Aldosterone

Base Information

• Chemical Name: Aldosterone
• CAS No.: 52-39-1
• Deprecated CAS: 10328-70-8,152-04-5,6251-69-0,47468-70-2,152-04-5
• Molecular Formula: C21H28O5
• Molecular Weight: 360.45
• Hs Code.: 29372900
• European Community (EC) Number: 200-139-9
• NSC Number: 73856
• UNII: 4964P6T9RB
• DSSTox Substance ID: DTXSID7022419
• Nikkaji Number: J4.130K
• Wikipedia: Aldosterone
• Wikidata: Q184564
• NCI Thesaurus Code: C219
• Pharos Ligand ID: 149UAM38VYZ3
• Metabolomics Workbench ID: 35389
• ChEMBL ID: CHEMBL273453
• Mol file: 52-39-1.mol

Synonyms:Aldosterone;Aldosterone, (+-)-Isomer;Aldosterone, (11 beta,17 alpha)-Isomer

Chemical Property of Aldosterone

Chemical Property:

• Appearance/Colour: white solid
• Vapor Pressure: 6.23E-16mmHg at 25°C
• Melting Point: 170-172 °C
• Refractive Index: 1.604
• Boiling Point: 568.1 °C at 760 mmHg
• PKA: 12.98±0.10(Predicted)
• Flash Point: 311.4 °C
• PSA: 91.67000
• Density: 1.28 g/cm³
• LogP: 1.84570
• Storage Temp.: 2-8°C
• Solubility.: Acetone (Slightly), Chloroform (Slightly), DMSO (Slightly), Methanol (Slightly)
• Water Solubility.: 51.18mg/L(37 oC)
• XLogP3: 1.1
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 3
• Exact Mass: 360.19367399
• Heavy Atom Count: 26
• Complexity: 682

Purity/Quality:

99% ^*data from raw suppliers

Aldosterone ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi,Xn,F
• Statements: 36/37/38-36-20/21/22-11
• Safety Statements: 22-24/25-36-26-36/37-16

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC12CCC(=O)C=C1CCC3C2C(CC4(C3CCC4C(=O)CO)C=O)O
• Isomeric SMILES: C[C@]12CCC(=O)C=C1CC[C@@H]3[C@@H]2[C@H](C[C@]4([C@H]3CC[C@@H]4C(=O)CO)C=O)O
• Recent ClinicalTrials: Studies on Aldosterone and Vascular Function
• Recent NIPH Clinical Trials: Transvenous RFA for primary aldosteronism
• 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.
• 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 The d-isomer of aldosterone is considered to be the biologically active isomer. 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. hypnotic, anastethic
• 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.

Technology Process of Aldosterone

There total 20 articles about Aldosterone which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

Pregnenolone (145-13-1) → Corticosterone (50-22-6) + aldosterone (52-39-1,47468-70-2) + 18,21-dihydroxy-4-pregnen-3,20-dione (10385-97-4)

Guidance literature:

With air; dibutyric cyclic AMP; NaHCO₃ buffer; normal male Sprague-Dawley rat adrenal glands after feeding for 72 h with 1 percent NaCl; at 37 ℃; for 3h; Product distribution; tritium labeled study;

DOI:10.1016/0039-128X(80)90082-3

Reference yield:

C21H30O2*C42H70O35 (117824-25-6) → 11-alpha-hydroxyprogesterone (80-75-1,22847-91-2) + 20-hydroxy-pregnan-18-oic acid (56143-33-0) + aldosterone (52-39-1,47468-70-2)

Guidance literature:

With potassium dihydrogenphosphate; magnesium sulfate heptahydrate; L-asparagine; D-glucose; In ethanol; water; at 30 ℃; for 72h; pH=5.5; Time; Concentration; Overall yield = 62.95 %Chromat.; Microbiological reaction;

DOI:10.3109/10242422.2014.894983

Reference yield:

Progesterone (57-83-0) → 11-alpha-hydroxyprogesterone (80-75-1,22847-91-2) + 20-hydroxy-pregnan-18-oic acid (56143-33-0) + aldosterone (52-39-1,47468-70-2)

Guidance literature:

With potassium dihydrogenphosphate; magnesium sulfate heptahydrate; L-asparagine; D-glucose; β‐cyclodextrin; In ethanol; water; at 30 ℃; for 48h; pH=5.5; Solvent; Reagent/catalyst; Time; Concentration; Overall yield = 87.15 %Chromat.; Microbiological reaction;

DOI:10.3109/10242422.2014.894983

upstream raw materials:

3,3;20,20-bis-ethanediyldioxy-11β,21-dihydroxy-pregn-5-en-18-al

Pregnenolone

aldosterone 21-acetate

11β,21-dihydroxy-3,20-dioxo-pregn-4-en-18-oic acid-11-lactone

Downstream raw materials:

11β,21-dihydroxy-3,20-dioxo-pregna-1,4-dien-18-al

rac-21-acetoxy-11β-hydroxy-3,20-dioxo-17βH-pregn-4-en-18-al

Aldosterone 18,21-diacetate

Refernces

• 1、 Dale,Holbrook,Melby. "Identification of 19-hydroxydeoxycorticosterone in regenerating rat adrenal incubations". . p. 601 - 609. Retrieved 2007/10/02.
• 2、 -. "Selenium-75 steroids". . . Retrieved 2008/06/13.