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Anita Oberholster

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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Anita Oberholster

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

  2. 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

  3. 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

  4. Figure: Ellagitannins Ribéreau-Gayon et al., (2006) Handbook of Enology

  5. 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

  6. Compounds Extracted from Oak: Volatile Methyloctalactone Eugenol Vanillin Syringaldehyde Coniferaldehyde Sinapaldehyde Ribéreau-Gayonet al., (2006) Handbook of Enology

  7. 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

  8. Compounds Extracted from Oak: Volatile Furfural Methyl-5-furfural Hydroxymethyl-5-furfural Cyclotene Maltol Isomaltol Ribéreau-Gayonet al., (2006) Handbook of Enology

  9. 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

  10. 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

  11. Compounds Extracted from Oak: Volatile Ribéreau-Gayonet al., (2006) Handbook of Enology

  12. 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

  13. 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

  14. 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

  15. 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.

  16. 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

  17. Influence of Barrel Storage Time Pérez-Prieto et al. (2003) J. Agric. Food Chem. 51: 5444-5449

  18. Influence of Barrel Storage Time Pérez-Prieto et al. (2003) J. Agric. Food Chem. 51: 5444-5449

  19. 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

  20. 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 .

  21. 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

  22. 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

  23. 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.

  24. Figure: Proanthocyanidins

  25. 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.

  26. Figure: Wine pigments Flavanyl-vinyl-pyranoanthocyanin Direct condensation Mateus et al., (2003) J. Agric. Food Chem. 51: 1919-1923; Reynolds (2010) Managing wine quality.

  27. 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

  28. 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.

  29. 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.

  30. 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.

  31. 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

  32. 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

  33. 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

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