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HomeProduct name listALDOSTERONE

ALDOSTERONE

Synonym(s):11β,21-Dihydroxy-3,20-dioxo-4-pregnen-18-al;11β,21-Dihydroxypregn-4-ene-3,18,20-trione;18-Aldocorticosterone;Aldosterone;Reichstein X

  • CAS NO.:52-39-1
  • Empirical Formula: C21H28O5
  • Molecular Weight: 360.45
  • MDL number: MFCD00051136
  • EINECS: 200-139-9
  • SAFETY DATA SHEET (SDS)
  • Update Date: 2024-12-18 14:15:30
ALDOSTERONE Structural

What is ALDOSTERONE?

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

The Uses of ALDOSTERONE

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

The Uses of ALDOSTERONE

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

The Uses of ALDOSTERONE

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.

The Uses of ALDOSTERONE

hypnotic, anastethic

The Uses of ALDOSTERONE

Imatinib intermediate

What are the applications of Application

Aldosterone is a MCR (mineralocorticoid receptor)

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) .

Synthesis_52-39-1

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.]

Properties of ALDOSTERONE

Melting point: 170-172°C
Boiling point: 412.46°C (rough estimate)
alpha  D23 +152.2° (anhydr; c = 2 in acetone); D25 +161° (c = 0.1 in chloroform)
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)
pka 12.98±0.10(Predicted)
form  Crystalline Powder
color  White
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 for ALDOSTERONE

Signal word Danger
Pictogram(s)
ghs
Flame
Flammables
GHS02
ghs
Exclamation Mark
Irritant
GHS07
GHS Hazard Statements H225:Flammable liquids
H319:Serious eye damage/eye irritation
Precautionary Statement Codes P210:Keep away from heat/sparks/open flames/hot surfaces. — No smoking.
P280:Wear protective gloves/protective clothing/eye protection/face protection.
P305+P351+P338:IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

Computed Descriptors for ALDOSTERONE

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