Alfred, 21, 159 #52 for whisky color, 263 Newton, Isaac, 374 Low wines, 5, 7, 24, 207, 208, 218, 222, 225, Niemcewicz, Julian Ursyn, 122 251 Nikka, 276 Lower explosive limit (LEL), 188 Non-random two-liquid (NRTL), 252 Lower flammability limit (LFL), 186 Nuclear magnetic resonance (NMR), 347 Lyne arm, 6, 11, 165

O M Oak M’Harry’s Practical Distiller, 259 and maturation, 259–277 M’Harry, Samuel, 122 aroma, 460, 461 Macallan, 110 barrels, 22, 40 The Macallan, 69, 71, 75, 106 charred barrels, 28, 39 Subject Index 511

charring, 306–310 Proof, 264, 265 constituents, 281–302 change and climate, 265 diffusivity, 277 Clarke, 7 extract, 354, 356, 362, 363 classes, 391, 392 new barrels, 39 Dicas, 391, 392 new charred barrels, 38–40, 42, 268, entry, 315 357 Gay-Lussac, 374 new uncharred barrels, 40 measurement, 374–387 seasoning, 302–306 Sikes, 2 slow vs. fast growth, 277 Tralles, 374 structure, 277–281 UK, 374 toasting, 306–310 definition, 388 Oats, 4, 5, 42, 85, 117 vs US, 388 Odor activity value (OAV), 64, 69 Proof gallon (PG), 374, 389 Odor referral, 46 Psychophysics, 54 Old Pulteney, 107 Puff von Schrick, Michael, 2 Old Weller, 400, 401 Puking, 189, 190 Olfactory epithelium, 46, 49 Pure Food and Drug Act, 34 Omission test, 77 Purifier, 165 Orange juice, 151 Pycnometer, 376 Organization Internationale de Métrologie Légale (OIML), 388 Oughtred, William, 371, 414 Q Quarter, 86, 117 Quartersawn boards, 280 P Pagoda, 112 R Panting, 189 R-index, 78 Partial least squares (PLS), 82, 109, 110 Rachilla, 84 Partition coefficient, 49, 178, 190 Raoult’s law, 199 Passions, 34 Receiver operating characteristic (ROC), 78 Pasteur, Louis, 163, 260 Rectifier, 24, 309 Patent still, 15 Red Book of Ossory, 2 Pear drops, 268 Redlich-Kister correction, 180 Peat, 107 Reflux, 220, 246 Penderyn, 105 Residence time, 251 Pennant, Thomas, 5 Rice hulls, 132 Pentosan, 136 Rittenhouse, 80 Pericarp, 84, 136 Roosevelt, Theodore, 37 Permeability, 132 Rouse, Prince Earl, Jr., 134 Persistence, 50 Royal Commission on Whisky, 21, 176, 261, pH, 264, 267 262 Philosophical bubbles, 375, 376 Rummager, 11 Phylloxera, 27 Rye, 4, 23, 29, 30, 40, 41, 79, 80, 82, 85, 90, Physiology, 276, 322 119, 122, 132, 262–264, 314, 315 Pigs, 122 Pitch rate, 146, 150 PK, 219 S Ponchon-Savarit diagram, 203 Saccharification, 125 Popcorn, 178, 188, 467 Sample dilution analysis (SDA), 81 Pressure oscillation, 22, 189 Saponification, 268 Principal component analysis (PCA), 312 Sawdust, 307 Prohibition, 29, 38, 39, 168, 263, 390, 394, 396, Schidrowitz, Philip, 42, 173, 251, 262, 270 397 Scotch Whisky Regulations, 21 512 Subject Index

Scottish Malt Distillers Limited (SMD), 174 Teed, Frank, 20 Scutellum, 84 Tennessee process, 309 Seagram, 39, 150, 268, 289, 315 Testa, 84 Select Committee on British and Foreign Thermal conductivity detector (TCD), 90, 363 Spirits, 18 Thermogram, 124 Sensory evaluation, 55 Thump keg, 168 Shackleton, Ernest Henry, 178 Tobacco, 309 Shakespeare, William, 3 Tovey, Charles, 16 Sherry, 259, 260, 262, 301, 316, 442 Trestarig, 4 Sieve tray, 121 Triangle test, 71 Sikes, Bartholomew, 388 Trigeminal nerve, 46 Singlings, 24, 259 Tun, 132 Slack malt, 130 Tyloses, 277 Slaking heat, 128–130 Slop odor, 263 Smith, Adam, 9 U Smith, Elizabeth Grant, 12 Ullage, 196, 368, 372–373, 418 Soap, 173, 189 United Distillers, 166 Solid-phase microextraction (SPME), 310 Upper flammability limit (UFL), 186 Sour mash, 158, 262, 263 Usher, Andrew, 17 Southern Comfort, 107 Usquebaugh, 3, 4 Spagirical operations, 374, 375 -baul, 5 Spirit whisky, 40 Springbank, vii, 118 V Stanyhurst, Richard, 2 Van Krevelen diagram, 320 Starch, 123 Van Laar’s model, 201 Stave, 280 Vapor liquid equilibrium (VLE), 198–205, 354 Steam, 22, 190 Ventilator, 112 Steely, barley, 85, 86 Virginia Gentleman, 106 Stein, Robert, 13 Viscosity, 91–95, 97, 110, 119, 128, 132, Stewart, Potter, 1 134–136, 337–338, 349, 405–410 Still Volstead act, 27 beer, 25 low wine, 6 wash, 6 W Stokes-Einstein relation, 349 Wantage, 372 Straight Warehouse vs. crooked, 37 bonded, 16, 27 whisky, 28, 34, 37, 38, 40 heated, 262 Strecker degredation, 104 Washback, 158, 173 Strike temperature, 129 Washington, George, 122, 186 Suntory, 293 Wet dog, 430 Surface tension, 193, 338, 378–380, 382, 383, Wheat, 9, 40 385, 401, 404, 405, 410 Whisky Sutton, Marvin ‘Popcorn’, 188 additives, 41, 316–321 crooked, 37 light, 39–41 T regulation Taft, William Howard, 37, 38 Scotland, 21 Tamdhu, 106 US, 40 Tannins, 264, 271, 273, 276, 277, 281, 288, science, 1–467 295, 303, 306, 315, 318 spirit, 40 Taste, 46 straight, 28, 34, 37, 38, 40 Taylor, Colonel Edmund Haynes, Jr., 33, 158 vs whiskey, vii Subject Index 513

Whisky Trust, 26, 33 Y Wild Turkey, 80, 400 Yates continuity correction, 77 Wiley, Harvey Washington, 34, 37, 38, 42, 43, Yoker, 15 166, 309 Young-Dupre equation, 378 Wilson, Alexander, 375 Young-Laplace pressure, 382, 383, 403 Wine gallon (WG), 374, 396, 415 YWorth, William, 374 Wort, 121, 132

X Z Xylem, 277 Zabetakis, Michael George, 186 Chemical Index

A 2-Acetylpyrrole, 108 Acetal, 182, 218, 225, 229, 247, 249, 464 2-Acetyl-1-pyrroline, 69, 178, 467 (aka 1,1-Diethoxyethane; Acetaldehyde (aka 1-(3,4-Dihydro-2H-pyrrol-5-yl)ethan- diethyl acetal) 1-one) Acetaldehyde, 70, 71, 81, 108, 111, 137, 145, 2-Acetylthiazole, 106, 356 147, 153, 180, 182, 212, 213, 218, Acids, 262, 263, 273 225, 229, 247, 249, 268, 274, 302, fixed, 264, 265, 267 363, 439 total, 264–266 Acetaldehyde diethyl acetal, 271, 274, 464 volatile, 265, 315 (aka Acetal; 1,1-Diethoxyethane) Acrolein, 138, 159, 160, 163, 182, 212, 213, Acetaldehyde 2,4-dinitrophenylhydrazone, 111 218, 225, 229, 247, 249, 442 Acetic acid, 59, 80, 108, 182, 208, 209, 218, (aka Prop-2-enal) 225, 229, 247, 249, 265, 268, 300, Acrolein diethyl acetal, 160 311, 363, 428 Active amyl alcohol, 148, 185, 425 α-Aceto-α-hydroxybutyric acid, 147, 148 (aka 2-Methylbutanol) Acetoin, 180, 182, 216–218, 225, 229, 247, Active valeric acid, 178 249, 445 Aconitic acid, 432 (aka 3-Hydroxybutan-2-one) Acutissimin α-Acetolactic acid, 147, 148 A, 282, 284 Acetone, 445 B, 282, 284 (aka Propan-2-one) Adenosine triphosphate, 145 Acetophenone, 446 (aka ATP) (aka 1-Phenylethanone) Adipic acid, 300 Acetosyringone, 294, 295, 311 ADP, 144, 145 Acetovanillone, 294, 295, 311, 456 Aesculetin, 297 (aka 1-(4-Hydroxy-3- Aesculin, 297 methoxyphenyl)ethanone) Alcohol dehydrogenase (ADH), 157 Acetyl, 216, 217 Aldehydes, 261–264, 270, 315 Acetyl-CoA, 144, 145 Aldol, 442 2-Acetylfuran, 108, 463 (aka 3-Hydroxybutanal) (aka 1-(Furan-2-yl)ethanone) Allyl alcohol, 182, 210, 211, 218, 225, 229, O-Acetyl-4-O-methylglucurono-β-D-xylan, 247, 249 291 4-Allyl-2,6-dimethoxyphenol, 456 Acetylpropionyl, 445 (aka 4-Allylsyringol) (aka Pentane-2,3-dione) 4-Allyl-2-methoxyphenol, 67, 69, 72, 75, 453 2-Acetylpyridine, 105 (aka Eugenol)

