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

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