4-Pregnene-11beta,17alpha,20beta,21-tetrol-3-one

Base Information

• Chemical Name: 4-Pregnene-11beta,17alpha,20beta,21-tetrol-3-one
• CAS No.: 116-58-5
• Molecular Formula: C21H32 O5
• Molecular Weight: 364.482
• UNII: 77U6C4OLOR
• DSSTox Substance ID: DTXSID40871599
• Metabolomics Workbench ID: 200424
• Nikkaji Number: J5.522K
• Wikidata: Q27266607
• Mol file: 116-58-5.mol

Synonyms:11 beta,17,20 beta,21-tetrahydroxypregn-4-en-3-one;11 beta,17,20,21-tetrahydroxypregn-4-en-3-one;20 alpha-dihydrocortisol;20 beta-dihydrocortisol;20-hydroxycortisol;20-hydroxycortisol, (11beta,20R)-isomer;20-hydroxycortisol, (11beta,20S)-isomer;20-hydroxycortisol, (3beta,11beta)-isomer;Reichstein's substance E

Chemical Property of 4-Pregnene-11beta,17alpha,20beta,21-tetrol-3-one

Chemical Property:

• Vapor Pressure: 3.34E-16mmHg at 25°C
• Melting Point: 125°C (rough estimate)
• Refractive Index: 1.6120 (estimate)
• Boiling Point: 586.6°C at 760 mmHg
• Flash Point: 322.6°C
• PSA: 97.99000
• Density: 1.29g/cm³
• LogP: 1.57340
• Storage Temp.: Refrigerator
• Solubility.: DMSO (Slightly), Methanol (Slightly)
• 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:

98%,99%, ^*data from raw suppliers

20β-Dihydrocortisol ^*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: 20β-Dihydrocortisol could be used as a potential non invasive diagnostic test of transmissible spongiform encephalopaties. 20β-Dihydrocortisol 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 4-Pregnene-11beta,17alpha,20beta,21-tetrol-3-one

There total 12 articles about 4-Pregnene-11beta,17alpha,20beta,21-tetrol-3-one 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: 80.0%

3,11β,17α,20R,21-pentahydroxypregn-4-ene → 11β,17α,20R,21-tetrahydroxypregn-4-en-3-one (116-58-5)

Guidance literature:

With [(η⁵-C₅Me₅)Ir(6,6'-dihydroxy-2,2'-bipyridine)(H₂O)]OTf₂; In water; tert-butyl alcohol; at 60 ℃; for 11h; chemoselective reaction;

DOI:10.1021/om5010258

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:

21-acetoxy-3-ethoxy-17-hydroxy-pregna-3,5-diene-11,20-dione (1852-65-9) → 11β,17α,20R,21-tetrahydroxypregn-4-en-3-one (116-58-5)

Guidance literature:

With lithium aluminium tetrahydride; diethyl ether; folgende Umsetzung mit wss.-methanol.H₂SO₄;

DOI:10.1021/ja01148a102

upstream raw materials:

HYDROCORTISONE

21-acetoxy-3-ethoxy-17-hydroxy-pregna-3,5-diene-11,20-dione

21-acetoxy-17-hydroxy-pregn-4-ene-3,11,20-trione-3-semicarbazone

Downstream raw materials:

Corticosterone

Refernces

• 1、 Ngo, Anh H.,Adams, Michael J.,Do, Loi H.. "Selective acceptorless dehydrogenation and hydrogenation by iridium catalysts enabling facile interconversion of glucocorticoids". . p. 6742 - 6745. Retrieved 2015/02/19.