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ALDOSTERONE

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ALDOSTERONE Basic information
Product Name:ALDOSTERONE
Synonyms:ELECTROCORTIN;11,21-Dihydroxy-3,20-dioxopregn-4-en-18-al;11beta,21-Dihydroxy-3,20-dioxo-pregn-4-en-18-al;18-Oxocorticosterone;21-dihydroxy-3,20-dioxo-1(11-beta)-pregn-4-en-18-a;21-dihydroxy-3,20-dioxo-1(11beta)-pregn-4-en-18-a;Aldocorten;Aldocortene
CAS:52-39-1
MF:C21H28O5
MW:360.45
EINECS:200-139-9
Product Categories:Steroid Hormones;A-AM;Aldehydes;Bioactive Small Molecules;Building Blocks;C13-C60;Carbonyl Compounds;Cell Biology;Cell Signaling and Neuroscience;Chemical Synthesis;Cytokines;Hormones;Organic Building Blocks;Isotope Labeled Compounds;Steroids;Intermediates & Fine Chemicals;Pharmaceuticals;TPI;Isolabel;Corticosteroid;Growth Factors and Hormones;Elisa Kit-Mouse Elisa Kit
Mol File:52-39-1.mol
ALDOSTERONE Structure
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)
Fp 2℃
storage temp. Sealed in dry,Room Temperature
solubility Acetone (Slightly), Chloroform (Slightly), DMSO (Slightly), Methanol (Slightly)
pka12.98±0.10(Predicted)
form Crystalline Powder
color White
Water Solubility 51.18mg/L(37 ºC)
Merck 13,224
BRN 3224996
CAS DataBase Reference52-39-1(CAS DataBase Reference)
EPA Substance Registry SystemAldosterone (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
22-24-25
HS Code 29372900
MSDS Information
ProviderLanguage
ACROS English
SigmaAldrich English
ALDOSTERONE Usage And Synthesis
DescriptionAldosterone 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 PropertiesWhite Solid
OriginatorAldosterone ,Sigma Chemical Company
UsesImatinib intermediate
UsesThe d-isomer of aldosterone is considered to be the biologically active isomer.
UsesA 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
UsesLabelled 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.
Useshypnotic, anastethic
DefinitionChEBI: 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.
Definitionaldosterone: 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 FunctionMineralocorticoid
Biological FunctionsAldosterone, 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 HazardAldosterone(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.
SynthesisAldosterone, 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 MethodsCrystallise 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.]
Tag:ALDOSTERONE(52-39-1) Related Product Information
D-ALDOSTERONE 21-ACETATE,ALDOSTERONE 21-ACETATE D-ALDOSTERONE 18,21-DIACETATE ALDOSTERONE 3-CMO : BSA ALDOSTERONE SECRETION INHIBITING FACTOR (1-35) (BOVINE) Aldosterone ELISA ALDOSTERONE, D-[1,2-3H(N)]-,[1,2-3H]ALDOSTERONE ANTI-ALDOSTERONE-3 ALDOSTERONE LABELING POSITION:3 ALDOSTERONE 3-CMO : HISTAMINE ALDOSTERONE SODIUM SULPHATE [1,2,6,7-3H]ALDOSTERONE,ALDOSTERONE, [1,2,6,7-3H]-,ALDOSTERONE, D [1,2,6,7-3H(N)] ALDOSTERONE 18,21-DIACETATE ALDOSTERONE GAMMA LACTONE Aldosterone, bis(O-trimethylsilyl-) D-ALDOSTERONE 21-HEMISUCCINATE*CRYSTALLINE ALDOSTERONE-3-BSA,RABBITANTI-:RIA ALDOSTERONE ANTI- KV FOR 3H MAb to Aldosterone Purified (1)