Formation of Two-Carbon Sugar Fragment at an Early Stage of the Browning Reaction of Sugar with Amine

Abstract

A product easily converted to glyoxal was found in an early stage of the reaction of sugar with amine in ethanol. Glyoxaldicyclohexylimine was isolated from the reaction mixture of d-glucose with cyclohexylamine. This finding suggested the formation of a similar type glyoxaldialkylimine in other reactions of sugar with amine. This two-carbon compound was assumed to be produced directly from sugar or glycosylamine, and a new pathway for sugar fragmentation was proposed.