ENRU

    Arrows to move, Enter to open

    Chemistry

    Aroma molecules

    More than 800 aroma compounds have been identified in wine, some of them at the level of nanograms per litre.23 A few are tied to a single grape or a single cellar process, and some work at tiny doses: for about 80% of a tasting panel, rotundone was detectable at 16 ng/L in red wine.1

    How little is enough

    Odour thresholds reported in the studies, on a logarithmic scale. Each step to the right is ten times more.

    0.1110100100010,000100,000ng/L
    4MMP0.8 ng/L in wine8
    IBMP2 ng/L in water2
    Rotundone16 ng/L in red wine1
    3MH60 ng/L in model solution7
    TDN2 µg/L in wine4
    cis-Whisky lactone20 µg/L in 12% alcohol solution17

    Ten molecules

    O

    C₁₅H₂₂O · PubChem 5321003

    Rotundone

    black pepper

    Rotundone, a sesquiterpene, was identified in 2008 as an aroma compound with a strong spicy, peppercorn aroma, and its concentration tracked the black pepper intensity rated by panels in Shiraz grapes and wines.1 Most panellists detected it at 16 ng/L in red wine, yet about 20% could not smell it even at 4000 ng/L in water.1 Black and white peppercorns contain roughly 10,000 times more of it than a very peppery wine.1

    NNO

    C₉H₁₄N₂O · PubChem 32594

    3-Isobutyl-2-methoxypyrazine (IBMP)

    green bell pepper

    IBMP gives grapes a bell pepper aroma and has a reported threshold of about 2 ng/L in water.2 Of 29 grape cultivars analysed at UC Davis, quantifiable levels were found only in Cabernet Franc, Cabernet Sauvignon, Merlot, Sauvignon Blanc and Sémillon.2 In Sauvignon Blanc the pea pod, capsicum character of methoxypyrazines, of which IBMP is the major one in grape berries, balances the passion fruit and grapefruit of varietal thiols, while excessive amounts reduce consumer acceptance, particularly in red wines.3

    C₁₃H₁₆ · PubChem 121677

    TDN (1,1,6-trimethyl-1,2-dihydronaphthalene)

    kerosene, petrol

    TDN is well known for the petrol aroma of aged Riesling.4 In young wines Riesling held 6.4 µg/L on average against 1.3 µg/L in other varieties, and 27 of 28 Rieslings exceeded the 2 µg/L detection threshold measured by a Cornell team.4 A Geisenheim study put the recognition threshold in young Riesling at 10–12 µg/L and found that serving the wine cooler, at about 11 °C, made the kerosene note easier to identify.5

    OHSH

    C₆H₁₄OS · PubChem 521348

    3-Mercaptohexan-1-ol (3MH)

    grapefruit, passion fruit

    3MH is one of the volatile thiols behind the varietal aroma of Sauvignon Blanc; the free thiol is not present in the juice and is released by yeast during alcoholic fermentation.6 Its two mirror-image forms have similar thresholds of 50 and 60 ng/L in model solution, but the R form recalls grapefruit and the S form passion fruit.7 It is also found in Sémillon wines, including sweet wines from grapes with noble rot.7

    OSH

    C₆H₁₂OS · PubChem 88290

    4-Mercapto-4-methylpentan-2-one (4MMP)

    blackcurrant

    4MMP has an odour threshold of 0.8 ng/L in wine, and in the Sauvignon Blanc wines analysed its levels were far above that threshold.8 Grape juice holds it as a non-volatile cysteine-bound precursor, which is cleaved during alcoholic fermentation.9 In red wines with a strong blackcurrant aroma, the concentration of 4MMP correlated very well with the intensity of that note.10

    OH

    C₁₀H₁₈O · PubChem 6549

    Linalool

    floral

    The floral and citrus notes of many white varieties are attributed to monoterpenes and monoterpene alcohols such as linalool.11 In Muscat Blanc à Petits Grains grapes linalool was the major aroma contributor.12 Monoterpenes matter in Muscat, Gewürztraminer and Riesling, where much of them sits in the berry as odourless glycosides that can be released during ripening, winemaking or ageing.13,11

