The estimation of androst-16-en-3α-ol in human urine. Partial synthesis of androstenol and of its β-glucosiduronic acid

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Abstract
The partial synthesis is described of androst-16-en-3[apha]-ol from androsterone, through the dehydration of androsterone acetate cyanohydrin, saponifica-tion, and decarboxylation of the derived aeti-16-enic acid. The synthesis of methyl (androst-16-en-3[alpha]-yl tri-O-acetyl-[beta]-D-glucopyranosid) uronate and the preparation from it of androst-6-en-3[alpha]-yl [beta]-D-gluco-siduronic acid are described. A method for the estimation of glucuro-nide-conjugated androst-16-en-3[aplha]-ol in human urine is described in detail. The procedure includes hydrolysis of the conjugate with [beta]-glucuronidase, separation of the androstenol by chromatography on alumina, and quantitative application of a colour reaction employing resorcylaldehyde and sulphuric acid in acetic acid. The specificity and limitations of the colour reaction have been studied. The precision of the whole method has been evaluated. Recoveries of androstenol, added to urine as the pure [beta]-glucosiduronic acid, exceeded 82% in the range 15-71 ug of androstenol/100 ml of urine and averaged 90.4 (S.D. [plus or minus] 5.3)%.