炭水化物系化合物の自動酸化分解(第7報)グルコースのアミノ-カルボニル反応において生成する色素について

概要

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Autoxidative cleavage of N-p-tolyl-D-glucosylamine (I) in ethanol solution containing p-toluidine yielded three pigments, X_1,X_3,and X_3,which were isolated together with other decomposition products. These pigments were identified with 2,3-dideoxo-2,3-di(p-tolylimino)-5-methylindoline (X_1) (reddish brown), 5,5'-dimethylindirubin (X_2)(violet), and 3-deoxo-3-(p-tolylimino)-5,5'-dimethylindirubin (X_3) (violet). These pigments were formed from the C_1 -C_2 fragment of the sugar and p-toluidine, and their structure was identified by synthesis from 5-methylisatin (X) by a different route. Free radical signal was detected in the electron spin resonance spectrum of the rection mixture of I and p-toluidine, and the signal was retained during the browning reaction which required a large amount of oxygen at the initial stage of the reaction. These results indicate that a free radicald formation was involved in this amino-carbonyl reaction and, therefore, the pigments obtained here were formed from C_1-C_2 fragments produced by the radical reaction between the sugar and the amine.
公益社団法人日本薬学会の論文
1973-01-25