Formation of pigment precursor (+)-1″-methylene-6″-hydroxy2H- furan-5″-one-catechin isomers from (+)-catechin and a degradation product of ascorbic acid in a model wine system

Célia Barril, Andrew C. Clark, Paul D. Prenzler, Peter Karuso, Geoffrey R. Scollary

Research output: Contribution to journalArticleResearchpeer-review

Abstract

The present study investigates the contribution of ascorbic acid to the formation of pigment precursors in model white wine systems containing (+)-catechin as the oxidizable phenolic substrate. The two main colorless products in these systems were structurally characterized as isomers of (+)-catechin substituted at either C6 or C8 on the A ring with a furan-type unit, namely, (+)-1 "-methylene-6"hydroxy-2H-furan-5"-one-6- catechin and (+)-1"-methylene-6"-hydroxy-2H-furan-5"-one-8- catechin. A known degradation product of ascorbic acid, L-xylosone, was separately prepared and, when reacted with (+)-catechin, generated the same (+)-furanone-catechin isomers as in model white wine systems. Incubation of these isomers in wine-like conditions yielded yellow xanthylium cation pigments. This study has shown that undesirable spoilage reactions (yellow coloration) can occur from a breakdown product of ascorbic acid-L-xylosone

LanguageEnglish
Pages9539-9546
Number of pages8
JournalJournal of Agricultural and Food Chemistry
Volume57
Issue number20
DOIs
Publication statusPublished - 28 Oct 2009

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Wine
Catechin
furans
catechin
Pigments
Isomers
Ascorbic Acid
isomers
wines
ascorbic acid
pigments
Degradation
degradation
white wines
Spoilage
spoilage
furan
Cations
cations
color

Cite this

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title = "Formation of pigment precursor (+)-1″-methylene-6″-hydroxy2H- furan-5″-one-catechin isomers from (+)-catechin and a degradation product of ascorbic acid in a model wine system",
abstract = "The present study investigates the contribution of ascorbic acid to the formation of pigment precursors in model white wine systems containing (+)-catechin as the oxidizable phenolic substrate. The two main colorless products in these systems were structurally characterized as isomers of (+)-catechin substituted at either C6 or C8 on the A ring with a furan-type unit, namely, (+)-1 {"}-methylene-6{"}hydroxy-2H-furan-5{"}-one-6- catechin and (+)-1{"}-methylene-6{"}-hydroxy-2H-furan-5{"}-one-8- catechin. A known degradation product of ascorbic acid, L-xylosone, was separately prepared and, when reacted with (+)-catechin, generated the same (+)-furanone-catechin isomers as in model white wine systems. Incubation of these isomers in wine-like conditions yielded yellow xanthylium cation pigments. This study has shown that undesirable spoilage reactions (yellow coloration) can occur from a breakdown product of ascorbic acid-L-xylosone",
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year = "2009",
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publisher = "American Chemical Society",
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Formation of pigment precursor (+)-1″-methylene-6″-hydroxy2H- furan-5″-one-catechin isomers from (+)-catechin and a degradation product of ascorbic acid in a model wine system. / Barril, Célia; Clark, Andrew C.; Prenzler, Paul D.; Karuso, Peter; Scollary, Geoffrey R.

In: Journal of Agricultural and Food Chemistry, Vol. 57, No. 20, 28.10.2009, p. 9539-9546.

Research output: Contribution to journalArticleResearchpeer-review

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AU - Barril, Célia

AU - Clark, Andrew C.

AU - Prenzler, Paul D.

AU - Karuso, Peter

AU - Scollary, Geoffrey R.

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