(-)-Columbianetin

Base Information

• Chemical Name: (-)-Columbianetin
• CAS No.: 52842-47-4
• Molecular Formula: C₁₄H₁₄O₄
• Molecular Weight: 246.263
• DSSTox Substance ID: DTXSID30331738
• Nikkaji Number: J89.726D
• Wikidata: Q27106206
• Metabolomics Workbench ID: 53090
• Mol file: 52842-47-4.mol

Synonyms:columbianetin;columbianetin, (+-)-isomer;columbianetin, (S)-isomer

Chemical Property of (-)-Columbianetin

Chemical Property:

• Vapor Pressure: 1.25E-08mmHg at 25°C
• Melting Point: 162.4 - 163.6 °C
• Boiling Point: 443°Cat760mmHg
• PKA: 14.34±0.29(Predicted)
• Flash Point: 171.9°C
• PSA: 59.67000
• Density: 1.334g/cm³
• LogP: 1.86740
• XLogP3: 1.9
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 1
• Exact Mass: 246.08920892
• Heavy Atom Count: 18
• Complexity: 387

Purity/Quality:

99%min ^*data from raw suppliers

(+)-COLUMBIANETIN 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)(C1CC2=C(O1)C=CC3=C2OC(=O)C=C3)O
• Isomeric SMILES: CC(C)([C@H]1CC2=C(O1)C=CC3=C2OC(=O)C=C3)O

Technology Process of (-)-Columbianetin

There total 17 articles about (-)-Columbianetin 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: 85.0%

osthenol (484-14-0) → columbianetin (1147-29-1,3804-70-4,26079-34-5,52842-47-4)

Guidance literature:

With potassium carbonate; 3-chloro-benzenecarboperoxoic acid; In dichloromethane; at 20 ℃; for 8h; Inert atmosphere;

DOI:10.1016/j.bmcl.2020.127633

Reference yield: 75.0%

C14H14O4 (1351118-96-1) → columbianetin (1147-29-1,3804-70-4,26079-34-5,52842-47-4)

Guidance literature:

With Echavarren's catalyst; In dichloromethane; for 16h; Inert atmosphere; Reflux;

DOI:10.1016/j.tetlet.2011.10.036

Reference yield: 71.0%

7-(2-methylbut-3-en-2-yloxy)-2H-chromen-2-one (27421-19-8) → columbianetin (1147-29-1,3804-70-4,26079-34-5,52842-47-4)

Guidance literature:

7-(2-methylbut-3-en-2-yloxy)-2H-chromen-2-one; With sodium hydrogencarbonate; In water; at 75 ℃; for 2h;

With 3-chloro-benzenecarboperoxoic acid; In water; at 50 ℃; for 20h;

DOI:10.1016/j.tetlet.2012.11.150

upstream raw materials:

osthenol

C₁₄H₁₄O₄

2-(1-hydroxy-1-methyl-ethyl)-2,3-dihydro-benzofuran-4-ol

7-hydroxy-2H-chromen-2-one

Refernces

• 1、 Ando, Tomomi,Nagumo, Mina,Ninomiya, Masayuki,Tanaka, Kaori,Linhardt, Robert J.,Koketsu, Mamoru. "Synthesis of coumarin derivatives and their cytoprotective effects on t-BHP-induced oxidative damage in HepG2 cells". supporting information. p. 2422 - 2425. Retrieved 2018/06/20.
• 2、 Marumoto, Shinsuke,Miyazawa, Mitsuo. "Structure-activity relationships for naturally occurring coumarins as β-secretase inhibitor". supporting information; experimental part. p. 784 - 788. Retrieved 2012/03/22.