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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
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2 -methoxy 3 isobutyl pyrazine (2 ppt)
Identified in Bell Peppers (1969)
Sensitive to light (1986)
Method for quantifying : (2003)
0
9 0
1 8 0
2 7 0
0 11 22 33 44
12
13
BerryAroma
BerryFlavor
VANILLABUTTERSCOTCH
MINT
CLOVE
SOY
Bell PepperAroma
VegyFlavor
BellPepper
Sites
Wines from two vineyard sites
WHAT CAUSES VEGY FLAVOR in WINE?
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SENSORY PCA – 19 wines (1986)
Clove
Mint
BerryF
BerryF
Vanilla
ButterscotchBellPepper
VegyF
Vegy
Soy
SpicyF
-3
-2
-1
0
1
2
3
4
5
6
-6 -4 -2 0 2 4 6
PC1(42.2%)P
C2(2
8.7
%)
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SOIL PCA
CEC
OMRootDepth
HardenpH
Texture
SoilAge
C:F %Gravel
Structure
Wt Fines
-4
-3
-2
-1
0
1
2
3
4
-4 -3 -2 -1 0 1 2 3 4
PC1 (26.4%)P
C2 (24.2
%)
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PLS of Soil and Vineyard factors versus Sensory
Noble and Elliot-Fiske, 1990
Soy
VegyVegyF
BellPepper BerryF
Berry
Butterscotch
VanillaMint
Clove
SpicyF
%Clay
SoilpH Structure
H20HoldingCap.
Year(younger)
SoilAge(older)
VineAge
Rootstock
WarmerClimate %Gravel
SoilinRootZone
-4
-2
0
2
4
6
8
-6 -4 -2 0 2 4 6
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BandAid
Spicy
Fruit by mouth
Berry
Vanilla
Eucalyptus
Green Bean
Soy
Vegetative by mouth
Black Pepper
Bell Pepper
PC1(39%)
PC
2(3
0%
)
Heymann (1986) Descriptive Analysis of Cabernet sauvignon
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Earthy
Vegetative
Body
Chemical
Animal
Vanilla
Spicy
AcidityBerry
Floral
AstringencyColor-
Intensity
Color-Hue
PC1(39%)
PC
2(3
1%
)
Sivertsen, et al.(1999). Classification of French red wines according to geographical origin by of multivariate data analyses
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passionfruit
persistenceart. fruit
citrus grapefruit
nutty
grassy
licorice
bodyfloral
37%
25%
Fischer, et al. (1999) The impact of geographic origin, vintage and wine estate on sensory properties of Vitis vinifera cv. Riesling
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Eucalyptus
Fresh Mint
Musty
Canned Veg
Bell Pepper
Cedar
Ethanol
Fresh Berry
CherryBlk Cherry
Karen Hein, 2005
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BP-B
BP-R
BP-S
Bell-Pepper
Bell Pepper1
Corn
C-B C-R
C-S
Corn1
MintM-B
M-R
M-S
BaseBerry
Raspberry
Strawberry
CANONICAL VARIATE ANALYSIS OF SPIKED WINE SAMPLES
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Morrison and Noble, 1990. Am. J. Enol. Vitic.41: 193 - 200.
