Epigallocatechin 3-O-p-coumarate

Base Information

• Chemical Name: Epigallocatechin 3-O-p-coumarate
• CAS No.: 89013-65-0
• Molecular Formula: C₂₄H₂₀O₉
• Molecular Weight: 452.417
• Wikidata: Q76390119
• Metabolomics Workbench ID: 21947
• ChEMBL ID: CHEMBL345400
• Mol file: 89013-65-0.mol

Synonyms:Epigallocatechin 3-O-p-coumarate;[(2R,3R)-5,7-dihydroxy-2-(3,4,5-trihydroxyphenyl)-3,4-dihydro-2H-chromen-3-yl] (E)-3-(4-hydroxyphenyl)prop-2-enoate;89013-65-0;CHEMBL345400;3-O-p-Coumaroylepigallocatechin;CHEBI:136601;(-)-Epigallocatechin 3-p-coumaroate;LMPK12020117;(-)-Epigallocatechin 3-O-p-coumaroate;5,7-dihydroxy-2-(3,4,5-trihydroxyphenyl)chroman-3-yl 3-(4-hydroxyphenyl)prop-2-enoate;[(2R,3R)-5,7-dihydroxy-2-(3,4,5-trihydroxyphenyl)chroman-3-yl] (E)-3-(4-hydroxyphenyl)prop-2-enoate

Chemical Property of Epigallocatechin 3-O-p-coumarate

Chemical Property:

• XLogP3: 2.3
• Hydrogen Bond Donor Count: 6
• Hydrogen Bond Acceptor Count: 9
• Rotatable Bond Count: 5
• Exact Mass: 452.11073221
• Heavy Atom Count: 33
• Complexity: 679

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: C1C(C(OC2=CC(=CC(=C21)O)O)C3=CC(=C(C(=C3)O)O)O)OC(=O)C=CC4=CC=C(C=C4)O
• Isomeric SMILES: C1[C@H]([C@H](OC2=CC(=CC(=C21)O)O)C3=CC(=C(C(=C3)O)O)O)OC(=O)/C=C/C4=CC=C(C=C4)O

Technology Process of Epigallocatechin 3-O-p-coumarate

There total 16 articles about Epigallocatechin 3-O-p-coumarate 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: 56.0%

C60H104O9Si6 → (-)-epigallocatechin 3-O-p-coumaroate (89013-65-0,110548-83-9)

Guidance literature:

With pyridine; pyridine hydrogenfluoride; In tetrahydrofuran; at 20 ℃; for 0.5h; Cooling with ice;

Reference yield: 56.0%

(2R,3R)-5,7-di((tert-butyldimethylsilyl)oxy)-2-(3,4,5-tri((tert-butyldimethylsilyl)oxy)phenyl)chroman-3-yl (E)-3-(4-((tert-butyldimethylsilyl)oxy)phenyl)acrylate → (-)-epigallocatechin 3-O-p-coumaroate (89013-65-0,110548-83-9)

Guidance literature:

With pyridine hydrogenfluoride; In tetrahydrofuran; at 20 ℃;

DOI:10.1039/c6ra23172a

Reference yield: 55.0%

4-O-acetyl-epigallocatechin trans-coumarate → (-)-epigallocatechin 3-O-p-coumaroate (89013-65-0,110548-83-9)

Guidance literature:

With ammonium acetate; water; In methanol; at 20 ℃; for 5h;

upstream raw materials:

4-tert-butyldimethylsilyloxicinnamic acid

(-)-epigallocatechin-3-gallate octa(tert-butyldimethylsilyl) ether

p-[(tert-butyldimethylsilyl)oxy]benzaldehyde

4-hydroxy-benzaldehyde

Downstream raw materials:

(E)-(2R,3R)-5,7-dimethoxy-2-(3,4,5-trimethoxyphenyl)chroman-3-yl 3-(4-methoxyphenyl)acrylate