3-Hydroxy-3',4',5,7-tetramethoxyflavone

Base Information

• Chemical Name: 3-Hydroxy-3',4',5,7-tetramethoxyflavone
• CAS No.: 1244-78-6
• Molecular Formula: C19H18 O7
• Molecular Weight: 358.348
• Hs Code.: 2914509090
• NSC Number: 102049
• UNII: UUX3TU2JXT
• DSSTox Substance ID: DTXSID40154319
• Nikkaji Number: J847.558J
• Wikidata: Q27158341
• Metabolomics Workbench ID: 25854
• ChEMBL ID: CHEMBL74675
• Mol file: 1244-78-6.mol

Synonyms:1244-78-6;3-Hydroxy-3',4',5,7-tetramethoxyflavone;Averionol;Quercetin 5,7,3',4'-tetramethyl ether;3',4',5,7-Tetramethylquercetin;5-hydroxy-7,3',4',5'-tetramethoxyflavone;UUX3TU2JXT;Flavone, 3-hydroxy-3',4',5,7-tetramethoxy-;NSC102049;NSC-102049;2-(3,4-Dimethoxyphenyl)-3-hydroxy-5,7-dimethoxy-4H-chromen-4-one;2-(3,4-dimethoxyphenyl)-3-hydroxy-5,7-dimethoxychromen-4-one;CHEBI:85124;QUERCETIN TETRAMETHYL (5,7,3',4') ETHER;NSC 102049;4H-1-Benzopyran-4-one, 2-(3,4-dimethoxyphenyl)-3-hydroxy-5,7-dimethoxy-;Spectrum_000784;3-Hydroxy-3,4, 5,7-tetramethoxyflavone;SpecPlus_000312;UNII-UUX3TU2JXT;Spectrum2_000711;Spectrum3_001253;Spectrum4_001473;Spectrum5_000145;BSPBio_002786;KBioGR_002045;KBioSS_001264;SPECTRUM300538;CHEMBL74675;DivK1c_006408;SPBio_000921;SCHEMBL3135319;Flavone,4',5,7-tetramethoxy-;KBio1_001352;KBio2_001264;KBio2_003832;KBio2_006400;KBio3_002286;DTXSID40154319;CCG-38364;LMPK12112771;AKOS005145745;3-Hydroxy-3',5,7-tetramethoxyflavone;SDCCGMLS-0066515.P001;NCGC00095598-01;NCGC00095598-02;NCGC00178472-01;NCI60_000056;3-hydroxy-5,7,3',4'-tetramethoxyflavone;Quercetin tetramethyl(3',4',5,7) ether;3-Hydroxy-3',4', 5,7-tetramethoxyflavone;3-Hydroxy-3/',4/',5,7-tetramethoxyflavone;F87819;QUERCETIN 3',4',5,7-TETRAMETHYL ETHER;A805642;SR-05000002615;SR-05000002615-1;BRD-K08825053-001-02-9;Q27158341;2-(3,4-dimethoxyphenyl)-3-hydroxy-5,7-dimethoxy-chromen-4-one;2-(3,4-dimethoxyphenyl)-5,7-dimethoxy-3-oxidanyl-chromen-4-one;4H-1-Benzopyran-4-one,4-dimethoxyphenyl)-3-hydroxy-5,7-dimethoxy-;2-(3,4-dimethoxyphenyl)-3-hydroxy-5,7-dimethoxy-1-benzopyran-4-one;2-(3,4-Dimethoxyphenyl)-3-hydroxy-5,7-dimethoxy-4H-1-benzopyran-4-one;4H-1-Benzopyran-4-one, 2-(3, 4-dimethoxyphenyl)-3-hydroxy-5,7-dimethoxy-;4H-1-Benzopyran-4-one, 2-(3,4-dimethoxyphenyl)-3-hydroxy-5,7-dimethoxy- (9CI)

Chemical Property of 3-Hydroxy-3',4',5,7-tetramethoxyflavone

Chemical Property:

