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IT was first reported by Womack & Koch [1932] that the urine of normal women yielded quantities ofandrogenic material which, as measured by the capon test, were of the same order as that yielded by the urine of normal men. This fact has been confirmed repeatedly [cf. Siebke, 1934; Dingemanse et al. 1935; 1937; Simpson et al. 1936; Callow, 1936; Koch, 1936; Gallagher et al. 1937; Callow, 1938; Callow et al. 1938] and, with the improved methods of extraction which have been used during the last two years, it is generally recognized that, although the average amount of urinary androgen is somewhat lower for women than for men, the limits ofnormal variation for the two sexes overlap. Nevertheless, there has been no report of attempts to identify chemically the androgenic compounds in the urine of normal, non-pregnant women, parallel with the work by Butenandt and his collaborators [1934; 1935; 1937], which established that androsterone and transdehydroandrosterone occurred in the urine of men, and indicated the presence of isoandrosterone and of epiaetiocholanediol. Work carried out in this laboratory [Callow et al. 1938] has shown that in respect of the ratio of methyleneketone, or " sterone " content (estimated colorimetrically) to comb-growth activity, no distinction can be made between urine extracts from men or women, but this rather vague evidence required amplification by more precise chemical analysis. With this end in view we undertook the more detailed fractionation of extracts of urine from both males and females. The concentration of androgenic activity in the neutral ketonic fraction ofmen's urine obtained by the use of Girard's reagent has been described in a previous paper [Callow et al. 1938]. When the ketonic resin was distilled at low pressure, volatile fractions were obtained, from the first of which the oxime of androsterone could be separated in the pure state in a yield of 02 mg. per 1. of original urine. Parallel with these experiments, a concentrate from women's urine was put through the same process. There was a striking similarity in the behaviour of the two types of extract in the whole course of the fractionation, and this culminated in the isolation from the women's urine concentrate of androsterone oxime in a yield of 044 mg. per 1. of original urine. The identity of the compound was confirmed by hydrolysis to androsterone and conversion of the latter into the benzoate. From a second fraction, distilling at a higher temperature, transdehydroandrosterone was isolated in small amount as the characteristic benzoate.

The isolation of androsterone and transdehydroandrosterone from the urine of normal women