Formation of Aromatic Compounds from Carbohydrates. IX. Reaction of D-Glucose and L-Lysine in Slightly Acidic, Aqueous Solution.

Abstract

The title reaction produced a humin-like precipitate In the supernatant, D-fructose and compounds comprising furans, pyrroles, phenols, and enols, were identified. The bicyclic products, 1-methyl-5-[5-(hydroxymethyl)-2-furfuryl]pyrrole-2-carboxaldehyde, 5-(5-formyl-2-furfuryloxymethyl)-1-methylpyrrole-2-carboxaldehyde, 5,5'-(oxydimethylene)bis[1-methylpyrrole-2-carboxaldehyde], 5-(hydroxymethyl)-1,1'-dimethyl-4,5'-methylenedipyrrole-2-carboxaldehyde, and 1-methyl-5-(3,4,5-trihydroxybenzyl)pyrrole-2-carboxaldehyde, are new. 2',4',5'-Trihydroxyacetophenone has not been identified previously as a degradation product of carbohydrates.