PHENOLIC SECRETS: Exploring Finishing Tannins in Maturation and

PHENOLIC SECRETS: Exploring Finishing Tannins in Maturation and

PHENOLIC SECRETS: Exploring Finishing Tannins in Maturation and Blending Time: 9:45am 10:45am Moderator: Tinus Els Speakers: Adolfo Alarcon Winemaker / Technical Liason, Trinchero Family Wine Estates Sabrina Lueck Instructor of Enology, Walla Walla Community College Richard Mansfield North American Winemaker, Winery Exchange Bernard Pradel Co-Founder, Toasted Oak Co. Finishing Tannins: Function, Fates, and Flavors Alternate Title: Sabrina reads literature so you dont have to! Sabrina Bitz Lueck Walla Walla Community College / College Cellars Today

Difference between fermentation, ageing, and finishing tannins Difference between hydrolysable and condensed tannins Different hydrolysable tannin species What do they do? Different oak aroma species What do they do? Compare 4 finishing tannin products using ETS Laboratories data Product Classes (Some Generalizations) Tannin source Protein reactivity Antioxidant activity Color stabilization Fermentation Tannin

Can include grape, oak, chestnut, exotic wood, gall nut Ageing Tannin Can include grape, oak, chestnut, exotic wood, gall nut Finishing Tannin Mainly oak, occasionally grape Yes (laccase protection) Yes No (or low) Yes Yes

Yes Yes Yes Some (maybe) Grape Tannins: Non-Hydrolysable (Condensed) Tannins Flavonoids (specifically procyanidins) Origin Grape seeds, skins, and stems Non-toasted oak, chestnut or exotic woods, gall nuts Function Provides tannic structure Monomers are bitter and astringent

Polymers are not bitter, but astringent Anti-oxidant activity reacts directly w/ O 2 Maybe control expression of reduced sulfur aromas? Quinone capture of volatile thiols Fate Buddying up with anthocyanins or other condensed tannins Precipitation during extended ageing (oxidation involved) Condensed tannin molecule (Scollary, 2010) Oak Tannins: Hydrolysable Tannins Non-flavonoid, ellagitannins and gallotannins Origin Toasted oak and gall nut Gallic acid can also come from stems Function Sensory impact is controversial Maybe synergistic impact Doesnt react well with salivary proteins No drying mouthfeel? Reacts pretty well with other stuff! Fate To hydrolyze (and react) Ellagitannin ellagic acid

Gallotannin gallic acid Vescalagin molecule (Waterhouse, 2002) Function/Fate: Compound Capture Influence of ellagic tannins on methanethiol in model solution 1.8 1.6 A few ellagitannins can capture grape or fermentation derived nucleophiles Sulfur based e.g. 3-sulfanylhaxan-1-ol grapefruit / tropical, methanethiol rotten cabbage Anthocyanins oenin forms anthocyanoellagitannin, bathychromatic shift 1.4 Concentration (g/L)g/L)

1.2 1 0.8 0.6 0.4 + O2 + H2O2 0.2 0 24 48

72 96 144 Storage time (h) Control Ellagic tannins + O2 +O2 (Chatonnet et al., 1992) Reduction to Roasted Oak aromatic aldehydes can perform more than just aroma masking. Furfural formed from oak wood hemicellulose degradation during toasting.

Chemical reaction occurs. + H2 S Furfural sweet caramel-like toast Furfurylthiol roasted Things on the ETS Oak Phenolics Panel Gallic acid antioxidant, derived from gallotannins, little/no sensory effect Ellagic acid antioxidant, derived from ellagitannins, little/no sensory effect Vescalin and castalin derived from vescalagin and castalagin, react w/ nucleophiles (reduced sulfur and others)

Vescalagin and castalagin reacts w/ nucleophiles (reduced sulfur and others) Complex ellagitannins other stuff, compounds that read as non condensed tannins, likely ellagitannins bound to other ellagitannins Total ellagitannins all the stuff! Things on the ETS Oak Aroma Panel Furfural + 5-methylfurfural butterscotch caramel cis-oak lactone Guaiacol + 4-methylguaiacol charred smoky spicy

Eugenol + Vanillin + trans-oak lactone raw oak coconut Isoeugenol clove vanilla Oak Aromas: Lignin Derived Flavors Guiacol charred Eugenol clove Lignin fills in spaces between other polysaccharides in cell walls. Provides mechanical strength. Lignin fragment 4-methylguiacol smoky spicy

Vanillin vanilla (structures from Gavin Sacks, Cornell University) Oak Aromas: Hemicellulose Derived Flavors Hemicellulose is a long chain of sugar Breakdown products taste/smell like cooked sugar Furfural sweet caramel-like 5-methylfurfural sweet caramel-like (structures from Gavin Sacks, Cornell University) Lets Look at Some Products Oak Phenolics and Oak Aroma Compounds in 4 Products Oak Phenolics in Products

gallic acid + ellagic acid ellagitannin monomers complex ellagitannins total ellagitannins 180 Concentration (mg/L gallic acid eq) 160 140 120 100 80 60

40 20 0 Product 1 Product 2 Product 3 Product 4 Expected Oak Phenolic Contribution to Wine (10 g/HL) gallic acid + ellagic acid ellagitannin monomers complex ellagitannins total ellagitannins

