ChemicalBook CAS DataBase List 64-85-7

64-85-7

Name	Desoxycorticosterone
CAS	64-85-7
EINECS(EC#)	200-596-4
Molecular Formula	C21H30O3
MDL Number	MFCD00003661
Molecular Weight	330.46
MOL File	64-85-7.mol

Synonyms

11-DEOXYCORTICOSTERONE 11-DESOXYCORTICOSTERONE 21-HYDROXY-4-PREGNENE-3,20-DIONE 21-hydroxypregn-4-ene-3,20-dione 21-HYDROXYPROGESTERONE 4-PREGNEN-21-OL-3,20-DIONE 4-PREGNENE-21-OL-3,20-DIONE CORTEXONE DELTA4-PREGNEN-21-OL-3,20-DIONE DEOXYCORTICOSTERONE DESOXYCORTICOSTERONE DESOXYCORTONE DOC HYDROXYPROGESTERONE, 21- KENDALL'S DESOXY COMPOUND B 'REICHSTEIN Q' REICHSTEIN'S COMPOUND ''Q'' REICHSTEIN'S SUBSTANCE Q (8S,10R,13S,17S)-17-(2-Hydroxy-acetyl)-10,13-dimethyl-1,2,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-cyclopenta[a]phenanthren-3-one 11-Dehydroxycorticosterone

Chemical Properties

Appearance	white to creamy-white crystalline powder
Melting point	138-144 °C
alpha	184 º (c=1, C2H5OH)
Boiling point	407.89°C (rough estimate)
density	1.0998 (rough estimate)
refractive index	1.5192 (estimate)
Fp	9℃
storage temp.	-20°C
solubility	Chloroform (Slightly), Methanol (Slightly)
form	Solid
pka	12.98±0.10(Predicted)
color	White to Pale Yellow
Optical Rotation	+17822 (c 1.5, ethanol)
Water Solubility	slightly soluble
Merck	13,2917
BRN	2062123
InChI	1S/C21H30O3/c1-20-9-7-14(23)11-13(20)3-4-15-16-5-6-18(19(24)12-22)21(16,2)10-8-17(15)20/h11,15-18,22H,3-10,12H2,1-2H3/t15-,16-,17-,18+,20-,21-/m0/s1
InChIKey	ZESRJSPZRDMNHY-YFWFAHHUSA-N
SMILES	[H][C@@]12CCC3=CC(=O)CC[C@]3(C)[C@@]1([H])CC[C@]4(C)[C@H](CC[C@@]24[H])C(=O)CO
LogP	2.880
CAS DataBase Reference	64-85-7(CAS DataBase Reference)
NIST Chemistry Reference	Deoxycorticosterone(64-85-7)
EPA Substance Registry System	64-85-7(EPA Substance)

Safety Data

Symbol(GHS)	GHS08
Signal word	Warning
Hazard statements	H351-H373
Precautionary statements	P201-P308+P313
Hazard Codes	Xn
Risk Statements	R40:Limited evidence of a carcinogenic effect. R48:Danger of serious damage to health by prolonged exposure. less more
Safety Statements	S22:Do not breathe dust . S24/25:Avoid contact with skin and eyes . less more
RIDADR	UN 2811 6.1/PG 2
WGK Germany	3
RTECS	HG0350000
Storage Class	11 - Combustible Solids
Hazard Classifications	Carc. 2 STOT RE 2

Hazard Information

Hazard

Toxic.

Chemical Properties

white to creamy-white crystalline powder

Uses

A mineralocorticoid that occurs in adrenal cortex. It acts as a precursor to Aldosterone (A514700).

Uses

Antiinflammatory;Corticoide

Definition

ChEBI: A mineralocorticoid that is progesterone substituted at position 21 by a hydroxy group.

General Description

11-Deoxycorticosterone is a steroid hormone produced in the adrenal glands that acts as a precursor for the hormone aldosterone. Levels of 11-deoxycorticosterone are measured by LC-MS/MS to aid in diagnosing disorders of steroid synthesis, such as 11-hydroxylase deficiency and glucocorticoid responsive hyperaldosteronism. This Certified Spiking Solution^? is suitable for use as starting material inlinearity standards, calibrators, and controls for numerous LC-MS/MS applications in endocrinology, clinical chemistry, and neonatal screening.

Mechanism of action

Desoxycorticosterone causes an increase in reabsorption of sodium ions and excretion of potassium ions from the renal tubules, which leads to increased tissue hydrophilicity. This facilitates an elevated volume of plasma and increased arterial pressure. Muscle tonicity and work capability are increased. It is used for an insufficiency of function of the adrenal cortex, myasthenia, asthenia, adynamia, and overall muscle weakness.

Synthesis

Desoxycorticosterone, 21-hydroxypregn-4-en-3,20-dione acetate (27.2.6), is synthesized in a number of ways, the easiest of which being iodination of progesterone at C21 in the methyl group, and subsequent reaction of the resulting iodo-derivative 27.2.5 with potassium acetate, which leads to formation of the desired desoxycorticosterone in the form of the acetate (27.2.6) .

Synthesis_64-85-7

Purification Methods

Crystallise 11-deoxycorticosterone from diethyl ether. [Schindler et al. Helv Chim Acta 24 360 1941, Steiger & Reichstein Helv Chim Acta 20 1164 1937.]

Material Safety Data Sheet(MSDS)

Spectrum Detail

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