16alpha,17-Epoxyprogesterone

Base Information

• Chemical Name: 16alpha,17-Epoxyprogesterone
• CAS No.: 1097-51-4
• Molecular Formula: C₂₁H₂₈O₃
• Molecular Weight: 328.452
• European Community (EC) Number: 214-147-5
• NSC Number: 18315
• UNII: F2DR02G069
• DSSTox Substance ID: DTXSID501318792
• Nikkaji Number: J66.979B
• Wikidata: Q27115861
• Pharos Ligand ID: NM3AA399QZ11
• ChEMBL ID: CHEMBL2112759
• Mol file: 1097-51-4.mol

Synonyms:16 alpha,17-epoxyprogesterone;16 alpha,17-epoxyprogesterone, (16beta,17alpha)-isomer;16,17-epoxy-4-pregnene-3,20-dione

Chemical Property of 16alpha,17-Epoxyprogesterone

Chemical Property:

• Appearance/Colour: white crystalline powder
• Vapor Pressure: 6.82E-09mmHg at 25°C
• Melting Point: 128 to 132oC
• Refractive Index: 168 ° (C=1, CHCl3)
• Boiling Point: 466.9 °C at 760 mmHg
• Flash Point: 204.4 °C
• PSA: 46.67000
• Density: 1.18 g/cm³
• LogP: 3.85480
• Storage Temp.: −20°C
• Solubility.: Chloroform, Methanol
• XLogP3: 2.9
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 1
• Exact Mass: 328.20384475
• Heavy Atom Count: 24
• Complexity: 679

Purity/Quality:

99% ^*data from raw suppliers

16α,17α-Epoxyprogesterone ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC(=O)C12C(O1)CC3C2(CCC4C3CCC5=CC(=O)CCC45C)C
• Isomeric SMILES: CC(=O)[C@]12[C@H](O1)C[C@@H]3[C@@]2(CC[C@H]4[C@H]3CCC5=CC(=O)CC[C@]45C)C
• Uses: 16α,17α-Epoxyprogesterone is hydrolyzed by Rhizopus nigricans for the synthesis of many steroidal drugs.

Technology Process of 16alpha,17-Epoxyprogesterone

There total 14 articles about 16alpha,17-Epoxyprogesterone 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: 100.0%

16α,17α-epoxy-pregnenolone → 16α,17α-epoxyprogesterone (1097-51-4,16356-47-1)

Guidance literature:

With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; ferric nitrate; In acetonitrile; for 16h; Reagent/catalyst; Reflux; Large scale;

Reference yield: 90.6%

20α-hydroxy-16α,17α-epoxypregn-4-en-3-one (2872-76-6) → 16α,17α-epoxyprogesterone (1097-51-4,16356-47-1)

Guidance literature:

With Jones reagent; In acetone; at 0 ℃; for 1h;

Reference yield: 22.0%

(3β,5α,16α)-16,17-epoxy-3-hydroxypregnan-20-one (1044-90-2,1097-50-3,74015-78-4,95044-31-8,113563-82-9) → 20α-hydroxy-16α,17α-epoxypregn-4-en-3-one (2872-76-6) + 16α,17α-epoxyprogesterone (1097-51-4,16356-47-1)

Guidance literature:

In water; dimethyl sulfoxide; at 28 ℃; for 40h; Rhodococcus sp. culture, maize extract, K2HPO4, NaH2PO4*12H2O, α,α-dipyridyl;

DOI:10.1007/BF00766462

upstream raw materials:

16-dehydroprogesterone

3β-hydroxy-16α,17α-epoxypregn-5-en-20-one

(3β,5α,16α)-16,17-epoxy-3-hydroxypregnan-20-one

16-dehydropregnenolone acetate

Downstream raw materials:

16β-Brom-17α-hydroxy-pregnen-(4)-dion-(3,20)

11α-hydroxy-16α,17α-epoxyprogesterone

Cortexolone

20,20-dimethoxy-16α,17α-epoxypregn-4-en-21-ol-3-one

Refernces

• 1、 Berg. "-". . p. 3350. Retrieved 1962.
• 2、 -. "fertile oxide synthesis method". . . Retrieved 2017/10/20.
• 3、 -. "Preparation method of betamethasone intermediate". Paragraph 0072; 0075. . Retrieved 2017/02/24.