METABOLISM OF THE STEROID HORMONES: THE ISOLATION OF AN ANDROGEN FROM HUMAN URINE CONTAINING AN 11-OXYGEN SUBSTITUTION IN THE STEROID RING1

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Abstract
10.5 mg./l. of androstanediol-3([alpha]), ll([beta])-17-one have been isolated from the unhydrolyzed urine of a girl suffering from virilism. This compound appears to be identical with a C-ll oxygen substituted steroid previously isolated from human urine by Mason. The androstanediol-3 ([alpha]), ll([beta])-17-one has been converted by dehydration into an androstenol-3([alpha])-17-one apparently identical with a substance previously iso- lated from hydrochloric acid hydrolyzed urine from the same patient. This conversion definitely establishes the presence of an 11-hydroxy substitution in the 11-oxygen compound and also narrows the possibilities of the unsaturation in the androstenol-3([alpha])-17-one to the 9:11 or 11:12 position. It has been demonstrated that androstanediol-3([alpha]), ll([beta])-17-one is approximately V as active as androsterone as measured by a chick comb method.