Quercetin 3,4'-dimethyl ether

Base Information

• Chemical Name: Quercetin 3,4'-dimethyl ether
• CAS No.: 33429-83-3
• Molecular Formula: C17H14O7
• Molecular Weight: 330.294
• NSC Number: 106970
• DSSTox Substance ID: DTXSID10418970
• Nikkaji Number: J94.537D
• Wikidata: Q27138349
• Metabolomics Workbench ID: 75266
• ChEMBL ID: CHEMBL309263
• Mol file: 33429-83-3.mol

Synonyms:5,7,3'-trihydroxy-3,4'-dimethoxyflavone

Chemical Property of Quercetin 3,4'-dimethyl ether

Chemical Property:

• Melting Point: 229-230 °C
• Boiling Point: 607 °C at 760 mmHg
• Flash Point: 227.3 °C
• Density: 1.55 g/cm³
• Storage Temp.: 2-8°C
• XLogP3: 2.8
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 3
• Exact Mass: 330.07395278
• Heavy Atom Count: 24
• Complexity: 517

Purity/Quality:

99% ^*data from raw suppliers

5,7-Dihydroxy-2-(3-hydroxy-4-methoxyphenyl)-3-methoxy-4H-chromen-4-one 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC1=C(C=C(C=C1)C2=C(C(=O)C3=C(C=C(C=C3O2)O)O)OC)O

Technology Process of Quercetin 3,4'-dimethyl ether

There total 7 articles about Quercetin 3,4'-dimethyl ether 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: 30.0%

quercetol (117-39-5,74893-81-5) + methyl iodide (74-88-4) → 3,3'-di-O-methylquercetin (4382-17-6) + 3,4'-O-dimethylquercetin (33429-83-3) + ombuin (529-40-8) + 2-(3,4-dihydroxyphenyl)-5-hydroxy-3,7-dimethoxychromen-4-one (2068-02-2) + ayanin (572-32-7) + 2-(3,4-dimethoxyphenyl)-3,5-dihydroxy-7-methoxy-4H-chromen-4-one (6068-80-0)

Guidance literature:

With potassium carbonate; In acetone; at 20 ℃; for 3h;

DOI:10.1007/s00044-019-02412-7

Reference yield: 11.9%

2-(3,4-Dihydroxy-phenyl)-5,7-dihydroxy-3-methoxy-chromen-4-on (1486-70-0) + dimethyl sulfate (77-78-1) → 3,4'-O-dimethylquercetin (33429-83-3) + 2-(3,4-dihydroxyphenyl)-5-hydroxy-3,7-dimethoxychromen-4-one (2068-02-2) + ayanin (572-32-7)

Guidance literature:

With potassium carbonate; In N,N-dimethyl-formamide; at 65 ℃; for 6h;

DOI:10.1016/j.bmc.2014.04.053

Reference yield:

rutin (153-18-4) → 3,4'-O-dimethylquercetin (33429-83-3) + 2-(3,4-dihydroxyphenyl)-5-hydroxy-3,7-dimethoxychromen-4-one (2068-02-2) + ayanin (572-32-7)

Guidance literature:

Multi-step reaction with 4 steps

1.1: potassium carbonate / N,N-dimethyl-formamide / 10 h / 20 °C / Inert atmosphere

1.2: 2 h / 80 °C

2.1: potassium carbonate / N,N-dimethyl-formamide / 6 h / 65 °C

3.1: hydrogen; palladium 10% on activated carbon / ethanol; tetrahydrofuran / 1 h / 20 °C / 375.04 Torr

4.1: potassium carbonate / N,N-dimethyl-formamide / 6 h / 65 °C

With palladium 10% on activated carbon; hydrogen; potassium carbonate; In tetrahydrofuran; ethanol; N,N-dimethyl-formamide;

DOI:10.1016/j.bmc.2014.04.053

upstream raw materials:

quercetol

methyl iodide

2-(3,4-Dihydroxy-phenyl)-5,7-dihydroxy-3-methoxy-chromen-4-on

dimethyl sulfate

Downstream raw materials:

tamarixetin

ayanin

retusin

3,5,7-triethoxy-2-(3-ethoxy-4-methoxy-phenyl)-chromen-4-one

Refernces

• 1、 Yamauchi, Kosei,Mitsunaga, Tohru,Inagaki, Mizuho,Suzuki, Tohru. "Synthesized quercetin derivatives stimulate melanogenesis in B16 melanoma cells by influencing the expression of melanin biosynthesis proteins MITF and p38 MAPK". . p. 3331 - 3340. Retrieved 2014/06/23.