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Anita Oberholster Impact of Oak on Wine Composition and Chemistry.
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Transcript of Anita Oberholster Impact of Oak on Wine Composition and Chemistry.
Anita Oberholster
Impact of Oak on Wine Composition and Chemistry
Introduction• Oak compounds extracted in to wine– Volatile– Non-volatile
• Influence of oak and wine composition on extraction
• Major wine compounds• Interaction of oak compounds with wine
constituents– Role of oxygen– Sensory impact
Compounds Extracted from Oak: Non-volatile
• Hydrolyzable tannins– Ellagitannins (up to 100 mg/L)– Most important monomers are vescalagin,
castalagin, less important are grandinin, roburin (Fig)
– More bitter then astringent, present in wine below detection limit, perhaps synergistic effect (Puech et al., 1999)
Ribéreau-Gayon et al., (2006) Handbook of Enology
Figure: Ellagitannins
Ribéreau-Gayon et al., (2006) Handbook of Enology
Non-volatile Extracts from Oak• Lignins• Triterpenes– Identified as the compounds contributing
sweetness to barrel-aged wines• Coumarins– Bitter glycosides aglycones – slightly acidic with
seasoning• Phenolic acid – gallic acid (50 mg/L)– Produced from ellagitannins and possibly lignin
• Polysaccharides – hemicelluloseMarchal et al. (2011) Anal. Chem. 83: 9629-9637Puech et al. (1999) Am. J. Enol. Vitic. 50: 469-478
Compounds Extracted from Oak: Volatile
Ribéreau-Gayon et al., (2006) Handbook of Enology
Methyloctalactone Eugenol
SyringaldehydeVanillin
Coniferaldehyde Sinapaldehyde
Compounds Extracted from Oak: Volatile
• Furanic aldehydes – Thermal degradation of polysaccharides
(hemicellulose)– Toasted almond aromas – below threshold
• Enolic compounds– Cyclotene, maltol, isomaltol– With heating, derived from hexoses– Caramel-toasty character– Contributions likely small due to high aroma
thresholdsRibéreau-Gayon et al. (2006) Handbook of EnologySpillman et al. (2004) Austr. J. Grape Wine Res. 10: 227-235
Compounds Extracted from Oak: Volatile
Ribéreau-Gayon et al., (2006) Handbook of Enology
Furfural Methyl-5-furfural Hydroxymethyl-5-furfural
IsomaltolMaltolCyclotene
Compounds Extracted from Oak: Volatile
• Volatile phenols – Degradation of lignan and polyols– Eugenol • Main volatile phenol• Smoky and spicy, reminiscent of cloves
• Phenol aldehydes– Relatively low amounts– Vanillin (vanilla and oaky notes)– Syringaldehyde, coniferaldehyde and
sinapaldehyde (small amounts)
Ribéreau-Gayon et al. (2006) Handbook of EnologySpillman et al. (2004) Austr. J. Grape Wine Res. 10: 227-235
Compounds Extracted from Oak: Volatile
• -methyl--octalactones – (cis and trans – coconut)
• Trans-2-nonenal, with trans-2-octanal and 1-decanal = “plank smell”– Attributed to unseasoned wood
Ribéreau-Gayon et al. (2006) Handbook of EnologySpillman et al. (2004) Austr. J. Grape Wine Res. 10: 227-235
Compounds Extracted from Oak: Volatile
Ribéreau-Gayon et al., (2006) Handbook of Enology
Influence of Wine and Oak Composition
• Wine composition– Alcohol content• Higher alcohol extraction of volatile compounds
• Oak composition– Depends mostly on geographical origin, then
specie and the tree itself• Only generalization is that American oak extract
higher cis/trans-oak lactone ratio compared to European species
– Seasoning, toasting and amount of times use• Much larger effect on oak composition
Garde-Cerdán and Ancín-Azpilicueta (2006) Trends Food Sci. 17: 438-447
Influence of Oak Composition• Allier vs Limousin (Ribéreau-Gayon et al., 2006)
– Ellagitannin Allier < Limousin– Volatiles Allier > Limousin
• Limousin vs Vosges vs Tronais vs Ohio (Spillman et al., 2004)
– Oak lactones + Eugenol Vosges > Tronais > Limousin
• Little diffr between Allier vs American (Pérez-Prieto et al., 2002)
– Except American oak-lactones
Pérez-Prieto et al. (2002) J. Agric. Food Chem. 50: 3272-3276Ribéreau-Gayon et al. (2006) Handbook of EnologySpillman et al. (2004) Austr. J. Grape Wine Res. 10: 216-226
Influence of Oak Composition• Generally with toasting– Furans with toasting level• Still mostly below aroma threshold
– Phenol aldehydes with toasting level– Oak lactones with toasting
Ribéreau-Gayon et al. (2006) Handbook of Enology
Influence of Winemaking on Oak Extracts
• Red wine – barrel aged• White wine – barrel fermented, aged on lees– Lees limit ellagic tannin conc in wine• Tannins fixed on yeast cell walls and mannoproteins
released from lees
• Barrel fermented wines – less wood aroma than barrel aged wines– Reduction of vanillin to vanillic alcohol
Marchal et al. (2011) Anal. Chem. 83: 9629-9637Puech et al. (1999) Am. J. Enol. Vitic. 50: 469-478.
