Journal
JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY
Volume 56, Issue 22, Pages 10980-10987Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jf8021496
Keywords
Malvidin-3-glucoside; 8-vinylcatechin; pyranoanthocyanins; pigments; red wine; mass spectrometry; NMR
Funding
- University of Adelaide (Australia)
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Reactions between malvidin-3-glucoside (mv3glc) and 8-vinylcatechin were carried out to synthesize pyranomv3glc-(+)-catechin pigment and to study the formation of intermediates. A rapid decrease of mv3g1c content concomitant with the formation of more complex structures such as mv3glc-vinylcatechin [precursor of pyranomv3glc-(+)-catechin pigment] and mv3glc-divinylcatechin was observed. On the other hand, 8-vinylcatechin undergoes acid-catalyzed dimerization in model wine solution, giving rise to 8-vinylcatechin dimers. These compounds were also found in the reaction between mv3glc and (+)-catechin mediated by acetaldehyde, which provides evidence for the formation of 8-vinylcatechin and its involvement in the formation of pyranoanthocyanins in aged red wines.
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