Cabernet sauvignon – differences too subtle to describe
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0123456
Vegetal
Black Pepper
Rose
Chocolate
Berry
Fruit by Mouth
Astringent
Veg by Mouth
12 UP 12 LO 25B UP 25B LNE 25B LSW
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0
0.05
0.1
0.15
0.2
0.25
0.3
0.35
0.4
25 LNE 25B LSW 25B UP 12 LO 12 UP
Fra
ctio
n A
vail
ab
le L
igh
t
0
5
10
15
20
25
30
35
40
25LNE
25BLSW
25BUP
12 LO 12 UP
M Iso B
Pyra
zin
e (
pp
t)
0
0.1
0.2
0.3
0.4
0.5
0.6
0.7
0.8
25 LNE 25BLSW
25B UP 12 LO 12 UP
Vig
or
(Pru
nin
g Y
ield
)Fraction Light Vigor
Pyrazine
0
1
2
3
4
5
6
7
25B LNE 25BLSW
12 LO 25B UP 12 UP
Inte
nsi
ty B
ell P
ep
per
Bell Pepper Aroma
Vegy Saga
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Buds/Vine
10 15 20 25 30 35 40 45 50
MIB
P (n
g/L)
-5
0
5
10
15
20
20002001
R2=0.7385***
R2=0.7007***
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IBMP (ng/L)
0 2 4 6 8 10 12 14 16 18 20
Ave
rage
Inte
nsity
Rat
ing
0
2
4
6
8
R2=0.5720***
R2=0.3541*
MIBP (ng/L)
0 2 4 6 8 10 12 14 16 18 20
Ave
rage
Inte
nsity
Rat
ing
2
4
6
8
20002001
A) Bell Pepper Aroma
IBMP (ng/L)
0 2 4 6 8 10 12 14 16 18 20
Ave
rage
Inte
nsity
Rat
ing
0
2
4
6
8 B) Vegetative Aroma
R2=0.5064**
R2=0.2091 (0.1)
R2=3702*
C) Vegetative Flavor by Mouth
R2=0.6394***
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Pruning: Pruning affects yield much more than pruning weight. Pruning to more buds/vine generally increases yield and decreases shoot length. Pruning to higher yield can lead to delayed sugar accumulation (probably when leaf area / fruit weight gets below 12 cm2 / gm), and at even higher yields decreased color in fruit, and in extreme cases decreased budbreak and fruitfulness the following year. Pruning to two times the standard crop load in Napa (4-bud spurs instead of 2-bud spurs) did not prevent ripening. Pruning to higher yields resulted in less veggy, less astringent, and more fruity attributes in Cabernet Sauvignon wines. And the veggy and astringent attributes were correlated with the concentration of MIBP (methoxypyrazine) and tannins in the wines. There were almost no significant differences in sensory attributes among wines made from vines with different cluster thinning treatments.
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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
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Compounds released in white wines
4-mercapto-4-methylpentan-2-one (4MMP) (also in Scheurebe) 0.8 ng/l*; range 0-40 -- box tree, broom flower; cat pee; conifer4-mercapto-4-methylpentan-2-ol (4MMPOH) 55 ng/l*; range 0-150 --
citrus zest; grapefruit3-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 skin3-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
Markers for great Sauvignon blancMarkers for great Sauvignon blanc
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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
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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
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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
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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
Glycosides in Red varieties
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floral
apple
honeyhoney
chocolatechocolate dried figdried fig
tobaccotobacco
Base wine
Napa Cabernet juiceglycoside hydrolysate
0
1
2
3
4
Juice glycoside hydrolysate
n=14 judges x 2 reps
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floral apple
honey
chocolatechocolate
dried figdried fig
tobaccotobacco Base wine
Napa Cabernet skinNapa Cabernet skinglycoside hydrolysateglycoside hydrolysate
Napa Cabernet skinNapa Cabernet skinglycoside hydrolysateglycoside hydrolysate
0
1
2
3
4
Skin glycoside hydrolysate
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PLS of Aroma attributes versus volatiles
floral
apple
honey
dried fig
chocolate
tobacco
volatiles
juices
skin extracts
Component 1
Component 2
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Volatiles related to the honey attribute
Norisoprenoids:•damascenone•hydroxydamascone
•dehydro ß ionone•TDN•vitispirane•actinidol
Benzene derivatives:•vanillin•acetovanillone•cinnamic acid
Monoterpenes:•ocimenol•furan linalool oxide •an ene diol
Others:•acetyl furan •ethyl decanoate•diethyl propanedioate
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PLS of Aroma attributes versus volatiles
floral
apple
honey
volatiles
juices
skin extracts
Component 1
Component 2
dried fig
chocolate
tobacco
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Volatiles associated with dried fig/tobacco
Benzene derivatives:•syringic acid•ethyl syringate•a methoxy phenol
Monoterpenes:•trimethyl vinyltetrahydropyran•furan linalool oxide
Others:•two unknowns•heptanoic acid•hexadecanoic acid•2-Et-3-Me maleic anhydride
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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 SO2
Homogenize skins/juice versus juice
Grape Berry Evaluation
Vineyard Variables:
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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?
FERMENTATION
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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
AGING
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Extraction of volatiles: vanillin, eugenol, oak lactone
Extraction: phenols, acids, lignins, CHO
Oak Aging
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Oak aging continuedVARIABLES:
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