© Springer Nature Switzerland AG 2019 515 G. H. Miller, Whisky Science, https://doi.org/10.1007/978-3-030-13732-8 516 Chemical Index

4-Allylsyringol, 304, 311, 456 2-Bromophenol, 458 (aka 4-Allyl-2,6-dimethoxyphenol) 4-Bromophenol, 458 1-(2-Aminophenyl)ethanone, 446 Butanal, 439 Amygdalin, 312 (aka Butyraldehyde) Amyl acetate, 50, 155, 436 Butane-2,3-diol, 424 (aka Pentyl acetate) meso-2,3-Butane diol, 180 Amyl alcohol, 144, 149, 150, 182, 210, 211, Butane-2,3-dione, 72, 73, 75, 77, 444 218, 225, 229, 247, 249, 260 (aka Diacetyl) (aka 1-Pentanol) Butane-1-thiol, 449 Amylase, 123 (aka n-Butyl mercaptan) α, 126–129 Butane-2-thiol, 449 β, 127–129 (aka sec-Butyl mercaptan) n-Amyl butyrate, 437 Butanoic acid, 178, 429 (aka Pentyl butanoate) (aka Butyric acid) tert-Amyl mercaptan, 449 1-Butanol, 180, 182, 185, 210, 211, 218, 225, (aka 2-Methylbutane-2-thiol) 229, 247, 249, 323, 424 Amylopectin, 122, 123, 125 (aka n-Butanol) structure, 124 2-Butanol, 424 Amylose, 122, 123, 125 (aka sec-Butanol) crystal structure, 123 Butan-2-one, 445 1,6-Anhydro-β-D-glucofuranose, 320 Butan-2-yl acetate, 437 1,6-Anhydro-β-D-glucopyranose, 320 (aka sec-Butyl acetate) Arabinic acid lactone, 317 (E)-But-2-enal, 142, 439 Arabinofuranose, 317 (aka trans-2-Butenal, crotonaldehyde) Arabinopyranose, 317 (E)-But-2-enedioic acid, 429 Arabinose, 135, 291, 292, 316, 317 (aka Fumaric acid) Arabinoxylan, 132, 136 4-(2-Butenylidene)-3,5,5-trimethylcyclohex-2- ATP, 144, 145 en-1-one, 309 (aka Adenosine triphosphate) Butyl acetate, 62, 436 Azelaic acid, 300 (aka n-Butyl acetate) sec-Butyl acetate, 437 (aka Butan-2-yl acetate) B tert-Butyl acetate, 62, 63, 437 Benzalacetone, 446 tert-Butyl alcohol, 182, 210, 211, 218, 225, (aka (E)-4-Phenylbut-3-en-2-one) 229, 247, 249, 424 Benzaldehyde, 47, 71, 108, 305, 311, 356, (aka 2-Methylpropan-2-ol) 442 n-Butyl mercaptan, 449 Benzene, 326 (aka Butane-1-thiol) Benzoic acid, 108, 300 sec-Butyl mercaptan, 449 Benzothiazole, 305 (aka Butane-2-thiol) 1,3-Benzothiazole, 171, 274, 275, 450 tert-Butyl mercaptan, 449 Benzothiophene, 171, 274, 275 (aka 2-Methylpropane-2-thiol) Benzylacetone, 446 5-Butyl-4-methyloxolan-2-one, 460 (aka 4-Phenylbutan-2-one) (aka Whisky lactone; β-Methyl-γ - Benyzl alcohol, 108, 426 octalactone) (aka Phenylmethanol) 5-Butyloxolan-2-one, 459 β-Bisabolene, 301 (aka γ -Octalactone) 1,3-Bisphosphoglycerate, 145 1-Butylsulfanylbutane, 449 Borneol, 301 (aka Di-n-butyl sulfide) Bourbonal, 47 Butyraldehyde, 108, 180, 182, 212, 213, 218, (aka Ethyl vanillin) 225, 229, 247, 249, 439 Brevifolin carboxylic acid, 288 (aka Butanal) Chemical Index 517

Butyric acid, 59, 80, 158, 182, 208, 209, 218, Coniferyl alcohol, 289, 292, 308, 311 225, 229, 247, 249, 266, 300, 429 Coniferyl aldehyde, 289, 293–296, 303, 309, (aka Butanoic acid) 313 Butyrolactone, 305 Copper, 90, 113–115, 169, 172, 190, 467 Copper thiocyanate, 113 Corundum, 332 C Coumaric acid, 313 Cadalene, 300 p-Coumaric acid, 137, 138, 162, 458 Cadinene, 301 ethyl ester, 438 δ, 300 (aka (E)-3-(4-Hydroxyphenyl)prop-2-enoic α-Cadinol, 300 acid) τ-Cadinol, 300 Coumarin, 297 Caffeic acid, 457 p-Coumaryl alcohol, 289, 292 ethyl ester, 438 Covellite, 170 (aka (E)-3-(3,4-Dihydroxyphenyl)prop-2- Creosol, 452 enoic acid) (aka 4-Methylguaiacol; 2-Methoxy-4- Caftaric acid, 458 methoxyphenol; p-Methylguaiacol) α-Calacorene, 300 m-Cresol, 108, 109, 184, 454 Calamenene, 300 (aka 3-Methylphenol) Capric acid, 266, 430 o-Cresol, 59, 107–109, 184, 295, 296, 454 (aka Decanoic acid) (aka 2-Methylphenol) Caproic acid, 266, 430 p-Cresol, 80, 108, 109, 184, 454 (aka Hexanoic acid) (aka 4-Methylphenol) Caprylic acid, 266, 430 Crotonaldehyde, 439 (aka Octanoic acid) (aka (E)-But-2-enal) Caramel, 292 Epi-Cubenol, 300 Caramelan, 320 Cuminaldehyde, 444 Carbon disulfide, 171 (aka 4-Propan-2-ylbenzaldehyde) Carbon tetrachloride, 326 Cuprous cyanide, 113 Carbonyl disulfide, 171 α-Curcumene, 300 Carbonyl sulfide, 138 Cyanidin, 138 Carboxyl ellagic acid, 288 Cyanogenic glycoside, 312 β-Carotene, 137 Cyanohydrin, 114 D-Carvone, 446 Cyclohexanone, 311, 445 (aka (5S)-2-Methyl-5-prop-1-en-2- Cyclohex-3-ene-1-carbaldehyde, 442 ylcyclohex-2-en-1-one) (aka 1,2,3,6-Tetrahydrobenzaldehyde) (R)-(-)-Carvone, 50 Cyclooctanecarboxaldehyde, 443 Castacrenin B, 284, 288 Cyclopentanone, 445 Castalagin, 282, 283, 465 Cyclotene, 308, 311, 428 Catechin, 464 (aka 2-Hydroxy-3-methyl-2- D-(+)-Catechin, 138 cyclopentenone) Cat urine ketone, 451 Cysteine, 158 (aka 4-Mercapto-4-methyl-2-pentanone) Cellulose, 134 Cinnamaldehyde, 443 D (aka (E)-3-Phenylprop-2-enal) β-Damascenone, 47, 67, 69, 72, 73, 75, 77, 80, Cinnamic acid, 108 176, 177, 190, 447 Citral, 52, 441 α-Damascone, 67 (aka Geranial; (E)-3,7-Dimethylocta-2,6- Decadienal, 138 dienal) (E,E)-2,4-Decadienal, 67, 70, 72, 73, 75, 142, Citronellal, 443 441 (aka 3,7-Dimethyloct-6-enal) (E,Z)-2,4-Decadienal, 142 CoA, 145 518 Chemical Index

