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Cortexolone

Cortexolone

IUPAC name	(8R,9S,10R,13S,14S,17R)-17-hydroxy-17-(2-hydroxy-1-oxoethyl)-10,13-dimethyl-2,6,7,8,9,11,12,14,15,16-decahydro-1H-cyclopenta[a]phenanthren-3-one
Identifiers
CAS number	152-58-9
PubChem	440707
SMILES	CC12CCC(=O)C=C1CCC3C2CCC4(C3CCC4(C(=O)CO)O)C
Properties
Molecular formula	C₂₁H₃₀O₄
Molar mass	346.4605
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) Infobox disclaimer and references

Cortexolone or cortodoxone or 11-deoxycortisol or 11-desoxycortisol or 11-deoxyhydrocortisone or 11-desoxyhydrocortisone or Reichstein's Substance S or, most commonly, Compound S, is a steroid that can be oxygenated to cortisol (hydrocortisone). It was first synthesized by Tadeusz Reichstein.

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On April 5, 1952, biochemist Durey Peterson and microbiologist Herbert Murray at Upjohn published the first report of a breakthrough fermentation process for the microbial 11α-oxygenation of steroids (e.g. progesterone) in a single step by common molds of the order Mucorales.^[1] 11α-oxygenation of Compound S produces 11α-hydrocortisone, which can be chemically oxidized to cortisone, or converted by further chemical steps to 11β-hydrocortisone (cortisol).

Subsequent fermentation processes for the microbial 11β-oxygenation of steroids in a single step were developed that could convert Compound S directly to 11β-hydrocortisone (cortisol).