    O

    C₁₀H₁₈O · PubChem 1712087

    cis-Rose oxide

    lychee

    Comparing lychee fruit with Gewürztraminer wine, Cornell researchers found that cis-rose oxide had the highest odour activity among their shared odorants and concluded that these shared odorants, above all cis-rose oxide, were responsible for the lychee aroma of the wine.14 It was not detected in the Chardonnay and Riesling control wines.14 In Gewürztraminer grapes, cis-rose oxide and geraniol were the major contributors to aroma.12

    OO

    C₄H₆O₂ · PubChem 650

    Diacetyl

    butter

    Diacetyl, a diketone that imparts a buttery aroma, is a major flavour metabolite of lactic acid bacteria; in wine its metabolism takes place during malolactic fermentation by Oenococcus oeni.15 Its formation depends on citric acid metabolism, and its final level on the bacterial strain, pH, temperature, sulphur dioxide, aeration and yeast lees.15 In Pinotage wines from Stellenbosch University trials, diacetyl correlated with the buttery character of wines that went through malolactic fermentation.16

    OO

    C₉H₁₆O₂ · PubChem 41285

    cis-Whisky lactone (oak lactone)

    coconut, wood

    The detection threshold of cis-whisky lactone in 12% alcohol solution is 20 µg/L, against 130 µg/L for the trans form, so at average concentrations in oak-aged red wines the cis form is above threshold and the trans form below it.17 In tests by a Bordeaux team on a reconstituted red-wine fruity aroma in model solution, both forms dulled red berry notes and strengthened blackberry and spicy ones.17 Whisky lactones give coconut-like odour impressions, and red wines aged with a large dose of oak chips scored higher for woody and coconut notes.18,19

    OOOH

    C₆H₈O₃ · PubChem 62835

    Sotolon

    curry, walnut

    Sotolon, a lactone, gives powerful Madeira-like, oxidised, curry and walnut notes and has been much studied in Jura flor wines, aged Roussillon sweet wines and old Port.20 In Jura yellow wines aged more than six years in barrel, its key role was confirmed at 112–387 µg/kg.21 The specific metabolism of flor yeasts, which grow as a film on the wine surface, explains the acetaldehyde and sotolon content of these wines.22