Influence of Barrel Size and Storage Time
• Different barrel sizes (225, 300, 500, 1000 L)– Smaller barrels > oak-related aroma
compounds, higher sensory scores• Rate of extraction depends on wine
composition and oak wood composition– Vanillin max 10-12 months• Transformed into vanillyl alcohol – less odoriferous
– Other volatile phenols max 10-12 months although mostly below aroma threshold
Garde-Cerdán amd Ancín-Azpilicueta (2006) Trends Food Sci. 17, 438-447Pérez-Prieto et al. (2003) J. Agric. Food Chem. 51: 5444-5449Rodríguez-Rodríguez and Gómez-Plaza (2011) Am. J. Enol. Vitic. 62 (3): 359-365
Influence of Barrel Storage Time
Pérez-Prieto et al. (2003) J. Agric. Food Chem. 51: 5444-5449
Influence of Barrel Storage Time
Pérez-Prieto et al. (2003) J. Agric. Food Chem. 51: 5444-5449
Influence of Barrel Storage Time
• Formation of ethylphenols– Ethylphenols, 4-ethyl phenol and 4-
ethylguaiacol• Produced by Brettanomyces/Dekkera contaminant
yeast• Decarboxylation of ferulic and coumaric acids• Higher conc in used barrels, increase with aging• 4-ethylphenol (horse, Band-aids)• 4-ethylguaiacol (smoky, spicy, cured bacon-like)
Garde-Cerdán amd Ancín-Azpilicueta (2006) Trends Food Sci. 17: 438-447Pérez-Prieto et al. (2003) J. Agric. Food Chem. 51: 5444-5449
Influence of New vs Used Barrels
• Greatest sensory diffr between used vs new barrels– lactones and vanillin conc– In used barrels – diffr size barrels less important
Garde-Cerdán amd Ancín-Azpilicueta (2006) Trends Food Sci. 17: 438-447Pérez-Prieto et al. (2003) J. Agric. Food Chem. 51: 5444-5449.
Oak: New Technologies• Entire surface area usable, not just 40% as in
the case with barrels• Comparing barrels, staves and oak chips– Additions according to similar surface area– Vanillin chips>stavesbarrel
• Oak chips vs barrel aged– Chips > coconut and vanilla character– Chips > bitterness and astringency– Oak chips wines > grassy and vegetal notes
compared to same wine barrel agedDel Alamo et al., 2004, Anal. Chim. Acta. 513 (1), 229-237; Garde-Cerdán amd Ancín-Azpilicueta (2006) Trends Food Sci. 17: 438-447; Ortega-Heras et al., 2010, Food Sci. Tech. 43, 1533-1541
The Use of Oak Chips• Alternative to give young wines woody tones
– similar to wine aged in barrels for 3 months– Similar phenol and color composition
• MOX + oak chips – similar color advantages to barrel– Lasting effect?
• Recommended for short aged red wine
Bautista-Ortin et al., 2008, Austr. J. Grape Wine Res. 14, 63-70.Del Alamo et al., 2004, Anal. Chim. Acta. 513 (1), 229-237Garde-Cerdán amd Ancín-Azpilicueta (2006) Trends Food Sci. 17: 438-447Ortega-Heras et al., 2010, Food Sci. Tech. 43: 1533-1541
• Flavonoids– Anthocyanins in skins• Red color, no taste
– Flavan-3-ols in skins and seeds • Oligomers and polymers of flavan-3-ols; proantho-
cyanidins (PA) or condensed tannins • Main contributors to bitterness and astringency
Most Important Grape Phenols
Prieur et al. (1994) Phytochem. 36, 781-784.Souquet et al. (1996) Phytochem. 43, (2), 509-512.
