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FLAVORS

Wine is well known for its incredible diversity of flavors. There are tens of thousands of compounds that contribute to each wine’s distinct fingerprint, and yet, flavor is the one thing winemakers have the least control over. Those seeking flavor concentration may lower yields, and those seeking fewer pyrazines may leaf thin and extend hang time, but at the end of the day, winemakers have very limited tools when it comes to shaping which flavors make it into the final wine. So before exploring individual flavors themselves, we choose to better understand their nature and how they fit into wine’s matrix. 

One of the key properties of virtually every flavor in wine is hydrophobicity, or the tendency to repel water. To put it simply, water is polar, and flavors are non-polar (like oil in water). They require alcohol as a solvent to remain in solution, which is one reason why de-alcoholized wines lose flavor before making it to the consumer. To better understand how hydrophobic flavors are we refer to their Log P values, otherwise known as the partition constant, which ranges from a scale of -3 (very hydrophilic) to +10 (extremely hydrophobic) (Cumming et al 2017). As you will see in the chart below, just about every wine flavor has a positive Log P value, indicating a degree of hydrophobicity. Why is this important to winemaking? Understanding hydrophobic interactions is key to unraveling some of wine's greatest mysteries and the key to harmonizing flavor and mouthfeel. 

In addition to alcohol, flavors will also interact with other non-polar compounds in wine. Tannins in particular are very hydrophobic compounds that when highly active can mute the aroma of wine giving it a closed aroma profile. This is very common amongst highly structured red wines, but this phenomenon also occurs with every wine style. This is because the majority of all phenolics in wine are Iron-Reactive Phenolics, and they are extracted primarily from the pulp. This means that non-astringent compounds in white wines, sparkling wines, and roses can also act as flavor-binding agents, the effect of which is just generally lower than for red wines. 

In general, a moderate amount of flavor suppression is a good thing. Wines that are too expressive jump out of the glass and can become dominated by a single characteristic. This is common amongst hot climate wines because they have little phenolic activity to balance aroma expression. These wines are often perceived as simple and lower quality because they also lack flavor concentration. Wines with moderate aroma suppression entice you into the glass and continue to evolve as they open up. 

When it comes to balancing flavors, it’s important to note that they also compete amongst themselves. Spoilage characteristics like Brettanomyces taint and cork taint (TCA) can suppress fruity esters and terpenes, a shift winemakers can detect even before identifying the spoilage aromas themselves. At these low levels, masked fruitiness may be perceived as increased complexity, but no winemaker encourages TCA because even at low levels it acts as a strong suppressor of our olfactory signals, clinging on and lingering in our noses and on our palates preventing us from smelling or tasting anything else (Takeuchi et al, 2013). 

Finally, alcohol and Iron-Reactive Phenolics are the key components that suppress aromas in wine, while volatile acidity is a key component that amplifies aromas in wine. This knowledge is exceptionally powerful when blending and shaping the different dimensions of your wine. It is important to note that a wine chemistry profile is insufficient for determining which lots are more closed or open. Enological analysis lends insight into the quantity of compounds, but we always accompany data with our palates because they are the only instruments that can provide a holistic assessment of wine quality. We, therefore, analyze the wine chemically and connect the dots organoleptically.

