Preparation, properties and metabolism of 5,6-monoepoxyretinoic acid

Abstract

1. Methyl retinoate has been converted into methyl 5,6-monoepoxyretinoate by reaction with monoperphthalic acid. The epoxy acid ester on alkaline hydrolysis gave 5,6-monoepoxyretinoic acid. 2. Treatment of the 5,6-monoepoxy compounds with ethanolic hydrochloric acid gave the corresponding 5,8-epoxy (furanoid) compounds. 3. With lithium aluminium hydride, the acid and the ester groups were selectively reduced to primary alcohols. 4. Administration of methyl 5,6-monoepoxyretinoate intraperitoneally and subcutaneously had good growth response in vitamin A-deficient rats. 5. 5,6-Monoepoxyretinoic acid, when given intraperitoneally as the sodium salt, was 157% as active as all-trans-retinyl acetate. 6. Methyl 5,6-monoepoxyretinoate was hydrolysed to the epoxy acid by rat-liver homogenate. It had 35% of the biological activity of all-trans-retinyl acetate in the rat when given orally.