Cortodoxone
| Cortodoxone | |
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(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 |
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Other names
11-Deoxycortisol; Cortoxelone; 17,21-Dihydroxypregn-4-ene-3,20-dione; 17,21-Dihydroxyprogesterone; 11-Desoxycortisol; 11-Deoxyhydrocortisone; 11-Desoxyhydrocortisone; Reichstein's Substance S; Compound S |
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| Identifiers | |
| CAS number | 152-58-9  |
| PubChem | 440707 |
| ChemSpider | 389582 |
| UNII | WDT5SLP0HQ |
| KEGG | D03595  |
| ChEBI | CHEBI:28324 |
| ChEMBL | CHEMBL253144 |
| Jmol-3D images | Image 1 |
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| Properties | |
| Molecular formula | C21H30O4 |
| Molar mass | 346.46 g mol−1 |
| Melting point |
215 °C |
 (verify) (what is:  / ?)Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) |
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| 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 glucocorticoid, though is less potent than cortisol. It can be synthesized from 17-hydroxyprogesterone. In 11β-hydroxylase deficiency, cortodoxone levels increase dramatically, causing hypertension (as opposed to 21α-hydroxylase deficiency, in which patients have hypotension from a lack of mineralocorticoids).
Cortodoxone can also be converted to androstenedione.[2] This could explain, at least in part, the marked increase in androstenedione levels in 11β-hydroxylase deficiency.[2]
See also
↑Jump back a sectionReferences
- ^ Peterson DH, Murray, HC (1952). "Microbiological oxygenation of steroids at carbon 11". J Am Chem Soc 74 (7): 1871–2. doi:10.1021/ja01127a531.
- ^ a b Auzéby A, Bogdan A, Touitou Y (January 1991). "Evidence for a new biologic pathway of androstenedione synthesis from 11-deoxycortisol". Steroids 56 (1): 33–6. PMID 2028480.
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