 
Odor Descriptor(s) Chemical Category  Chemical  Odor Detection Threshold Hydrophobic Constant (Log P) o/w 
Rose Taint Cycloalkane 1,1,3,5-tetramethylcyclohexane   5.15
Kerosene, petrol Isoprenoid 1,1,6‐Trimethyl‐1,2dihydronapthalene (TDN) 2 µg/L (ppb) 5.129
Grape, fruity Ester: Fatty acid ethyl ester Ethyl decanoate 200 µg/L (ppb) 4.861
Floral, rose   Isoprenoid Farnesol 20 µg/L (ppb) 4.828
Floral, apple, green Isoprenoid Nerolidol 10 µg/L (ppb) 4.682
Musty, moldy Anisole Tribromoanisole (TBA) 4-8 ng/L (ppt) 4.1
Fatty, rancid Volatile fatty acid Decanoic acid 1 (mg/L) 4.09
Baked/stewed apple, quince, honey, floral Isoprenoid β-Damascenone 0.05 µg/L (ppb) 4.042
Black Pepper Isoprenoid (-)-Rotundone  0.016 µg/L (ppb) 4.04
Violet, wood, raspberry Isoprenoid β‐Ionone 0.09 µg/L (ppb) 3.995
Citrus, aldehydic, sweet, waxy, orange peel Aldehyde Decanal 1.25 µg/L (ppb) 3.97
Peach, fruity Ester: Fatty acid ethyl ester Ethyl octanoate (ethyl caprylate) 5 µg/L (ppb) 3.842
Cork taint, musty, moldy, baby carrots Anisole Trichloroanisole (TCA) 1.4-3 ng/L (ppt) 3.74
Floral, citrus Isoprenoid Geraniol 30 µg/L (ppb) 3.56
Petrichor, earthy, beetroot, muddy Bicyclic alcohol Geosmin 25-50 ng/L (ppt) 3.497
Citrus, floral, green Isoprenoid Nerol 300-400 µg/L (ppb) 3.47
Coconut Ester: Lactone γ–Dodecalactone 7 µg/L (ppb) 3.47
Citrus, waxy, aldehydic, rose, fresh, orris, orange peel, fatty Aldehyde Nonanal 2.5 µg/L (ppb) 3.461
Fatty, green, cucumber, aldehydic, citrus Aldehyde (E)‐2‐nonenal 0.6 µg/L (ppb) 3.319
Floral, rose, citrus Isoprenoid β-Citronellol 100 µg/L (ppb) 3.239
Rose, floral, green Isoprenoid (–)‐cis‐Rose oxide 0.2 µg/L (ppb) 3.186
Onion Alkyl disulfide Diethyl disulfide (DEDS) 4 µg/L (ppb) 3.169
Fatty, rancid Volatile fatty acid Octanoic (caprylic) acid 0.5 (mg/L) 3.05
Cinnamon Ester: Fatty acid ethyl ester Ethyl cinnamate 1.1 µg/L (ppb) 2.99
Citrus, floral, muscat Isoprenoid Linalool 15-25 µg/L (ppb) 2.97
Citrus, aldehydic, waxy, orange peel, green herbal, fresh, fatty Aldehyde Octanal 2.5 µg/L (ppb) 2.951
Earthy, camphor-like Monoterpene (–)2-Methylisoborneol (MIB) 30-55 ng/L (ppt) 2.931
Bell Pepper Pyrazine "SBMP" 3-secbutyl-2-methoxypyrazine   2.924
Green apple, sweet, banana Ester: Acetate ester Hexyl acetate 1800 µg/L (ppb) 2.87
Spicy, herbal Terpenoid p-menth-1-en-9-al (Carvomenthenal)   2.858
Green Apple, Guava, Strawberry, Anise Ester: Fatty acid ethyl ester Ethyl hexanoate (ethyl caproate) 14 µg/L (ppb) 2.823
Fresh cucumber, fatty, green, herbal, banana, waxy, green leaf Aldehyde (E)‐2‐octenal 3 µg/L (ppb) 2.809
Sweet   Ester: Fatty acid ethyl ester Ethyl 2-methylpropanoate 15 µg/L (ppb) 2.758
Smoke, struck flint Aryl thiol Benzenemethanethiol (BMT) 0.3 ng/L (ppt) 2.739
Fatty, peach Ester: Lactone γ–Decalactone 0.7 µg/L (ppb) 2.72
Lilac, floral, woody Isoprenoid α-Terpineol 250 µg/L (ppb) 2.67
Strawberry Ester: Fatty acid ethyl ester Ethyl 4-methylpentanoate 0.75 µg/L (ppb) 2.667
