11-beta,17-alpha,21-Trihydroxy-6-alpha-methylpregn-4-ene-3,20-dione

Base Information

• Chemical Name: 11-beta,17-alpha,21-Trihydroxy-6-alpha-methylpregn-4-ene-3,20-dione
• CAS No.: 1625-39-4
• Molecular Formula: C22H32 O5
• Molecular Weight: 376.493
• European Community (EC) Number: 216-614-9
• NSC Number: 19618
• UNII: 7XQ6AER9QE
• DSSTox Substance ID: DTXSID301313722
• Nikkaji Number: J195.253F
• ChEMBL ID: CHEMBL3250348
• Mol file: 1625-39-4.mol

Synonyms:1625-39-4;11-beta,17-alpha,21-Trihydroxy-6-alpha-methylpregn-4-ene-3,20-dione;6alpha-methylhydrocortisone;7XQ6AER9QE;(6S,8S,9S,10R,11S,13S,14S,17R)-11,17-dihydroxy-17-(2-hydroxyacetyl)-6,10,13-trimethyl-2,6,7,8,9,11,12,14,15,16-decahydro-1H-cyclopenta[a]phenanthren-3-one;EINECS 216-614-9;NSC-19618;6|A-Methylcortisol;NSC19618;NSC 19618;PREMEDROL;UNII-7XQ6AER9QE;SCHEMBL137529;6.ALPHA.-METHYLCORTISOL;CHEMBL3250348;DTXSID301313722;6.ALPHA.-METHYLHYDROCORTISONE;U-7240;METHYLPREDNISOLONE IMPURITY F [EP IMPURITY];11beta,17,21-trihydroxy-6alpha-methyl-4-pregnene-3,20-dione;11beta,17,21-Trihydroxy-6alpha-methylpregn-4-ene-3,20-dione;11.BETA.,17,21-TRIHYDROXY-6.ALPHA.-METHYLPREGN-4-ENE-3,20-DIONE;6.ALPHA.-METHYL-11.BETA.,17.ALPHA.,21-TRIHYDROXY-4-PREGNENE-3,20-DIONE;PREGN-4-ENE-3,20-DIONE, 11,17,21-TRIHYDROXY-6-METHYL-, (6.ALPHA.,11.BETA.)-;(6S,8S,9S,10R,11S,13S,14S,17R)-11,17-dihydroxy-17-(2-hydroxyacetyl)-6,10,13-trimethyl-6,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3(2H)-one

Chemical Property of 11-beta,17-alpha,21-Trihydroxy-6-alpha-methylpregn-4-ene-3,20-dione

Chemical Property:

• Vapor Pressure: 2.83E-15mmHg at 25°C
• Melting Point: 203-208 °C
• Boiling Point: 568.2°Cat760mmHg
• PKA: 12.47±0.70(Predicted)
• Flash Point: 311.5°C
• PSA: 94.83000
• Density: 1.26g/cm³
• LogP: 2.02760
• Storage Temp.: Refrigerator
• Solubility.: Acetone (Slightly), Chloroform (Very Slightly, Heated), DMSO (Slightly), Methano
• XLogP3: 1.9
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 2
• Exact Mass: 376.22497412
• Heavy Atom Count: 27
• Complexity: 714

Purity/Quality:

99%, ^*data from raw suppliers

6α-MethylHydrocortisone ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1CC2C3CCC(C3(CC(C2C4(C1=CC(=O)CC4)C)O)C)(C(=O)CO)O
• Isomeric SMILES: C[C@H]1C[C@H]2[C@@H]3CC[C@@]([C@]3(C[C@@H]([C@@H]2[C@@]4(C1=CC(=O)CC4)C)O)C)(C(=O)CO)O
• Uses: A metabolite of Cortisone (C696500).

Technology Process of 11-beta,17-alpha,21-Trihydroxy-6-alpha-methylpregn-4-ene-3,20-dione

There total 23 articles about 11-beta,17-alpha,21-Trihydroxy-6-alpha-methylpregn-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:

Methylprednisolone (83-43-2) → 11β,17α,21-trihydroxy-6α-methylpregna-4-ene-3,20-dione (1625-39-4)

Guidance literature:

With hydrogen; Wilkinson's catalyst; In ethanol; ethyl acetate; at 20 ℃; for 168h; under 760.051 Torr;

Reference yield:

6-methine hydrocortisone → 11β,17α,21-trihydroxy-6α-methylpregna-4-ene-3,20-dione (1625-39-4)

Guidance literature:

With 5%-palladium/activated carbon; In chloroform; cyclohexene; at 45 - 60 ℃; Solvent;

Reference yield:

21-acetoxy-11β-hydroxy-6α-methyl-pregna-4,17(20)c-dien-3-one (3386-05-8,14423-18-8,75110-33-7) → 11β,17α,21-trihydroxy-6α-methylpregna-4-ene-3,20-dione (1625-39-4)

Guidance literature:

Multi-step reaction with 2 steps

1: diacetoxy-phenyl-iodan; OsO₄; pyridine / Reagens 4: tert-Butylalkohol

2: Hydrolysis

With pyridine; osmium(VIII) oxide; [bis(acetoxy)iodo]benzene;

DOI:10.1021/ja01604a078

upstream raw materials:

5,11β,17,21-tetrahydroxy-6β-methyl-5α-pregnane-3,20-dione

21-acetoxy-11β,17-dihydroxy-6α-methyl-pregn-4-ene-3,20-dione

21-acetoxy-11β-hydroxy-6α-methyl-pregna-4,17(20)c-dien-3-one

3,3;20,20-bis-ethanediyldioxy-6β-methyl-5α-pregnane-5,11β,17,21-tetraol

Downstream raw materials:

21-acetoxy-11β,17-dihydroxy-6α-methyl-pregn-4-ene-3,20-dione

21-fluoro-11β,17-dihydroxy-6α-methyl-pregn-4-ene-3,20-dione

11β,17-dihydroxy-6α-methyl-pregn-4-ene-3,20-dione

Refernces

• 1、 -. "NOVEL COMPOUNDS". Page/Page column 17. . Retrieved 2010/10/19.
• 2、 -. "STEROIDAL [3, 2-C] PYRAZOLE COMPOUNDS, WITH GLUCOCORTICOID ACTIVITY". Page/Page column 144. . Retrieved 2009/05/29.