3'-Hydroxy-5,6,7,4'-tetramethoxyflavone

Base Information

• Chemical Name: 3'-Hydroxy-5,6,7,4'-tetramethoxyflavone
• CAS No.: 21764-09-0
• Molecular Formula: C19H18 O7
• Molecular Weight: 358.348
• Hs Code.: 2914509090
• European Community (EC) Number: 686-159-2
• DSSTox Substance ID: DTXSID70427265
• Nikkaji Number: J428.538G
• Wikidata: Q82239960
• Pharos Ligand ID: ALY5SLTQ32BA
• Metabolomics Workbench ID: 24324
• ChEMBL ID: CHEMBL124885
• Mol file: 21764-09-0.mol

Synonyms:eupatorin-5-methyl ether

Chemical Property of 3'-Hydroxy-5,6,7,4'-tetramethoxyflavone

Chemical Property:

• Melting Point: 179-180°C
• Boiling Point: 573.7°Cat760mmHg
• PKA: 9.99±0.10(Predicted)
• Flash Point: 207.4°C
• PSA: 87.36000
• Density: 1.309g/cm³
• LogP: 3.20000
• Storage Temp.: Refrigerator, under inert atmosphere
• Solubility.: DMSO (Slightly), Methanol (Slightly)
• XLogP3: 2.7
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 5
• Exact Mass: 358.10525291
• Heavy Atom Count: 26
• Complexity: 534

Purity/Quality:

≥98% ^*data from raw suppliers

Eupatorin5-MethylEther ^*data from reagent suppliers

Safty Information:

• Pictogram(s): T
• Hazard Codes: T
• Statements: 25
• Safety Statements: 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)O
• Uses: Sinensetin, eupatorin, 3''-hydroxy-5,6,7,4''-tetramethoxyflavone and rosmarinic acid contents and antioxidative effect of Orthosiphon stamineus from Malaysia.

Technology Process of 3'-Hydroxy-5,6,7,4'-tetramethoxyflavone

There total 3 articles about 3'-Hydroxy-5,6,7,4'-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: 20.0%

2-[1-(3-Hydroxy-4-methoxy-phenyl)-meth-(Z)-ylidene]-4,5,6-trimethoxy-benzofuran-3-one (527750-40-9) → 2-(3,4dihydroxyphenyl)-5-hydroxy-7-[3,4,5-trihydroxy-6-(hydroxymethyl)(2H-3,4,5,6 tetrahydropyran-2-yloxy)]chromen-4-one (21764-09-0)

Guidance literature:

With potassium cyanide; In ethanol; dichloromethane; for 12h; Heating;

DOI:10.1016/j.bmcl.2003.07.003

Reference yield:

(3,4,5-trimethoxyphenoxy)acetic acid (65876-10-0) → 2-(3,4dihydroxyphenyl)-5-hydroxy-7-[3,4,5-trihydroxy-6-(hydroxymethyl)(2H-3,4,5,6 tetrahydropyran-2-yloxy)]chromen-4-one (21764-09-0)

Guidance literature:

Multi-step reaction with 3 steps

1: 60 percent / polyphosphoric acid / 8 h / 80 °C

2: 31 percent / Al₂O₃ / CH₂Cl₂ / 20 °C

3: 20 percent / KCN / ethanol; CH₂Cl₂ / 12 h / Heating

With potassium cyanide; aluminum oxide; PPA; In ethanol; dichloromethane; 1: Friedel-Crafts reaction;

DOI:10.1016/j.bmcl.2003.07.003

Reference yield:

6-hydroxy-2,3,4-trimethoxyacetophenone (22248-14-2) → 2-(3,4dihydroxyphenyl)-5-hydroxy-7-[3,4,5-trihydroxy-6-(hydroxymethyl)(2H-3,4,5,6 tetrahydropyran-2-yloxy)]chromen-4-one (21764-09-0)

Guidance literature:

Multi-step reaction with 2 steps

1: potassium-t-butoxide / ethanol / 85 °C

2: iodine / dimethyl sulfoxide / 100 °C

With potassium-t-butoxide; iodine; In ethanol; dimethyl sulfoxide;

DOI:10.1021/acs.jafc.1c07509

upstream raw materials:

2-[1-(3-Hydroxy-4-methoxy-phenyl)-meth-(Z)-ylidene]-4,5,6-trimethoxy-benzofuran-3-one

(3,4,5-trimethoxyphenoxy)acetic acid

6-hydroxy-2,3,4-trimethoxyacetophenone

Downstream raw materials:

eupatorin

Refernces

• 1、 Lawrence, Nicholas J.,Rennison, David,McGown, Alan T.,Hadfield, John A.. "The total synthesis of an aurone isolated from Uvaria hamiltonii: Aurones and flavones as anticancer agents". . p. 3759 - 3763. Retrieved 2007/10/03.