• Vapor Pressure: 5.7E-13mmHg at 25°C
• Melting Point: 195.6 °C
• Boiling Point: 550.9°Cat760mmHg
• PKA: 7.98±0.20(Predicted)
• Flash Point: 198.3°C
• PSA: 87.36000
• Density: 1.325g/cm³
• LogP: 3.20000
• XLogP3: 2.9
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 5
• Exact Mass: 358.10525291
• Heavy Atom Count: 26
• Complexity: 546

Purity/Quality:

99%, ^*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(O2)C=C(C=C3OC)OC)O)OC

Technology Process of 3-Hydroxy-3',4',5,7-tetramethoxyflavone

There total 32 articles about 3-Hydroxy-3',4',5,7-tetramethoxyflavone 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: 92.2%

5,7,3',4'-O-tetramethylrutin (58528-03-3) → 2-(3,4-dimethoxyphenyl)-3-hydroxy-5,7-dimethoxy-4H-4-chromenone (1244-78-6)

Guidance literature:

With hydrogenchloride; In water; for 1h; Reflux;

DOI:10.3390/molecules19044791

Reference yield: 86.0%

2-(3,4-dimethoxyphenyl)-5,7-dimethoxy-4H-chromen-4-one (855-97-0) → 2-(3,4-dimethoxyphenyl)-3-hydroxy-5,7-dimethoxy-4H-4-chromenone (1244-78-6)

Guidance literature:

With 3,3-dimethyldioxirane; In dichloromethane; acetone; at 0 - 20 ℃; for 0.5h;

DOI:10.1016/j.tet.2004.01.023

Reference yield: 85.0%

C9H10O5 + 3,4-dimethoxy-benzaldehyde (120-14-9) → 2-(3,4-dimethoxyphenyl)-3-hydroxy-5,7-dimethoxy-4H-4-chromenone (1244-78-6)

Guidance literature:

With pyrrolidine; oxygen; In water; at 50 ℃; under 760.051 Torr;

DOI:10.1021/acs.joc.0c01869

upstream raw materials:

diazomethane

quercetol

pentamethyl quercetin

(2R^*,3S^*,4R^*)-flavan-3,4-diol

Downstream raw materials:

2-(3,4-dimethoxy-phenyl)-5,7-dimethoxy-3-(tri-O-acetyl-α-L-arabinopyranosyloxy)-chromen-4-one

3-(3',4',5,7-tetramethoxyflavonyl-3-oxy)propan-1-ol

quercetin 5,7,3',4'-tetramethyl ether-3-acetate

pentamethyl quercetin

Refernces

• 1、 Zapesockonaya,Ban'kovskii. "-". . . Retrieved 1965.
• 2、 Sakurai, Atsushi,Okumura, Yasuaki. "Chemical Studies on the Mistletoe. V. The Structure of Taxillusin, a New Flavonoid Glycoside Isolated from Taxillus kaempferi". . p. 542 - 544. Retrieved 1983.
• 3、 Wang, Gang-Qiang,Yan, Li-Li,Wang, Qiu-An. "Synthesis and antiproliferative activity of flavonoid triazolyl glycosides". . p. 119 - 124. Retrieved 2018.
• 4、 Yang, Hao-Jie,Li, Ya-Nan,Yan, Chen,Yang, Jue,Zeng, Yan-Rong,Yi, Ping,Li, Yan-Mei,Hao, Xiao-Jiang,Yuan, Chun-Mao. "Discovery and synthesis of rocaglaol derivatives inducing apoptosis in HCT116 cells via suppression of MAPK signaling pathway". . . Retrieved 2021/03/16.
• 5、 Chen, Hongping,Ding, Haiyan,Hu, Yuan,Li, Dan,Liu, Youping,You, Qiang. "Pharmacokinetics and Metabolites of 12 Bioactive Polymethoxyflavones in Rat Plasma". . p. 12705 - 12716. Retrieved 2021/11/17.