379-68-0 Usage
Description
18-Hydroxy-11-deoxycorticosterone (18-OH-DOC) is a mineralocorticoid hormone secreted by the zona fasciculata of the adrenal gland. It plays a crucial role in the regulation of electrolyte balance and blood pressure. Its biosynthesis is regulated by adrenocorticotropic hormone (ACTH) and angiotensin II, which increases 18-OH-DOC production in isolated human adrenal glomerulosa 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. It is also an analog of corticosterone, a glucocorticoid involved in the body's stress response and immune system regulation.
Uses
Used in Pharmaceutical Industry:
18-Hydroxy-11-deoxycorticosterone is used as a pharmaceutical intermediate for the synthesis of other adrenocortical steroids, such as aldosterone, which is essential for maintaining electrolyte balance and blood pressure. Its role in the regulation of these physiological processes makes it a valuable compound for the development of medications targeting adrenal gland-related disorders.
Used in Medical Research:
18-OH-DOC is used as a research tool in the study of adrenal gland function, mineralocorticoid action, and the pathophysiology of various diseases, including type 2 diabetes. Elevated plasma levels of 18-OH-DOC in a db/db mouse model of type 2 diabetes highlight its potential as a biomarker or therapeutic target for further investigation.
Used in Endocrinology:
As a mineralocorticoid, 18-Hydroxy-11-deoxycorticosterone is involved in the regulation of electrolyte balance and blood pressure. It is used in endocrinology to study the role of the adrenal gland in these processes and to understand the underlying mechanisms of related disorders, such as hypertension and electrolyte imbalances.
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.]
Check Digit Verification of cas no
The CAS Registry Mumber 379-68-0 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 3,7 and 9 respectively; the second part has 2 digits, 6 and 8 respectively.
Calculate Digit Verification of CAS Registry Number 379-68:
(5*3)+(4*7)+(3*9)+(2*6)+(1*8)=90
90 % 10 = 0
So 379-68-0 is a valid CAS Registry Number.
InChI:InChI=1/C21H30O4/c1-20-8-6-14(24)10-13(20)2-3-15-16(20)7-9-21(12-23)17(15)4-5-18(21)19(25)11-22/h10,15-18,22-23H,2-9,11-12H2,1H3/t15-,16+,17+,18-,20+,21-/m1/s1
379-68-0Relevant articles and documents
Inhibition of aldosterone formation by cortisol in rat adrenal mitochondria
Matkovic, Laura,Gomez-Sanchez, Celso E.,Lantos, Carlos P.,Cozza, Eduardo N.
, p. 447 - 452 (1995)
In this work we confirm by a metabolic method the existence of at least two enzymes with 11β- and 18-hydroxylase activities in rat adrenal mitochondria.The method was based on the ability of cortisol (F), a foreign alternative substrate, to inhibit competitively metabolite productions from various precursors.F inhibited a) aldosterone (ALDO) production from 11-deoxycorticosterone (DOC) without affecting the yields of corticosterone (B) and 18-hydroxy-11-deoxycorticosterone (18-OHDOC); b) 18-hydroxycorticosterone and aldosterone productions from B (Ki = 2.5 +/- 0.5 μM); and c) ALDO production from 18-OHDOC.These results suggest the existence of two categories of enzymes with both 11β- and 18-hydroxylase activities, one comprising those that catalyze the conversions of DOC to B and 18-OHDOC (F-insensitive reactions ) and the other one comprising the enzymes involved in the conversions of B to 18-OHB and ALDO and that of 18-OHDOC to ALDO (F-sensitive reactions ).The cloned enzymes CYP11B1 and CYP11B2 would pertain respectively to the FIS and FS categories. - Keywords: aldosterone; adrenal; cytochrome P450; 11β,18-hydroxylases; steroidogenesis; Cortisol