Decalactone (aka Tartaric acid) δ, 460 α, β-Dihydroxyisovaleric acid, 148 (aka 6-Pentyloxan-2-one) 2,3-Dihydroxy-3-methylvaleric acid, 147, 148 γ , 47, 67, 69, 73, 75, 161, 459 (aka α, β-Dihydroxyisovaleric acid) (aka 5-Hexyloxolan-2-one) (E)-3-(3,4-Dihydroxyphenyl)prop-2-enoic γ -Decalactone, 300 acid, 457 1-Decanal, 142, 307, 359, 443 (aka Caffeic acid) Decanoic acid, 300, 430 2,3-Dihydroxypropanal, 442 (aka Capric acid) (aka D-Glyceraldehyde) 1-Decanol, 59, 359, 427 Di-isopropyl sulfide, 449 2-Decanol, 427 (aka 2-Propan-2-ylsulfanylpropane) Decan-2-one, 446 1,3-Dimethoxy-2-hydroxybenzene, 455 Decan-3-one, 446 (aka Syringol) 2,4,7-Decatrienal, 142 2,6-Dimethoxyphenol, 80 (E)-2-Decenal, 67, 72, 73, 75, 142, 443 Dimethyl amine, 112, 113 (aka trans-2-Decenal) 3,3-Dimethylbutan-2-one, 445 trans-2-Decenal, 443 (aka Pinacolone) (aka (E)-2-Decenal) 3,4-Dimethyl-1,3-cyclohexane- (Z)-2-Decenal, 142 carboxaldehyde, 443 (aka cis-2-Decenal) Dimethyl disulfide, 138, 171, 274, 275, 448 (Z)-Dec-7-en-5-olide, 462 2,4-Dimethyl furan, 311 (aka Jasmine lactone; 6-[(Z)-Pent-2- 2,6-Dimethylheptan-4-one, 446 enyl]oxan-2-one) (E)-2,2-Dimethylhept-4-enal, 443 Delphinidin, 138 Dimethyl nitrosamine, 113 5-Deoxy myo-Inositol, 317 (E)-3,7-Dimethylocta-2,6-dienal, 441 33-Deoxy-33-carboxyvescalagin, 465 (aka Citral; Geranial) Diacetyl, 59, 180, 182, 216–218, 225, 229, 247, 2,7-Dimethylocta-1,6-dien-3-ol, 427 249, 321, 444 (aka Linalool) (aka Butane-2,3-dione) (Z)-3,7-Dimethyl-2,6-octadien-1-ol, 427 Diastase, 126–129 (aka Nerol) 2,4-Dibromophenol, 107, 458 3,7-Dimethyloct-6-enal, 443 2,6-Dibromophenol, 105, 107, 458 (aka Citronellal) Di-n-butyl sulfide, 449 2,4-Dimethylpentan-3-one, 445 (aka 1-Butylsulfanylbutane) 2,3-Dimethylphenol, 458 Dichloromethane, 304 (aka 2,3-Xylenol) 1,1-Diethoxyethane, 67, 69–73, 75, 274, 464 2,3-Dimethylpyrazine, 105, 106, 466 (aka Acetal; Acetaldehyde diethyl acetal) 2,5-Dimethylpyrazine, 51, 104–106, 108, 356, Diethyl disulfide, 157, 448 466 Diethyl ether, 302 2,6-Dimethylpyridine, 105 2,3-Diethylpyrazine, 106 3,4-Dimethylpyridine, 105 2,6-Diethylpyrazine, 108 Dimethyl sulfide, 59, 61, 70, 100, 138, 171, Diethyl sulfide, 448 275, 447 Dihydroconiferyl alcohol, 309 Dimethyl sulfoxide, 100 2,3-Dihydrofuran, 311 2,5-Dimethylthiophene, 171 Dihydrokaempferol-3-O-α-L-rhamnoside, 464 Dimethyl trisulfide, 59, 171, 172, 190, 274, Dihydro-2-methyl-3(2H)-thiophenone, 171, 275, 448 275 (5E)-6,10-Dimethylundeca-5,9-dien-2-one, 5,6-Dihydro-2H-pyran-2-one, 311 446 1-(3,4-Dihydro-2H-pyrrol-5-yl)ethan-1-one, (aka Geranylacetone) 467 2,4-Dinitrophenylhydrazine, 111 (aka 2-Acetyl-1-pyrroline) Dissolved solids, 273, 363 Dihydroquercetin-3-O-α-L-rhamnoside, 464 Djurleite, 170 Dihydroxyacetone phosphate, 145 DMDS, see Dimethyl disulfide 2,3-Dihydroxybutanedioic acid, 432 DMTS, see Dimethyl trisulfide Chemical Index 519

γ -Dodecalactone, 67, 69, 73, 75, 161, 460 Ethyl caproate, 153, 358, 434 (aka 5-Octyloxolan-2-one) (aka Ethyl hexanoate) Dodecanal, 359, 444 Ethyl caprylate, 153, 175, 358, 435 Dodecanoic acid, 431 (aka Ethyl octanoate) (aka Lauric acid) Ethyl carbamate, 112–116, 190 1-Dodecanol, 355, 359, 428 (aka Urethane) Dodecan-2-one, 446 trans-Ethylcinnamate, 67, 69, 72, 73, 75, 80, (Z)-6-Dodecen-γ -lactone, 67, 69 438 (aka Ethyl 3-phenylprop-2-enoate) Ethyl decanoate, 155, 356, 357, 359, 360, 362, E 435 EDTA, 114, 115 (aka Ethyl caprate) (aka Ethylenediaminetetraacetic acid) 3-Ethyl-2,5-dimethylpyrazine, 69 Ethyl isovalerate, 249 Ethyl dodecanoate, 356, 360–362, 435 Elemol, 300 (aka Ethyl laurate) Ellagic acid, 276, 295, 303, 313, 465 Ethylenediaminetetraacetic acid, 115 Ellagic acid rhamnoside, 287 (aka EDTA) Ellagitannin, 282 Ethyl 3-ethoxypropionate, 160 Enanthic acid, 266, 430 Ethyl formate, 436 (aka Heptanoic acid) 4-Ethylguaiacol, 108, 109, 162, 184, 304, 452 Entropy, 326 (aka 4-Ethyl-2-methoxyphenol; p- Epicatechin, 464 Ethylguaiacol) Epiheterodentrin, 116 p-Ethylguaiacol, 311, 452 trans-4,5-Epoxy-trans-2-decenal, 142 (aka 4-Ethyl-2-methoxyphenol; 4- Esters, 262–264, 269, 273, 315 Ethylguaiacol) Ethanal, 157 Ethyl heptanoate, 436 1,1-Ethanediol, 274 Ethyl hexadecanoate, 108, 356, 358, 360–362, Ethanethiol, 157, 171, 178, 449 433 (aka Ethyl mercaptan) (aka Ethyl palmitate) Ethanol, 70–73, 75, 77, 144, 147, 179, 207, Ethyl (E)-hexadec-9-enoate, 433 249, 253–258 (aka Ethyl palmitoleate) Ethanol lignin, 289, 292, 296 2-Ethylhexanal, 442 4-Ethenyl-2-methoxyphenol, 453 Ethyl hexanoate, 48, 59, 67, 69–73, 75, 80, 137, (aka Vinylguaiacol) 155, 311, 356, 434 4-Ethenylphenol, 455 (aka Ethyl caproate) (aka 4-Vinylphenol; p-Vinylphenol) 2-Ethylhex-2-enal, 442 Ethers, 262 Ethyl hydrogen succinate, 437 1-Ethoxyethanol, 274 (aka 4-Ethoxy-4-oxobutanoic acid) 4-Ethoxy-4-oxobutanoic acid, 437 Ethyl 3-Hydroxyhexanoate, 69 (aka Ethyl hydrogen succinate) Ethyl 4-hydroxy-3-methoxybenzoate, 456 3-Ethoxypropionaldehyde diethyl acetal, 160 (aka Ethyl vanillate) Ethyl acetate, 59, 70, 71, 155, 175, 268, 269, (S)-Ethyl-2-hydroxy-3-methylbutanoate, 69, 274, 356, 363, 434 73, 75, 438 Ethyl 2-amino-4-(methylsulfanyl)butanoate, Ethyl-2-hydroxy-3-methylpentanoate, 73 450 (2R,4S)-Ethyl-2-hydroxy-3-methylpentanoate, (aka Ethyl methionate) 75 2-Ethylbutanal, 439 (2S,3S)-Ethyl-2-hydroxy-3-methylpentanoate, Ethyl butanoate, 51, 67, 69–73, 75, 432 69, 72, 73, 75, 438 (aka Ethyl butyrate) Ethyl 2-hydroxypropanoate, 432 Ethyl butyrate, 59, 62, 80, 153, 158, 356, 358, (aka Ethyl lactate) 432 Ethyl isobutyrate, 80, 182, 214, 215, 218, 225, (aka Ethyl butanoate) 229, 247, 249, 437 Ethyl caprate, 153, 169, 175, 358, 435 (aka Ethyl 2-methylpropanoate) (aka Ethyl decanoate) 520 Chemical Index

