ALDOSTERONE Chemical Properties

Melting point:

170-172°C

alpha 

D23 +152.2° (anhydr; c = 2 in acetone); D25 +161° (c = 0.1 in chloroform)

Boiling point:

412.46°C (rough estimate)

Density 

1.28

refractive index 

1.6120 (estimate)

Flash point:

2℃

storage temp. 

Sealed in dry,Room Temperature

solubility 

Acetone (Slightly), Chloroform (Slightly), DMSO (Slightly), Methanol (Slightly)

form 

Crystalline Powder

pka

12.98±0.10(Predicted)

color 

White

optical activity

+14523 (c 0.99, acetone)

Water Solubility 

51.18mg/L(37 ºC)

Merck 

13,224

BRN 

3224996

CAS DataBase Reference

52-39-1(CAS DataBase Reference)

EPA Substance Registry System

Aldosterone (52-39-1)

Safety Information

Hazard Codes 

Xi,Xn,F

Risk Statements 

36/37/38-36-20/21/22-11

Safety Statements 

22-24/25-36-26-36/37-16

RIDADR 

UN 1648 3 / PGII

WGK Germany 

3

RTECS 

TU4523000

F 

22-24-25

HS Code 

29372900

MSDS

• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS

ALDOSTERONE Usage And Synthesis

Description

Aldosterone is a mineralocorticosteroid that takes part in the regulation of electrolytic balance in the organism. Aldosterone lowers excretion of sodium ions from the body, thus increasing their reabsorption and increasing secretion of potassium ions in renal tubules. Being a competitive antagonist of aldosterone, spironlactone blocks aldosterone receptors, thus increasing excretion of sodium, chloride, and corresponding equivalents of water with urine, thus retaining the amount of potassium ions in the organism. Spironolactone is used both individually as well as in combination with thiazides, since it lowers kaliuresis caused by thiazide diuretics.

Chemical Properties

White Solid

Originator

Aldosterone ,Sigma Chemical Company

Uses

A labelled adrenocortical steroid which exerts regulatory influence on metabolism of electrolytes and water. Biologically active aldosterone isomer; a mineralocorticoid produced by the adrenal cortex that induces urinary excretion of K+ and renal re

Uses

The d-isomer of aldosterone is considered to be the biologically active isomer.

Uses

Labelled Aldosterone. Aldosterone is an adrenocortical steroid which exerts regulatory influence on metabolism of electrolytes and water. Biologically active aldosterone isomer; a mineralocorticoid pr oduced by the adrenal cortex that induces urinary excretion of K+ and renal reabsorptioon of Na+. Exists as an equilibrium mixture of the aldehyde and the hemiacetal.

Uses

Imatinib intermediate

Uses

hypnotic, anastethic

Definition

ChEBI: A pregnane-based steroidal hormone produced by the outer-section (zona glomerulosa) of the adrenal cortex in the adrenal gland, and acts on the distal tubules and collecting ducts of the kidney to cause the conservation of sodium, secretion of potassium, i creased water retention, and increased blood pressure. The overall effect of aldosterone is to increase reabsorption of ions and water in the kidney.

Definition

aldosterone: A hormone producedby the adrenal glands that controlsexcretion of sodium by the kidneysand thereby maintains the balance ofsalt and water in the body fluids.

Therapeutic Function

Mineralocorticoid

Biological Functions

Aldosterone, produced by the adrenal cortex, acts at epithelial cells in the distal tubule of the nephron to increase the reabsorption of sodium and is therefore considered an important hormone in the regulation of electrolyte balance. Aldosterone exerts its effects at the nephron through mineralocorticoid receptors, which translocate to the nucleus upon aldosterone binding and exert genomic effects leading to increased sodium reabsorption. In addition to the epithelial effects of aldosterone at mineralocorticoid receptors, nonepithelial cells, including cardiac muscle and vascular smooth muscle cells and cells in the brain, can respond to aldosterone and result in left ventricular hypertrophy, cardiac and vascular fibrosis, and stimulation of sympathetic nervous system activity.
Spironolactone (Aldactone), an antagonist of the aldosterone mineralocorticoid receptor, is used to treat primary aldosteronism, essential hypertension, and congestive heart failure. In the treatment of hypertension resulting from adrenal adenoma (primary aldosteronism) and in patients with essential hypertension, spironolactone lowers blood pressure primarily through blockade of epithelial mineralocorticoid receptors in the kidney, reductions in sodium and water reabsorption, and diuresis.The use of spironolactone in the treatment of essential hypertension is typically restricted to patients who do not respond appropriately to other agents and is often used in combination drug therapy. In large-scale clinical trials in patients with severe heart failure, administration of spironolactone markedly reduced morbidity and mortality without reducing blood pressure. Spironolactone is used to treat patients with moderate to severe heart failure who exhibit symptoms and ventricular dysfunction despite treatment with an ACE inhibitor or a diuretic.
Adverse effects of spironolactone therapy include hyperkalemia, gastrointestinal problems, gynecomastia (breast enlargement in males), and impotence. Gynecomastia and impotence arising from spironolactone treatment are results of significant blockade of the androgen and mineralocorticoid receptors.Novel selective mineralocorticoid receptor antagonists, such as eplerenone, are in clinical trials.

Health Hazard

Aldosterone(Aldocortin; electrocortin; mineralocorticoid; 18-oxocorticosterone): (1)Maintenance of normal electrolyte blood balances;(2)Prolongs survival of adrenalectomized animals;(3)Accelerates gluconeogenesis;(4)Regulates kidney function.

Synthesis

Aldosterone, 11|?,21-dihydroxypregn-4-en-2,18,20-trione (27.2.4), is synthesized from 21-O-acetylcorticosterone, which when reacted with nitrosyl chloride in pyridine gives the nitrite 27.2.1. When photochemically irradiated, this compound is transformed to the oxime 27.2.2, which is hydrolyzed by nitrous acid and forms the semiacetal 27.2.3, which is an acetate of the desired aldosterone. Alkaline hydrolysis of the acetyl group of this compound leads to the desired aldosterone (27.2.4) .

Purification Methods

Crystallise aldosterone from aqueous acetone. It exists in solution as an equilibrium mixture of free aldehyde and its cyclic hemiacetal, favouring the hemiacetal. The 21-acetate crystallises from Me2CO/Et2O or CH2Cl2/EtOAc and has m 198-199o, [] D +121.7o (c 0.7, CHCl3). [Barton et al. J Chem Soc Perkin Trans 1 2243 1975, Beilstein 8 IV 3491.]

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