Cortodoxone

Cortodoxone
IUPAC name (8R,9S,10R,13S,14S,17R)-17-hydroxy-17-(2-hydroxyacetyl)-10,13-dimethyl-2,6,7,8,9,11,12,14,15,16-decahydro-1H-cyclopenta[a]phenanthren-3-one
Other names 11-Deoxycortisol; Cortoxelone; 17,21-Dihydroxypregn-4-ene-3,20-dione; 11-Desoxycortisol; 11-Deoxyhydrocortisone; 11-Desoxyhydrocortisone; Reichstein's Substance S; Compound S
Identifiers
CAS number	152-58-9 Y
PubChem	440707
ChemSpider	389582 Y
UNII	WDT5SLP0HQ Y
KEGG	D03595 N
ChEBI	CHEBI:28324 N
ChEMBL	CHEMBL253144 N
Jmol-3D images	Image 1
SMILES O=C4\C=C2/[C@]([C@H]1CC[C@@]3([C@@](O)(C(=O)CO)CC[C@H]3[C@@H]1CC2)C)(C)CC4
InChI InChI=1S/C21H30O4/c1-19-8-5-14(23)11-13(19)3-4-15-16(19)6-9-20(2)17(15)7-10-21(20,25)18(24)12-22/h11,15-17,22,25H,3-10,12H2,1-2H3/t15-,16+,17+,19+,20+,21+/m1/s1 Y Key: WHBHBVVOGNECLV-OBQKJFGGSA-N Y InChI=1/C21H30O4/c1-19-8-5-14(23)11-13(19)3-4-15-16(19)6-9-20(2)17(15)7-10-21(20,25)18(24)12-22/h11,15-17,22,25H,3-10,12H2,1-2H3/t15-,16+,17+,19+,20+,21+/m1/s1 Key: WHBHBVVOGNECLV-OBQKJFGGBG
Properties
Molecular formula	C21H30O4
Molar mass	346.46 g mol−1
Melting point	215 °C
N (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

Cortodoxone, also known as cortexolone or 11-deoxycortisol, is a steroid that can be oxygenated to cortisol (hydrocortisone). It was first synthesized by Tadeusz Reichstein.

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 cortodoxone produces 11α-hydrocortisone, which can be chemically oxidized to cortisone, or converted by further chemical steps to cortisol.

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

Cortodoxone functions as a mineralocorticoid, though is less potent than cortisol. It can be synthesized from 17-hydroxyprogesterone. In 11-beta-hydroxylase deficiency, cortodoxone levels increase dramatically, causing hypertension (as opposed to 21-alpha-hydroxylase deficiency, in which patients have hypotension from a lack of mineralocorticoids).

References

1. ^ Peterson DH, Murray, HC (1952). "Microbiological oxygenation of steroids at carbon 11". J Am Chem Soc 74 (7): 1871–2. doi:10.1021/ja01127a531.