Ethyl isovalerate, 80, 182, 214, 215, 218, 225, Ethyl palmitoleate, 361, 433 229, 247, 437 (aka Ethyl (E)-hexadec-9-enoate) (aka Ethyl-3-methylbutanoate) Ethyl pentadecanoate, 438 Ethyl lactate, 163, 432 Ethyl pentanoate, 69–71, 436 (aka Ethyl 2-hydroxypropanoate) (aka Ethyl valerate) Ethyl laurate, 59, 169, 175, 401, 402, 435 3-Ethylphenol, 70, 73, 75 (aka Ethyl dodecanoate) 4-Ethenylphenol, 455 Ethyl levulinate, 437 4-Ethylphenol, 67, 72, 73, 75, 80 (aka Ethyl 4-oxopentanoate) (aka p-Ethylphenol) Ethyl linoleate, 108, 169, 433 p-Ethylphenol, 107, 108, 162, 455 (aka Ethyl (9Z,12Z)-octadeca-9,12- (aka 4-Ethylphenol) dienoate) Ethyl phenylacetate, 67, 69, 75 Ethyl mercaptan, 449 (aka Ethyl 2-phenylacetate) (aka Ethanethiol) Ethyl 3-phenylprop-2-enoate, 438 Ethyl methionate, 275, 450 (aka trans-Ethylcinnamate) (aka Ethyl 2-Amino-4- Ethyl propanoate, 69–71, 73, 75, 80, 432 (methylsulfanyl)butanoate) (aka Ethyl propionate) 4-Ethyl-2-methoxyphenol, 67, 69, 72, 73, 75, Ethyl propionate, 48, 62, 63, 432 80, 311, 452 (aka Ethyl propanoate) (aka 4-Ethylguaiacol; p-Ethylguaiacol) Ethylpyrazine, 106 (S)-Ethyl-2-methylbutanoate, 67, 69–73, 75, 2-Ethylpyrazine, 108, 467 438 3-Ethylpyridine, 105 Ethyl-3-methylbutanoate, 67, 69–73, 75, 437 4-Ethylpyridine, 106 (aka Ethyl isovalerate) Ethyl pyridine-3-carboxylate, 437 Ethyl 2-methylpropanoate, 67, 69–73, 75, 437 (aka Ethyl nicotinate) (aka Ethyl isobutyrate) Ethyl pyruvate, 436 2-Ethyl-3-methylpyrazine, 106, 467 (aka Ethyl 2-oxopropanoate) 3-Ethyl-2-methylpyrazine, 69 Ethyl stearate, 433 5-Ethyl-2-methylpyrazine, 106 (aka Ethyl octadecanoate) Ethyl 3-(methylthio)propanoate, 171, 275 Ethyl syringate, 294, 295 Ethyl myristate, 108, 175, 432 Ethyl tetradecanoate, 432 (aka Ethyl tetradecanoate) (aka Ethyl myristate) Ethyl nicotinate, 437 Ethyl tridecanoate, 438 (aka Ethyl pyridine-3-carboxylate) Ethyl undecanoate, 437 Ethyl nonanoate, 436 Ethyl valerate, 436 Ethyl (9Z,12Z)-octadeca-9,12-dienoate, 433 (aka Ethyl pentanoate) (aka Ethyl linoleate) Ethyl vanillate, 80, 294, 295, 456 Ethyl octadecanoate, 433 (aka Ethyl 4-hydroxy-3-methoxybenzoate) (aka Ethyl stearate) Ethyl vanillin, 47 Ethyl (E)-octadec-9-enoate, 433 (aka Bourbonal) (aka Ethyl oleate) Ethyl vinyl ketone, 445 Ethyl octanoate, 48, 51, 67, 69, 72, 73, 75, 137, (aka 1-Penten-3-one) 155, 356, 435 α-Eudesmol, 300 (aka Ethyl caprylate) β-Eudesmol, 300 Ethyl oleate, 108, 169, 433 γ -Eudesmol, 300 (aka Ethyl (E)-octadec-9-enoate) Eugenol, 59, 80, 295, 296, 298, 304, 308, 311, 5-Ethyloxolan-2-one, 459 313, 453 (aka γ -Hexalactone) (aka 4-Allyl-2-methoxyphenol) Ethyl 4-oxopentanoate, 437 (aka Ethyl levulinate) Ethyl 2-oxopropanoate, 436 F (aka Ethyl pyruvate) Ferulic acid, 135–138, 162, 174, 175, 190, 294, Ethyl palmitate, 108, 169, 175, 401, 402, 433 313, 457 (aka Ethyl hexadecanoate) ethyl ester, 438 Chemical Index 521

(aka (E)-3-(4-Hydroxy-3- (aka 3,4,5-Trihydroxybenzoic acid) methoxyphenyl)prop-2-enoic Geosmin, 59 acid) Geranial, 441 Flavin mononucleotide (FMN), 154 (aka Citral; (E)-3,7-Dimethylocta-2,6- Floroglucin, 317 dienal) Folin-Denis reagent, 271 Geraniol, 59 Formaldehyde, 108, 439 Geranyl acetate, 301 Formic acid, 59, 182, 208, 209, 218, 225, 247, Geranylacetone, 446 249 (aka (5E)-6,10-Dimethylundeca-5,9-dien- Frucose, 143 2-one) α-D-Fructofuranose, 319 Gibberelic acid, 86 β-D-Fructofuranose, 319, 320 β-Glucan, 132, 134–136, 143 α-D-Fructopyranose, 319 Glucitol, 317 β-D-Fructopyranose, 319 Glucoamylase, 143 Fructose, 291, 316, 317 Glucomannan, 291 D, 319 2-Keto-D-gluconic acid, 316, 317 Fructose-1,6-bisphosphate, 145 Glucopyranose, 317 Fructose-6-phosphate, 145 α-D-Glucopyranose, 319, 320 Fumaric acid, 300, 429 β-D-Glucopyranose, 319, 320 (aka (E)-But-2-enedioic acid) Glucose, 122, 125, 128, 129, 143–145, 291, Furan-2-carbaldehyde, 463 292, 317, 321 (aka Furfural) α, 127 Furancarboxylic acid, 300 α-D, 124 2,5-Furandicarboxylic acid, 300 β-D, 124 2-Furanmethanol, 463 D, 147, 319 (aka Furfuryl alcohol, 5- β-Glucose, 135 hydroxymethylfuran) Glucose-6-phosphate, 145 3-Furanmethanol, 311 α-Glucosidase, 126–129 2-(5H) Furanone, 311 D-Glyceraldehyde, 442 1-(Furan-2-yl)ethanone, 305, 311, 463 (aka 2,3-Dihydroxypropanal) (aka 2-Acetylfuran) Glyceraldehyde-3-phosphate, 145 (E)-3-(Furan-2-yl)prop-2-enal, 464 Glyceric acid, 317 (aka Furylacrolein) Glycerol, 144, 145, 159, 291, 316, 317, 323 Furfural, 19, 22, 59, 103, 107, 108, 167, 175, Glycerol-3-phosphate, 145 176, 180, 182, 190, 216–218, 225, Glyoxal, 321, 444 229, 247, 249, 262–264, 269, 270, (aka Oxaldehyde) 305, 307, 308, 311, 356, 463 Glyoxylic acid, 431, 444 (aka Furan-2-carbaldehyde) (aka Oxaldehydic acid) Furfurol, 19 Gramine, 112, 113 Furfuryl alcohol, 305, 463 Grandinin, 282, 283, 465 (aka 2-Furanmethanol) Grapefruit mercaptan, 47 1-Furfurylpyrrole, 108 (aka (R)-2-(4-Methylcyclohex- 2-Furoic acid, 108 3-enyl)propane-2-thiol, Furylacrolein, 464 1-p-menthene-8-thiol) (aka (E)-3-(Furan-2-yl)prop-2-enal) Grasshopper ketone, 177 Fuschin sulfite, 269 Guaiacol, 47, 51, 59, 80, 107–109, 184, 304, Fusel oil, 169, 260–262, 271 307, 308, 311, 323, 451 (aka 2-Methoxyphenol) Guaiacylpropane, 311 G Galactose, 291, 292, 316, 317 D-Galacturonic acid, 151, 152 H Gallic acid, 276, 295, 298, 303, 317, 458 Hemicellulose, 134, 136, 287, 291, 309 ethyl ester, 438 Heptadecanoic acid, 266 522 Chemical Index

