Chemistry of Wine Flavor (ACS Symposium Series, No. 714)

249 Pages·1999·20.54 MB·English

by  Andrew L. Waterhouse

Chemistry of Wine Flavor
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ACS SYMPOSIUM SERIES 714
Chemistry of Wine Flavor
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NIV g | d University of California at Davis
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American Chemical Society, Washington, DC
Library of Congress Cataloging-in-Publication Data
Chemistry of Wine Flavor / Andrew L. Waterhouse, editor, Susan E. Ebeler,
editor.
p. cm.—(ACS symposium series , ISSN 0097-6156 ; 714)
"Developed from a symposium sponsored by the Division of Agricultural
01 and Food Chemistry at the 213th National Meeting of the American Chemical
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w Society, San Francisco, California, April 13-17, 1997"—T.p. verso.
4.f
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7 Includes bibliographical references (p. - ) and index.
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st 7, 200921/bk-199 I1S.B WNin 0e-8 a4n1d2 -w3i5n9e2 -m9a king—Chemistry—Congresses.
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g1 I. Waterhouse, Andrew Leo. II. Ebeleer, Susan E., 1961- . III. American
Au10. Chemical Society. Division of Agricultural and Food Chemistry. IV. American
on oi: Chemical Society. Meeting (213th : 1997 : San Francisco, Calif.) V. Series.
UNIV org | d TP544.C45 1998
N cs. 663'.2—dc21 98-34175
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PRINhttp:// The paper used in this publication meets the minimum requirements of American National Standard for
y n Information Sciences—Permanence of Paper for Printed Library Materials, ANSI Z39.48-1984.
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nloade3, 200 Copyright © 1998 American Chemical Society
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ACS Symposium Series
Mary E. Castellion Omkaram Nalamasu
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u0 Douglas A. Smith
Aug10.1 University of Kansas The DAS Group, Inc.
NIV on g | doi: LNaabwisrceon Fcoeo dPs. KGrloeumpa nn Martin R. Tant
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Oa Richard N. Loeppky
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DJul at Urbana-Champaign DuPont Company
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Foreword
THE ACS SYMPOSIUM SERIES was first published in 1974 to provide
a mechanism for publishing symposia quickly in book form. The pur­
pose of the series is to publish timely, comprehensive books devel­
1 oped from ACS-sponsored symposia based on current scientific re­
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w search. Occasionally, books are developed from symposia sponsored
14.f by other organizations when the topic is of keen interest to the chem­
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st 7, 200921/bk-199 itse rreesvBt iteeofw otrheede aafgourrde ieaeipnnpcgre o.t poSr ipoamutebe l iapsnahdp a e crbsoo mmopkar,y et hhbeee n pesrixvocepl uocdsoeevdde itrnaab goleer d aoenrf dtc oof onbrtee tintnet­sr
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Au10. focus the book; others may be added to provide comprehensiveness.
on oi: When appropriate, overview or introductory chapters are added.
NIV g | d Drafts of chapters are peer-reviewed prior to final acceptance or re­
Uor jection, and manuscripts are prepared in camera-ready format.
ON acs. As a rule, only original research papers and original review pa­
CETpubs. pers are included in the volumes. Verbatim reproductions of previ­
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Preface
The complexity of wine composition has always challenged chemists and, as a
1 result , there have been many meetings to discuss the chemistry and the related
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pr flavors. Scientific interest in these flavors has led to an increased understanding
14. of wine chemistry, biochemistry, and sensory perception, and meetings of the
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Aug10.1 this volume is derived.
on oi: The first five chapters of this book focus on the grape derived and varietal
NIV g | d flavors of wines. Many of these compounds occur as nonvolatile glycosidic fla­
Uor vor precursors and the separation and analysis of these precursors have been a
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PRINhttp:// tartitlelmionp tr aton gceh aanradc tleorwizeer . varietal flavors with sensory thresholds in the parts per
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de00 those formed during the primary yeast fermentation and any secondary bacterial
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n J yeast fermentations) or are still not well understood. The effects of grape com­
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u to an increased understanding of the pathways by which fermentation flavors are
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formed. These topics are discussed in Chapters 6-9.
The contribution of polyphenols to the bitter taste and astringent mouthfeel
of wine is the focus of Chapters 10-12. The effects of grape growing region,
wine processing (filtration and fining), and aging are discussed as they relate to
polyphenol composition and taste. Finally, the characterization of aromas related
