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Impact of Oak on Wine Composition and Chemistry. Anita Oberholster. 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

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introduction
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
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-Gayonet al., (2006) Handbook of Enology

figure ellagitannins
Figure: Ellagitannins

Ribéreau-Gayon et al., (2006) Handbook of Enology

non volatile extracts from oak
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 – hemicellulose

Marchal et al. (2011) Anal. Chem. 83: 9629-9637

Puech et al. (1999) Am. J. Enol. Vitic. 50: 469-478

compounds extracted from oak volatile
Compounds Extracted from Oak: Volatile

Methyloctalactone

Eugenol

Vanillin

Syringaldehyde

Coniferaldehyde

Sinapaldehyde

Ribéreau-Gayonet al., (2006) Handbook of Enology

compounds extracted from oak volatile1
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 thresholds

Ribéreau-Gayon et al. (2006) Handbook of Enology

Spillman et al. (2004) Austr. J. Grape Wine Res. 10: 227-235

compounds extracted from oak volatile2
Compounds Extracted from Oak: Volatile

Furfural

Methyl-5-furfural

Hydroxymethyl-5-furfural

Cyclotene

Maltol

Isomaltol

Ribéreau-Gayonet al., (2006) Handbook of Enology

compounds extracted from oak volatile3
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 Enology

Spillman et al. (2004) Austr. J. Grape Wine Res. 10: 227-235

compounds extracted from oak volatile4
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 Enology

Spillman et al. (2004) Austr. J. Grape Wine Res. 10: 227-235

compounds extracted from oak volatile5
Compounds Extracted from Oak: Volatile

Ribéreau-Gayonet al., (2006) Handbook of Enology

influence of wine and oak composition
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
Influence of Oak Composition
  • Allier vsLimousin(Ribéreau-Gayon et al., 2006)
    • Ellagitannin Allier < Limousin
    • Volatiles Allier > Limousin
    • Limousinvs Vosges vsTronaisvs Ohio (Spillman et al., 2004)
    • Oak lactones + Eugenol Vosges > Tronais > Limousin
    • Little diffr between Allier vs American (Pérez-Prietoet al., 2002)
    • Except American  oak-lactones

Pérez-Prieto et al. (2002) J. Agric. Food Chem. 50: 3272-3276

Ribéreau-Gayonet al. (2006) Handbook of Enology

Spillman et al. (2004) Austr. J. Grape Wine Res. 10: 216-226

influence of oak composition1
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
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: 9629-9637

Puech et al. (1999) Am. J. Enol. Vitic. 50: 469-478.

influence of barrel size and storage time
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-CerdánamdAncín-Azpilicueta(2006) Trends Food Sci. 17, 438-447

Pérez-Prieto et al. (2003) J. Agric. Food Chem. 51: 5444-5449

Rodríguez-Rodríguez and Gómez-Plaza (2011) Am. J. Enol. Vitic. 62 (3): 359-365

influence of barrel storage time
Influence of Barrel Storage Time

Pérez-Prieto et al. (2003) J. Agric. Food Chem. 51: 5444-5449

influence of barrel storage time1
Influence of Barrel Storage Time

Pérez-Prieto et al. (2003) J. Agric. Food Chem. 51: 5444-5449

influence of barrel storage time2
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-CerdánamdAncín-Azpilicueta (2006) Trends Food Sci. 17: 438-447

Pérez-Prieto et al. (2003) J. Agric. Food Chem. 51: 5444-5449

influence of new vs used barrels
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-CerdánamdAncín-Azpilicueta (2006) Trends Food Sci. 17: 438-447

Pérez-Prieto et al. (2003) J. Agric. Food Chem. 51: 5444-5449

.

oak new technologies
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>stavesbarrel
  • 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 aged

Del Alamo et al., 2004, Anal. Chim. Acta. 513 (1), 229-237; Garde-CerdánamdAncín-Azpilicueta (2006) Trends Food Sci. 17: 438-447; Ortega-Heras et al., 2010, Food Sci. Tech. 43, 1533-1541

the use of oak chips
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), 229-237

Garde-CerdánamdAncín-Azpilicueta (2006) Trends Food Sci. 17: 438-447

Ortega-Heras et al., 2010, Food Sci. Tech. 43: 1533-1541

most important grape phenols
Most Important Grape Phenols
  • 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

Prieuret al. (1994) Phytochem. 36, 781-784.

Souquetet al. (1996)Phytochem. 43, (2), 509-512.

wine tannin
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; Guyotet al., (1996) Phytochem. 42: 12789-1288.

figure wine pigments
Figure: Wine pigments

Flavanyl-vinyl-pyranoanthocyanin

Direct condensation

Mateus et al., (2003) J. Agric. Food Chem. 51: 1919-1923; Reynolds (2010) Managing wine quality.

role of oxygen during barrel aging
Role of Oxygen during Barrel Aging
  • O2initial 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 O2diffusion 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

Del Ãlamo et al.,(2010) Anal. Chim. Acta660:92-101

Ribéreau-Gayonet al., (2006) Handbook of Enology

influence of ellagitannnin on wine tannin
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-Lópezet al., 2010; Del Ãlamo et al., 2010)
    • Malv-3-gluc and cat mediated reactions by oak-derived furfural, methyl-furfural and vanillin – modelsolutions(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 tannin1
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 tannin2
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. 14:260-270

Saucier et al. (2006) J. Agric. Food Chem. 54 (19): 7349-7354

Vivas and Glories (1996)Am. J. Enol. Vitic. 47: 103-107.

influence of ellagitannnin on wine tannin3
Influence of Ellagitannnin on Wine Tannin
  • 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

Cano-López et al., (2010) Food Chem. 119: 191-195

Gómez-Plaza and Cano-López (2011) Food Chem. 125: 1131-1140

concluding remarks
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 remarks1
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