Isolation of Δ3:5-androstadiene-17-one from the urine of a man with a malignant tumour of the adrenal cortex

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Abstract
A [male] patient with a malignant tumor of the adrenal gland excreted an excessive amount of oestrogenic hormone, and showed concomitant signs of feminism. An attempt to isolate this hormone from the urine was not successful, but the results were consistent with the view that the hormone was oestrone. From 30 1 of urine were isolated 0.75 gm. of p-cresol, and 3 ketonic compounds which have not hitherto been recognized as urinary constituents. The chief of these, of which 0.4 gm. was isolated, has been shown by analysis and by its artificial preparation by dehydration of de-hydroandrosterone to be [DELTA]3:5-androstadiene-17-one. This ketone had weak comb-growth promoting activity in capons, but had no oestrogenic activity or cortical hormone activity. The other 2 compounds were isolated only in amounts insufficient for adequate characterization but analysis of their derivatives suggests that they are represented by the formulae C19H28O3 and C21H32O3. Neither of these had appreciable oestrogenic activity.

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