Letter | Published:

Oxidation of Cholesterol and Dehydroandrosterone by Means of Osmic Acid

Nature volume 140, page 466 (11 September 1937) | Download Citation



UNSATURATED compounds are known to add, under the action of osmic acid, two hydroxyl groups at the place of their double bond1, these groups being in cis-exposition with regard to each other. The reaction course is analogous to that produced by KMnO4. However, action of the latter on cholesterol2 yields but 4–5 per cent of cis-cholestan-triol. Thus KMnO4 is unsuitable for the oxidation of the double bond in sterol-derived hormones, in particular in dehydro-androsterone.

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  1. 1.

    Details in the recent paper by , Ann., 522, 75 (1936), where the literature is cited.

  2. 2.

    , Ber., 40, 257 (1907).

  3. 3.

    , and , “Dehydroandrosterone oxide”, in press in Journal Obshchei Chimii and Bull. Soc. Chim. de France.

  4. 4.

    Criegee (loc. cit.) mentions having obtained some cis-diols of the sterol group ; he does not give any details, nor mention what sterols he worked with.

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  1. Laboratory of Sterol and Hormone Chemistry, All-Union Institute of Experimental Medicine, Moscow.

    • M. USHAKOV
    •  & A. LUTENBERG


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