11beta,16alpha,17,21-Tetrahydroxypregn-4-ene-3,20-dione

Base Information

• Chemical Name: 11beta,16alpha,17,21-Tetrahydroxypregn-4-ene-3,20-dione
• CAS No.: 1171-81-9
• Molecular Formula: C21H30 O6
• Molecular Weight: 378.466
• European Community (EC) Number: 214-627-4
• DSSTox Substance ID: DTXSID90922287
• Nikkaji Number: J203.430A
• Wikidata: Q82895691
• Mol file: 1171-81-9.mol

Synonyms:1171-81-9;11beta,16alpha,17,21-Tetrahydroxypregn-4-ene-3,20-dione;EINECS 214-627-4;(8S,9S,10R,11S,13S,14S,16R,17S)-11,16,17-trihydroxy-17-(2-hydroxyacetyl)-10,13-dimethyl-2,6,7,8,9,11,12,14,15,16-decahydro-1H-cyclopenta[a]phenanthren-3-one;16a-Hydroxycortisol;SCHEMBL141635;DTXSID90922287;11,16,17,21-tetrahydroxypregn-4-ene-3,20-dione

Chemical Property of 11beta,16alpha,17,21-Tetrahydroxypregn-4-ene-3,20-dione

Chemical Property:

• Vapor Pressure: 3.14E-16mmHg at 25°C
• Melting Point: >217°C (dec.)
• Boiling Point: 587.1°C at 760 mmHg
• Flash Point: 322.9°C
• PSA: 115.06000
• Density: 1.35g/cm³
• LogP: 0.75240
• Storage Temp.: -20°C Freezer
• Solubility.: DMSO (slightly), Methanol (Slightly, Heated)
• XLogP3: 1.2
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 2
• Exact Mass: 378.20423867
• Heavy Atom Count: 27
• Complexity: 716

Purity/Quality:

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

16α-Hydroxycortisol ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC12CCC(=O)C=C1CCC3C2C(CC4(C3CC(C4(C(=O)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]3C[C@H]([C@@]4(C(=O)CO)O)O)C)O
• Uses: 11β,16α,17,21-Tetrahydroxypregn-4-ene-3,20-dione is a metabolite of Hydroxycortisone (H714615), a steroid hormone, more specifically a glucocorticoid, produced by the zona fasciculata of the adrenal gland. 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 11beta,16alpha,17,21-Tetrahydroxypregn-4-ene-3,20-dione

There total 5 articles about 11beta,16alpha,17,21-Tetrahydroxypregn-4-ene-3,20-dione 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: 85.0%

16-OH-prednisolone → 11β,16α,17,21-tetrahydroxy-pregn-4-ene-3,20-dione (1171-81-9)

Guidance literature:

With hydrogen; Wilkinson's catalyst; In ethanol; toluene; at 20 ℃; for 72h; under 760.051 Torr;

Reference yield:

pregna-4,16-dien-11β,21-diol-3,20-dione 21-acetate (21720-47-8) → 11β,16α,17,21-tetrahydroxy-pregn-4-ene-3,20-dione (1171-81-9)

Guidance literature:

With osmium(VIII) oxide;

DOI:10.1021/ja01590a038

Reference yield:

3,3;20,20-bis-ethanediyldioxy-pregn-5-ene-11β,16α,17,21-tetraol (911668-61-6) → 11β,16α,17,21-tetrahydroxy-pregn-4-ene-3,20-dione (1171-81-9)

Guidance literature:

With sulfuric acid;

DOI:10.1021/ja01590a038

upstream raw materials:

pregna-4,16-dien-11β,21-diol-3,20-dione 21-acetate

3,3;20,20-bis-ethanediyldioxy-pregn-5-ene-11β,16α,17,21-tetraol

3,3;20,20-bis-ethanediyldioxy-pregna-5,16-diene-11β,21-diol

Downstream raw materials:

triamcinolone acetonide

triamcinolone diacetate

16α,21-diacetoxy-9-fluoro-17-hydroxy-pregna-1,4-diene-3,11,20-trione

16α,21-diacetoxy-9-chloro-11β,17-dihydroxy-pregna-1,4-diene-3,20-dione

Refernces

• 1、 -. "STEROID DERIVATIVES ACTING AS GLUCOCORTICOSTEROID RECEPTOR AGONISTS". Page/Page column 56-57. . Retrieved 2009/07/25.