Quercetin 3,3'-dimethyl ether

Base Information

• Chemical Name: Quercetin 3,3'-dimethyl ether
• CAS No.: 4382-17-6
• Molecular Formula: C17H14O7
• Molecular Weight: 330.294
• Hs Code.: 2914509090
• NSC Number: 254669
• UNII: J03N0KJ42I
• DSSTox Substance ID: DTXSID60195941
• Nikkaji Number: J910E
• Wikidata: Q27280983
• Metabolomics Workbench ID: 75265
• ChEMBL ID: CHEMBL511363
• Mol file: 4382-17-6.mol

Synonyms:3,3'-di-O-methylquercetin;3,3'-dimethoxyquercetin

Chemical Property of Quercetin 3,3'-dimethyl ether

Chemical Property:

• Vapor Pressure: 3.19E-15mmHg at 25°C
• Melting Point: 257-258 °C
• Boiling Point: 604.8°C at 760 mmHg
• PKA: 6.31±0.40(Predicted)
• Flash Point: 226.4°C
• PSA: 109.36000
• Density: 1.55g/cm³
• LogP: 2.59400
• 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:

Analysis control,97.5% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

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

Technology Process of Quercetin 3,3'-dimethyl ether

There total 6 articles about Quercetin 3,3'-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:

2-(3,4-Dihydroxy-phenyl)-5,7-dihydroxy-3-methoxy-chromen-4-on (1486-70-0) + S-adenosyl-L-methionine (485-80-3,15519-60-5,60018-85-1,60018-86-2,79845-28-6) → 3,3'-di-O-methylquercetin (4382-17-6)

Guidance literature:

With Citrus reticulata O-methyltransferase gene-pET₃₂a recombinant; In aq. buffer; at 37 ℃; for 2h; pH=8; Enzymatic reaction;

DOI:10.3390/molecules25040858

Reference yield:

quercetin 3,3'-dimethyl ether 7-rutinoside → 3,3'-di-O-methylquercetin (4382-17-6)

Guidance literature:

With hydrogenchloride; at 110 ℃; for 4h;

DOI:10.1016/S0031-9422(97)01113-8

upstream raw materials:

quercetol

methyl iodide

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

S-adenosyl-L-methionine

Downstream raw materials:

6-prenyl-5,7,4'-trihydroxy-3,3'-dimethoxyflavone

8-prenyl-5,7,4'-trihydroxy-3,3'-dimethoxyflavone

4',5-dihydroxy-3,3'-dimethoxy-7-(3-methylbut-2-enyloxy)flavone

7,4'-diacetyloxy-5-hydroxy-3,3'-dimethoxyflavone

Refernces

• 1、 Liu, Xiaojuan,Wang, Yue,Chen, Yezhi,Xu, Shuting,Gong, Qin,Zhao, Chenning,Cao, Jinping,Sun, Chongde. "Characterization of a Flavonoid 3’/5’/7-O-Methyltransferase from Citrus reticulata and Evaluation of the in Vitro Cytotoxicity of Its Methylated Products". . . Retrieved 2020/02/25.
• 2、 Woo, Won Sick,Choi, Jae Sue,Kang, Sam Sik. "A FLAVONOL GLUCOSIDE FROM TYPHA LATIFOLIA". . p. 2881 - 2882. Retrieved 2007/10/02.