Beta-Cortol

Base Information

• Chemical Name: Beta-Cortol
• CAS No.: 667-65-2
• Molecular Formula: C₂₁H₃₆O₅
• Molecular Weight: 368.514
• NSC Number: 58792
• UNII: K5O9P9J39F
• DSSTox Substance ID: DTXSID50289060
• Nikkaji Number: J7.083A
• Wikidata: Q27161442
• Metabolomics Workbench ID: 38772
• Mol file: 667-65-2.mol

Synonyms:Beta-Cortol;667-65-2;20beta-Cortol;beta-Cortol [MI];NSC-58792;b-cortol;UNII-K5O9P9J39F;K5O9P9J39F;(3R,5R,8S,9S,10S,11S,13S,14S,17R)-17-[(1R)-1,2-dihydroxyethyl]-10,13-dimethyl-1,2,3,4,5,6,7,8,9,11,12,14,15,16-tetradecahydrocyclopenta[a]phenanthrene-3,11,17-triol;Pregnane-3,11,17,20,21-pentol, (3alpha,5beta,11beta,20R)-;Pregnane-3,11,17,20,21-pentol, (3.alpha.,5.beta.,11.beta.,20R)-;Cortol-20beta;.BETA.-CORTOL;20.BETA.-CORTOL;.BETA.-CORTOL [MI];SCHEMBL14983098;CHEBI:89257;DTXSID50289060;NSC58792;AKOS040740723;MS-25921;HY-113418;CS-0059428;Pregnane-3alpha,11beta,17,20beta,21-pentol;3alpha,11beta,17,20beta,21-Pentahydroxypregnane;5beta-Pregnane-3alpha,11beta,17,20R,21-pentol;5beta-Pregnan-3alpha,11beta,20,20beta,21-pentol;Q27161442;5beta-Pregnane-3alpha,11beta,17alpha,20beta,21-pentol;(3alpha,5beta,11beta,20R) Pregnane-3,11,17,20,21-pentol;5beta-Pregnane-3alpha,11beta,17,20beta,21-pentol 20beta-Cortol;Pregnane-3,17,20,21-pentol, (3.alpha.,5.beta.,11.beta.,20R)-

Chemical Property of Beta-Cortol

Chemical Property:

• Vapor Pressure: 4.28E-15mmHg at 25°C
• Boiling Point: 564.5°C at 760 mmHg
• PKA: 14.06±0.70(Predicted)
• Flash Point: 255°C
• PSA: 101.15000
• Density: 1.252g/cm³
• LogP: 1.44510
• Storage Temp.: Hygroscopic, -20°C Freezer, Under inert atmosphere
• Solubility.: DMSO, Ethanol (Slightly), Methanol (Very Slightly), Pyridine (Slightly)
• XLogP3: 2.1
• Hydrogen Bond Donor Count: 5
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 2
• Exact Mass: 368.25627424
• Heavy Atom Count: 26
• Complexity: 555

Purity/Quality:

99% ^*data from raw suppliers

β-Cortol ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC12CCC(CC1CCC3C2C(CC4(C3CCC4(C(CO)O)O)C)O)O
• Isomeric SMILES: C[C@]12CC[C@H](C[C@H]1CC[C@@H]3[C@@H]2[C@H](C[C@]4([C@H]3CC[C@@]4([C@@H](CO)O)O)C)O)O
• Uses: β-Cortol is a metabolite of cortisol (H714615), a steroid hormone, more specifically a glucocorticoid, produced by the zona fasciculata of the adrenal gland. Cortisol is released in response to stress and a low level of blood glucocorticoids. Its primary functions are to increase blood sugar through gluconeogenesis; suppress the immune system; and aid in fat, protein and carbohydrate metabolism.

Technology Process of Beta-Cortol

There total 7 articles about Beta-Cortol 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:

→ β-cortol (667-65-2)

Guidance literature:

With acetic acid;

DOI:10.1021/ja01148a102

Reference yield:

21-acetoxy-3α,11β,17α-trihydroxy-5β-pregnan-20-one 3-tert-butyldimethylsilyl ether (83274-68-4) → β-cortol (667-65-2)

Guidance literature:

Multi-step reaction with 4 steps

1: NaBH₄ / ethanol; tetrahydrofuran / 0.5 h / Ambient temperature

2: pyridine

3: 180 mg / 50percent H₂SO₄ / acetone / 0.17 h / Ambient temperature

4: saponification

With sodium tetrahydroborate; sulfuric acid; In tetrahydrofuran; pyridine; ethanol; acetone;

DOI:10.1248/cpb.32.4023

Reference yield:

methyl 20α-acetoxy-3α-tert-butyldimethylsilyloxy-17α-hydroxy-11-oxo-5β-pregnan-21-oate (93206-76-9) → β-cortol (667-65-2)

Guidance literature:

Multi-step reaction with 4 steps

1: 18 mg / LiAlH₄ / diethyl ether / 1 h / Ambient temperature

2: pyridine

3: 180 mg / 50percent H₂SO₄ / acetone / 0.17 h / Ambient temperature

4: saponification

With lithium aluminium tetrahydride; sulfuric acid; In pyridine; diethyl ether; acetone;

DOI:10.1248/cpb.32.4023

upstream raw materials:

3α,20β_F,21-triacetoxy-17-hydroxy-5β-pregnan-11-one

20β-cortol 20,21-diacetate

21-acetoxy-3α,11β,17α-trihydroxy-5β-pregnan-20-one 3-tert-butyldimethylsilyl ether

methyl 20α-acetoxy-3α-tert-butyldimethylsilyloxy-17α-hydroxy-11-oxo-5β-pregnan-21-oate

Downstream raw materials:

11β-hydroxyetiocholanolone

Refernces