Epicatechin-3-gallate

Base Information

• Chemical Name: Epicatechin-3-gallate
• CAS No.: 863-03-6
• Molecular Formula: C₂₂H₁₈O₁₀
• Molecular Weight: 442.379
• Nikkaji Number: J676.226C
• Wikidata: Q27145772
• NCI Thesaurus Code: C68454
• Metabolomics Workbench ID: 21922
• ChEMBL ID: CHEMBL126142
• Mol file: 863-03-6.mol

Synonyms:epicatechin gallate;epicatechin gallate, (2R-cis)-isomer;epicatechin-3-gallate;epicatechin-3-galloyl ester;epicatechin-3-O-gallate

Chemical Property of Epicatechin-3-gallate

Chemical Property:

• Vapor Pressure: 3.33E-31mmHg at 25°C
• Boiling Point: 861.7°C at 760 mmHg
• PKA: 7.75±0.25(Predicted)
• Flash Point: 305°C
• Density: 1.8g/cm³
• XLogP3: 1.5
• Hydrogen Bond Donor Count: 7
• Hydrogen Bond Acceptor Count: 10
• Rotatable Bond Count: 4
• Exact Mass: 442.08999677
• Heavy Atom Count: 32
• Complexity: 649

Purity/Quality:

98.5% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

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

Technology Process of Epicatechin-3-gallate

There total 41 articles about Epicatechin-3-gallate 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: 98.0%

(-)-(2R,3R)-5,7-bis(benzyloxy)-2-[3,4-bis(benzyloxy)phenyl]chroman-3-yl 3,4,5-tris(benzyloxy)benzoate (256236-30-3) → (-)-epicatechin gallate (863-03-6,10517-25-6,13445-34-6,17431-25-3,20819-16-3,25615-05-8,130405-40-2,1257-08-5)

Guidance literature:

With 5% Pd(OH)₂/C; hydrogen; In tetrahydrofuran; methanol; water; at 20 ℃; for 0.5h;

DOI:10.1039/c003464a

Reference yield:

platanoside-A (1255211-38-1) → β-D-glucose (492-61-5) + cyanidin (13306-05-3) + (-)-epicatechin gallate (863-03-6,10517-25-6,13445-34-6,17431-25-3,20819-16-3,25615-05-8,130405-40-2,1257-08-5)

Guidance literature:

With hydrogenchloride; water; In ethanol; for 2h; Inert atmosphere; Reflux;

DOI:10.1007/s10600-010-9616-3

Reference yield:

platanoside-B (1255211-63-2) → β-D-glucose (492-61-5) + cyanidin (13306-05-3) + O-β-(6-O-galloyl)-glucopyranoside (7253-25-0,34781-46-9) + (-)-epicatechin gallate (863-03-6,10517-25-6,13445-34-6,17431-25-3,20819-16-3,25615-05-8,130405-40-2,1257-08-5)

Guidance literature:

With hydrogenchloride; water; In ethanol; Inert atmosphere; Reflux;

DOI:10.1007/s10600-010-9616-3

upstream raw materials:

proanthocyanidin B₆

(-)-epigallocatechin (4β-8)-(-)-epigallocatechin 3-O-gallate

phenylmethanethiol

epigallocatechin 3-O-gallate-(4β->6)-epicatechin 3-O-gallate

Downstream raw materials:

(2R,3R)-5,7-dimethoxy-2-(3,4-dimethoxyphenyl)-3,4-dihydrobenzopyran-3-ol 3,4,5-trimethoxybenzoate

(-)-ECG-7TBS

theaflavate C

bistheaflavate A

Refernces

• 1、 Sakakibara, Takumi,Sawada, Yoshiharu,Wang, Jilite,Nagaoka, Satoshi,Yanase, Emiko. "Molecular Mechanism by Which Tea Catechins Decrease the Micellar Solubility of Cholesterol". . . Retrieved 2019/07/03.
• 2、 Vyas, Sandeep,Manon, Benu,Vir Singh, Tej,Dev Sharma, Pritam,Sharma, Manu. "Potential O-acyl-substituted (-)-epicatechin gallate prodrugs as inhibitors of DMBA/TPA-induced squamous cell carcinoma of skin in swiss albino mice". experimental part. p. 599 - 613. Retrieved 2011/11/12.