7-Hydroxy-2',4',5'-trimethoxyisoflavone

Base Information

• Chemical Name: 7-Hydroxy-2',4',5'-trimethoxyisoflavone
• CAS No.: 29096-94-4
• Molecular Formula: C18H16O6
• Molecular Weight: 328.321
• ChEMBL ID: CHEMBL455048
• DSSTox Substance ID: DTXSID20571702
• Metabolomics Workbench ID: 22227
• Nikkaji Number: J2.798.749D
• Wikidata: Q27149369
• Mol file: 29096-94-4.mol

Synonyms:7-Hydroxy-2',4',5'-trimethoxyisoflavone;29096-94-4;CHEBI:80369;7-HYDROXY-3-(2,4,5-TRIMETHOXYPHENYL)CHROMEN-4-ONE;7-Hydroxy-3-(2,4,5-trimethoxyphenyl)-4H-chromen-4-one;7-hydroxy-3-(2,4,5-trimethoxyphenyl)-4H-1-benzopyran-4-one;CHEMBL455048;DTXSID20571702;LMPK12050089;XH161600;7-Hydroxy-2?,4?,5?-trimethoxyisoflavone;7-hydroxy -2',4',5'-trimethoxyisoflavone;Q27149369

Chemical Property of 7-Hydroxy-2',4',5'-trimethoxyisoflavone

Chemical Property:

• XLogP3: 2.7
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 4
• Exact Mass: 328.09468823
• Heavy Atom Count: 24
• Complexity: 490

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC1=CC(=C(C=C1C2=COC3=C(C2=O)C=CC(=C3)O)OC)OC

Technology Process of 7-Hydroxy-2',4',5'-trimethoxyisoflavone

There total 18 articles about 7-Hydroxy-2',4',5'-trimethoxyisoflavone 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: 87.1%

7-((tetrahydro-2H-pyran-2-yl)oxy)-3-(2,4,5-trimethoxyphenyl)-4H-chromen-4-one (1616247-85-8) → 7-hydroxy-3-(2,4,5-trimethoxyphenyl)-4H-chromen-4-one (29096-94-4)

Guidance literature:

With toluene-4-sulfonic acid; In tetrahydrofuran; methanol; at 60 ℃; for 1h;

DOI:10.1016/j.bmcl.2014.04.121

Reference yield:

asaraldehyde (4460-86-0,14374-62-0) → 7-hydroxy-3-(2,4,5-trimethoxyphenyl)-4H-chromen-4-one (29096-94-4)

Guidance literature:

Multi-step reaction with 4 steps

1: 85.3 percent / 50percent aq. KOH / ethanol / 24 h / Ambient temperature

2: thallium nitrate / CHCl₃ / Ambient temperature

3: H₂, triethylamine / 10percent Pd/C / ethyl acetate / 760 Torr / Ambient temperature

4: 5percent HCl / methanol / 2 h / Heating

With hydrogenchloride; potassium hydroxide; thallium(I) nitrate; hydrogen; triethylamine; palladium on activated charcoal; In methanol; ethanol; chloroform; ethyl acetate;

Reference yield:

2',4'-bis(benzyloxy)-2,4,5-trimethoxychalcone (91735-52-3) → 7-hydroxy-3-(2,4,5-trimethoxyphenyl)-4H-chromen-4-one (29096-94-4)

Guidance literature:

Multi-step reaction with 3 steps

1: thallium nitrate / CHCl₃ / Ambient temperature

2: H₂, triethylamine / 10percent Pd/C / ethyl acetate / 760 Torr / Ambient temperature

3: 5percent HCl / methanol / 2 h / Heating

With hydrogenchloride; thallium(I) nitrate; hydrogen; triethylamine; palladium on activated charcoal; In methanol; chloroform; ethyl acetate;

upstream raw materials:

asaraldehyde

2',4'-bis(benzyloxy)-2,4,5-trimethoxychalcone

4'-Benzyloxy-2'-hydroxy-2,4,5-trimethoxychalcone

2',4'-Dibenzyloxy-2,4,5-trimethoxychalcone

Downstream raw materials:

2',4',5'-trimethoxy-6'',6''-dimethylpyrano(2'',3'':7,8)isoflavone

7-((3-methylbut-2-en-1-yl)oxy)-3-(2,4,5-trimethoxyphenyl)-4H-chromen-4-one

4-oxo-3-(2,4,5-trimethoxyphenyl)-4H-chromen-7-yl-3-methoxybenzoate

7-(1-oxo-2-(3-(trifluoromethyl)phenyl)ethoxy)-3-(2,4,5-trimethoxyphenyl)-4H-chromen-4-one

Refernces

• 1、 Nishiyama, Kiyotoshi,Esaki, Sachiko,Deguchi, Ikuko,Sugiyama, Naoko,Kamiya, Shintaro. "Syntheses of Isoflavones and Isoflavone Glycosides, and Their Inhibitory Activity against Bovine Liver &β-Galactosidase". . p. 107 - 114. Retrieved 2007/10/02.