| Identification | Back Directory | [Name]
18-HYDROXY-11-DEOXYCORTICOSTERONE | [CAS]
379-68-0 | [Synonyms]
18-HYDROXY DOC
18-HYDROXYDEOXYCORTICOSTERONE
4-PREGNEN-18,21-DIOL-3,20-DIONE
4-PREGNENE-18,21-DIOL-3,20-DIONE
11-DEOXY-18-HYDROXYCORTICOSTERONE
18-HYDROXY-11-DEOXYCORTICOSTERONE
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
18-Hydroxy-21-hydroxypregna-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
(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
(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
(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 | [EINECS(EC#)]
206-834-3 | [Molecular Formula]
C21H30O4 | [MDL Number]
MFCD00010486 | [MOL File]
379-68-0.mol | [Molecular Weight]
346.46 |
| Chemical Properties | Back Directory | [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) |
| Hazard Information | Back Directory | [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. | [Definition]
ChEBI: 18-hydroxydeoxycorticosterone is a 21-hydroxy steroid, a 3-oxo-Delta(4) steroid, a 20-oxo steroid and a 18-hydroxy steroid. | [storage]
Store at -20°C | [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.] | [References]
[1] L M BRALEY G H W. The effect of angiotensin II and saralasin on 18-hydroxy-11-deoxycorticosterone production by isolated human adrenal glomerulosa cells.[J]. Journal of Clinical Endocrinology & Metabolism, 1979, 49 4: 600-603. DOI: 10.1210/jcem-49-4-600
[2] JOHN CARROLL James C M Pavel Komanicky. The relationship between plasma 18-hydroxy-11-deoxycorticosterone levels and production of hypertension in the rat[J]. Journal of steroid biochemistry, 1981, 14 10: Pages 989-995. DOI: 10.1016/0022-4731(81)90206-5
[3] MüLLER J. The conversion of 18-hydroxycorticosterone and 18-hydroxy-11-deoxycorticosterone to aldosterone by rat adrenal tissue: Evidence for an alternative biosynthetic pathway[J]. Journal of steroid biochemistry, 1980, 13 3: Pages 245-251. DOI: 10.1016/0022-4731(80)90001-1
[4] ANDRZEJ SLOMINSKI. Metabolism of progesterone to DOC, corticosterone and 18OHDOC in cultured human melanoma cells[J]. FEBS Letters, 1999, 455 3: 364-366. DOI: 10.1016/s0014-5793(99)00889-3
[5] PIETER GIESBERTZ. Metabolite profiling in plasma and tissues of ob/ob and db/db mice identifies novel markers of obesity and type 2 diabetes.[J]. Diabetologia, 2015, 58 9: 2133-2143. DOI: 10.1007/s00125-015-3656-y |
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