18-substituted steroids--9[1]. Studies on the stability of aldosterone in dilute alkali
Abstract:
In the presence of dilute alkali at room temperature aldosterone undergoes rearrangement to form an isomeric compound identified as 11 beta, 18;18,21-diepoxy-20,21-dihydroxypregn-4-en-3-one. The presence of dissolved oxygen causes simultaneous degradation to form 11 beta, 18-epoxy-18-hydroxy-3-oxo-17(beta H)-androst-4-ene-17 alpha-carboxylic acid. Under similar alkaline conditions at reflux temperature in aqueous methanol aldosterone undergoes rearrangement to form (20S)-20,21-dihydroxy-3-oxo-pregn-4-eno-18,11 beta-lactone accompanied by an intramolecular aldol type condensation to form 11 beta, 21-dihydroxy-18,21-cyclopregna-4,18(21)-diene-3,20-dione. Identical products were formed from 17-isoaldosterone. The mechanisms of these reactions are discussed.
Related Concept Videos
Hormones of the Adrenal Glands
The adrenal cortex, a powerhouse of hormone synthesis, generates over two dozen corticosteroid hormones. The zona glomerulosa produces mineralocorticoids, exemplified by aldosterone, influencing the electrolyte composition of body fluids. The synthesis of glucocorticoids such as cortisol and corticosterone...
Adrenal Gland Disorders
Adrenal insufficiency, characterized by insufficient cortisol and aldosterone production, leads to conditions like Addison's disease. This disorder, affecting the adrenal cortex, exhibits symptoms such as skin bronzing, dehydration, low blood pressure, fatigue, and weight loss. Congenital adrenal hyperplasia, a genetic ailment causing...
Antihypertensive Drugs: Potassium-Sparing Diuretics
Heart Failure Drugs: Inhibitors of Renin-Angiotensin System
Drug Product Stability
Pharmaceutical Alternatives: Stability-Related Therapeutic Nonequivalence


