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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 Table A.1 A compilation of aroma threshold data Compound Descriptor Threshold [ppb] By In References Alcohols Methanol Alcohol, solvent 10,000,000 T Beer [528] Ethanol Ethanol-like 2,000,000 rO Water [198] Ethanol-like 990,000 dO Water [198] Alcohol, strong 14,000,000 T Beer [528] 1-Propanol Alcohol 800,000 T Beer [528] 306,100 O White wine at 10% [207] >720,000 O 34% Spirit [723] 2-Propanol Alcohol 1,500,000 T Beer [528] 1-Butanol Malty, solvent-like 4300 rO Water [198] Malty, solvent-like 590 dO Water [198] 500 O Water [131] Alcohol 450,000 T Beer [528] >5000 O 34% Spirit [723] 2-Methylpropan-1-ol (aka isobutyl alcohol) Malty 2300 rO Water [198] Malty 550 dO Water [198] Alcohol 200,000 T Beer [528] 75,000 O 9.4% (w/w) Spirit [722] 40,000 O 10% (w/w) Ethanol [321] 75,000 O 34% Spirit [723] 2-Butanol Alcohol 16,000 T Beer [528] >10,000 O 34% Spirit [723] 2-Methylpropan-2-ol (aka tert-butyl alcohol) Alcohol 1,600,000 T Beer [528] Butane-2,3-diol Rubber, sweetish, warming, diacetyl 4,500,000 T Beer [528] A Threshold Data 425 1-Pentanol Alcohol, medicinal 80,000 T Beer [528] 64,430 O Whitewineat10% [207] 3-Methylbutanol (aka isoamyl alcohol) Malty 980 rO Water [198] Malty 220 dO Water [198] 250 O Water [131] 4000 T Water [680, 681] Alcohol, banana, sweetish, aromatic 70,000 T Beer [528] 7000 O 9.4% (w/w) Spirit [722] 7000 O 10% Ethanol [790] 310,000 T 12% Ethanol [680, 681] 330,000 T Dry Riesling [680, 681] 300,000 T Ugni Blanc [680, 681] 30,000 O 10% (w/w) Ethanol [321] 6500 O 34% Spirit [723] Malty 56,100 O 40% Ethanol [656, 658] 2-Methyl-1-butanol Malty, solvent-like 3700 rO Water [198] Malty, solvent-like 1200 dO Water [198] Alcohol, banana, medicinal, solvent 65,000 T Beer [528] 32,000 O 34% Spirit [723] 2-Pentanol Alcohol, fruity, raspberry, nutty, ether 45,000 T Beer [528] 3-Pentanol Alcohol, medicinal, ether, nutty, fruity 50,000 T Beer [528] 1-Penten-3-ol 400 O Water [131] Pungent, alcoholic, solvent 350 T Beer [528] (continued) 426 A Threshold Data Table A.1 (continued) Compound Descriptor Threshold [ppb] By In References 1-Hexanol 400 O Water [131] Coconut, green leaves, unpleasant 400,000 T Beer [528] 5200 O 9.4% (w/w) Spirit [722] 5200 O 10% Ethanol [790] 8000 O 10% (w/w) Ethanol [321] 5200 O 34% Spirit [723] 5280 O White wine at 10% [207] 1080 O White wine at 10% [207] 2-Hexanol Coconut 400,000 T Beer [528] (E)-2-Hexen-1-ol Bitter, green leaves 15,000 T Beer [528] (Z)-3-Hexen-1-ol Lettuce-like 13 rO Water [198] Lettuce-like 3.9 dO Water [198] 70 O Water [131] Green leaves, banana, sweetish 13,000 T Beer [528] 400 O 10% (w/w) Ethanol [321] 1-Heptanol Coconut 1000 T Beer [528] 2450 O White wine at 10% [207] 2-Heptanol Coconut 250 T Beer [528] 1-Hepten-3-ol Green leaves 150 T Beer [528] Phenylmethanol (aka benzyl alcohol) Almonds, bitter 900,000 T Beer [528] 1-Octanol Coconut, walnut, oily 900 T Beer [528] 820 O White wine at 10% [207] 1100 O 34% Spirit [723] (S)-(+)-2-Octanol Coconut, walnut, oily 40 T Beer [528] 1-Octen-3-ol Green leaves, perfumed, sweetish 200 T Beer [528] 2-Phenylethanol Flowery, honey-like 390 rO Water [198] A Threshold Data 427 