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
Identifiers
CAS Number	152-58-9 Y
3D model (Jmol)	Interactive image
ChEBI	CHEBI:28324 N
ChEMBL	ChEMBL253144 N
ChemSpider	389582 Y
ECHA InfoCard	100.005.279
IUPHAR/BPS	5100
KEGG	D03595 N
PubChem	440707
UNII	WDT5SLP0HQ Y
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 N Key: WHBHBVVOGNECLV-OBQKJFGGSA-N 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	346.47 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).
N  (what is YN ?)
Infobox references

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

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. 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. This could explain, at least in part, the marked increase in androstenedione levels in 11β-hydroxylase deficiency.