Wine flavor chemistry
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Wine Flavor Chemistry. Flavor is the psychological interpretation of the physiological response to a physical stimulus Milton Bailey, University of Missouri, 1986. WHAT CAUSES VEGY FLAVOR in WINE?. 2 -methoxy 3 isobutyl pyrazine (2 ppt) Identified in Bell Peppers (1969)

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Wine Flavor Chemistry

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Wine flavor chemistry

Wine Flavor Chemistry

  • Flavor is the psychological interpretation of the physiological response to a physical stimulus

    • Milton Bailey, University of Missouri, 1986


What causes vegy flavor in wine

WHAT CAUSES VEGY FLAVOR in WINE?

2 -methoxy 3 isobutyl pyrazine (2 ppt)

Identified in Bell Peppers (1969)

Sensitive to light (1986)

Method for quantifying : (2003)


Wine flavor chemistry

SENSORY PCA – 19 wines (1986)


Wine flavor chemistry

SOIL PCA


Pls of soil and vineyard factors versus sensory

PLS of Soil and Vineyard factors versus Sensory

Noble and Elliot-Fiske, 1990


Wine flavor chemistry

Heymann (1986) Descriptive Analysis of Cabernet sauvignon


Wine flavor chemistry

Sivertsen, et al.(1999). Classification of French red wines according to geographical origin by of multivariate data analyses


Wine flavor chemistry

Fischer, et al. (1999) The impact of geographic origin, vintage and wine estate on sensory properties of Vitis vinifera cv. Riesling


Wine flavor chemistry

Karen Hein, 2005


Wine flavor chemistry

CANONICAL VARIATE ANALYSIS OF SPIKED WINE SAMPLES


Wine flavor chemistry

Cabernet sauvignon – differences too subtle to describe

Morrison and Noble, 1990. Am. J. Enol. Vitic.41: 193 - 200.


Wine flavor chemistry

Vegy Saga

Fraction Light

Vigor

Bell Pepper Aroma

Pyrazine


Evaluation of 96 bordeaux red wines

Evaluation of 96 Bordeaux red wines

  • IBMP is the contributor to vegetal aroma in Cabernet sauvignon; Cabernet franc and Sauvignon blanc

  • Compound only found in a minority of Merlot


Compounds released in white wines

Compounds released in white wines

Markers for great Sauvignon blanc

4-mercapto-4-methylpentan-2-one (4MMP) (also in Scheurebe)

0.8 ng/l*; range 0-40 -- box tree, broom flower; cat pee; conifer

4-mercapto-4-methylpentan-2-ol (4MMPOH) 55 ng/l*; range 0-150 -- citrus zest; grapefruit

3-mercapto-3-methylbutan-1-ol (3MMB) 1,500 ng/l*; range 30-150 – cooked leeks

3-mercaptohexan-1-ol (3MH) 60 ng/l*; range 200-5,000 – grapefruit; passion fruit; passion fruit skin

3-mercaptohexylacetate (3MHA) (also in Merlot, Cabernet sauvignon) 4.2 ng/l*; range 0-500 – box tree; passion fruit; sweet sweaty

Aqueous 12% alcohol solution with 5g/l tartaric acid; pH 3.5 25 J, triangle; 50% correct

increases during fermentation as these potent thiols released from their S-cysteine conjugate precursors


Thiols in other varieties

Thiols in other varieties

  • 4MMP and A3MH (3-mercaptohexylacetate [box tree]):

    • Impact on aromas of Colombard and Muscat d’Alsace wines

    • As well as on young wines from Petit manseng*

  • 3MH

    • Contributes passion fruit and grapefruit to Gewurtztraminer, Riesling, Petit manseng and botrytized Semillon

      *White variety, South West France – may be Albarino: floral fruity flavors, a distinct lemon and fruit salad flavor & high acidity increasing popularity in Languedoc & California

Tominaga et al. (2000) AJEV 51(2):178-182


Production location and extraction of s cysteine conjugates

Production, location and extraction of S-Cysteine Conjugates

  • Moderate water stress favor S-cysteine conjugate (P-thiol) formation; severe prolonged stress limits production

  • Location of P-thiolsdiffer as f(volatile thiol)

    • P-4MMP and P-4MMPOH -- 80% in juice

    • P-3MH – 50:50 between juice and skin

  • Upto 19 hours skin contact

    • Some ↑ in P-4MMP and P-4MMPOH (20% + 30%)

    • 50% ↑ in P-3MH (even more extracted if skin contact at 18C vs 10C)

