Isomeric influence on the oxidative coloration of phenolic compounds in a model white wine: comparison of (+)-catechin and (-)-epicatechin

J Agric Food Chem. 2005 Dec 28;53(26):9993-8. doi: 10.1021/jf0511648.

Abstract

The reactions of (+)-catechin and (-)-epicatechin with glyoxylic acid were studied in a model white wine solution. When the reactions were performed in darkness at 45 degrees C, the (-)-epicatechin concentration decreased more rapidly than that of (+)-catechin, and the (-)-epicatechin sample had twice the 440 nm absorbance of the (+)-catechin sample after the 14 day incubation period. The main pigments generated were identified as xanthylium cation pigments regardless of the isomeric character of the phenolic compound. Using a combination of absorbance and ion current data, the xanthylium cation pigments generated from (-)-epicatechin were found to have combined molar absorptivity coefficients 1.8 times that of the xanthylium cation pigments generated from (+)-catechin. The implication of these results on the development of an index of white wine oxidation susceptibility is discussed.

Publication types

  • Comparative Study
  • Research Support, Non-U.S. Gov't

MeSH terms

  • Algorithms
  • Catechin / analysis*
  • Chromatography, Liquid
  • Color
  • Glyoxylates / analysis
  • Isomerism
  • Mass Spectrometry
  • Oxidation-Reduction
  • Phenols / analysis*
  • Spectrophotometry, Ultraviolet
  • Wine / analysis*

Substances

  • Glyoxylates
  • Phenols
  • Catechin
  • glyoxylic acid