Eupatorin

Base Information

• Chemical Name: Eupatorin
• CAS No.: 855-96-9
• Molecular Formula: C18H16O7
• Molecular Weight: 344.321
• Hs Code.: 2932999099
• European Community (EC) Number: 663-133-9
• NSC Number: 106402
• UNII: 3J474AV6MY
• DSSTox Substance ID: DTXSID20234704
• Nikkaji Number: J7.145E
• Wikidata: Q3060386
• Pharos Ligand ID: JZ549ATBM16L
• Metabolomics Workbench ID: 24322
• ChEMBL ID: CHEMBL487402
• Mol file: 855-96-9.mol

Synonyms:3',5-dihydroxy-4',6,7-trimethoxyflavone;eupatorin

Chemical Property of Eupatorin

Chemical Property:

• Melting Point: 194-196°C
• Boiling Point: 587 °C at 760 mmHg
• PKA: 6.31±0.40(Predicted)
• Flash Point: 216 °C
• PSA: 98.36000
• Density: 1.387 g/cm³
• LogP: 2.89700
• Storage Temp.: room temp
• Solubility.: DMSO: >10mg/mL
• Water Solubility.: Insoluble in water. Soluble in chloroform and methanol.
• XLogP3: 2.9
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 4
• Exact Mass: 344.08960285
• Heavy Atom Count: 25
• Complexity: 520

Purity/Quality:

≥98% ^*data from raw suppliers

Eupatorin ^*data from reagent suppliers

Safty Information:

• Pictogram(s): T
• Hazard Codes: T
• Statements: 36/37/38-25
• Safety Statements: 26-36-45

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)O)O
• Uses: Eupatorin is a flavanoid with antiproliferative activity in cells expressing the CYP1 family. Eupatorin also displays antioxidant and anti-inflammatory activity. 3',5-Dihydroxy-4',6,7-trimethoxyflavone is an important raw material and intermediate used in organic synthesis, pharmaceuticals and agrochemicals.

Technology Process of Eupatorin

There total 4 articles about Eupatorin 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:

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) → eupatorin (855-96-9)

Guidance literature:

With hydrogenchloride; In water monomer; at 85 ℃;

DOI:10.1021/acs.jafc.1c07509

Reference yield:

(E)-3-(3-Hydroxy-4-methoxy-phenyl)-1-(6-hydroxy-2,3,4-trimethoxy-phenyl)-propenone (37656-97-6) → eupatorin (855-96-9)

Guidance literature:

Multi-step reaction with 2 steps

1: iodine / dimethyl sulfoxide / 100 °C

2: hydrogenchloride / water monomer / 85 °C

With hydrogenchloride; iodine; In water monomer; dimethyl sulfoxide;

DOI:10.1021/acs.jafc.1c07509

Reference yield:

3,4,5-trimethoxyphenol (642-71-7) → eupatorin (855-96-9)

Guidance literature:

Multi-step reaction with 4 steps

1: boron trifluoride diethyl ether complex / 85 °C

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

3: iodine / dimethyl sulfoxide / 100 °C

4: hydrogenchloride / water monomer / 85 °C

With hydrogenchloride; boron trifluoride diethyl ether complex; potassium-t-butoxide; iodine; In ethanol; water monomer; dimethyl sulfoxide;

DOI:10.1021/acs.jafc.1c07509

upstream raw materials:

(E)-3-(3-Hydroxy-4-methoxy-phenyl)-1-(6-hydroxy-2,3,4-trimethoxy-phenyl)-propenone

2-(3,4dihydroxyphenyl)-5-hydroxy-7-[3,4,5-trihydroxy-6-(hydroxymethyl)(2H-3,4,5,6 tetrahydropyran-2-yloxy)]chromen-4-one

3,4,5-trimethoxyphenol

6-hydroxy-2,3,4-trimethoxyacetophenone

Downstream raw materials:

Isovanillic acid

2,3-dimethoxy-1,6-dihydroxybenzene

Refernces