Flowery, honey-like 140 dO Water [198] Roses, sweetish, perfumed 125,000 T Beer [528] 7500 O 9.4% (w/w) Spirit [722] 7500 O 10% Ethanol [790] 10,000 O 10% (w/w) Ethanol [321] 2000 dO 23% (v/v) Grain whisky [447] Floral 80,000 rO 23% (v/v) Grain whisky [447] 7500 O 34% Spirit [723] Flowery 2600 O 40% Ethanol [658] 4-(2-Hydroxyethyl)phenol (aka tyrosol) Bitter, chemical 200,000 T Beer [528] 1-Nonanol Coconut, walnut, oily 80 T Beer [528] 310 O Deflavored white wine at 10% [207] 2-Nonanol Coconut 75 T Beer [528] 1-Decanol Coconut, walnut, oily, rancid 180 T Beer [528] 360 O White wine at 10% [207] 210 O 34% Spirit [723] 2-Decanol Coconut, aniseed 15 T Beer [528] (Z)-3,7-Dimethyl-2,6-octadien-1-ol Lime, flowery (hyacinth, rose) 500 T Beer [528] (aka nerol) 2,7-Dimethylocta-1,6-dien-3-ol (aka linalool) 6 O Water [131] Aniseed, terpenoid 80 T Beer [528] 15 O 10% (w/w) Ethanol [321] (R)-2,7-Dimethylocta-1,6-dien-3-ol Citrus-like, bergamot-like 0.17 rO Water [198] Citrus-like, bergamot-like 0.087 dO Water [198] 2-(4-Methyl-1-cyclohex-3-enyl)propan-2-ol 350 O Water [131] (aka α-terpineol) Almonds, solvent 414,000 T Beer [528] (continued) 428 A Threshold Data Table A.1 (continued) Compound Descriptor Threshold [ppb] By In References 1-Undecanol Fatty acids, coconut 500 T Beer [528] 2-Undecanol Perfumed, sweetish, coconut, varnish, 70 T Beer [528] musty 1-Dodecanol Fatty acids, coconut, banana 400 T Beer [528] 1001 O White wine at 10% [207] 1000 O 34% Spirit [723] 1-Tetradecanol 5000 O 34% Spirit [723] 1-Hexadecanol 1100 O 34% Spirit [723] Maltol (aka 3-hydroxy-2-methylpyran-4-one) Sweet, cotton candy, burnt sugar 35,000 O Water [654] Fruity, cotton candy, sour 13,000 T Water [654] Caramel, fragrant 11,400 O White wine [777] 8000 dO 23% (v/v) Grain whisky [447] Sweet 36,000 rO 23% (v/v) Grain whisky [447] Cyclotene (aka 2-hydroxy-3-methyl-2- Maple 300 O Water [583] cyclopentenone) Caramel, maple 3100 O White wine [777] Acids Acetic acid Vinegar 180,000 rO Water [198] Vinegar 99,000 dO Water [198] 200,000 O 10% (w/w) Ethanol [321] 24,000 dO 23% (v/v) Grain whisky [447] Sour 233,000 rO 23% (v/v) Grain whisky [447] 26,000 O 34% Spirit [723] 3-Methylbutanoic acid (aka isovaleric acid) Sweaty 1200 rO Water [198] A Threshold Data 429 Sweaty 490 dO Water [198] Cheese, old hops, sweaty 1500 T Beer [528] 700 O 9.4% (w/w) Spirit [722] 700 O 10% Ethanol [790] 100 dO 23% (v/v) Grain whisky [447] Sweaty 300 rO 23% (v/v) Grain whisky [447] 750 O 34% Spirit [723] Butanoic acid (aka butyric acid) Sweaty 7700 rO Water [198] Sweaty 2400 dO Water [198] Buttery, cheesy, sweaty 2200 T Beer [528] 4000 O 9.4% (w/w) Spirit [722] 4000 O 10% Ethanol [790] 10,000 O 10% (w/w) Ethanol [321] 3400 O 34% Spirit [723] (E)-But-2-enedioic acid (aka fumaric acid) Acid 400,000 T Beer [528] 2-Methylpropanoic acid (aka isobutyric acid) Sweaty, cheesy 29,000 rO Water [198] Sweaty, cheesy 16,000 dO Water [198] Sweaty, bitter, sour 30,000 T Beer [528] 8000 O 9.4% (w/w) Spirit [722] 8100 O 10% Ethanol [790] 200,000 O 10% (w/w) Ethanol [321] 8200 O 34% Spirit [723] Propanoic acid (aka propionic
