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J Agric Food Chem. 2009 Oct 28;57(20):9539-46. doi: 10.1021/jf902198e.

Formation of pigment precursor (+)-1''-methylene-6''-hydroxy-2H-furan-5''-one-catechin isomers from (+)-catechin and a degradation product of ascorbic acid in a model wine system.

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National Wine and Grape Industry Centre, Charles Sturt University, Locked Bag 588, Wagga Wagga, NSW 2678, Australia.


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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