4H-1-Benzopyran-4-one, 5-hydroxy-3,7-dimethoxy-2-phenyl-

Base Information

• Chemical Name: 4H-1-Benzopyran-4-one, 5-hydroxy-3,7-dimethoxy-2-phenyl-
• CAS No.: 70786-48-0
• Molecular Formula: C17H14O5
• Molecular Weight: 298.295
• NSC Number: 749214
• DSSTox Substance ID: DTXSID60221037
• Nikkaji Number: J1.609.655E
• Wikidata: Q83098619
• Metabolomics Workbench ID: 24740
• ChEMBL ID: CHEMBL1097683
• Mol file: 70786-48-0.mol

Synonyms:3,7-dimethylgalangin

Chemical Property of 4H-1-Benzopyran-4-one, 5-hydroxy-3,7-dimethoxy-2-phenyl-

Chemical Property:

• Vapor Pressure: 1.56E-11mmHg at 25°C
• Boiling Point: 522.5°C at 760 mmHg
• Flash Point: 196.3°C
• Density: 1.36g/cm³
• XLogP3: 3.5
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 3
• Exact Mass: 298.08412354
• Heavy Atom Count: 22
• Complexity: 452

Purity/Quality:

≥98% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC1=CC(=C2C(=C1)OC(=C(C2=O)OC)C3=CC=CC=C3)O

Technology Process of 4H-1-Benzopyran-4-one, 5-hydroxy-3,7-dimethoxy-2-phenyl-

There total 14 articles about 4H-1-Benzopyran-4-one, 5-hydroxy-3,7-dimethoxy-2-phenyl- 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: 78.0%

3,5,7-trimethoxyflavone (26964-29-4) → 5-hydroxy-3,7-dimethoxyflavone (70786-48-0)

Guidance literature:

3,5,7-trimethoxyflavone; With boron tribromide; In dichloromethane; at 0 - 20 ℃; for 4h;

With water; In dichloromethane;

DOI:10.5012/bkcs.2012.33.4.1379

Reference yield:

2'-hydroxy-2,4',6'-trimethoxyacetophenone (17874-42-9) → 5-hydroxy-3,7-dimethoxyflavone (70786-48-0)

Guidance literature:

Multi-step reaction with 3 steps

1: lithium diisopropyl amide / tetrahydrofuran

2: sulfuric acid; acetic acid / 0.5 h / 80 °C

3: boron tribromide / dichloromethane / 4 h / 0 - 20 °C

With sulfuric acid; boron tribromide; acetic acid; lithium diisopropyl amide; In tetrahydrofuran; dichloromethane;

DOI:10.5012/bkcs.2012.33.4.1379

Reference yield:

3,5-dimethoxyphenol (500-99-2) → 5-hydroxy-3,7-dimethoxyflavone (70786-48-0)

Guidance literature:

Multi-step reaction with 4 steps

1: aluminum (III) chloride / 1,1,2,2-tetrachloroethane / 20 °C

2: lithium diisopropyl amide / tetrahydrofuran

3: sulfuric acid; acetic acid / 0.5 h / 80 °C

4: boron tribromide / dichloromethane / 4 h / 0 - 20 °C

With aluminum (III) chloride; sulfuric acid; boron tribromide; acetic acid; lithium diisopropyl amide; In tetrahydrofuran; dichloromethane; 1,1,2,2-tetrachloroethane;

DOI:10.5012/bkcs.2012.33.4.1379

upstream raw materials:

methanol

galangin

sodium methylate

methyl iodide

Downstream raw materials:

5-acetoxy-3,7-dimethoxyflavone

3,5,7-trimethoxyflavone

isalpinin

5,8-dihydroxy-3,7-dimethoxyflavone

Refernces

• 1、 Parmar, Virinder S.,Gupta, Sandhya,Sinha, Rita,Sharma, Sunil K.. "Synthesis of some commonly occurring 2-phenyl-4H-1-benzopyran-4-ones: Revised structures for three natural products". . p. 244 - 256. Retrieved 2007/10/02.
• 2、 Dwivedi, P.,Kapoor, N. K.,Khanna, R. N.. "Synthesis of Platanetin - A Naturally Occuring Prenylated Flavone". . p. 77 - 78. Retrieved 2007/10/02.