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VEN124 Section VI

VEN124 Section VI. Wine Aroma and Flavor: Putting It All Together. Lecture 19:. The Flavor and Aroma Compounds of Wine. Distribution of Aroma Compounds in White Wines. “Canadian Muscat”. Muscats. Traminer. Fruity (Terpenes). Rieslings. Chardonnay Sauvignon blanc.

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VEN124 Section VI

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  1. VEN124 Section VI Wine Aroma and Flavor: Putting It All Together

  2. Lecture 19: The Flavor and Aroma Compounds of Wine

  3. Distribution of Aroma Compounds in White Wines “Canadian Muscat” Muscats Traminer Fruity (Terpenes) Rieslings Chardonnay Sauvignon blanc Chenin blanc Fr. Columbard Vegetal

  4. Classes of Flavor/Aroma Compounds • Pyrazines

  5. Pyrazines R = -CH2-CH-CH3 -CH2-CH3 -CH3 N R CH3 Bell pepper Potato N O-CH3 Peanut

  6. Pyrazines • Derived from grape • Not microbial in origin • Vegetal characters • Bell pepper • Chili • Bean • Carrot • Potato • Peanut • Roasted Barley

  7. Classes of Flavor/Aroma Compounds • Pyrazines • Terpenes

  8. Terpenes • Fruity fruit/floral aromas from grapes • Can be produced by some yeasts and molds (but not by Saccharomyces) • Derived from isoprene units • May be unbound or bound (as glycosides) • Only unbound terpenes can be detected

  9. Terpenes Formed from isoprene units 1 C 2 C 3 C 4 5 C C The double bond can occur anywhere in the 5-member structure

  10. Terpenes • Monoterpenes: C10 • Higher terpenes: C10

  11. Terpenes Can occur as: hydrocarbons alcohols aldehydes ketones esters

  12. Monoterpene Hydrocarbons 4 CH3 3 5 2 1 1 2 C 3 CH3 CH2 4 5 Limonene

  13. Monoterpene Alcohols CH3 CH3 CH2OH OH H CH2 C C CH3 CH3 CH3 CH3 Geraniol Linalool

  14. Monoterpene Aldehydes CH3 CH3 H CHO H CHO C C CH3 CH3 CH3 CH3 Geranial Neral

  15. Higher Terpenes • Includes napthalene derivatives • From plants • Fruit characters • Fuel characters

  16. Higher Terpenes O CH2 C CH3 Grapefruit

  17. Higher Terpenes CH3 CH3 CH3 Trimethyl Dihydronapthalene “Kerosene”

  18. Classes of Flavor/Aroma Compounds • Pyrazines • Terpenes • Shikimic acid derivatives

  19. Shikimic Acid Derivatives • Derived from aromatic amino acid metabolism • Produced by plants, microbes, oak extraction

  20. Shikimic Acid Derivatives H O C OCH3 OH Vanillin

  21. Classes of Flavor/Aroma Compounds • Pyrazines • Terpenes • Shikimic acid derivatives • Lactones

  22. Lactones • Oxygen-containing 5-member ring compound • From grapes, microbes, oak extraction • Typical characters: cotton candy, generic candy, generic fruit, coconut, buttery

  23. Lactones O CH2OH O O C4H9 CH3 Furfuryl Alcohol Methyl Lactone

  24. Classes of Flavor/Aroma Compounds • Pyrazines • Terpenes • Shikimic acid derivatives • Lactones • Esters

  25. Esters • From reaction of an alcohol and an acyl-CoA molecule • Formed mainly by microbes, but can come from plant • Readily hydrolyzed at wine pH

  26. Esters O R1-OH R2-CCoA O R1-O-C-R2

  27. Esters Alcohol: ethanol or alcohol from amino acid, purine, pyrimidine degradation Acid: acetic acid or acid from amino acid degradation, fatty acid biosynthesis

  28. Esters • Ethyl acetate: nail polish remover/glue • Ethyl laurate: soap • Isoamyl acetate: banana • Phenethyl acetate: rose oil

  29. Esters • Short chain: fruity, floral • Long chain: perfume,soap • Lower concentration: fruity, floral • Higher concentrations: perfume

  30. Ester Formation Influenced By: • Temperature • Higher temperature: increased loss • Volatilization • Hydrolysis • Oxygen exposure • Stimulate fatty acid biosynthesis • Nitrogen source availability • Precursor availability • Strain/genetic background • As much as 10-fold difference in level of production

  31. Classes of Flavor/Aroma Compounds • Pyrazines • Terpenes • Shikimic acid derivatives • Lactones • Esters • Higher alcohols

  32. Higher Alcohols • Made mostly by microbes, can be made by plants • From amino acid degradation/ biosynthesis Fusel oils Aromatic amino acid derivatives

  33. The Fusel Oils • 3-Methylbutanol • 2-Methylbutanol • Isobutanol • Propanol

  34. Classes of Flavor/Aroma Compounds • Pyrazines • Terpenes • Shikimic acid derivatives • Lactones • Esters • Higher alcohols • Acids

  35. Acids • From plant or microbes • Sourness • Other characters: • Rancid (butyric acid) • Pungent (acetic acid)

  36. Acids Most Sour Least Sour Citrate Fumarate Malate Lactate Succinate Tartrate

  37. Acetic Acid Legal Limits: US CA OIV White: 1.2 g/L 1.1g/L 0.98g/L Red: 1.4 g/L 1.2g/L 0.98g/L Threshold of Detection:  1 g/L

  38. Classes of Flavor/Aroma Compounds • Pyrazines • Terpenes • Shikimic acid derivatives • Lactones • Esters • Higher alcohols • Acids • Phenolic compounds

  39. Phenolic Compounds • Bitterness • Astringency • Produced by plant • Can be converted into vinyl phenols by microbes (spoilage characters)

  40. Bitterness Flavanols OH OH HO O OH OH Catechin

  41. Astringency Flavanols and Non-flavinoids OH OH HO OH OH CH HC C=O O HOOC-CH-CH-COOH COOH Gallic acid Caftaric acid OH

  42. Classes of Flavor/Aroma Compounds • Pyrazines • Terpenes • Shikimic acid derivatives • Lactones • Esters • Higher alcohols • Acids • Phenolic compounds • Sulfur-containing compounds

  43. Sulfur-Containing Compounds • Low thresholds of detection • Generally produced by microbes • Degradation of sulfur containing amino acids • Spontaneous reactions from microbially-derived sulfides

  44. Sulfur-Containing Compounds • Sulfides • Thiols • Sulfoxides

  45. Sulfides • H2S (hydrogen sulfide): rotten egg • CH3-S-CH3 (dimethyl sulfide): cabbage, canned corn • CH3-S-S-CH3 (dimethyl disulfide): clam

  46. Sulfur-Containing Compounds • Sulfides • Thiols • Sulfoxides

  47. Thiols • CH3-SH (methanethiol): rubber • CH3-CH2-SH (ethanethiol): onion, rubber, skunk

  48. Sulfur-Containing Compounds • Sulfides • Thiols • Sulfoxides

  49. Sulfoxides • CH3-SO-CH3 (dimethyl sulfoxide): plastic, rubber hose

  50. Sulfur-Containing Compounds • Sulfides • Thiols • Sulfoxides • Thio alcohols

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