to wine maturation, aging in oak cooperage, the cork stopper, and the role of
component interactions on flavor volatility and perception are the focus of the
final four chapters of the book.
The authors, whose chapters appear in this book, represent a cross-section
of the current generation of international experts in the field of wine flavor
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chemistry. But like all science, current research in wine chemistry builds on the
findings of pioneers in the field. For instance, early studies on wine phenolics by
Vernon L. Singleton and on wine and sherry volatiles by A. Dinsmoor Webb
have been further developed by other scientists and former colleagues in other
parts of the world. Although not all of the early wine chemists are individually
named in this book, their contributions were essential for achieving our current
state of knowledge. As such, this ACS Wine Flavor Chemistry Symposium rep­
resented an exciting mixture of topics, scientific history, and recent discoveries,
and this proceedings presents one of the most current collections of research on
wine flavor chemistry that is available.
1 We thank the contributors, Diane Eschenbaum for administrative assistance,
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14. making the symposium a success: The American Society for Enology and Viti­
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NIV g | d Department of Viticulture and Enology
Uor University of California at Davis
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Chapter 1
Analysis, Structure, and Reactivity of Labile Terpenoid
Aroma Precursors in Riesling Wine
Peter Winterhalter1, Beate Baderschneider, and Bernd Bonnländer
1
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ch Institut für Pharmazie und Lebensmittelchemie, Universität Erlangen at Nürnberg,
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1 Schuhstrasse 19, D-91052 Erlangen, Germany
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N cs. well as two ß-D-glucopyranosides of 3-hydroxy-7,8-didehydro-ß-ionol.
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Cp aroma volatiles is discussed. In addition, the identification of uncommon
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by on 2-ethyl-3-methylmaleimide as well as the ß-D-glucose ester of 10,11-di-
ed 09 hydroxy-3,7,11-trimethyl-2,6-dodecadienoic acid.
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n J structures in recent days is mainly due to their role as flavour precursors (9-16).
d o Especially during a prolonged storage of wine, the acid-catalyzed degradation of
he such glycoconjugates is considered to make an important contribution to the typical
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Reasons for Elucidating the Total Structure of Glycosidic Aroma Precursors
Glycosidic aroma precursors are conveniently isolated from grape juice and wine by
selective retention on either C^-reversed phase adsorbent (19) or Amberlite XAD-2
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(20), followed by the desorption of the retained glycosides using ethyl acetate or
methanol as the eluting solvent. Once a precursor concentrate has been obtained,
two lines of investigations can be pursued. The first rapid approach consists of a
HRGC-MS analysis of the aglycon fraction obtained after enzymatic hydrolysis. On
this basis, some information about the bound aroma fraction is immediately
obtained. This approach, however, does not give absolute proof of glycoconjugation.
1Current address: Institut für Lebensmittelchemie, Technische Universität Braunschweig, Schleinitzstrasse
20, D-38106 Braunschweig, Germany.
© 1999 American Chemical Society 1
2
In a recent study (21), the formation of artifacts during enzymatic hydrolyses has
been reported. High concentrations of fungal-derived hydrolases were found to
almost completely oxidize some of the aglycon moieties. Glycosides with homo-
allylic glycosidic linkages were found to be particularly susceptible to this
oxidation. One example is the hydrolysis of glucoconjugated 3-hydroxy-B-damas-
cone 1. Upon enzymatic hydrolysis with a fungal-derived enzyme preparation,
glucoside 1 did not liberate the intact aglycon 2, instead oxidized products, i.e. the
oxodamascones 3 and 4, were obtained as cleavage products. This observation
emphasizes the need to confirm the structures of the glycoconjugates by isolating
and characterizing the individual glycoconjugates.
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N Ucs.or Figure 1. Artifact formation observed after incubation with fungal-derived
Oa glycosidase preparations (21).
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d b9 o conjugates may show considerable differences in their reactivity. The importance of
de00 glycoconjugation for the formation of aroma volatiles is demonstrated in the case of
ownloay 23, 2 vpiattitseprinr aonfe v6o lfaotrilme aptrioodnu. cWts,h earmeaosn gth we hfircehe iasgolmyceorinc 5vAiti swpiarsa nfeosu n6d w teor ey ioenldly a p rwesheonlet
Dul in minor quantities (15 %), the glucoconjugated form 5 almost exclusively forms the
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OH 6
5A R = H 15%
5 R = Glc > 90 %
Figure 2. Influence of glycoconjugation on the rate of product formation,
example vitispirane 6 formation from nonvolatile precursors 5 and 5A.