Prune, minty, anise Ketone 3‐Methyl‐2,4‐nonanedione 0.016 µg/L (ppb) 2.661
Strawberry Ester: Fatty acid ethyl ester Ethyl 3-methylpentanoate 0.5 µg/L (ppb) 2.65
Coconut Ester: Lactone (4S,5S)‐3‐Methylγ‐octalactone (cis‐oak lactone) 25 µg/L (ppb) 2.631
Medicinal, phenolic Volatile phenol 4‐Vinylphenol (4VP) 180 µg/L (ppb) 2.615
Medicinal, pharmaceutical, barnyard, horse Volatile phenol 4-Ethylphenol (4EP) 368-600 µg/L (ppb) 2.58
Horsey Volatile phenol 4-ethylcatechol (4EC) 774 µg/L (ppb) 2.58
Smoke, phenolic Volatile phenol 4‐Vinylguaiacol (4VG) 40 µg/L (ppb) 2.573
Coriander, green, sweet, oily Monoterpene 6-methyl-5-hepten-2-ol (Coriander heptenol)   2.57
Bell Pepper, vegetal Pyrazine 3‐Isobutyl‐2‐methoxypyrazine (IBMP) 2-60 ng/L (ppt) 2.547
Passionfruit, box tree Thiol 3‐Mercaptohexyl acetate  (3‐MHA) 4 ng/L (ppt) 2.539
Mushroom, metallic Higher alcohol 1‐Octen‐3‐ol 20-40 µg/L (ppb) 2.519
Eucalyptus, fresh, minty, bay leaf Isoprenoid 1,8-cineole (Eucalyptol) 1.1-3.5 µg/L (ppb) 2.512
Smoky, spice, clove Volatile phenol 4-ethylguaiacol (4EG)  11-33 µg/L (ppb) 2.434
Bell Pepper, asparagus, earth, peas Pyrazine 3-Isopropyl-2-methoxypyrazine (IPMP) 0.3-2 ng/L (ppt) 2.414
Hyacinth flower, citrus Isoprenoid Hotrienol 111 µg/L (ppb) 2.408
Plastic, medicinal, paint, phenolic Chlorophenol 2,6‐Dichlorophenol (2,6‐DCP) 32 ng/L (ppt) 2.36
Meaty, roasted, burnt, bacon, smoke, ham Volatile phenol Allyl-4-syringol   2.338
Rose, honey, tropical Ester: Acetate ester 2-Phenylethyl acetate 2400 µg/L (ppb) 2.3
Clove, spice Volatile phenol Eugenol (4‐Allyl‐2‐methoxyphenol) 6 µg/L (ppb) 2.27
Banana, ripe, sweet Ester: Acetate ester Isoamyl acetate  30-160 µg/L (ppb) 2.26
Mushroom, metallic Ketone 1‐Octen‐3‐one 70 ng/L (ppt) 2.18
Fruity  Ester: Fatty acid ethyl ester Ethyl 3-methylbutanoate (ethyl isovalerate) 3 µg/L (ppb) 2.158
Apple  Ester: Fatty acid ethyl ester Ethyl 2-methylbutanoate 18 µg/L (ppb) 2.158
Chemical, plastic, rubber, mothballs  Biogenic amine Indole 23 µg/L (ppb) 2.14
Phenolic, gasoline, ethereal, anise Anisole Methoxybenzene   2.11
Plastic, medicinal, paint, phenolic Chlorophenol 2,4‐Dichlorophenol (2,4‐DCP) 896 ng/L (ppt) 2.1
Grassy  Higher alcohol 1‐Hexanol 8 mg/L (ppm) 2.03
Rubber S‐Heterocycle Benzothiazole (BT) 50 ng/L (ppt) 2.01
Coconut Ester: Lactone (4S,5R)‐3‐Methylγ‐octalactone (trans‐oak lactone) 110 µg/L (ppb) 1.968
Coconut  Isoprenoid 4-hydroxy-3-methyloctanoic acid gamma-lactone (whiskey lactone) 67 µg/L (ppb) 1.968
Leather Volatile phenol Meta‐Cresol (3‐methylphenol) 20 µg/L (ppb) 1.96
Garlic, rubber  Alkyl disulfide Diethyl sulfide (DES) 1 µg/L (ppb) 1.95
Phenolic, animal Volatile phenol Ortho-Cresol   1.95
Peach  Ester: Lactone γ–Nonalactone 25 µg/L (ppb) 1.942
Cooked meat, fish Aryl thiol 2‐Methyl‐3‐furanthiol (MFT) 3 ng/L (ppt) 1.941
Phenolic, animal Volatile phenol Para-Cresol   1.94
Smoke Taint, ash Volatile phenol 4‐Methylguaiacol (2‐Methoxy‐4methylphenol) 4-21 µg/L (ppb) 1.925
