Abstract
THE discovery that carbon atom C4 of the cholesterol molecule is the first point of attack by oxygen, leading to the formation of cis ”5:6-cholestene-3: 4-diol, suggested that this reactive primary oxidation product may play an important role in the metabolism of cholesterol and the sexual hormones. Experimental confirmation of this view was obtained by feeding experiments, which showed that the diol, as well as its intermediate dehydration product cholestenone, were converted into coprosterol by the animal organism1. We have now obtained by mild oxidation of the 3 monoacetate (or 3-benzoate) of the cis-diol what is probably the oxide of 4-ketochole-stenol 3-acetate (or 3-benzoate). These compounds yield on hydrolysis a highly reactive substance C27H42O2 (I) which possesses the typical grouping —C = COH—CO— of diosphenol (buchu-camphor) (II).
Similar content being viewed by others
Article PDF
References
Rosenheim and Webster, NATURE, 136, 474 (1935). Rosenheim and Starling, J. Chem. Soc., 377 (1937); cf. Schoenheimer, Rittenberg and Graff, J. Biol. Chem., 111, 185 (1935).
Walker and Read, J. Chem. Soc., 238 (1934).
Inhoffer, Ber., 69, 1702 (1936).
Butenandt and Schramm, Ber., 69, 2289 (1936).
Author information
Authors and Affiliations
Rights and permissions
About this article
Cite this article
ROSENHEIM, O., KING, H. Cholesterol and the Adrenal Cortical Hormone. Nature 139, 1015 (1937). https://doi.org/10.1038/1391015a0
Issue Date:
DOI: https://doi.org/10.1038/1391015a0
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.