    Sources

    1. From wine to pepper: rotundone, an obscure sesquiterpene, is a potent spicy aroma compound (J Agric Food Chem 56:3738-44). Wood C, Siebert TE, Parker M et al., 2008. level 3
    2. 2-Methoxy-3-isobutylpyrazine in grape berries and its dependence on genotype (Phytochemistry 71:2190-8). Koch A, Doyle CL, Matthews MA, Williams LE, Ebeler SE (UC Davis), 2010. level 3
    3. Genetic analysis of the biosynthesis of 2-methoxy-3-isobutylpyrazine, a major grape-derived aroma compound impacting wine quality (Plant Physiol 162:604-15). Guillaumie S et al. (ISVV Bordeaux), 2013. level 3
    4. Sensory threshold of 1,1,6-trimethyl-1,2-dihydronaphthalene (TDN) and concentrations in young Riesling and non-Riesling wines (J Agric Food Chem 60:2998-3004). Sacks GL et al. (Cornell University), 2012. level 3
    5. 1,1,6-Trimethyl-1,2-dihydronaphthalene (TDN) Sensory Thresholds in Riesling Wine (Foods 9:606). Tarasov A et al. (Hochschule Geisenheim University), 2020. level 3
    6. Yeast genes involved in sulfur and nitrogen metabolism affect the production of volatile thiols from Sauvignon Blanc musts (Appl Microbiol Biotechnol 97:223-35). Harsch MJ, Gardner RC, 2013. level 3
    7. Stereoisomeric distribution of 3-mercaptohexan-1-ol and 3-mercaptohexyl acetate in dry and sweet white wines made from Vitis vinifera (Var. Sauvignon Blanc and Semillon) (J Agric Food Chem 54:7251-5). Tominaga T, Niclass Y, Frerot E, Dubourdieu D, 2006. level 3
    8. Quantitative determination of sulfur-containing wine odorants at sub parts per billion levels. 2. (J Agric Food Chem 51:3243-8). Schneider R, Kotseridis Y, Ray JL, Augier C, Baumes R, 2003. level 3
    9. Engineering volatile thiol release in Saccharomyces cerevisiae for improved wine aroma (Yeast 24:561-74). Swiegers JH et al., 2007. level 3
    10. Influence of volatile thiols in the development of blackcurrant aroma in red wine (Food Chem 142:242-8). Rigou P, Triay A, Razungles A, 2014. level 3
    11. Biosynthesis of wine aroma: transcript profiles ... parallel monoterpenol glycoside accumulation in Gewurztraminer grapes (Planta 236:919-29). Martin DM, Chiang A, Lund ST, Bohlmann J, 2012. level 3
    12. Monoterpenyl Glycosyltransferases Differentially Contribute to Production of Monoterpenyl Glycosides in Two Aromatic Vitis vinifera Varieties (Front Plant Sci 8:1226). Li XY, Wen YQ, Meng N, Qian X, Pan QH, 2017. level 3
    13. Coexpression of alpha-L-arabinofuranosidase and beta-glucosidase in Saccharomyces cerevisiae (FEMS Yeast Res 11:88-103). Zietsman AJ, de Klerk D, van Rensburg P, 2011. level 3
    14. Similarities in the aroma chemistry of Gewurztraminer variety wines and lychee (Litchi chinesis sonn.) fruit (J Agric Food Chem 47:665-70). Ong PK, Acree TE (Cornell University), 1999. level 3
    15. The 'buttery' attribute of wine--diacetyl--desirability, spoilage and beyond (Int J Food Microbiol 96:235-52). Bartowsky EJ, Henschke PA (AWRI), 2004. level 3
    16. The relationships between consumer liking, sensory and chemical attributes of Vitis vinifera L. cv. Pinotage wines elaborated with different Oenococcus oeni starter cultures (J Sci Food Agric 93:2829-40). Malherbe S et al. (Stellenbosch University), 2013. level 3
    17. Impact of Whisky Lactone Diastereoisomers on Red Wine Fruity Aromatic Expression in Model Solution (J Agric Food Chem 68:10808-14). Cameleyre M, Madrelle V, Lytra G, Barbe JC (ISVV), 2020. level 3
    18. Characterization of the key odorants in goji wines in three levels of sweetness by applications of sensomics approach (Food Chem 461:140803). Zheng Y et al., 2024. level 3
    19. Impact of alternative technique to ageing using oak chips in alcoholic or in malolactic fermentation on volatile and sensory composition of red wines (Food Chem 134:851-63). Gomez Garcia-Carpintero E et al., 2012. level 3
    20. How sotolon can impart a Madeira off-flavor to aged beers (J Agric Food Chem 63:2886-92). Scholtes C, Nizet S, Collin S (UCLouvain), 2015. level 3
    21. Main odorants in Jura flor-sherry wines. Relative contributions of sotolon, abhexon, and theaspirane-derived compounds (J Agric Food Chem 60:380-7). Collin S, Nizet S, Claeys Bouuaert T, Despatures PM, 2012. level 3
    22. Flor yeasts of Saccharomyces cerevisiae--their ecology, genetics and metabolism (Int J Food Microbiol 167:269-75). Alexandre H (Universite de Bourgogne), 2013. level 3
    23. Instrumental and sensory approaches for the characterization of compounds responsible for wine aroma (Chem Biodivers 5:1170-83). Barbe JC, Pineau B, Ferreira AC, 2008. level 3