Fatty, rancid, cheese Volatile fatty acid Hexanoic (caproic) acid 0.4 (mg/L) 1.92
Disinfectant Chlorophenol 6‐Chloro‐o‐cresol (6CC) 70 ng/L (ppt) 1.9
Artificial grape, Concord grapes (Vitis labrusca)  Ester Methyl anthranilate (MA) 300 µg/L (ppb) 1.88
Phenolic, smoke, spice, clove, caramel Volatile phenol Methyl-4-syringol   1.859
Pineapple, apple, fruity Ester: Fatty acid ethyl ester Ethyl butanoate 20 µg/L (ppb) 1.804
Bell Pepper Pyrazine 3-Ethyl-2-methoxypyrazine   1.8
Green, sweet, floral Aldehyde Phenylacetaldehyde 1 µg/L (ppb) 1.78
Banana, cherry, tropical Ester: Acetate ester 2‐Methylpropyl acetate (isobutyl acetate) 1600 µg/L (ppb) 1.78
Onion, cabbage, asparagus Alkyl disulfide Dimethyl disulfide (DMDS) 10-29 µg/L (ppb) 1.77
Roasted coffee Aryl thiol 2‐Furanmethanethiol (2‐furfurylthiol (FFT)) 0.4 ng/L (ppt) 1.727
Rose Taint Ketone 6-methyl-3,5-heptadien-2-one (methyl heptadienone)   1.679
Cork taint, fungal, earth, must,  Pyrazine 2‐Methoxy‐3,5-dimethylpyrazine (MDMP) 2 ng/L (ppt) 1.672
Passionfruit, grapefruit Volatile thiol 3‐Mercaptohexanol (3MH) 0.00006 mg/L (ppm) 1.644
Grapefruit, passionfruit Thiol 3‐Mercaptohexan‐1‐ol (3‐MH) 60 ng/L (ppt) 1.644
Coconut, woody, sweet Isoprenoid Wine Lactone  0.01 µg/L (ppb) 1.634
Corn tortilla, mothball, acacia Ketone ortho-Aminoacetophenone (o-AAP) 0.5 µg/L (ppb) 1.63
Fruity, wasabi, tropical, horseradish Ester Allyl propionate   1.599
Meaty, dirty, cooked, phenolic, rubbery Biogenic amine Tyramine   1.585
  Biogenic amine Tryptamine   1.55
Chemical, ink Volatile phenol Phenol 30 µg/L (ppb) 1.46
Fishy, ammonia Biogenic amine Triethylamine   1.45
Putrefaction Onion, rubber Alkyl thiol Ethanethiol (EtSH) 1 µg/L (ppb) 1.442
Coconut  Ester: Lactone γ–Octalactone 7 µg/L (ppb) 1.432
Box tree, guava Thiol 4‐Mercapto‐4‐methylpentan‐2one (4‐MMP) 3 ng/L (ppt) 1.432
Fishy Biogenic amine Phenylethylamine   1.41
Unpleasant ammonia Biogenic amine Isoamylamine   1.41
Maple syrup Ketone Sotolon 8 µg/L (ppb) 1.4
Garlic, onion Thioester Ethyl thioacetate (EtSAc) 10 µg/L (ppb) 1.369
Rose, honey Higher alcohol 2-Phenylethanol (β‐phenylethanol) 14 mg/L (ppm) 1.36
Smoke Taint, sweet Volatile phenol Guaiacol (2‐methoxyphenol) 4-23 µg/L ppb 1.32
Solvent, fusel Higher alcohol 2-Methyl-1-butanol (active amyl alcohol) 1.2 mg/L (ppm) 1.29
Citrus Thiol 4‐Mercapto‐4‐methylpentan‐2‐ol (4‐MMPOH) 55 ng/L (ppt) 1.278
Chocolate, unripe banana, leafy, apple, cheese,  Aldehyde 3‐Methylbutanal (Isovaleraldehyde) 4 µg/L (ppb) 1.267
Cocoa, musty, phenolic, coffee, nutty, malty, fermented, fatty, alcoholic Aldehyde 2‐Methylbutanal 16 µg/L (ppb) 1.267
Vanilla Volatile phenol Vanillin (4‐hydroxy‐3methoxybenzaldehyde) 200 µg/L (ppb) 1.21
Rancid, sweat, cheese Volatile fatty acid 3-Methylbutanoic (isovaleric) acid 0.03 mg/L (ppm) 1.16
Solvent, fusel, burnt Higher alcohol 3-Methyl-1-butanol (isoamyl alcohol) 30 mg/L (ppm) 1.16
Smoke, medicinal  Volatile phenol Syringol (2,6‐dimethoxyphenol) 57 µg/L (ppb) 1.15
