Deoxycorticosterone

Title: Deoxycorticosterone
CAS Registry Number: 64-85-7
CAS Name: 21-Hydroxypregn-4-ene-3,20-dione
Additional Names: 4-pregnen-21-ol-3,20-dione; 21-hydroxyprogesterone; desoxycorticosterone; 11-deoxycorticosterone; cortexone; desoxycortone; Kendall's desoxy compound B; Reichstein's substance Q
Molecular Formula: C21H30O3
Molecular Weight: 330.46
Percent Composition: C 76.33%, H 9.15%, O 14.52%
Literature References: Occurs in adrenal cortex: Reichstein, von Euw, Helv. Chim. Acta 21, 1197 (1938); Steiger, Reichstein, ibid. 20, 1164 (1937). Numerous prepns from other steroids: Schindler et al., ibid. 24, 371 (1941); Reichstein, DE 875353 (1953 to Schering); Bockmühl et al., DE 871153 (1953 to Hoechst); Wettstein et al., US 2778776 (1957 to Ciba); NL 89575 (1958 to Organon); Kaspar et al., DE 1028572 (1958 to Schering). Isoln from the prothoracal glands of the water beetle, Dytiscus marginalis: Schildknecht et al., Angew. Chem. 78, 392 (1966).
Properties: Plates from ether, mp 141-142°. [a]D22 +178° (alc). uv max: 240 nm. Freely sol in alcohol, acetone.
Melting point: mp 141-142°
Optical Rotation: [a]D22 +178° (alc)
Absorption maximum: uv max: 240 nm
Derivative Type: Acetate see Deoxycortiscosterone Acetate
Derivative Type: Tetraacetyl-b-D-glucoside
Molecular Formula: C35H48O12
Molecular Weight: 660.75
Percent Composition: C 63.62%, H 7.32%, O 29.06%
Properties: Clusters of needles from 50% alc, mp 176-176.5°. [a]D24 +80° (c = 0.515 in chloroform). Believed to occur in nature in this glycosidic form: Johnson, J. Am. Chem. Soc. 63, 3238 (1941).
Melting point: mp 176-176.5°
Optical Rotation: [a]D24 +80° (c = 0.515 in chloroform)
Therap-Cat: Mineralocorticoid.
Keywords: Mineralocorticoid.
Deoxycorticosterone Acetate Deoxydihydrostreptomycin Deoxyepinephrine Deoxyribonucleic Acid Depreotide

11-Deoxycorticosterone
11-Deoxycorticosterone.svg
Systematic (IUPAC) name
(1S,2R,10S,11S,14S,15S)-14-(2-hydroxyacetyl)-2,15-dimethyltetracyclo[8.7.0.02,7.011,15]heptadec-6-en-5-one
Clinical data
Legal status  ?
Identifiers
CAS number 64-85-7 YesY
56-47-3 (acetate ester)
ATC code H02AA03
PubChem CID 6166
ChemSpider 5932 YesY
UNII 40GP35YQ49 YesY
ChEBI CHEBI:16973 YesY
ChEMBL CHEMBL1498 YesY
Synonyms 11-Desoxycorticosterone; Deoxycorticosterone; 21-Hydroxyprogesterone; Cortexone; Deoxycortone; Desoxycortone; DOC
Chemical data
Formula C21H30O3 
Mol. mass 330.461 g/mol
 YesY (what is this?)  (verify)

11-Deoxycorticosterone (DOC), or simply deoxycorticosterone, also known as 21-hydroxyprogesterone, is a steroid hormone produced by the adrenal gland that possesses mineralocorticoid activity and acts as a precursor to aldosterone. It has no significant glucocorticoid activity.[1] As its names indicate, 11-deoxycorticosterone can be understood as the 21-hydroxy- variant of progesterone or as the 11-deoxy- variant of corticosterone.