Heptadienal, 138 (aka (Z)-Hex-3-enal) (E,E)-2,4-Heptadienal, 142 trans-3-Hexenal, 142 (E,Z)-2,4-Heptadienal, 142 (Z)-Hex-3-enal, 139, 440 γ -Heptalactone, 459 (aka cis-3-Hexenal) (aka 5-Propyloxolan-2-one) Hex-3-enoic acid, 430 1-Heptanal, 50, 142, 440 (E)-2-Hexen-1-ol, 426 2-Heptanal, 440 (Z)-3-Hexen-1-ol, 47, 59, 426 Heptanoic acid, 300, 430 Hexyl acetate, 69, 73 (aka Enanthic acid) n-Hexyl acetate, 436 1-Heptanol, 59, 108, 426 5-Hexyloxolan-2-one, 459 2-Heptanol, 108, 426 (aka γ -Decalactone) 3-Heptanol, 108 Homoserine, 100 Heptan-2-one, 47, 51, 69, 445 Hordenine, 112, 113 Heptan-3-one, 445 Hydrazine, 261 Heptan-4-one, 445 Hydrochloric acid, 303 (E)-2-Heptenal, 67, 142, 440 Hydrogen cyanate, 114 (aka trans-2-Heptenal) Hydrogen sulfide, 59, 138, 156–158, 171 trans-2-Heptenal, 142 Hydroperoxide lyase, 99, 139 cis-4-Heptenal, 440 (9Z,11E)-13-Hydroperoxy-9,11- (aka (Z)-Hept-4-enal) octadecadienoic acid, 99 (Z)-Hept-4-enal, 440 (10E,12Z)-9-Hydroperoxy-10,12- (aka cis-4-Heptenal) octadecadienoic acid, 99 1-Hepten-3-ol, 426 (9Z,11E,15Z)-13-Hydroperoxy-9,11,15- Heptyl butanoate, 437 octadecatrienoic acid, 139 (aka sec-Heptyl butyrate) (10E,12Z,15E)-9-Hydroperoxy-1-,12,15- sec-Heptyl butyrate, 437 octadecatrienoic acid, 139 (aka Heptyl butanoate) 3-Hydroxybutanal, 442 n-Heptyl acetate, 436 (aka Aldol) Hexadecanoate-L,D-glucopyranoside, 317 3-Hydroxybutan-2-one, 445 Hexadecanoic acid, 317, 431 (aka Acetoin) (aka Palmitic acid) 4-[(E)-3-Hydroxybut-1-enyl]-3,5,5- 1-Hexadecanol, 428 trimethylcyclohex-2-en-1-one, (9Z)-Hexadec-9-enoic acid, 431 309 (aka Palmitoleic acid) α-Hydroxy-β-carboxybutyrate, 147 trans-2-cis-4-Hexadienal, 442 β-Hydroxy-β-carboxybutyrate, 147 (aka (2E,4Z)-Hexa-2,4-dienal) α-Hydroxy-β-carboxyisocaproate, 147 (2E,4Z)-Hexa-2,4-dienal, 442 β-Hydroxy-β-carboxyisocaproate, 147 (aka trans-2-cis-4-Hexadienal) 3-Hydroxy-β-damascone, 177 2,3-(S)-Hexahydroxydiphenoyl-D-glucose, 4-Hydroxy-3,5-dimethoxy benzaldehyde, 456 290 (aka Syringaldehyde) γ -Hexalactone, 459 4-Hydroxy-3,5-dimethoxybenzoic acid, 456 (aka 5-Ethyloxolan-2-one) (aka Syringic acid) Hexanal, 59, 63, 99, 142, 359, 439 3-(4-Hydroxy-3,5-dimethoxyphenol)prop-2- Hexane-2,3-dione, 445 enal, 458 Hexanoic acid, 300, 430 (aka Sinapaldehyde) (aka Caproic acid) (E)-3-(4-Hydroxy-3,5-dimethoxyphenyl)prop- 1-Hexanol, 359, 426 2-enoic acid, 458 2-Hexanol, 426 (aka Sinapic acid) Hexan-2-one, 445 3-Hydroxy-4,5-dimethylfuran-2(5H)-one, 67, (E)-Hex-2-enal, 138, 139, 440 69, 462 (aka trans-2-Hexenal) (aka Sotolon) trans-2-Hexenal, 142, 440 7-Hydroxy-3,7-dimethyloctanal, 444 (aka (E)-Hex-2-enal) 4-(2-Hydroxyethyl)phenol, 427 cis-3-Hexenal, 142, 440 (aka Tyrosol) Chemical Index 523

4-Hydroxy-3-methoxy benzaldehyde, 67, 69, (aka (E)-4-(2,6,6-Trimethylcyclohexen- 70, 72, 73, 75, 77, 78, 457 1-yl)but-3-en-2-one) (aka Vanillin) Iron oxide, 169 4-Hydroxy-3-methoxybenzoic acid, 458 Isoamyl isovalerate, 433 (aka Vanillic acid) (aka 3-Methylbutyl 3-methylbutanoate) 1-(4-Hydroxy-3-methoxyphenyl)ethanone, 456 Isoamyl acetate, 51, 59, 77, 80, 153, 175, 269, (aka Acetovanillone) 435 (E)-3-(4-Hydroxy-3-methoxyphenyl)prop-2- (aka 3-Methylbutyl acetate) enoic acid, 457 Isoamyl alcohol, 148, 175, 179, 182, 185, 210, (aka Ferulic acid) 211, 218, 225, 229, 247, 249, 363, 4-Hydroxy-2-methylacetophenone, 311 425 3-Hydroxy-3-methylbutan-2-one, 445 (aka 3-Methylbutanol) 2-Hydroxy-3-methyl-2-cyclopentenone, 307, Isoamyl caprate, 175, 433 308, 428 (aka 3-Methylbutyl decanoate) (aka Cyclotene) Isoamyl caproate, 433 2-Hydroxy-4-methyl-2-cyclopentenone, 108 (aka 3-Methylbutyl hexanoate) 5-Hydroxymethylfuran, 108 Isoamyl caprylate, 433 (aka 2-Furanmethanol) (aka 3-Methylbutyl octanoate) 5-(Hydroxymethyl)furan-2-carbaldehyde, 463 Isoamyl formate, 182, 214, 215, 218, 225, 229, (aka 5-(Hydroxymethyl)furfural) 247, 249, 436 5-(Hydroxymethyl)furfural, 303, 305, 307, (aka 3-Methylbutyl formate) 309, 311, 463 Isoamyl isobutyrate, 433 (aka 5-(Hydroxymethyl)furan-2- (aka 3-Methylbutyl 2-methylpropanoate) carbaldehyde) Isoamyl mercaptan, 449 3-Hydroxy-2-methylpyran-4-one, 428 (aka 3-Methyl-1-butanethiol) (aka Maltol) Isoamyl nonanoate, 437 2-Hydroxy-4-(methylthio)butyric acid, 157 (aka 3-Methylbutyl nonanoate) 2-Hydroxy-2-phenylacetic acid, 431 Isoamyl propionate, 437 (aka Mandelic acid) (aka 3-Methylbutyl propanoate) 2-(4-Hydroxyphenly)ethanal, 146 Isoamyl n-valerate, 433 2-(4-Hydroxyphenly)ethanol, 146 (aka Pentyl 3-methylbutanoate) (Z)-3-Hydroxy-2-Phenylprop-2-enal, 443 Isobutanal, 441 (E)-3-(4-Hydroxyphenyl)prop-2-enoic acid, (aka Isobutyraldehyde; 2-Methylpropanal) 458 Isobutanol, 144, 147–150, 175, 179, 182, 185, (aka p-Coumaric acid) 210, 211, 218, 225, 229, 247, 249, 2-Hydroxypropanoic acid, 431 363, 424 (aka Lactic acid) (aka 2-Methylpropan-1-ol) 3-Hydroxypropionaldehyde, 159, 160 Isobutyl acetate, 155, 433 3-Hydroxypropionic acid, 159, 160 (aka 2-Methylpropyl acetate) 2-Hydroxybutyric acid, 157 Isobutyl formate, 182, 214, 215, 218, 225, 229, 247, 249, 436 (aka 2-Methylpropyl formate) I Isobutyl mercaptan, 449 2-(Indol-3-yl)-ethanal, 146 (aka 2-Methylpropane-1-thiol) 2-(Indol-3-yl)-ethanol, 146 2-Isobutylthiazole, 450 Inositol, 292, 316, 317 (aka 2-(2-Methylpropyl)-1,3-thiazole) myo-Inositol, 316, 317 Isobutyraldehyde, 47, 108, 147, 148, 182, 212, Iodine, 105, 467 213, 218, 225, 229, 247, 249, 441 Ionone (aka Isobutanal; 2-Methylpropanal) α, 59, 137, 447 Isobutyric acid, 182, 208, 209, 218, 225, 229, (aka (E)-4-(2,6,6-Trimethylcyclohex-2- 247, 249, 266, 300, 429 en-1-yl)but-3-en-2-one) (aka 2-Methylpropanoic acid) β, 47, 59, 67, 69, 80, 137, 300, 447 Isoeugenol, 304, 309, 311 Isoleucine, 146–148 524 Chemical Index