Canned Corn, cabbage, asparagus, truffle Alkyl sulfide Dimethylsulfide (DMS) 10-25 µg/L (ppb) 0.977
Rancid, butter, cheese Volatile fatty acid 2-Methylpropanoic (isobutyric) acid 2 (mg/L) 0.94
Putrefaction Onion, rubber Alkyl thiol Methanethiol (MeSH) 1-2 µg/L (ppb) 0.932
Sweet, port-like Ketone 2‐Methyl‐4‐hydroxymethyldioxolane and dioxane isomers 0.1 g/L  0.9
Cheese, egg Thioester Methyl thioacetate (MeSAc) 50 µg/L (ppb) 0.859
Licorice, green fruit Ketone 1,1‐Diethoxyethane (acetal) 1400 µg/L (ppb) 0.84
Mousy  Cyclic imine 2-Ethyl-3,4,5,6-tetrahydropyridine (ETHP) 4-18 µg/L (ppb) 0.8
Rancid, sweat, cheese Volatile fatty acid Butanoic (butyric) acid 0.2 mg/L (ppm) 0.79
Solvent Higher alcohol 2-Methyl-1-propanol (isobutanol) 40 mg/L (ppm) 0.76
Sulfurous, blackberry, natural gas S‐Heterocycle 2‐Methyltetrahydrothiophen‐3‐one (MTHT) 90 ng/L (ppt) 0.758
Fresh, aldehydic, banana, green, melon, cheese Aldehyde 2‐Methylpropanal (Isobutyraldehyde) 6 µg/L (ppb) 0.74
Nail polish remover Ester: Fatty acid ethyl ester Ethyl acetate 12 mg/L (ppm) 0.73
Mousy  Cyclic imine 2-Acetyl-3,4,5,6-tetrahydropyradine (ATHP) 4-18 µg/L (ppb) 0.508
Rotten Eggs Sulfide Hydrogen sulfide (H2S) 1 µg/L (ppb) 0.5
Cooked potato, musty, cabbage Aldehyde Methional 0.5 µg/L (ppb) 0.436
Boiled Potato, cauliflower Alkyl disulfide 3-Methylsulfanyl-1-propanol (methionol) 1 mg/L (ppm) 0.417
Caramel  Aldehyde Furfural 15 mg/L (ppm) 0.41
Pungent, rancid Volatile fatty acid Propanoic (propionic) acid 8 (mg/L) 0.33
Fishy, oily, rancid, sweaty  Biogenic amine Trimethylamine   0.16
Mousy  Cyclic imine 2-acetyl-1-pyrroline (APY) 0.1-18 µg/L (ppb) -0.019
Ammonia, fishy Biogenic amine Ethylamine   -0.13
Vinegar/Volatile Acidity (VA) Volatile fatty acid Acetic acid 0.6-0.9 g/L -0.17
Oxidized, aldehydic, bruised apple Aldehyde Acetaldehyde (Ethanal) 100 mg/L (ppm) -0.34
Butter, cream Ketone Acetoin 0.15 g/L -0.36
Sperm, dead-animal Biogenic amine Cadaverine   -0.49
  Biogenic amine Spermine   -0.543
  Biogenic amine Methylamine   -0.57
Caramel, sweet Ester: Lactone γ–Butyrolactone unknown (high) -0.64
Animal, rotting fish Biogenic amine  Putrescine   -0.7
  Biogenic amine Histamine   -0.7
  Biogenic amine Spermidine   -1
Ammonia  Biogenic amine Ethanolamine   -1.308
Buttery, popcorn Ketone Diacetyl 0.1-3 mg/L (ppm) -1.34
  Biogenic amine Diamine-propane   -1.4
  Biogenic amine Agmatine   -1.55

References

Cumming, Hemi, and Christoph Rücker. “Octanol–Water Partition Coefficient Measurement by a Simple 1 H NMR Method.” ACS Omega 2, no. 9 (September 30, 2017): 6244–49. https://doi.org/10.1021/acsomega.7b01102.

Takeuchi H, Kato H, Kurahashi T. 2,4,6-trichloroanisole is a potent suppressor of olfactory signal transduction. Proc Natl Acad Sci U S A. 2013 Oct 1;110(40):16235-40. doi: 10.1073/pnas.1300764110. Epub 2013 Sep 16. PMID: 24043819; PMCID: PMC3791788.

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