Figure: Proanthocyanidins
Wine tannin• Depends on grape composition• Extraction • Presence of wood or oenological
(commercial/exogenous) tannin addition – ellagitannin and/or gallotannin
• Main polymerization reactions– Oxidation reactions – Condensation with aldehydes (Fig. 4)– Direct reactions
Atanasova et al., (2002) Tetrahedron Lett. 43: 6151-6153; Es-Safi et al., (1999) J. Agric. Food Chem. 47:2096-2102;Fulcrand et al., (1996) J. Chromatogr. 752:85-91; Guyot et al., (1996) Phytochem. 42: 12789-1288.
Figure: Wine pigments
Direct condensation
Mateus et al., (2003) J. Agric. Food Chem. 51: 1919-1923; Reynolds (2010) Managing wine quality.
Flavanyl-vinyl-pyranoanthocyanin
Role of Oxygen during Barrel Aging
Del Ãlamo et al.,(2010) Anal. Chim. Acta 660:92-101Ribéreau-Gayon et al., (2006) Handbook of Enology
• O2 initial filling of barrel up to 6 mg/L (0.5 mg/L)
• O2 penetration through the barrel estimated at 1.66 and 2.5 ml.L-1.month-1 (1st month 1-5 mgL-
1.month-1, < 1 ml.L-1.month-1 )• Difficult to determine – used by phenols in
wine + ellagitannins– Age of barrel will effect O2 diffusion rate– Slow down due to plugging of wood pores
with wine deposits • Topping up barrels – 0.25 mg/L (very little)* Values in italics – my own measurments
Influence of Ellagitannnin on Wine Tannin
• [Ellagitannins] low in wine due to– Wood seasoning and toasting ellagitannins– Chemical transformation in wine due to oxidation,
polymerization and hydrolysis (8 - 21 mg/L castalagin and 2 - 7 mg/L vescalagin )
• Pyranoanthocyanins and other polymeric pigments with barrel maturation (Cano-López et al., 2010; Del Ãlamo et al., 2010)
– Malv-3-gluc and cat mediated reactions by oak-derived furfural, methyl-furfural and vanillin – model solutions (Sousa et al., 2010 and Pissarra et al., 2004)
Cano-López et al., (2010) Food Chem. 119: 191-195; Chassaing et al. (2010) Eur. J. Org. Chem. 1:55-63; Del Ãlamo et al., (2010) Anal. Chim. Acta 660:92-101; Pissarra et al., (2004) Anal. Chim. Acta 513: 215-221; Moutounet et al. (1989) Sci. Aliments. 9: 35-41; Sousa et al. (2010) J. Agric. Food Chem. 58: 5664-5669.
Influence of Ellagitannnin on Wine Tannin
• Saucier et al. (2006) also identified 5 ellagitannin derivatives in oak aged Bordeaux wine– Total 2 mg/L, catechin- and epicatechin-
ellagitannin derivatives
Saucier et al. (2006) J. Agric. Food Chem. 54 (19): 7349-7354.
Influence of Ellagitannnin on Wine Tannin
• Barrel aging enhances color stability and decrease astringency– Protecting grape phenols against oxidation– Slow O2 exposure, formation of acetaldehyde
– anthocyanin-tannin interaction by CH3CHO, furfural and other compounds that mediate polymerization reactions
Chassaing et al. (2010) Eur. J. Org. Chem. 1:55-63 Jordão et al. (2008)Austr. J. Grape Wine Res. 14:260-270Saucier et al. (2006) J. Agric. Food Chem. 54 (19): 7349-7354Vivas and Glories (1996) Am. J. Enol. Vitic. 47: 103-107.
Influence of Ellagitannnin on Wine Tannin
Cano-López et al., (2010) Food Chem. 119: 191-195Gómez-Plaza and Cano-López (2011) Food Chem. 125: 1131-1140
• Micro-oxygenation (MOX) – Color density, similar to barrel aging (Gómez-
Plaza and Cano-López, 2011)
– No wood aromas• Comparison between MOX and barrel aging
(Cano-López et al., 2010) – Similar color density (CD) after 3 months– After 6 months bottle aging: barrel> MOX– MOX hue or tint
Concluding remarks• No easy answers on best choice of barrel
for specific wine• Personal experience and some rough
guides – Light toasting – more coconut, oaky aromas– Medium toasting best for most well-balanced
wines– Heavy toasting cover herbaceous notes best
Concluding remarks• Chips alternative for short aged red wines
in lower price range– No data available on comparison between
MOX + chips/stave and barrel aging– MOX alone give similar color advantages, but
not long term