Degradation of (+)-Cyanidanol-3 by Sodium Sulfite in Aqueous Solution. II. Reactivity of Several (+)-Cyanidanol-3 Derivatives with Sodium Sulfite

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The reactivity of several (+)-cyanidanol-3 (cianidanol) derivatives with sodium sulfite in aqueous solution was investigated at pH 7.5 and 60℃. 5,7-O-Dimethylcianidanol was degraded by sodium sulfite to yield a water-soluble degradation product, which was assumed to be 5,7-O-dimethylepicatechin carrying the sodium sulfonate function in place of the aliphatic hydroxy group at the C-3 position. The degradation by sodium sulfite was inhibited by the addition of boric acid and by lowering the pH of the solution to 3.0. On the other hand, 3', 4'-O-dimethylcianidanol and 5,7,3', 4'-O-tetramethylcianidanol were very stable in aqueous solution containing sodium sulfite. The mechanism of the attack of sulfite ion and/or bisulfite ion at the C-3 position of the dissociated form of cianidanol or 5,7-O-dimethylcianidanol is discussed.
公益社団法人日本薬学会の論文
1984-08-25