Letter | Published:

Oxidation of Cholesterol and Dehydroandrosterone by Means of Osmic Acid

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

Subjects

Abstract

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.

Access optionsAccess options

Rent or Buy article

Get time limited or full article access on ReadCube.

from$8.99

All prices are NET prices.

References

  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.

Download references

Author information

Affiliations

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

    • M. USHAKOV
    •  & A. LUTENBERG

Authors

  1. Search for M. USHAKOV in:

  2. Search for A. LUTENBERG in:

About this article

Publication history

Published

DOI

https://doi.org/10.1038/140466b0

Further reading

Comments

By submitting a comment you agree to abide by our Terms and Community Guidelines. If you find something abusive or that does not comply with our terms or guidelines please flag it as inappropriate.