Betamethasone 9,11-Epoxide

Base Information

• Chemical Name: Betamethasone 9,11-Epoxide
• CAS No.: 981-34-0
• Molecular Formula: C22H28O5
• Molecular Weight: 372.461
• Hs Code.: 2918990090
• European Community (EC) Number: 213-563-4
• UNII: M9AY9BSI41
• DSSTox Substance ID: DTXSID601020538
• Nikkaji Number: J298.581K
• Wikidata: Q27283711
• Mol file: 981-34-0.mol

Synonyms:981-34-0;Betamethasone 9,11-Epoxide;16-beta Methyl Epoxide;(4aS,4bS,5aS,6aS,7R,8S,9aS,9bS)-7-Hydroxy-7-(2-hydroxyacetyl)-4a,6a,8-trimethyl-5a,6,6a,7,8,9,9a,9b,10,11-decahydrocyclopenta[1,2]phenanthro[4,4a-b]oxiren-2(4aH)-one;UNII-M9AY9BSI41;M9AY9BSI41;EINECS 213-563-4;9beta,11beta-Epoxy-17alpha,21-dihydroxy-16beta-methylene-pregna-1,4-diene-3,20-dione;9beta,11beta-Epoxy-17,21-dihydroxy-16beta-methylpregna-1,4-diene-3,20-dione;(9beta,11beta,16beta)-9,11-Epoxy-17,21-dihydroxy-16-methylpregna-1,4-diene-3,20-dione;(1S,2S,10S,11S,13S,14R,15S,17S)-14-hydroxy-14-(2-hydroxyacetyl)-2,13,15-trimethyl-18-oxapentacyclo[8.8.0.01,17.02,7.011,15]octadeca-3,6-dien-5-one;C22H28O5;Pregna-1,4-diene-3,20-dione, 9,11-epoxy-17,21-dihydroxy-16-methyl-, (9.beta.,11.beta.,16.beta.)-;9,11?-Epoxy-17,21-dihydroxy-16?-methyl-9?-pregna-1,4-diene-3,20-dione;16-beta-Methyl epoxide;SCHEMBL5262836;9|A,11|A-Epoxy-17,21-dihydroxy-16|A-methylpregna-1,4-diene-3,20-dione;Pregna-1,4-dieno-3,20-diona, 9,11-epoxi-17,21-dihidroxi-16-metil-, (9?,11?,16?)-;DTXSID601020538;14622-47-0;AMY27801;MFCD09038712;AKOS017343721;CS-T-49076;CS-W006439;AS-17685;BETAMETHASONE IMPURITY E [EP IMPURITY];C77355;A855442;W-100093;Q27283711;BECLOMETHASONE DIPROPIONATE IMPURITY R [EP IMPURITY];9 beta ,11 beta -Epoxy-17,21-dihydroxy-16 beta -methylpregna-1,4-diene-3,20-dione;16alpha-Methyl epoxide(db-11);17alpha,21-dihydroxy-9alpha,11alpha,epoxy-16alpha-methylpregn-1,4-diene-3,20-dione;9,11.BETA.-EPOXY-17,21-DIHYDROXY-16.BETA.-METHYL-9.BETA.-PREGNA-1,4-DIENE-3,20-DIONE;9.BETA.-PREGNA-1,4-DIENE-3,20-DIONE, 9,11.BETA.-EPOXY-17,21-DIHYDROXY-16.BETA.-METHYL-

Chemical Property of Betamethasone 9,11-Epoxide

Chemical Property:

• Appearance/Colour: off-white solid
• Vapor Pressure: 4.09E-15mmHg at 25°C
• Melting Point: 210-220 °C
• Refractive Index: 1.616
• Boiling Point: 564.9 °C at 760 mmHg
• PKA: 12.56±0.70(Predicted)
• Flash Point: 198.1 °C
• PSA: 87.13000
• Density: 1.32 g/cm³
• LogP: 1.88420
• Storage Temp.: Refrigerator
• XLogP3: 2
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 2
• Exact Mass: 372.19367399
• Heavy Atom Count: 27
• Complexity: 814

Purity/Quality:

99.9% ^*data from raw suppliers

Betamethasone 9,11-epoxide ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1CC2C3CCC4=CC(=O)C=CC4(C35C(O5)CC2(C1(C(=O)CO)O)C)C
• Isomeric SMILES: C[C@H]1C[C@H]2[C@@H]3CCC4=CC(=O)C=C[C@@]4([C@]35[C@@H](O5)C[C@@]2([C@]1(C(=O)CO)O)C)C
• Uses: Metabolite of Beclometasone (131000) A metabolite of Mometasone furoate. Low solubility in most solvent.

Technology Process of Betamethasone 9,11-Epoxide

There total 20 articles about Betamethasone 9,11-Epoxide 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: 83.0%

21-acetoxy-17α-hydroxy-9β,11β-epoxy-16β-methylpregna-4-ene-3,20-dione → 9β,11β-epoxy-17α,21-dihydroxy-16β-methylpregna-1,4-diene-3,20-dione (981-34-0)

Guidance literature:

With D-Glucose; In aq. phosphate buffer; for 76h; Microbiological reaction;

DOI:10.3184/174751917X14925986241025

Reference yield: 75.0%

C25H33BrO7 → 9β,11β-epoxy-17α,21-dihydroxy-16β-methylpregna-1,4-diene-3,20-dione (981-34-0)

Guidance literature:

In dichloromethane; water; at 25 - 30 ℃; for 1h; Inert atmosphere;

Reference yield:

Acetic acid 2-((8S,9R,10S,11S,13S,14S,16S,17R)-9-bromo-11,17-dihydroxy-10,13,16-trimethyl-3-oxo-6,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-3H-cyclopenta[a]phenanthren-17-yl)-2-oxo-ethyl ester → 9β,11β-epoxy-17α,21-dihydroxy-16β-methylpregna-1,4-diene-3,20-dione (981-34-0)

Guidance literature:

With sodium hydroxide; sodium sulfite; In methanol; water; at 10 ℃; for 3h;

upstream raw materials:

C₂₆H₃₆O₉S

17α-hydroxy-16β-methyl-21-ethoxycarbonyloxypregna-1,4,9(11)-triene-3,20-dione

androst-4,9⁽¹¹⁾-dien-3,17-dione

Downstream raw materials:

betamethasone

beclomethasone

beclomethasone 17-monopropionate

beclomethasone 17,21-dipropionate

Refernces

• 1、 Tang, Jie,Liu, Xirong,Zeng, Chunlin,Meng, Hao,Tian, Mi,Guo, Cancheng. "A novel route for the preparation of betamethasone from 9α-hydroxyandrost-4-ene-3,17-dione (9αOH-AD) by chemical synthesis and fermentation". . p. 266 - 270. Retrieved 2017/06/19.
• 2、 Fu, Xiaoyong,Tann, Chou-Hong,Thiruvengadam. "Process improvements in the synthesis of corticosteroid 9,11β-epoxides". . p. 376 - 382. Retrieved 2013/09/07.