18-HYDROXY-11-DEOXYCORTICOSTERONE Chemical 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 Information

Safety Statements 

22-24/25

18-HYDROXY-11-DEOXYCORTICOSTERONE Usage And Synthesis

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.

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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