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    SUPPLEMENTARY INFORMATION 1: Identity for Natural Flavor Complexes as Evaluated by the Expert Panel The Identification Description as Reviewed by the FEMA FEMA No.1 FEMA Primary Name Expert Panel Rebaudioside M ≥80%; Rebaudioside D 5-20%; Total 4895 Rebaudioside M steviol glycosides ≥95%. Glutamic acid 35-40%; Other amino acids 1-2%; Total Corynebacterium glutamicum corn nitrogen 6-7%; Aliphatic primary alcohols, aldehydes, 4907 syrup fermentation product carboxylic acids, acetals and esters containing additional oxygenated functional groups 1-2%; Minerals 9-11% Inosine 5´-monophosphate 20-25%; Amino acids 7-8%; Corynebacterium stationis corn 4908 Minerals 23-25%; water 28-37%; Other nucleotides 1-2%; syrup fermentation product Total nitrogen 5-8% Supraglucosylated steviol glycosides 70-80%; Rebaudioside Glucosylated steviol glycosides, 4909 A 14-20%; Steviol glycosides not further glucosylated, each 70-80% individually, not to exceed 3%; Maltodextrin 3-10% Supraglucosylated steviol glycosides 30-40%; Rebaudioside Glucosylated steviol glycosides, A 5-8%; Not more than 4% stevioside; All other individual 4910 40% steviol glycosides not further glucosylated <3%; Maltodextrin 45-60% Stevioside 70-80%; Rebaudioside A 13-18%; Steviobioside 1- 3%; Rebaudioside C 2-3%; Total glycosides (including 4911 Stevia extract stevioside, 70% Rebaudioside D, Rebaudioside B, Rebaudioside F, Dulcoside A, and Rubusoside) <3% Derived from hibiscus blossom calyces (Hibiscus sabdariffa L.) , Hibiscus blossom extract is measured as water 30-60%; 4912 Hibiscus
  • New Natural Agonists of the Transient Receptor Potential Ankyrin 1 (TRPA1

    New Natural Agonists of the Transient Receptor Potential Ankyrin 1 (TRPA1

    www.nature.com/scientificreports OPEN New natural agonists of the transient receptor potential Ankyrin 1 (TRPA1) channel Coline Legrand, Jenny Meylan Merlini, Carole de Senarclens‑Bezençon & Stéphanie Michlig* The transient receptor potential (TRP) channels family are cationic channels involved in various physiological processes as pain, infammation, metabolism, swallowing function, gut motility, thermoregulation or adipogenesis. In the oral cavity, TRP channels are involved in chemesthesis, the sensory chemical transduction of spicy ingredients. Among them, TRPA1 is activated by natural molecules producing pungent, tingling or irritating sensations during their consumption. TRPA1 can be activated by diferent chemicals found in plants or spices such as the electrophiles isothiocyanates, thiosulfnates or unsaturated aldehydes. TRPA1 has been as well associated to various physiological mechanisms like gut motility, infammation or pain. Cinnamaldehyde, its well known potent agonist from cinnamon, is reported to impact metabolism and exert anti-obesity and anti-hyperglycemic efects. Recently, a structurally similar molecule to cinnamaldehyde, cuminaldehyde was shown to possess anti-obesity and anti-hyperglycemic efect as well. We hypothesized that both cinnamaldehyde and cuminaldehyde might exert this metabolic efects through TRPA1 activation and evaluated the impact of cuminaldehyde on TRPA1. The results presented here show that cuminaldehyde activates TRPA1 as well. Additionally, a new natural agonist of TRPA1, tiglic aldehyde, was identifed