A New Reductone derived from D-Glucuronolactone by Alkali. I. Isolation of 3-Keto-4, 5-dideoxy-trans-4, 5-dehydro-glucuronic Acid

Abstract

An aqueous solution of D-glucuronolactone (I) produces a yellow color by alkali. This yellow substance (II) was isolated from the precipitates obtained by treating I in dimethylformamide with potassium hydroxide in methanol at 70°. It had a strong reducing character, indicating the presence of oxo-ene-diol grouping in the molecule, and gave fumaric acid (VI) and 4-oxo-glutaconic acid (IV) on periodic acid oxidation. The structure of 3-keto-4, 5-dideoxy-trans-4, 5-dehydro-glucuronic acid was proposed to this new reductone.