Isomaltol, 305 (aka 2,7-Dimethylocta-1,6-dien-3-ol) Isomaltose, 130, 131 Linoleic acid, 98, 99, 136, 138, 140, 142, 169, Isomerase, 99 266, 300, 307, 431 Isopropanol, 50, 179, 182, 210, 211, 218, 225, (aka (9Z,12Z)-9,12-Octadecadienoic acid) 229, 247, 249 Linolenic acid, 98, 136, 138, 139, 142, 300, Isopropyl acetate, 182, 214, 215, 218, 225, 229, 317 247, 249 2-Butanol, 185 α-Isopropylmalate, 148 2,3-Lutidine, 106 β-Isopropylmalate, 148 2,6-Lutidine, 106 2-Isopropyl-3-methoxypyrazine, 67, 467 Lyoniresinol, 276, 466 3-Isopropyl-2-methoxypyrazine, 69 2-Isopropyl-5-methyl-2-hexenal, 103 4-Isopropylpyridine, 106 M Isorhamnetin-3-O-β-D-glucopyranoside, 464 Macarangioside E, 309, 310 Isovaleraldehyde, 108, 147, 442 Malic acid, 158, 317 (aka 3-Methylbutanal) Maltase, 127–129 Isovaleric acid, 47, 59, 80, 178, 266, 300, 429 Maltol, 59, 305, 307, 308, 428 (aka 3-Methylbutanoic acid) (aka 3-Hydroxy-2-methylpyran-4-one) Maltose, 125, 127, 130, 131, 143, 320 Maltotetrose, 143 J Maltotriose, 143 Jasmine lactone, 462 Mandelic acid, 431 (aka (Z)-Dec-7-en-5-olide; 6-[(Z)-Pent-2- (aka 2-Hydroxy-2-phenylacetic acid) enyl]oxan-2-one) α-D-Mannopyranose, 319 β-D-Mannopyranose, 319 Mannose, 291, 292, 317 K D, 319 α-Ketobutyrate, 147, 157 Megastigmatrienone, 298, 309, 310 α-Ketobutyric acid, 148 (aka 4-(2-Butenylidene)-3,5,5- α-Keto-β-carboxybutyrate, 147 trimethylcyclohex-2-en-1-one) α-Ketoisocaproate, 147 4-Mercapto-4-methyl-2-pentanone, 161, 451 α-Ketoisocaproic acid, 148 (aka Cat urine ketone) Ketoisophorone, 309, 310 Mesaconic acid, 300 (aka 2,6,6-Trimethyl-2-cyclohexene-1,4- Mesityl oxide, 59, 161, 445 dione) (aka 4-Methyl-3-penten-2-one) α-Ketoisovalerate, 147 Methanethiol, 138, 157, 171, 449 α-Ketoisovaleric acid, 148 (aka Methylmercaptan) α-Keto-β-methylvaleric acid, 147 Methanol, 151, 179, 210, 211, 219, 252–258, 303, 323, 424 1-p-Menthene-8-thiol, 47 L (aka Grapefruit mercaptan; Lactic acid, 158, 163, 431 (R)-2-(4-Methylcyclohex-3- (aka 2-Hydroxypropanoic acid) enyl)propane-2-thiol) Lactonitrile, 114 Methional, 157, 449 Lauric acid, 266, 300, 431 (aka 3-Methylsulfanylpropanal) (aka Dodecanoic acid) Methionine, 100, 138, 146, 157 Leucine, 146–148 Methionol, 157 Leucoanthocyanidin, 138 Methionyl acetate, 275, 450 Lignin, 281, 289, 309 (aka 3-Methylsulfanylpropyl acetate) Limit dextrinase, 127–129 Methonine, 157 Limonene, 47, 52, 464 6-Methoxy-m-cresol, 457 (aka 1-Methyl-4-(1-methylethenyl)- (aka 5-Methyl-2-methoxyphenol) cyclohexene) Methoxyeugenol, 311 Linalool, 52, 427 p-Methoxyguaiacol Chemical Index 525

(aka Creosol; 4-Methylguaiacol; 2-Methylbutyric acid, 300 2-Methoxy-4-methoxyphenol) 3-Methylbutyric acid, 69, 108, 300 2-Methoxy-3-isopropylpyrazine, 69 Methyl caprate, 437 2-Methoxy-4-methylphenol, 452 (aka Methyl decanoate) (aka Creosol; 4-Methylguaiacol; 4-Methylcyclohexan-1-one, 446 p-Methylguaiacol) (R)-2-(4-Methylcyclohex-3-enyl)propane-2- 2-Methoxyphenol, 67, 69, 70, 72, 75, 107, 451 thiol, 47 (aka Guaiacol) (aka Grapefruit mercaptan; 1-p-Menthene- 2-Methylphenol, 73 8-thiol) 4-Methylphenol, 69 2-(4-Methyl-1-cyclohex-3-enyl)propan-2-ol, Methoxysuccinic acid, 300 427 Methyl acetate, 436 (aka α-Terpineol) 2-Methyl-5-acetylpyrazine, 108 Methyl decanoate, 437 4-Methylacetophenone, 67, 69 (aka Methyl caprate) 5-Methylbenzoic acid, 317 4-Methyl-2,3-dihydrofuran, 311 2-Methylbutanal, 59, 70, 71, 146, 442 Methyl formate, 436 3-Methylbutanal, 59, 70–73, 75, 77, 103, 146, (aka Methyl methanoate) 442 α-Methyl furan, 311 (aka Isovaleraldehyde) 5-Methylfuran-2-carbaldehyde, 463 2-Methylbutane-2-thiol, 449 (aka 5-Methylfurfural) (aka tert-Amyl mercaptan) 3-Methyl-2,5-furandione, 311 3-Methyl-1-butanethiol, 449 5-Methyl-2(3H)-furanone, 311 (aka Isoamyl mercaptan) 2-Methylfurfural, 307 2-Methylbutanoic acid, 178 5-Methylfurfural, 103, 107, 108, 305, 307, 309, 3-Methylbutanoic acid, 178, 429 311, 463 (aka Isovaleric acid) (aka 5-Methylfuran-2-carbaldehyde) 2-Methylbutanol, 73, 75, 144, 146, 147, 425 4-O-Methyl-α-D-glucuronic acid, 291 (aka Active amyl alcohol) 4-Methylguaiacol, 51, 108, 109, 137, 162, 184, 3-Methylbutanol, 67, 69–73, 75, 77, 144, 146, 304, 307, 308, 452 147, 425 (aka Cresol; 2-Methoxy-4-methoxyphenol; (aka Isoamyl alcohol) p-Methylguaiacol) 3-Methylbutan-2-one, 445 p-Methylguaiacol, 311, 452 3-Methylbutanol, 80, 311 2-Methylhepta-2-trans-4-dien-6-one, 446 2-Methylbutyl acetate, 73, 75 6-Methylheptan-3-one, 446 3-Methylbutyl acetate, 67, 69–73, 75, 77, 435 2-Methylhept-2-en-6-one, 446 (aka Isoamyl acetate) 5-Methylhexan-2-one, 445 3-Methylbutyl decanoate, 433 Methyl 2-hydroxybenzoate, 432 (aka Isoamyl caprate) (aka Methyl salicylate) 3-Methylbutyl formate, 436 3-Methyl-4-hydroxyoctanoic acid, 300 (aka Isoamyl formate) 2-Methyl iso-borneol, 59 3-Methylbutyl hexanoate, 433 Methyl mercaptan, 449 (aka Isoamyl caproate) (aka Methanethiol) 3-Methylbutyl 3-methylbutanoate, 433 Methyl methanoate, 436 (aka Isoamyl isovalerate) (aka Methyl formate) 3-Methylbutyl 2-methylpropanoate, 433 S-Methylmethionine, 100 (aka Isoamyl isobutyrate) 4-Methyl-2-methoxyphenol, 72, 73, 75 3-Methylbutyl nonanoate, 437 5-Methyl-2-methoxyphenol, 69, 72, 73, 75, (aka Isoamyl nonanoate) 457 3-Methylbutyl octanoate, 433 (aka 6-Methoxy-m-cresol) (aka Isoamyl caprylate) 1-Methyl-4-(1-methylethenyl)-cyclohexene, 3-Methylbutyl propanoate, 437 464 (aka Isoamyl propionate) (aka Limonene) 2-Methyl-1-butyraldehyde, 148 Methyl-(2-methyl-3-furyl)disulfide, 59, 171, (aka β-Methylbutyraldehyde) 448 526 Chemical Index

