Preparation, properties and metabolism of 5,6-monoepoxyretinoic acid.
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.
D000085:Acetates; D000143:Acids; D000535:Aluminum; D000818:Animals; D001681:Biological Assay; D055598:Chemical Phenomena; D002621:Chemistry; D002625:Chemistry, Organic; D002845:Chromatography; D002855:Chromatography, Thin Layer; D004988:Ethers, Cyclic; D005663:Furans; D007274:Injections, Intraperitoneal; D007279:Injections, Subcutaneous; D008094:Lithium; D008297:Male; D055601:Organic Chemistry Phenomena; D051381:Rats; D013053:Spectrophotometry; D014801:Vitamin A; D014802:Vitamin A Deficiency / Q000378:metabolism
D000085:Acetates; D000143:Acids; D004988:Ethers, Cyclic; D005663:Furans; D014801:Vitamin A; D008094:Lithium; D000535:Aluminum