18-HYDROXY-11-DEOXYCORTICOSTERONE

18-HYDROXY-11-DEOXYCORTICOSTERONE Structure
CAS No.
379-68-0
Chemical Name:
18-HYDROXY-11-DEOXYCORTICOSTERONE
Synonyms
18-HYDROXY DOC;18-HYDROXYDEOXYCORTICOSTERONE;4-PREGNEN-18,21-DIOL-3,20-DIONE;4-PREGNENE-18,21-DIOL-3,20-DIONE;18-HYDROXY-11-DEOXYCORTICOSTERONE;11-DEOXY-18-HYDROXYCORTICOSTERONE;18,21-dihydroxypregn-4-ene-3,20-dione;18,21-DIHYDROXY-4-PREGNENE-3,20-DIONE;Pregn-4-ene-3,20-dione, 18,21-dihydroxy-;18,20-EPOXY-20,21-DIHYDROXY-4-PREGNEN-3-ONE
CBNumber:
CB0164085
Molecular Formula:
C21H30O4
Molecular Weight:
346.46
MOL File:
379-68-0.mol
Modify Date:
2023/5/25 18:00:55

18-HYDROXY-11-DEOXYCORTICOSTERONE Properties

Melting point 171-173 °C
storage temp. 2-8°C
solubility Chloroform (Slightly, Sonicated), Methanol (Slightly, Heated)
form Solid
color White to Off-White
LogP 1.571 (est)

SAFETY

Risk and Safety Statements

Safety Statements  22-24/25

18-HYDROXY-11-DEOXYCORTICOSTERONE Chemical Properties,Uses,Production

Description

18-hydroxy-11-deoxy Corticosterone (18-OH-DOC) is a mineralocorticoid secreted by the zona fasciculata of the adrenal gland. Its biosynthesis is regulated by adrenocorticotropic hormone (ACTH; ) as well as angiotensin II , which increases 18-OH-DOC production in isolated human adrenal glomerulosa cells. 18-OH-DOC can be formed via conversion of 11-deoxy corticosterone (DOC; ) in human SK-MEL188 melanoma cells. 18-OH-DOC is an intermediate in the metabolism of progesterone and can be converted to aldosterone by the capsular portion of rat adrenal glands. Continuous infusion of 18-OH-DOC (200 μg/rat per day) increases systolic blood pressure in uninephrectomized saline-drinking rats. Plasma levels of 18-OH-DOC are elevated in a db/db mouse model of type 2 diabetes.

Uses

11-Deoxy-18-hydroxycorticosterone is an analog of Corticosterone (C695700); a glucocorticoid and intermediate in the biosynthesis of Aldosterone (A514700) which is an adrenocortical steroid isolated from the adrenal cortex.

Purification Methods

Recrystallise 18-hydroxy-11-deoxycorticosterone from Et2O/Me2CO to give crystals m 200-205o. When it is recrystallised from M2CO, it has m 191-195o. It has UV with max at 240nm. The 21-O-acetoxy-18-hydroxy derivative has m 158-159o (from Et2O/*C6H6), and the 21-O-acetoxy-18,20-epoxy derivative has m 149-154o (from Et2O). [Kahnt et al. Helv Chim Acta 38 1237 1955; Pappo J Am Chem Soc 81 1010 1959.]

18-HYDROXY-11-DEOXYCORTICOSTERONE Preparation Products And Raw materials

Raw materials

Preparation Products

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(8R,9S,10R,13R,14S,17S)-17-(2-hydroxyethanoyl)-13-(hydroxymethyl)-10-methyl-1,2,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-3-one (8R,9S,10R,13R,14S,17S)-17-glycoloyl-10-methyl-13-methylol-1,2,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-3-one 11-DEOXY-18-HYDROXYCORTICOSTERONE 18-HYDROXY-11-DEOXYCORTICOSTERONE 18-HYDROXYDEOXYCORTICOSTERONE 18-HYDROXY DOC 18,20-EPOXY-20,21-DIHYDROXY-4-PREGNEN-3-ONE 18,21-DIHYDROXY-4-PREGNENE-3,20-DIONE 4-PREGNENE-18,21-DIOL-3,20-DIONE 4-PREGNEN-18,21-DIOL-3,20-DIONE 18,21-dihydroxypregn-4-ene-3,20-dione 11-Deoxy-18-hydroxycorticosterone, 18,20-Epoxy-20,21-dihydroxy-4-pregnen-3-one, 18,21-Dihydroxy-4-pregnene-3,20-dione 18-Hydroxy-21-hydroxypregna-4-ene-3,20-dione (8R,9S,10R,13R,14S,17S)-17-(2-hydroxyacetyl)-13-(hydroxymethyl)-10-methyl-1,2,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-3-one Pregn-4-ene-3,20-dione, 18,21-dihydroxy- 379-68-0