(11beta)-11,21-dihydroxypregna-1,4-diene-3,20-dione

Base Information

• Chemical Name: (11beta)-11,21-dihydroxypregna-1,4-diene-3,20-dione
• CAS No.: 13479-38-4
• Molecular Formula: C₂₁H₂₈O₄
• Molecular Weight: 344.4446
• UNII: FY7AZ5TJU4
• DSSTox Substance ID: DTXSID90928764
• Nikkaji Number: J836.370F
• Wikidata: Q76415723
• Mol file: 13479-38-4.mol

Synonyms:13479-38-4;17-Deoxyprednisolone;1,2-Didehydrocorticosterone;Pregna-1,4-diene-3,20-dione, 11,21-dihydroxy-, (11beta)-;FY7AZ5TJU4;UNII-FY7AZ5TJU4;(8S,9S,10R,11S,13S,14S,17S)-11-hydroxy-17-(2-hydroxyacetyl)-10,13-dimethyl-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthren-3-one;11,21-Dihydroxypregna-1,4-diene-3,20-dione (11beta)-;(11beta)-11,21-Dihydroxypregna-1,4-diene-3,20-dione;1-Dehydrocorticosterone;2a3i;SCHEMBL6271311;.DELTA.1-CORTICOSTERONE;DTXSID90928764;PREDNISOLONE IMPURITY I [EP IMPURITY];11,21-dihydroxypregna-1,4-diene-3,20-dione;11.BETA.,21-DIHYDROXYPREGNA-1,4-DIENE-3,20-DIONE;(11.BETA.)-11,21-DIHYDROXYPREGNA-1,4-DIENE-3,20-DIONE;11?,21-Dihydroxypregna-1,4-diene-3,20-dione (17-Desoxyprednisolone);PREGNA-1,4-DIENE-3,20-DIONE, 11,21-DIHYDROXY-, (11.BETA.)-;(8S,9S,10R,11S,13S,14S,17S)-11-Hydroxy-17-(2-hydroxyacetyl)-10,13-dimethyl-6,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-3H-cyclopenta[a]phenanthren-3-one

Chemical Property of (11beta)-11,21-dihydroxypregna-1,4-diene-3,20-dione

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Boiling Point: 532.789°C at 760 mmHg
• Flash Point: 290.094°C
• Density: 1.241g/cm³
• XLogP3: 2.1
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 2
• Exact Mass: 344.19875937
• Heavy Atom Count: 25
• Complexity: 677

Purity/Quality:

HPLC≥98% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC12CC(C3C(C1CCC2C(=O)CO)CCC4=CC(=O)C=CC34C)O
• Isomeric SMILES: C[C@]12C[C@@H]([C@H]3[C@H]([C@@H]1CC[C@@H]2C(=O)CO)CCC4=CC(=O)C=C[C@]34C)O

Technology Process of (11beta)-11,21-dihydroxypregna-1,4-diene-3,20-dione

There total 9 articles about (11beta)-11,21-dihydroxypregna-1,4-diene-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: 80.0%

prednisolon (50-24-8,8056-11-9) → 11β,21-dihydroxy-1,4-pregnadiene-3,20-dione (13479-38-4)

Guidance literature:

With trimethylsilyl iodide; In acetonitrile; for 1h; Ambient temperature;

DOI:10.1248/cpb.34.3722

Reference yield:

Corticosterone (50-22-6) → 11β,21-dihydroxy-1,4-pregnadiene-3,20-dione (13479-38-4)

Guidance literature:

mit Hilfe von Calonectria decora;

DOI:10.1002/hlca.19550380328

Reference yield:

11β-hydroxy-3-oxo-5β-androstane-17β-carboxylic acid (110247-37-5) → 11β,21-dihydroxy-1,4-pregnadiene-3,20-dione (13479-38-4)

Guidance literature:

Multi-step reaction with 2 steps

1: bromine; acetic acid / Erhitzen des Reaktionsprodukts mit 2,4,6-Trimethyl-pyridin

2: beim aufeinanderfolgenden Behandeln mit Oxalylchlorid, mit Diazomethan, mit Essigsaeure, und mit wss.KHCO₃

With bromine; acetic acid;

upstream raw materials:

Corticosterone

(10R,11S,13S,17S)-11-hydroxy-10,13-dimethyl-3-oxo-6,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-3H-cyclopenta[a]phenanthrene-17-carboxylic acid

prednisolon

11β-hydroxy-3-oxo-5β-androstane-17β-carboxylic acid

Refernces

• 1、 -. "Cytotoxic nucleoside-corticosteroid phosphodiesters". . . Retrieved 2008/06/13.