3-Methyl-2,4-nonadione, 69 5-Methyl-2-thiophene-carboxaldehyde, 171, β-Methyl-γ -octalactone, 305, 460 274, 275 (aka Whisky lactone; 5-Butyl-4- 2-Methylthiophene-3-ol, 450 methyloxolan-2-one) 3-(Methylthio)propanal, 146, 171, 275 2-Methyl-1-pentanol, 108 3-(Methylthio)propanol, 146, 171, 275 4-Methylpentan-2-one, 445 3-(Methylthio)propyl acetate, 171, 275 4-Methyl-3-penten-2-one, 445 4-Methylumbelliferone, 297 (aka Mesityl oxide) 4-Methylvaleric acid, 108 2-Methylphenol, 72, 75, 454 4-Methyl-5-vinylthiazole, 106 (aka o-Cresol) 3-Methoxy-4-hydrophenol 1-O-β-D(6- 3-Methylphenol, 73, 75, 454 O-galloyl)glucopyranoside, (aka m-Cresol) 290 4-Methylphenol, 73, 75, 454 Muurolene, 301 (aka p-Cresol) Myristic acid, 266, 300, 431 2-Methylpropanal, 70–73, 75, 77, 146, 441 (aka Tetradecanoic acid) (aka Isobutanal; Isobutyraldehyde) Myrtenol, 300 2-Methylpropane-1-thiol, 449 (aka Isobutyl mercaptan) 2-Methylpropane-2-thiol, 449 N (aka tert-Butyl mercaptan) NAD, 144, 145 2-Methylpropan-1-ol, 59, 67, 69, 80, 146, 424 (aka Nicotineamide adenine dinucleotide) (aka Isobutanol) NADH, 144, 145 2-Methylpropan-2-ol, 424 Naphthalene, 59 (aka tert-Butyl alcohol) Neoxanthin, 176, 177, 190 2-Methylpropanoic acid, 429 Nerol, 427 (aka Isobutyric acid) (aka (Z)-3,7-Dimethyl-2,6-octadien-1-ol) (5S)-2-Methyl-5-prop-1-en-2-ylcyclohex-2-en- Nicotine, 323 1-one, 446 Nicotineamide adenine dinucleotide, 144 (aka D-Carvone) Ninhydrin, 87, 88 2-Methylpropionic acid, 108 Nitrobenzene, 303 2-Methylpropyl acetate, 433 Nitrogen oxides (NOX), 90 (aka Isobutyl acetate) Nonadienal 2-Methylpropyl formate, 436 (2E,4E), 67, 69, 72, 73, 75, 142, 443 (aka Isobutyl formate) (2E,6Z), 67, 69, 72, 73, 75, 138, 139, 142, 2-(2-Methylpropyl)-1,3-thiazole, 450 443 (aka 2-Isobutylthiazole) (aka Violet leaf aldehyde) 2-Methylpyrazine, 105, 106, 466 (3Z,6Z), 139 2-Methylpyridine, 105 Nonalactone 3-Methylpyridine, 105 δ, 67, 69 Methyl salicylate, 432 γ , 67, 69, 70, 72, 73, 75, 77, 80, 459 (aka Methyl 2-hydroxybenzoate) (aka 5-Pentyloxolan-2-one) Methylsuccinic acid, 300 γ -Nonalactone, 300 3-Methylsulfanylpropanal, 449 Nonanal, 67, 142, 440 (aka Methional) Nonanoic acid, 300, 430 3-Methylsulfanylpropyl acetate, 450 (aka Pelargonic acid) (aka Methionyl acetate) Nonanol, 108 4-Methylsyringol, 304 1-Nonanol, 427 2-Methylthio acetaldehyde, 449 2-Nonanol, 427 Methyl thioacetate, 171 2-Nonanone, 69, 446 4-Methylthiobutan-2-ol, 450 2-Nonenal, 59 2-Methylthio ethanol, 449 (E)-2-Nonenal, 67, 69, 72, 73, 75, 99, 142, 163, 4-Methylthio-2-oxobutyric acid, 157 307, 441 2-Methylthiophene, 171 (aka trans-2-Nonenal) trans-2-Nonenal, 441 Chemical Index 527

(aka (E)-2-Nonenal) Octyl hexanoate, 437 (Z)-2-Nonenal, 69, 142 (aka Octyl caproate) (aka cis-2-Nonenal) 5-Octyloxolan-2-one, 460 trans-3-Nonenal, 142 (aka γ -Dodecalactone) (Z)-3-Nonenal, 99, 142 2,3-di-O-galloyl-glucose, 290 (aka cis-3-Nonenal) 3-O-galloyl-glucose, 290 Nonenoic acid, 300 6-O-galloyl-glucose, 290 (E)-Non-2-enoic acid, 431 Oleic acid, 98, 108, 136, 142, 161, 169, 266, (E)-Non-2-en-4-one, 445 300, 431 (aka (9Z)-Octadec-9-enoic acid) Oxalacetic acid, 444 O (aka 2-Oxobutanedioic acid) Octacecanoic acid, 317 Oxaldehyde, 444 (9Z,12Z)-9,12-Octadecadienoic acid, 431 (aka Glyoxal) (aka Linoleic acid) Oxaldehydic acid, 431, 444 Octadecanoic acid, 431 (aka Glyoxylic acid) (aka Stearic acid) Oxalic acid, 300 9-Octadecanoic acid, 317 2-Oxobutanedioic acid, 444 (9Z)-Octadec-9-enoic acid, 431 (aka Oxalacetic acid) (aka Oleic acid) (9Z)-12-Oxo-9-dodecenoic acid, 99, 139 cis-2,cis-5-Octadienal, 142 3-Oxo-α-ionol, 309, 310 1,cis-5-Octadien-3-hydroperoxide, 142 (aka 4-[(E)-3-Hydroxybut-1-enyl]-3,5,5- 1,cis-5-Octadien-3-one, 142 trimethylcyclohex-2-en-1-one) 3,5-Octadien-2-one, 142 9-Oxo-nonanolic acid, 99, 139 Octalactone 2-Oxo-3-phenylpropanoic acid, 431 δ, 459 (aka Phenylpyruvic acid) (aka 6-Propyloxan-2-one) 2-Oxopropanal, 178 γ , 69, 459 2-Oxopropanoic acid, 431 (aka 5-Butyloxolan-2-one) (aka Pyruvic acid) Octanal, 142, 359, 440 Octanoic acid, 300, 430 (aka Caprylic acid) P 1-Octanol, 359, 426 Palmitic acid, 98, 136, 169, 266, 300, 431 (S)-(+)-2-Octanol, 426 (aka Hexadecanoic acid) Octan-2-one, 446 Palmitoleic acid, 161, 266, 300, 431 Octan-3-one, 446 (aka (9Z)-Hexadec-9-enoic acid) Octenal, 138 Paraldehyde, 81 (E)-2-Octenal, 307, 440 Pectin, 151, 152 (aka trans-2-Octenal) Pedunculagin, 282, 285 trans-2-Octenal, 142, 440 Pelargonic acid, 266, 430 (aka (E)-2-Octenal) (aka Nonanoic acid) (Z)-2-Octenal, 142 Pentadecanoic acid, 266, 300, 431 (aka cis-2-Octenal) Pentadecenoic acid, 300 1-Octen-3-hydroperoxide, 142 1,2,3,4,6-Pentagalloyl-β-d-glucose, 465 1-Octen-3-ol, 426 Pentanal, 138, 140, 142, 439 1-Octen-3-one, 142, 446 (aka Valeraldehyde) 3-Octen-1-one, 307 Pentane, 142 n-Octyl acetate, 436 Pentane-2,3-dione, 445 Octyl butanoate, 437 (aka Acetylpropionyl) (aka n-Octyl butyrate) Pentanoic acid, 430 n-Octyl butyrate, 437 (aka Valeric acid) (aka Octyl butanoate) 1-Pentanol, 425 Octyl caproate, 437 (aka Amyl alcohol) (aka Octyl hexanoate) 2-Pentanol, 425 528 Chemical Index

3-Pentanol, 425 2-Phenylprop-2-enal, 443 Pentan-2-one, 445 (aka 2-Phenylacrolein) Pentan-3-one, 445 (E)-3-Phenylprop-2-enal, 443 cis-2-Pentenal, 142 (aka Cinnamaldehyde) trans-2-Pentenal, 142 Phenylpyruvic acid, 431 1-Penten-3-ol, 425 (aka 2-Oxo-3-phenylpropanoic acid) cis-Pent-2-en-1-ol, 108 2-Phosphoglycerate, 145 1-Penten-3-one, 142, 445 3-Phosphoglycerate, 145 (aka Ethyl vinyl ketone) Phosphomolybdic acid, 271 6-[(Z)-Pent-2-enyl]oxan-2-one, 462 Phosphoric acid, 316, 317 (aka Jasmine lactone; (Z)-Dec-7-en-5- Phthalic acid, 300 olide) 3-Picoline, 106 Pentyl acetate, 436 Pimelic acid, 300 (aka Amyl acetate) Pinacolone, 445 Pentyl butanoate, 437 (aka 3,3-Dimethylbutan-2-one) (aka n-Amyl butyrate) 1H-Pirrole-2-carboxaldehyde, 305 2-Pentylfuran, 463 Procyanidin Pentyl 3-methylbutanoate, 433 B1, 465 (aka Isoamyl n-valerate) B2, 466 5-Pentyloxolan-2-one, 459 B3, 466 (aka γ -Nonalactone) C1, 466 6-Pentyloxan-2-one, 460 Proline, 178 (aka δ-Decalactone) Propanal, 108, 142, 439 6-Pentylpyran-2-one, 462 1,3-Propanediol, 159 2-Phenethylacetate, 155 Propane-1-thiol, 449 Phenol, 107–109, 184, 304, 311, 454 (aka n-Propyl mercaptan) 2-Phenoxyethanol, 305 1,1,3-Propanetriol, 159, 160 Phenylacetaldehyde, 69 Propanoic acid, 429 2-Phenylacetaldehyde, 146, 442 (aka Propionic acid) Phenylacetic acid, 108 Propanol, 144, 149, 150 2-Phenylacetic acid, 67, 69, 80, 431 1-Propanol, 137, 147, 175, 179, 182, 185, 210, 2-Phenylacrolein, 443 211, 218, 225, 229, 247, 249, 323, (aka 2-Phenylprop-2-enal) 424 Phenylalanine, 146 (aka Propanol; n-Propanol; n-Propyl 4-Phenylbutan-2-one, 446 alcohol) (aka Benzylacetone) 2-Propanol, 424 (E)-4-Phenylbut-3-en-2-one, 446 Propan-2-one, 445 (aka Benzalacetone) (aka Acetone) Phenylethanol, 59 4-Propan-2-ylbenzaldehyde, 444 2-Phenylethanol, 51, 67, 69, 70, 72, 73, 75, 80, (aka Cuminaldehyde) 108, 144, 146, 149, 150, 175, 305, 2-Propan-2-ylsulfanylpropane, 449 311, 427 (aka Di-isopropyl sulfide) 1-Phenylethanone, 446 Prop-2-enal, 442 (aka Acetophenone) (aka Acrolein) 2-Phenylethyl acetate, 67, 69, 72, 73, 75, 80, Propionaldehyde, 147, 180, 182, 212, 213, 218, 153, 175, 311, 434 225, 229, 247, 249 (aka β-Phenylethyl acetate) Propionic acid, 108, 182, 208, 209, 218, 225, β-Phenylethyl acetate, 434 229, 247, 249, 266, 300, 429 (aka 2-Phenylethyl acetate) (aka Propanoic acid) 2-Phenylethyl propanoate, 67 Propiovanillone, 294, 295 Phenylmethanol, 305, 426 Propyl acetate, 62, 436 (aka Benzyl alcohol) (aka n-Propyl acetate) 2-Phenylpropanal, 443 2-Propyl furan, 311 3-Phenylpropanol, 108 4-Propylguaiacol, 457 Chemical Index 529

