Abstract
Two substances have been isolated from the urine of men which resemble the male hormone in their ability to stimulate the growth of the capon's comb1. One of these, androsterone, described in detail by Butenandt and Tscherning2, has -been produced artificially by Ruzicka and his collaborators3 by means of the oxidative decomposition of epi-dihydro-Cholesterol acetate, and has thereby been recognised as 3-epi-oxy-allo-aetio-cholanone-(17). A second oxyketone containing two hydrogen atoms less has been obtained by Butenandt and Dannenbaum4 from an unsaturated chloroketone, C19H27OC1, occurring in extracts of urine, by replacement of the chlorine atom by a hydroxyl group. On carrying out the analogous replacement reaction using the saturated chloroketone, androsterone was obtained. These reactions leave the question unanswered as to the position of the double bond and the steric position of the hydroxyl group.
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References
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Helv. Chim. Acta, 17, 1389; 1934.
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OPPENAUER, R. Synthesis of Dehydroandrosterone by the Decomposition of -Sitosterol from Soya Beans. Nature 135, 1039 (1935). https://doi.org/10.1038/1351039a0
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DOI: https://doi.org/10.1038/1351039a0
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