20alpha-Dihydrocortisol

Base Information

• Chemical Name: 20alpha-Dihydrocortisol
• CAS No.: 1719-79-5
• Molecular Formula: C₂₁H₃₂O₅
• Molecular Weight: 364.482
• NSC Number: 82878
• Nikkaji Number: J658.564G
• Metabolomics Workbench ID: 200425
• ChEMBL ID: CHEMBL488842
• Mol file: 1719-79-5.mol

Synonyms:20alpha-Dihydrocortisol;1719-79-5;NSC-82878;(8S,9S,10R,11S,13S,14S,17R)-17-[(1S)-1,2-dihydroxyethyl]-11,17-dihydroxy-10,13-dimethyl-2,6,7,8,9,11,12,14,15,16-decahydro-1H-cyclopenta[a]phenanthren-3-one;20-alpha-Dihydrocortisol;MLS002694142;20alpha-hydroxycortisol;CHEMBL488842;SCHEMBL2903879;NSC82878

Chemical Property of 20alpha-Dihydrocortisol

Chemical Property:

• Vapor Pressure: 3.34E-16mmHg at 25°C
• Boiling Point: 586.6ºC at 760 mmHg
• Flash Point: 322.6 ºC
• PSA: 94.83000
• Density: 1.29 g/cm³
• LogP: 1.86150
• XLogP3: 0.8
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 2
• Exact Mass: 364.22497412
• Heavy Atom Count: 26
• Complexity: 644

Purity/Quality:

99%min ^*data from raw suppliers

20-ALPHA-DIHYDROCORTISOL 98.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC12CCC(=O)C=C1CCC3C2C(CC4(C3CCC4(C(CO)O)O)C)O
• Isomeric SMILES: C[C@]12CCC(=O)C=C1CC[C@@H]3[C@@H]2[C@H](C[C@]4([C@H]3CC[C@@]4([C@H](CO)O)O)C)O
• Uses: 20α-Dihydrocortisol is a metabolite of Cortisol (H714615) which is a topical corticosteroid (1), more specifically a glucocorticoid, produced by the zona fasciculata of the adrenal gland (2). Cortisol is released in response to stress and a low level of blood glucocorticoids. Its primary functions are to increase blood sugar through gluconeogenesis (3); suppress the immune system; and aid in fat, protein and carbohydrate metabolism.

Technology Process of 20alpha-Dihydrocortisol

There total 10 articles about 20alpha-Dihydrocortisol 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: 50.0%

HYDROCORTISONE (50-23-7) → 11β,17α,20β,21-tetrahydroxypregn-4-en-3-one (1719-79-5) + 11β,17α,20R,21-tetrahydroxypregn-4-en-3-one (116-58-5)

Guidance literature:

With sodium tetrahydroborate; calcium chloride; In water; ethyl acetate; at -27 ℃; for 2h;

DOI:10.1016/0039-128X(83)90125-3

Reference yield:

→ 11β,17,20β,21-Tetrahydroxy-pregn-4-en-3-on (116-58-5,1719-79-5,1921-46-6,2899-95-8)

Guidance literature:

17α,20α,21-Trihydroxypregn-4-en-3-on, Einw. v. Pellicularia; (Nebenprod.: 17α,19,20α,21-tetrahydroxypregn-4-en-3-on);

Reference yield:

→ 11β,17,20α,21-Tetrahydroxy-pregn-4-en-3-on (116-58-5,1719-79-5,1921-46-6,2899-95-8)

Guidance literature:

Hydrocortison, Actinomyces albus 3006;

upstream raw materials:

20α-dihydrocortisol 21-acetate

HYDROCORTISONE

21-acetoxy-11β-hydroxy-pregna-4,17(20)c-dien-3-one

Refernces

• 1、 Han,Monder. "Asymmetric reduction of steroidal 20-ketones: Chemical synthesis of corticosteroid derivatives containing the 20α, 21-diol and 17α, 20α, 21-triol side chains". . p. 619 - 626. Retrieved 2007/10/02.