Quercetin 7,3',4'-trimethyl ether

Base Information

• Chemical Name: Quercetin 7,3',4'-trimethyl ether
• CAS No.: 6068-80-0
• Molecular Formula: C18H16 O7
• Molecular Weight: 344.321
• DSSTox Substance ID: DTXSID00976115
• Nikkaji Number: J94.542K
• Wikidata: Q27138366
• Metabolomics Workbench ID: 25741
• ChEMBL ID: CHEMBL1689343
• Mol file: 6068-80-0.mol

Synonyms:6068-80-0;Quercetin 7,3',4'-trimethyl ether;3',4',7-Trimethylquercetin;3,5-Dihydroxy-7,3',4'-trimethoxyflavone;3',4',7-TRIMETHOXYQUERCETIN;347TRIMETHOXYQUERCETIN;2-(3,4-dimethoxyphenyl)-3,5-dihydroxy-7-methoxychromen-4-one;2-(3,4-dimethoxyphenyl)-3,5-dihydroxy-7-methoxy-4H-chromen-4-one;CHEBI:70024;2-(3,4-dimethoxyphenyl)-3,5-dihydroxy-7-methoxy-4H-1-Benzopyran-4-one;4H-1-Benzopyran-4-one, 2-(3,4-dimethoxyphenyl)-3,5-dihydroxy-7-methoxy-;SCHEMBL1250547;CHEMBL1689343;DTXSID00976115;HY-N7641;LMPK12112658;Quercetin 3',4',7-trimethyl ether;MS-25272;3,5-dihydroxy-3',4',7-trimethoxyflavone;CS-0134915;Flavone, 3,5-dihydroxy-3',4',7-trimethoxy-;Q27138366

Chemical Property of Quercetin 7,3',4'-trimethyl ether

Chemical Property:

• Vapor Pressure: 2.42E-13mmHg at 25°C
• Boiling Point: 559.2°C at 760 mmHg
• Flash Point: 204.9°C
• PSA: 98.36000
• Density: 1.407g/cm³
• LogP: 2.89700
• XLogP3: 2.5
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 4
• Exact Mass: 344.08960285
• Heavy Atom Count: 25
• Complexity: 532

Purity/Quality:

98.5% ^*data from raw 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)OC)O)O)OC

Technology Process of Quercetin 7,3',4'-trimethyl ether

There total 10 articles about Quercetin 7,3',4'-trimethyl 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: 91.0%

rutin (153-18-4) + methyl iodide (74-88-4) → 2-(3,4-dimethoxyphenyl)-3,5-dihydroxy-7-methoxy-4H-chromen-4-one (6068-80-0)

Guidance literature:

rutin; methyl iodide; With potassium carbonate; In N,N-dimethyl-formamide; at 40 ℃; for 3h; Inert atmosphere;

With hydrogenchloride; In ethanol; water; at 70 ℃; for 2h;

DOI:10.1016/j.ejmech.2012.04.044

Reference yield: 87.0%

2-(3,4-Dimethoxy-phenyl)-5-hydroxy-7-methoxy-3-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-((2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyl-tetrahydro-pyran-2-yloxymethyl)-tetrahydro-pyran-2-yloxy]-chromen-4-one → 2-(3,4-dimethoxyphenyl)-3,5-dihydroxy-7-methoxy-4H-chromen-4-one (6068-80-0)

Guidance literature:

With hydrogenchloride; methanol; for 2h; Heating;

DOI:10.1248/cpb.50.788

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

upstream raw materials:

3,4-dimethoxybenzoic anhydride

2-benzoyloxy-1-(2,6-dihydroxy-4-methoxy-phenyl)-ethanone

rutin

methyl iodide

Downstream raw materials:

3,5-diacetoxy-2-(3,4-dimethoxy-phenyl)-7-methoxy-chromen-4-one

Refernces

• 1、 Pabuprapap, Wachirachai,Wassanatip, Yanisa,Khetkam, Pichit,Chaichompoo, Waraluck,Kunkaewom, Sukanya,Senabud, Pongpan,Hata, Janejira,Chokchaisiri, Ratchanaporn,Svasti, Saovaros,Suksamrarn, Apichart. "Quercetin analogs with high fetal hemoglobin-inducing activity". . p. 1755 - 1765. Retrieved 2019/08/02.
• 2、 Shi, Zhi-Hao,Li, Nian-Guang,Tang, Yu-Ping,Wei-Li,Lian-Yin,Yang, Jian-Ping,Hao-Tang,Duan, Jin-Ao. "Metabolism-based synthesis, biologic evaluation and SARs analysis of O-methylated analogs of quercetin as thrombin inhibitors". experimental part. p. 210 - 222. Retrieved 2012/09/07.