The isolation of 16α-hydroxydehydroepiandrosterone (3β:16α-dihydroxyandrost-5-en-17-one) from the urine of normal men

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Abstract
It has been shown by paper chromatography that when urine from normal males is boiled for 1 hour at neutral pH and extracted with chloroform these extracts contain two "blue-tetrazolium"-reducing compounds X and Y which are not present in extracts of unboiled urine. By treatment with acid at room temperature X was converted into a blue-tetrazolium- reducing compound Xa, which had a higher Rf than X and the same Rf as Y. Xa has been isolated from extracts of urine and characterized as the hitherto undescribed steroid 16 [alpha]-hydroxydehydroepiandrosterone. By analogy with 6 [beta]-hydroxy-3,5-cycloandrostan-17-one which arises from the hydrolysis in neutral solution of dehydroepiandrosterone sulfate and which is transformed bv acid into dehydroepiandrosterone it is considered that X is 6 3,16 [alpha]-dihydroxy-3,5-cycloandrostan-17-one formed from the 3 B-sulfate of 16 a-hydroxydehydroepiandrosterone. 16 [alpha]-hydroxydehydroepiandrosterone was shown to be a metabolite of dehydroepiandrosterone, and it is suggested that it is an intermediate in the transformation of dehydroepiandrosterone into androst-5-ene-3 [beta],16 [alpha],17[beta]-triol.