Sinensetin

Base Information

• Chemical Name: Sinensetin
• CAS No.: 2306-27-6
• Molecular Formula: C20H20O7
• Molecular Weight: 372.375
• Hs Code.: 29329990
• European Community (EC) Number: 803-609-7
• UNII: 240LNZ51AT
• DSSTox Substance ID: DTXSID60177626
• Nikkaji Number: J94.519F
• Wikipedia: Sinensetin
• Wikidata: Q3484909
• Metabolomics Workbench ID: 24333
• ChEMBL ID: CHEMBL226507
• Mol file: 2306-27-6.mol

Synonyms:3',4',5,6,7-pentamethoxyflavone;sinensetin

Chemical Property of Sinensetin

Chemical Property:

• Appearance/Colour: pale creamy yellow powder
• Vapor Pressure: 4.73E-12mmHg at 25°C
• Melting Point: 174-176°C
• Refractive Index: 1.565
• Boiling Point: 547.76 °C at 760 mmHg
• Flash Point: 240.561 °C
• PSA: 76.36000
• Density: 1.244 g/cm³
• LogP: 3.50300
• Storage Temp.: 2-8°C
• Solubility.: DMSO: soluble3mg/mL, clear (warmed)
• 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:

≥96% ^*data from raw suppliers

Sinensetin ^*data from reagent suppliers

Safty Information:

• Pictogram(s): T
• Hazard Codes: T
• Statements: 25
• Safety Statements: 22-24/25-45

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC1=C(C=C(C=C1)C2=CC(=O)C3=C(C(=C(C=C3O2)OC)OC)OC)OC
• Uses: Sinensetin, eupatorin, 3'-hydroxy-5,6,7,4'-tetramethoxyflavone and rosmarinic acid contents and antioxidative effect of Orthosiphon stamineus from Malaysia. antiangiogenesis, antidiabetic Sinensetin exhibits anti-fungal, anti-histamine activity; induce cell differentiation, inhibition of linoleic acid oxidation, inhibition of white blood cells in the human zona protein Interleukin -1-i nduced expression of tissue factor.

Technology Process of Sinensetin

There total 22 articles about Sinensetin 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: 81.0%

3,4-dimethoxybenzoic acid chloride (3535-37-3) + Eudesmic acid (118-41-2) → sinensetin (2306-27-6,27181-91-5)

Guidance literature:

3,4-dimethoxybenzoic acid chloride; Eudesmic acid; With triethylamine; In dichloromethane; at 0 - 20 ℃; for 2h;

With trimethylsilyl trifluoromethanesulfonate; triethylamine; In dichloromethane; at 95 ℃; for 2h;

Reference yield: 76.0%

2'-hydroxy-3,4,4',5',6'-pentamethoxychalcone (65602-54-2) → sinensetin (2306-27-6,27181-91-5)

Guidance literature:

With sulfuric acid; In dimethyl sulfoxide; Heating;

DOI:10.1080/14786419.2021.1961136

Reference yield: 71.0%

(E)-3-(3,4-dimethoxyphenyl)-1-(6-hydroxy-2,3,4-trimethoxyphenyl)prop-2-en-1-one (114021-62-4) → sinensetin (2306-27-6,27181-91-5)

Guidance literature:

With pyridine; iodine; for 8h; Heating;

DOI:10.1016/j.tet.2004.01.023

upstream raw materials:

(E)-3-(3,4-dimethoxyphenyl)-1-(6-hydroxy-2,3,4-trimethoxyphenyl)prop-2-en-1-one

3,6-dihydroxy-2,4-dimethoxyacetophenone

3,4-dimethoxybenzoic anhydride

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

Downstream raw materials:

gardenin B

5-hydroxy-4',6,7-trimethoxyflavone

5-desmethylsinensetin

artemetin

Refernces

• 1、 Morita et al.. "-". . p. 421,423. Retrieved 1973.
• 2、 -. "Nobiletin derivative or pharmaceutically acceptable salt thereof as well as preparation method and application thereof". . . Retrieved 2019/12/09.
• 3、 Kumar, Rohitesh,Lu, Yuting,Elliott, Alysha G.,Kavanagh, Angela M.,Cooper, Matthew A.,Davis, Rohan A.. "Semi-synthesis and NMR spectral assignments of flavonoid and chalcone derivatives". . p. 880 - 886. Retrieved 2016/10/25.