(-)-TEPHROSIN

Base Information

• Chemical Name: (-)-TEPHROSIN
• CAS No.: 76-80-2
• Molecular Formula: C23H22O7
• Molecular Weight: 410.423
• European Community (EC) Number: 804-719-8
• UNII: 9C081V83CC
• DSSTox Substance ID: DTXSID20878627
• Nikkaji Number: J2.265.546I
• Wikipedia: Tephrosin
• Wikidata: Q7701343
• Metabolomics Workbench ID: 22693
• ChEMBL ID: CHEMBL241806
• Mol file: 76-80-2.mol

Synonyms:3H-Bis[1]benzopyrano[3,4-b:6‘,5‘-e]pyran-7(7aH)-one, 13,13a-dihydro-7a-hydroxy-9,10-dimethoxy-3,3-dimethyl-, (7aR-cis)-;Tephrosin;

Chemical Property of (-)-TEPHROSIN

Chemical Property:

• Vapor Pressure: 2.11E-16mmHg at 25°C
• Melting Point: 198° (218-220°)
• Refractive Index: 1.5300 (estimate)
• Boiling Point: 623.4°C at 760 mmHg
• PKA: 10.47±0.40(Predicted)
• Flash Point: 219.3°C
• PSA: 83.45000
• Density: 1.341g/cm³
• LogP: 3.11190
• Storage Temp.: ?20°C
• XLogP3: 3
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 2
• Exact Mass: 410.13655304
• Heavy Atom Count: 30
• Complexity: 720

Purity/Quality:

98%, ^*data from raw suppliers

Tephrosin ^*data from reagent suppliers

Safty Information:

• Hazard Codes: N
• Statements: 50
• Safety Statements: 61

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1(C=CC2=C(O1)C=CC3=C2OC4COC5=CC(=C(C=C5C4(C3=O)O)OC)OC)C
• Isomeric SMILES: CC1(C=CC2=C(O1)C=CC3=C2O[C@@H]4COC5=CC(=C(C=C5[C@@]4(C3=O)O)OC)OC)C
• Uses: Tephrosin as a natural rotenoid obtained from Tephrosia vogelii and displays anticancer activity.

Technology Process of (-)-TEPHROSIN

There total 75 articles about (-)-TEPHROSIN 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: 90.0%

cis-deguelin (522-17-8,54324-46-8,110508-99-1,123000-18-0) → (+/-)-tephrosin (76-80-2,561-35-3,16277-84-2,110549-03-6)

Guidance literature:

With copper(I) oxide; 1,3,4,6,7,8-hexahydro-2H-pyrimido[1,2-a]pyrimidine; oxygen; In dimethyl sulfoxide; at 20 ℃; for 5h;

DOI:10.1021/acs.jnatprod.7b00794

Reference yield: 53.0%

(-)-deguelin (522-17-8,54324-46-8,110508-99-1,123000-18-0) → (±)-12a-epi-tephrosin (76-80-2,561-35-3,16277-84-2,110549-03-6) + (+/-)-tephrosin (76-80-2,561-35-3,16277-84-2,110549-03-6)

Guidance literature:

With copper(I) oxide; 1,3,4,6,7,8-hexahydro-2H-pyrimido[1,2-a]pyrimidine; oxygen; In dimethyl sulfoxide; at 20 ℃; for 4.5h;

DOI:10.1055/s-0037-1611654

Reference yield: 53.0%

(-)-deguelin (522-17-8,54324-46-8,110508-99-1,123000-18-0) → (±)-12a-epi-tephrosin (76-80-2,561-35-3,16277-84-2,110549-03-6) + (+/-)-tephrosin (76-80-2,561-35-3,16277-84-2,110549-03-6)

Guidance literature:

With copper(I) oxide; 1,3,4,6,7,8-hexahydro-2H-pyrimido[1,2-a]pyrimidine; oxygen; In dimethyl sulfoxide; at 20 ℃; for 4.5h;

DOI:10.1055/s-0037-1611654

upstream raw materials:

3-fluorophenol

2-(3-fluorophenoxy)tetrahydro-2H-pyran

Downstream raw materials:

(-)-deguelin

Refernces

• 1、 Xu, Shengtao,Wang, Guangyu,Xu, Feijie,Li, Wenlong,Lin, Aijun,Yao, Hequan,Xu, Jinyi. "Concise Total Synthesis of (±)-Deguelin and (±)-Tephrosin Using a Vinyl Iodide as a Key Building Block". . p. 1055 - 1059. Retrieved 2018/05/07.
• 2、 Garcia, Jose,Barluenga, Sofia,Beebe, Kristin,Neckers, Len,Winssinger, Nicolas. "Concise modular asymmetric synthesis of deguelin, tephrosin and investigation into their mode of action". body text. p. 9767 - 9771. Retrieved 2010/10/21.