The Origin of 3,5-Cycloandrostan-6β-ol-17-one (i-Androsten-6β-ol-17-one) in Urinary Extracts

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

“…Since the R, of chromatographically purified Y was unaffected by this treatment it seems probable that Xa and Y may be identical, but no rigid proofthat this is so has been obtained. The liberation of X from a chloroform-insoluble precursor in urine by boiling and the transformation by acid treatment of X into Xa (with higher R.) appeared to be strikingly analogous to the hydrolysis of sodium dehydroepiandrosterone sulphate by boiling in neutral aqueous solution with the formation of i-androstanolone and the transformation of the latter into dehydroepiandrosterone by acid (Teich et al 1953). Accordingly, the working hypothesis was adopted that Xa might be a steroid of the 5-en-3,B-ol class, that X might be the corresponding 6fl-hydroxy-3:5-cyclo compound, and that the parent substance present in urine might be the 3-sulphate of Xa.…”

The isolation of 3β-hydroxy-Δ5-steroids from the urine of normal men

“…without adjustment of pH. It would appear from the work of Dingemanse, Huis in't Veld & Hartogh-Katz (1952), Teich, Rogers, Lieberman, Engel & Davis (1953) and Fotherby et al (1957) that the major reaction product resulting from boiling a solution of the sulphate of a 3fl-hydroxy-A5-* Present address: Clinical Endocrinology Research Unit (Medical Research Council), University of Edinburgh. steroid at neutral pH is the 3:5-cyclo-6f-hydroxy steroid accompanied by a small amount of the 3flhydroxy-A/5-steroid.…”