Comparative studies of bile salts. 16-Deoxymyxinol, a second bile alcohol from hagfish

Abstract

1. Material containing the less polar sulphate previously noticed in hagfish bile salts gave, after dioxan–trichloroacetic acid cleavage, 16-deoxymyxinol [3β,7α,-26(27)-trihydroxy-5α-cholestane]. 2. Anodic coupling of 3β-hydroxy-5β-cholanoic acid and the mixed half esters of dl-methylsuccinic acid, followed by lithium aluminium hydride reduction, yielded 3β,26(27)-dihydroxy-5β-cholestane. 3. 16-Deoxymyxinol, the third known bile alcohol having the 3β-hydroxy-5α-hydrogen configuration, poses again the question of how the 3β-hydroxyl group of cholesterol can be ‘retained’ in biosynthesis of primitive bile salts.