Eupalitin

Base Information

• Chemical Name: Eupalitin
• CAS No.: 29536-41-2
• Molecular Formula: C17H14 O7
• Molecular Weight: 330.294
• Hs Code.: 2914509090
• UNII: P5KF23690D
• DSSTox Substance ID: DTXSID20183723
• Nikkaji Number: J21.597J
• Wikipedia: Eupalitin
• Wikidata: Q10859709
• Metabolomics Workbench ID: 25953
• Mol file: 29536-41-2.mol

Synonyms:3,5,4'-trihydroxy-6,7-dimethoxyflavone

Chemical Property of Eupalitin

Chemical Property:

• Vapor Pressure: 1.18E-14mmHg at 25°C
• Melting Point: 289-292℃
• Boiling Point: 587.7°Cat760mmHg
• PKA: 6.16±0.40(Predicted)
• Flash Point: 219.7°C
• PSA: 109.36000
• Density: 1.507g/cm³
• LogP: 2.59400
• XLogP3: 2.8
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 3
• Exact Mass: 330.07395278
• Heavy Atom Count: 24
• Complexity: 509

Purity/Quality:

98% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC1=C(C(=C2C(=C1)OC(=C(C2=O)O)C3=CC=C(C=C3)O)O)OC

Technology Process of Eupalitin

There total 9 articles about Eupalitin 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: 85.0%

2-(4-Benzyloxy-phenyl)-3,5-dihydroxy-6,7-dimethoxy-chromen-4-one (124910-03-8) → 3,5,4'-trihydroxy-6,7-dimethoxy-flavone (29536-41-2)

Guidance literature:

With hydrogen; palladium on activated charcoal; In methanol; ethyl acetate;

Reference yield:

sesuvioside A (1312097-78-1) → 3,5,4'-trihydroxy-6,7-dimethoxy-flavone (29536-41-2) + L-Rhamnose (3615-41-6,478518-52-4) + D-Galactose (59-23-4)

Guidance literature:

With hydrogenchloride; In 1,4-dioxane; water; at 80 ℃; for 4h;

DOI:10.1016/j.tet.2011.04.041

Reference yield:

p-(benzyloxy)benzoic acid anhydride (1486-49-3) → 3,5,4'-trihydroxy-6,7-dimethoxy-flavone (29536-41-2)

Guidance literature:

Multi-step reaction with 6 steps

1: 1.) potassium benzoate, 2.) K₂CO₃ / 1.) 170/180 deg C, 8 h, 2.) acetone, reflux, 2.5-4 h

2: 88 percent / AlBr₃ / acetonitrile / 0.33 h / 0 - 5 °C

3: 82 percent / K₂CO₃ / acetone / Heating

4: 91 percent / AlBr₃ / acetonitrile / 1 h / Ambient temperature

5: 86 percent / K₂CO₃ / methanol / 2 h / Heating

6: 85 percent / H₂ / 10percent palladium on charcoal / ethyl acetate; methanol

With aluminum tri-bromide; hydrogen; Potassium benzoate; potassium carbonate; palladium on activated charcoal; In methanol; ethyl acetate; acetone; acetonitrile;

upstream raw materials:

2-(4-Benzyloxy-phenyl)-3,5-dihydroxy-6,7-dimethoxy-chromen-4-one

p-(benzyloxy)benzoic acid anhydride

1-(3,6-dihydroxy-2,4-dimethoxy-phenyl)-2-methoxy-ethanone

2-(4-benzyloxy-phenyl)-5-hydroxy-3,6,7-trimethoxy-chromen-4-one

Downstream raw materials:

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

Refernces

• 1、 Horie, Tokunaru,Kawamura, Yasuhiko,Tsukayama, Masao,Yoshizaki, Shiro. "STUDIES OF THE SELECTIVE O-ALKYLATION AND DEALKYLATION OF FLAVONOIDS. XII. A NEW, CONVENIENT METHOD FOR SYNTHESIZING 3,5-DIHYDROXY-6,7-DIMETHOXYFLAVONES FROM 3,5,6,7-TETRAMETHOXYFLAVONES". . p. 1216 - 1220. Retrieved 2007/10/02.