Peyrot des Gachons, Catherine: Aroma Potential of Sauvignon blanc grapes, PhD Dissertation Bordeaux


Transformation of p thiols into varietal aromas

Transformation of p-thiols into varietal aromas

  • Transformation % low (1 month after fermentation) – due to yeast lyases

    • 1.4% for P-4MMP; 3% for P-4MMPOH; 4.2% for P-3MH

  • Not much transformed? Or Lost? Or metabolized or unstable? – do not yet know

  • Do know that P-thiol disappearance is correlated with thiol appearance

Peyrot des Gachons, Catherine: Aroma Potential of Sauvignon blanc grapes, PhD Dissertation Bordeaux


Glycosides in red varieties

Glycosides in Red varieties

Norisoprenoids/norterpenoids from carotenes Beta-damascenone

Shiraz stalky, earthy, cigar, and tobacco aromas

black pepper aroma by GCO not id’d

Cabernet Sauvignon and Merlot dried fig, tobacco and chocolate aromas

Zinfandel Preliminary studies: Not much contribution


Wine flavor chemistry

Juice glycoside hydrolysate

Napa Cabernet juice

glycoside hydrolysate

floral

4

Base wine

3

tobacco

2

apple

1

0

honey

dried fig

chocolate

n=14 judges x 2 reps


Wine flavor chemistry

Skin glycoside hydrolysate

Napa Cabernet skin

glycoside hydrolysate

4

floral

Base wine

3

tobacco

apple

2

1

0

dried fig

honey

chocolate


Pls of aroma attributes versus volatiles

PLS of Aroma attributes versus volatiles

Component 2

volatiles

honey

floral

juices

dried fig

apple

tobacco

skin extracts

chocolate

Component 1


Volatiles related to the honey attribute

Volatiles related to the honey attribute

  • Norisoprenoids:

    • damascenone

    • hydroxydamascone

  • dehydro ß ionone

    • TDN

    • vitispirane

    • actinidol

  • Benzene derivatives:

    • vanillin

    • acetovanillone

    • cinnamic acid

  • Others:

    • acetyl furan

    • ethyl decanoate

    • diethyl propanedioate

  • Monoterpenes:

    • ocimenol

    • furan linalool oxide

    • an ene diol


Wine flavor chemistry

PLS of Aroma attributes versus volatiles

volatiles

honey

Component 2

floral

juices

dried fig

apple

tobacco

chocolate

skin extracts

Component 1


Volatiles associated with dried fig tobacco

Volatiles associated with dried fig/tobacco

  • Benzene derivatives:

    • syringic acid

    • ethyl syringate

    • a methoxy phenol

  • Others:

    • two unknowns

    • heptanoic acid

    • hexadecanoic acid

    • 2-Et-3-Me maleic anhydride

  • Monoterpenes:

    • trimethyl vinyltetrahydropyran

    • furan linalool oxide


Vineyard variables

Vineyard Variables:

Trellising or leaf removal increases light

< 2-methoxy 3 isobutyl pyrazine

> norisoprenoids

Maturity

How to assess pH, TA, °B?

Grape Must Evaluation (evaluate in < 1 hour)Rinse and Crush grapes, add 20 ppm SO2Homogenize skins/juice versus juice

Grape Berry Evaluation


Fermentation

FERMENTATION

Temperature:

Cool: retain more volatilesWarmer: more esters but lose more (fruity) low MW

Yeast strain:? Biggest issue is H2S production

“Natural” versus inoculation

Skin Contact Time/Cap Management

Increase K, pH, phenols, anthocyanins

Centrifuging?


Aging

AGING

Terpene glycosides hydrolyze, but terpenes interconvert to less fruity forms

Vitaspirane and 1,1,6 trimethyl 1,2 dihydronaphthalene increase

Esters hydrolyze slowly: Acetate esters & higher MW faster.

Acids esterify; pH; Tannins polymerize

Oxidation reactions


Oak aging

Oak Aging

Extraction of volatiles: vanillin, eugenol, oak lactone

Extraction: phenols, acids, lignins, CHO


Oak aging continued

Oak aging continued

VARIABLES:

Source oak (Am  Vanillin; Fr  Phenols, extract)

Sawn vs split

Air vs kiln drying Air  Vanillin; Kiln HMF

Air drying in cool vs hot area

Hot  Vanillin ,Oak lactone

Hot  vanilla, caramel, buttery

Steamed or bent over fire

Degree toasting  Furfural,  Vanillin


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