9 Concentration (mg/L gallic acid eq) 8 7 6 5 4 3 2 1 0

Product 1 Product 2 Product 3 Product 4 Oak Volatiles Panel (10 g/HL) furfural + 5 methylfurfural cis-oak lactone + trans-oak lactone eugenol + isoeugenol vanillin guaiacol + 4-methylguaiacol 300 Concentration (g/L)g/L)

250 200 150 100 50 0 Product 1 Product 2 Product 3 Product 4 Odor Activity Values 10

furfural + 5 methylfurfural cis-oak lactone + trans-oak lactone eugenol + isoeugenol vanillin guaiacol + 4-methylguaiacol Value = 17 Importance of a compound to the odor of a sample OAV = concentration / detection threshold 9 8 Odor Activity Value 7 6

5 4 3 2 1 0 Product 1 Product 2 Product 3 Product 4 Detection thresholds from Chatonnet 1995 Thank You References Chatonnet, P. 1995. Influence des proceeds de tonnellerie et des techniques dlevage sur la composition et la qualit des vins levs en fts de chne. PhD Thesis. Universit de Bordeaux, Bordeaux, FR. He, F., Liang, N., Mu, L., Pan, Q., Wang, J. Reeves, M., and C. Duan. 2012. Anthocyanins and their variation in red wines I; monomeric anthocyanins and their color expression. Molecules. 17: 1571-1601.

He, F., Liang, N., Mu, L., Pan, Q., Wang, J. Reeves, M., and C. Duan. 2012. Anthocyanins and their variation in red wines II; anthocyanin derived pigments and their color evolution. Molecules. 17:1483-1519. Kontoudakis, N. 2010. Grape phenolic maturity; Determination methods and consequences on wine phenolic composition. Thesis, Rovira i Virgili University, Tarragona. Loch, R. 2002. Micro-oxygenation: a large winery case study. In ASVO Proceedings of Seminar Use of gases in winemaking. Allen, M. (ed), pp. 45-53. Australian Society for Viticulture and Oenology. Adelaide. Ribreau-Gayon, P., Glories, Y., Maujean, A., and D. Dubourdieu. 2006. Handbook of Enology Volume 2; The Chemistry of Wine Stabilization and Treatments. John Wiley & Sons Ltd, Chichester, United Kingdom. Waterhouse, A. 2002. Wine Phenolics. Ann. N.Y. Acad. Sci. 957: 21-36. Thank You to Our Session Sponsor:

Recently Viewed Presentations

  • The Preliminary Thesis - Council Rock School District

    The Preliminary Thesis - Council Rock School District

    with your thesis. If everyone agrees on first sight, your thesis is too obvious, and not worth writing about. Analytical, not evaluative. A critical analysis of a literary work is not the place to praise or blame works of literature:...
  • Use Inverse Matrices to Solve Linear Systems

    Use Inverse Matrices to Solve Linear Systems

    Square Matrix. Although a matrix may have any number of rows and columns, square matrices have properties that we can use to solve systems of equations A square matrix is one of the form ?×?, where . n. is a...
  • Organic Chemistry - newburyparkhighschool.net

    Organic Chemistry - newburyparkhighschool.net

    Molecular Formulas. Molecular: actual number of atoms of each present. It can be deduced if both the empirical formula and relative molecular mass, M r, are known.. Example:What is the molecular formula of a compound with relative molecular mass, M....
  • CRS PPT Fresh Template Eng MK1471 22Sep14

    CRS PPT Fresh Template Eng MK1471 22Sep14

    Operations in Emergencies:Staff Care - Stress & Stress Management. Welcome to this introduction to staff care in emergencies. The staff care presentations will give you an overview of challenges you and your staff may face in maintaining health and wellbeing...
  • Ephrata Community Hospitals POCT Competency Program- Then and

    Ephrata Community Hospitals POCT Competency Program- Then and

    Ephrata Community Hospital's POCT Competency Program- Then and Now By Beverly McAllister Laboratory Operations Manager Demographics 135 bed Community Hospital Located in Lancaster County, PA 12 types of Point-of-care tests 6 POC tests brought in-house within the last 3 years...
  • Choices in Relationships

    Choices in Relationships

    You can't marry siblings, cousins, parent & child Sociological Factors Operative in Mate Selection The homogamy theory of mate selection states that we tend to be attracted to and become involved with those who are similar to us in age,...
  • Belmont Abbey College Cuthbert Allen Lecture Science, Ethics ...

    Belmont Abbey College Cuthbert Allen Lecture Science, Ethics ...

    " Psalm 34:3 (NIV) DOXOLOGYPraise God for the myriad gifts ... I have given every green plant for food." (NRSV) Genesis 9:3-4 - "Every moving thing that lives shall be food for you; and just as I gave you green...
  • web.stanford.edu

    web.stanford.edu

    Implementation Lucene Mysql Ted Grenager's Crawler Source Jakarta HTTPClient Improving Software Package Search Quality Dan Fingal and Jamie Nicolson The Problem Search engines for softare packages typically perform poorly Tend to search project name an blurb only For example… Sourceforge.org...