(aka 4-Propyl-2-methoxyphenol) Sinapic acid, 458 n-Propyl mercaptan, 449 (aka (E)-3-(4-Hydroxy-3,5- (aka Propane-1-thiol) dimethoxyphenyl)prop-2-enoic 4-Propyl-2-methoxyphenol, 69, 75, 457 acid) (aka 4-Propylguaiacol) Sinapic alcohol, 289 6-Propyloxan-2-one, 459 Sinapyl alcohol, 289, 292 (aka δ-Octalactone) Sitosterol β-D-glucoside, 297 5-Propyloxolan-2-one, 459 Sodium 4-hydrazino-benzenesulfonate, 261 (aka γ -Heptalactone) Sodium hydroxide, 303 2-Propylpyrazine, 108 Sodium hypochlorite, 115 Protocatechuic acid, 458 Sodium sulfide, 59 ethyl ester, 438 Sodium tungstate, 271 Proto-quercitol, 288, 292 Sotolon, 301, 302, 462 Pryene, 343 (aka 3-Hydroxy-4,5-dimethylfuran-2(5H)- Pyruvic acid, 144, 145, 147, 148 one) Punicalagin, 282, 285 Stearic acid, 98, 136, 266, 300, 431 Pyrazine, 356, 466 (aka Octadecanoic acid) Pyrazines, 102, 105, 119, 288 Suberic acid, 300 Pyridine, 106, 466 Succinic acid, 300 Pyridines, 104, 105, 288 Sucrose, 143, 320 Pyruvic acid, 431 Sulfur dioxide, 171 (aka 2-Oxopropanoic acid) Syringaldehyde, 80, 289, 293–296, 298, 303, 311, 313, 456 (aka 4-Hydroxy-3,5-dimethoxy Q benzaldehyde) Quercetin-3-O-β-D-galactopyranoside, 464 β β Syringetin-3-O- -D-glucopyranoside, 464 Quercetin-3-O- -D-glucuropyranoside, 464 Syringic acid, 294, 295, 303, 313, 317, 456 Quercitrin, 464 ethyl ester, 438 (aka 4-Hydroxy-3,5-dimethoxybenzoic R acid) Rhamnose, 291, 292 Syringol, 304, 311, 455 Ribofuranose, 316, 317 (aka 1,3-Dimethoxy-2-hydroxybenzene) Ribopyranose, 316, 317 Roburin A, 283, 465 T B, 283, 465 Tannic acid, 273, 465 C, 283, 465 Tannin, 138, 296, 315 D, 283, 465 condensed, 139, 281, 282 dimers, 282 hydrolyzable, 282 E, 282, 283, 465 polymeric, 466 Ruhemann’s purple, 88 Tartaric acid, 432 (aka 2,3-Dihydroxybutanedioic acid) Terpenes, 300, 301 S Terpineol, 301 S-adenosyl-L-methionine, 100 α-Terpineol, 427 Scopoletin, 296, 297, 303 (aka 2-(4-Methyl-1-cyclohex-3- Scopolin, 297 enyl)propan-2-ol) Sebacic acid, 300 Tetradecanoic acid, 431 S-Ethyl thioacetate, 157 (aka Myristic acid) Silica, 169 1-Tetradecanol, 359, 428 Simethicone, 173, 190 Tetradecenoic acid, 300 Sinapaldehyde, 289, 293–296, 303, 313, 458 1,2,3,6-Tetrahydrobenzaldehyde, 442 (aka 3-(4-Hydroxy-3,5- (aka Cyclohex-3-ene-1-carbaldehyde) dimethoxyphenol)prop-2-enal) 1,2,3,5-Tetrahydroxycyclohexane, 317 530 Chemical Index

Tetramethylpyrazine, 106 V 2,3,5,6-Tetramethylpyrazine, 466 Valeonic acid bilactone, 286 Theonine, 148 Valeraldehyde, 108, 180, 182, 212, 213, 218, Thiazole, 106 225, 229, 247, 249, 439 1,3-Thiazole, 449 (aka Pentanal) Thiocyanate, 114 Valeric acid, 108, 182, 208, 209, 218, 225, 229, Thiomenthone, 59 247, 249, 266, 300, 430 2-Thiophencarboxaldehyde, 274, 275 (aka Pentanoic acid) (aka Formylthiophene) Valine, 146–148 Thiophene, 171 Vanillic acid, 138, 294, 295, 303, 311, 313, 2-Thiophenecarboxaldehyde, 171 317, 458 Threonine, 147, 302 ethyl ester, 438 2,4,6-Tribromophenol, 107, 458 (aka 4-Hydroxy-3-methoxybenzoic acid) 1,2,4-Trichloro-3-methoxybenzene, 464 Vanillin, 47, 59, 78, 80, 162, 289, 293–296, (aka 2,3,6-Trichloroanisole) 298, 303, 309, 311, 313, 457 2,3,6-Trichloroanisole, 464 (aka 4-Hydroxy-3-methoxy benzaldehyde) (aka 1,2,4-Trichloro-3-methoxybenzene) Verbenone, 301 2,4,6-Trichloroanisole, 59 Vescalagin, 282, 283, 465 Tridecanoic acid, 266, 431 4-Vinylguaiacol, 59, 136, 137, 162, 175, 190, Tridecan-2-one, 446 304, 309, 453 2,3,5-Triethylpyrazine, 108 (aka 4-Ethenyl-2-methoxyphenol) Trigalloyl glucose, 286 p-Vinylguaiacol, 80 3,4,5-Trihydroxybenzoic acid, 458 4-Vinylphenol, 455 (aka Gallic acid) (aka p-Ethenylphenol; 4-Ethenylphenol) Trimethylbenzoic acid, 300 p-Vinylphenol, 137, 162, 455 2,6,6-Trimethyl-2-cyclohexene-1,4-dione, 309 (aka 4-Vinylphenol; 4-Ethenylphenol) (E)-4-(2,6,6-Trimethylcyclohexen-1-yl)but-3- Violet leaf aldehyde, 443 en-2-one, 447 (aka (2E,6Z)-Nonadienal) (aka β-Ionone) (E)-4-(2,6,6-Trimethylcyclohex-2-en-1-yl)but- 3-en-2-one, 447 W (aka α-Ionone) Whisky tannin, 289 2,3,4-Trimethylpyrazine, 466 Whiskylactone 2,3,5-Trimethylpyrazine, 105, 106, 108, 466 whisky lactone Trithioacetaldehyde, 157 trans,(3S,4R), 69 Tryptophan, 146 Whisky lactone, 59, 298, 460 Tyrosine, 146 cis, 80, 311 Tyrosol, 427 (3R,4R), 298 (aka 4-(2-Hydroxyethyl)phenol) (3S,4S), 67, 69, 72, 73, 75, 77, 78, 298 precursor, 298, 299 trans, 80 U (3R,4S), 298 Umbelliferone, 297 (3S,4R), 67, 72, 73, 75, 298 Undecanal, 441, 444 (aka β-Methyl-γ -octalactone; 5-Butyl-4- Undecanoic acid, 266, 300, 430 methyloxolan-2-one) 1-Undecanol, 428 2-Undecanol, 428 Undecan-2-one, 446 X Undec-10-enal, 444 2,3-Xylenol, 458 trans-2-Undecenal, 142 (aka 2,3-Dimethylphenol) Undec-9-enal, 444 2,6-Xylenol, 295, 296 Urea, 114 Xylopyranose, 317 Urethane, 112 Xylose, 135, 176, 291, 292, 317 (aka Ethylcarbamate)