On the Synthesis and Metabolism of Cholest-4-en-7alpha-ol-3-one. Bile acids and steroids 156.

Abstract

A new method of synthesis of cholest-4-en-7[alpha]-ol-3-one is described. This compound was prepared from chenodeoxycholic acid in a yield of about 5% by electrolytic coupling of chenodeoxycholic acid with isovaleric acid, oxidation of the resulting 5[beta]-cholestane-3[alpha], 7[alpha]-diol to 5 [beta]-cholestan-7 [alpha]-ol-3-one, and dehydro- genation of this compound with selenium dioxide. Tritium-labeled cholest-4-en-7[alpha]-ol-3-one, prepared from randomly tritium-labeled chenodeoxycholic acid, was converted, when administered in trace amounts, mainly into cholic and chenodeoxycholic acids in the bile fistula rat.