11-Deoxycortisol

11-Deoxycortisol
Names
	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; 11-Deoxycortisone; Cortoxelone; 17α,21-Dihydroxypregn-4-ene-3,20-dione; 17α,21-Dihydroxyprogesterone; 11-Desoxycortisol; 11-Deoxyhydrocortisone; 11-Desoxyhydrocortisone; 17α-Hydroxy-11-deoxycorticosterone; Reichstein's Substance S; Compound S; Cortodoxone; Cortexolone,
Identifiers
CAS Number	152-58-9 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:28324 ;
ChEMBL	ChEMBL253144 ;
ChemSpider	389582 ;
ECHA InfoCard	100.005.279
IUPHAR/BPS	5100;
KEGG	D03595 ;
PubChem CID	440707;
UNII	WDT5SLP0HQ ;
CompTox Dashboard (EPA)	DTXSID8045642 ;
	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 Key: WHBHBVVOGNECLV-OBQKJFGGSA-N ; 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;
	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;
Properties
Chemical formula	C21H30O4
Molar mass	346.467 g·mol−1
Melting point	215 °C (419 °F; 488 K)
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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	Infobox references

11-Deoxycortisol, also known as cortodoxone (INN) or cortexolone, as well as 17α,21-dihydroxyprogesterone or 17α,21-dihydroxypregn-4-ene-3,20-dione,[1] is a glucocorticoid steroid hormone. It was first synthesized by Tadeusz Reichstein, and has also been referred to as Reichstein's Substance.[1]

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.[2] 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).

11-Deoxycortisol acts as a glucocorticoid, though is less potent than cortisol. It can be synthesized from 17α-hydroxyprogesterone. In 11β-hydroxylase deficiency, 11-deoxycortisol levels increase dramatically, causing hypertension (as opposed to 21-hydroxylase deficiency, in which patients have low blood pressure from a lack of mineralocorticoids).

11-Deoxycortisol can also be converted to androstenedione.[3] This could explain, at least in part, the marked increase in androstenedione levels in 11β-hydroxylase deficiency.[3]

References

R.A. Hill; H.L.J. Makin; D.N. Kirk; G.M. Murphy (23 May 1991). Dictionary of Steroids. CRC Press. pp. 338–. ISBN 978-0-412-27060-4.
Peterson DH; Murray, HC (1952). "Microbiological oxygenation of steroids at carbon 11". J Am Chem Soc. 74 (7): 1871–2. doi:10.1021/ja01127a531.
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. doi:10.1016/0039-128X(91)90112-9. PMID 2028480.

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[HillMakin1991-1] R.A. Hill; H.L.J. Makin; D.N. Kirk; G.M. Murphy (23 May 1991). Dictionary of Steroids. CRC Press. pp. 338–. ISBN 978-0-412-27060-4.

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

[pmid2028480-3] 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. doi:10.1016/0039-128X(91)90112-9. PMID 2028480.

11-Deoxycortisol

See also

References