Allotetrahydrocortisone

Base Information

• Chemical Name: Allotetrahydrocortisone
• CAS No.: 547-77-3
• Molecular Formula: C21H32 O5
• Molecular Weight: 364.482
• European Community (EC) Number: 208-936-3
• UNII: 76SK258VML
• DSSTox Substance ID: DTXSID30878592
• Nikkaji Number: J39.554D
• Wikidata: Q27266508
• Mol file: 547-77-3.mol

Synonyms:Allotetrahydrocortisone;547-77-3;UNII-76SK258VML;76SK258VML;Reichstein's substance Dehydro-C;EINECS 208-936-3;(3R,5S,8S,9S,10S,13S,14S,17R)-3,17-dihydroxy-17-(2-hydroxyacetyl)-10,13-dimethyl-2,3,4,5,6,7,8,9,12,14,15,16-dodecahydro-1H-cyclopenta[a]phenanthren-11-one;5-alpha-PREGNAN-3-beta, 17,21-TRIOL-11,20-DIONE;11-dehydro c;3alpha,17,21-Trihydroxy-5alpha-pregnane-11,20-dione;C21H32O5;(3-alpha,5-alpha)-3,17,21-Trihydroxypregnane-11,20-dione;SCHEMBL1184192;DTXSID30878592;ALLOTETRAHYDROCORTISONE [MI];Q27266508

Chemical Property of Allotetrahydrocortisone

Chemical Property:

• Vapor Pressure: 4E-14mmHg at 25°C
• Melting Point: 212-214°
• Boiling Point: 544.5°Cat760mmHg
• PKA: 12.38±0.70(Predicted)
• Flash Point: 297.1°C
• PSA: 94.83000
• Density: 1.249g/cm³
• LogP: 1.86150
• XLogP3: 2.2
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 2
• Exact Mass: 364.22497412
• Heavy Atom Count: 26
• Complexity: 632

Purity/Quality:

99% ^*data from raw suppliers

Allotetrahydrocortisone ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC12CCC(CC1CCC3C2C(=O)CC4(C3CCC4(C(=O)CO)O)C)O
• Isomeric SMILES: C[C@]12CC[C@H](C[C@@H]1CC[C@@H]3[C@@H]2C(=O)C[C@]4([C@H]3CC[C@@]4(C(=O)CO)O)C)O
• Uses: Allotetrahydrocortisone is a metabolite of Cortisone (C696500), a glucocorticoid, anti-inflammatory agent.

Technology Process of Allotetrahydrocortisone

There total 7 articles about Allotetrahydrocortisone 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:

21-acetoxy-3β,17-dihydroxy-5α-pregnane-11,20-dione (1856-12-8) → 3α,17α,21-trihydroxy-5α-pregnane-11,20-dione (547-77-3)

Guidance literature:

With pyridine; p-toluenesulfonyl chloride; aufeinanderfolgende Umsetzung mit Kaliumacetat und Essigsaeure sowie mit wss.-aethanol.KHCO₃;

Reference yield:

3α,21-bis-formyloxy-17-hydroxy-5α-pregnane-11,20-dione (113455-07-5) → 3α,17α,21-trihydroxy-5α-pregnane-11,20-dione (547-77-3)

Guidance literature:

With potassium hydrogencarbonate;

DOI:10.1002/hlca.19580410610

Reference yield:

3α,11β,17α,21-tetrahydroxy-5α-pregnan-20-one (302-91-0) → 3α,17α,21-trihydroxy-5α-pregnane-11,20-dione (547-77-3)

Guidance literature:

Multi-step reaction with 3 steps

1: acetic acid anhydride; pyridine

2: CrO₃

3: aqueous methanol.KHCO₃

With pyridine; chromium(VI) oxide; acetic anhydride; potassium hydrogencarbonate;

DOI:10.1002/hlca.19580410610

upstream raw materials:

3α,21-bis-formyloxy-17-hydroxy-5α-pregnane-11,20-dione

21-acetoxy-3β,17-dihydroxy-5α-pregnane-11,20-dione

3α,11β,17α,21-tetrahydroxy-5α-pregnan-20-one

3α,21-bis-formyloxy-11β,17-dihydroxy-5α-pregnan-20-one

Refernces