Topterone

Base Information

• Chemical Name: Topterone
• CAS No.: 60607-35-4
• Molecular Formula: C22H34 O2
• Molecular Weight: 330.511
• European Community (EC) Number: 262-321-4
• UNII: 77WPB17ZK1
• DSSTox Substance ID: DTXSID20209417
• Nikkaji Number: J18.529I
• Wikipedia: Topterone
• Wikidata: Q15633967
• NCI Thesaurus Code: C74122
• Metabolomics Workbench ID: 155862
• ChEMBL ID: CHEMBL2107659
• Mol file: 60607-35-4.mol

Synonyms:17-propyltestosterone;topterone;Win 17,665

Chemical Property of Topterone

Chemical Property:

• Vapor Pressure: 2.18E-10mmHg at 25°C
• Melting Point: 114.6-116.0 °C(Solv: benzene (71-43-2); hexane (110-54-3))
• Boiling Point: 459.8°C at 760 mmHg
• PKA: 15.13±0.60(Predicted)
• Flash Point: 195.7°C
• PSA: 37.30000
• Density: 1.08g/cm³
• LogP: 5.04950
• XLogP3: 4.2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 330.255880323
• Heavy Atom Count: 24
• Complexity: 579

Purity/Quality:

98%Min ^*data from raw suppliers

Topterone ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCCC1(CCC2C1(CCC3C2CCC4=CC(=O)CCC34C)C)O
• Isomeric SMILES: CCC[C@@]1(CC[C@@H]2[C@@]1(CC[C@H]3[C@H]2CCC4=CC(=O)CC[C@]34C)C)O
• Uses: Topterone functions as steroidal antiandrogen drug. Also, the are used in acne and androgenic alopecia treatment.

Technology Process of Topterone

There total 3 articles about Topterone 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:

C24H38O3 → 17α-propyltestosterone (60607-35-4)

Guidance literature:

With hydrogenchloride; In tetrahydrofuran; acetone; for 12h; Yield given;

DOI:10.1016/0040-4039(94)88011-5

Reference yield:

3,3-ethylenedioxy-5-androsten-17-one (3754-63-0) → 17α-propyltestosterone (60607-35-4)

Guidance literature:

Multi-step reaction with 2 steps

1: 1.) Ce(III)Cl₃ / 1.) THF, -78 deg C, 1.5 h; 2.) THF, -40 deg C, 4 h

2: 9 percent aq. HCl / acetone; tetrahydrofuran / 12 h

With hydrogenchloride; cerium(III) chloride; In tetrahydrofuran; acetone;

DOI:10.1016/0040-4039(94)88011-5

Reference yield:

→ 17β-Hydroxy-3-oxo-17α-propyl-androsten-(4) (60607-35-4)

Guidance literature:

3β.17β-Dihydroxy-17α-propyl-androsten-(5), Aluminiumisopropylat, Cyclohexan, Toluol, 40 min, sieden;

DOI:10.1021/ja01467a047

upstream raw materials:

3,3-ethylenedioxy-5-androsten-17-one

Refernces