Isosinensetin

Base Information

• Chemical Name: Isosinensetin
• CAS No.: 17290-70-9
• Molecular Formula: C20H20O7
• Molecular Weight: 372.375
• Hs Code.: 2932999099
• UNII: 63Z99S38LE
• DSSTox Substance ID: DTXSID80348199
• Nikkaji Number: J282.485J
• Wikidata: Q27263667
• Metabolomics Workbench ID: 24486
• ChEMBL ID: CHEMBL451707
• Mol file: 17290-70-9.mol

Synonyms:Isosinensetin;17290-70-9;6-Demethoxynobiletin;5,7,8,3',4'-pentamethoxyflavone;2-(3,4-Dimethoxyphenyl)-5,7,8-trimethoxy-4H-chromen-4-one;6-Demethoxylnobiletin;2-(3,4-dimethoxyphenyl)-5,7,8-trimethoxychromen-4-one;UNII-63Z99S38LE;Flavone, 3',4',5,7,8-pentamethoxy-;63Z99S38LE;DTXSID80348199;4H-1-Benzopyran-4-one, 2-(3,4-dimethoxyphenyl)-5,7,8-trimethoxy-;3',4',5,7,8-Pentamethoxyflavone;SCHEMBL987761;CHEMBL451707;DTXCID60299271;CHEBI:175779;HY-N1941;LMPK12111403;AKOS016012041;AC-34952;AS-57493;XI161836;CS-0018252;FT-0775464;Isosinensetin3',4' ,5,7,8-pentamethoxyflavone;A881826;Q27263667;2-(3,4-Dimethoxyphenyl)-5,7,8-trimethoxy-4H-1-benzopyran-4-one;2-(3,4-Dimethoxyphenyl)-5,7,8-trimethoxy-4H-chromen-4-one #;2-(3,4-DimethoIsosinensetinxyphenyl)-5,7,8-trimethoxy-4H-chromen-4-one

Chemical Property of Isosinensetin

Chemical Property:

• Melting Point: 198-199℃
• Boiling Point: 565.3±50.0 °C(Predicted)
• PSA: 76.36000
• Density: 1.244±0.06 g/cm3(Predicted)
• LogP: 3.50300
• Storage Temp.: 2-8°C
• XLogP3: 3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 6
• Exact Mass: 372.12090297
• Heavy Atom Count: 27
• Complexity: 548

Purity/Quality:

95%-98% ^*data from raw suppliers

Isosinensetin ^*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=CC(=O)C3=C(O2)C(=C(C=C3OC)OC)OC)OC

Technology Process of Isosinensetin

There total 18 articles about Isosinensetin 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: 83.0%

1-(2-hydroxy-3,4,6-trimethoxyphenyl)-3-(3,4-dimethoxyphenyl)-1,3-propanedione (114866-05-6) → isosinensetin (17290-70-9)

Guidance literature:

With sulfuric acid; In acetic acid; for 0.025h; Heating; Microwave irradiation;

DOI:10.3987/COM-07-11054

Reference yield: 59.0%

5,8-dihydroxy-7-methoxy-2-(3,4-dimethoxyphenyl)-4-benzopyrone (71847-58-0) + dimethyl sulfate (77-78-1) → 5-hydroxy-3’,4’,7,8-tetramethoxyflavone (13003-74-2) + isosinensetin (17290-70-9)

Guidance literature:

With potassium carbonate; In acetone; for 1h; Heating;

DOI:10.1016/j.tet.2004.01.023

Reference yield:

5-hydroxy-3',4',7-trimethoxyflavone (29080-58-8) → isosinensetin (17290-70-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 93 percent / dimethyl dioxirane / acetone; CH₂Cl₂ / 0.33 h / 0 - 20 °C

2: 41 percent / K₂CO₃ / acetone / 1 h / Heating

With 3,3-dimethyldioxirane; potassium carbonate; In dichloromethane; acetone;

DOI:10.1016/j.tet.2004.01.023

upstream raw materials:

2'-hydroxy-3,4,3',4',6'-pentamethoxychalcone

5,8-dihydroxy-7-methoxy-2-(3,4-dimethoxyphenyl)-4-benzopyrone

dimethyl sulfate

3′,4′,5,7,8-pentahydroxyflavone

Downstream raw materials:

3',4',5,6,7-pentahydroxyflavone

5-hydroxy-3’,4’,7,8-tetramethoxyflavone

3′,4′,5,7,8-pentahydroxyflavone

Refernces

• 1、 Chu, Han-Wei,Wu, Huan-Ting,Lee, Yean-Jang. "Regioselective hydroxylation of 2-hydroxychalcones by dimethyldioxirane towards polymethoxylated flavonoids". . p. 2647 - 2655. Retrieved 2007/10/03.
• 2、 Shaw, S. C.,Azad, R.,Mandal, S. P.,Gandhi, R. S.. "Syntheses of 6-Hydroxyluteolin and Sinensetin by Wessely - Moser Rearrangement". . p. 107 - 109. Retrieved 2007/10/02.