Carbocations and the Complex Flavor and Bouquet of Wine: Mechanistic Aspects of Terpene Biosynthesis in Wine Grapes

Henry B Wedler; Ryan P Pemberton; Dean J Tantillo

doi:10.3390/molecules200610781

Carbocations and the Complex Flavor and Bouquet of Wine: Mechanistic Aspects of Terpene Biosynthesis in Wine Grapes

Molecules. 2015 Jun 11;20(6):10781-92. doi: 10.3390/molecules200610781.

Authors

Henry B Wedler¹, Ryan P Pemberton², Dean J Tantillo³

Affiliations

¹ Department of Chemistry, University of California, Davis, One Shields Avenue, Davis, CA 95616, USA. hbwedler@ucdavis.edu.
² Department of Chemistry, University of California, Davis, One Shields Avenue, Davis, CA 95616, USA. pemberton@ucdavis.edu.
³ Department of Chemistry, University of California, Davis, One Shields Avenue, Davis, CA 95616, USA. djtantillo@ucdavis.edu.

Abstract

Computational chemistry approaches for studying the formation of terpenes/terpenoids in wines are presented, using five particular terpenes/terpenoids (1,8-cineole, α-ylangene, botrydial, rotundone, and the wine lactone), volatile compounds (or their precursors) found in wine and/or wine grapes, as representative examples. Through these examples, we show how modern computational quantum chemistry can be employed as an effective tool for assessing the validity of proposed mechanisms for terpene/terpenoid formation.

Keywords: aroma; biosynthesis; mechanism; quantum chemistry; terpene; wine.

Publication types

Research Support, U.S. Gov't, Non-P.H.S.
Review

MeSH terms

Cyclohexanols / chemistry
Eucalyptol
Flavoring Agents / chemistry
Fruit / metabolism
Humans
Monoterpenes / chemistry
Sesquiterpenes / chemistry
Sesquiterpenes / metabolism
Taste*
Terpenes / metabolism*
Vitis / chemistry*
Wine*

Substances

Cyclohexanols
Flavoring Agents
Monoterpenes
Sesquiterpenes
Terpenes
rotundone
Eucalyptol