(-)-Epicatechin gallate

Base Information

• Chemical Name: (-)-Epicatechin gallate
• CAS No.: 1257-08-5
• Molecular Formula: C₂₂H₁₈O₁₀
• Molecular Weight: 442.379
• Hs Code.: 29329990
• European Community (EC) Number: 603-088-4
• UNII: 92587OVD8Z
• DSSTox Substance ID: DTXSID70925231
• Nikkaji Number: J277.682K
• Wikipedia: Epicatechin_gallate
• Wikidata: Q5382492
• Pharos Ligand ID: 3MRW8BM6R5AH
• Metabolomics Workbench ID: 21920
• ChEMBL ID: CHEMBL36327
• Mol file: 1257-08-5.mol

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

Chemical Property of (-)-Epicatechin gallate

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 257-258 °C
• Refractive Index: 1.769
• Boiling Point: 861.7 °C at 760 mmHg
• PKA: 7.75±0.25(Predicted)
• Flash Point: 305 °C
• PSA: 177.14000
• Density: 1.8 g/cm³
• LogP: 2.52760
• Storage Temp.: 2-8°C
• Solubility.: Acetone (Sparingly), DMSO (Slightly), Methanol (Slightly)
• Water Solubility.: Soluble in water, acetone, DMSO, methanol.
• 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:

99% ^*data from raw suppliers

(-)-Epicatechin gallate ^*data from reagent suppliers

Safty Information:

• Safety Statements: 24/25

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
• Uses: One of the catechin isomers and a potent antioxidant that can modulate a wide range of membrane proteins. Its bilayer-modifying potency was tested using gramicidin A (gA) channels as probes. All the c atechins alter gA channel function and modify bilayer properties, with a 500-fold range in potency. The gallate group causes current block, as evident by brief downward current transitions. An antioxidant investigated as an adjunct treatment of some methyicillin resistant bacteria. (-)-Epicatechin gallate is polyphenols which are abundant in green and black teas. (-)-Epicatechin gallate (ECG) is a natural catechin with a single galloyl group. The hydroxyl groups of ECG contribute to its potent antioxidant activity and facilitate the killing of methicillin-resistant strains of S. aureus.

Technology Process of (-)-Epicatechin gallate

There total 41 articles about (-)-Epicatechin 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-dihydroxy-2-(3',4'-dihydroxy-phenyl)chroman-3-yl 3'',5''-dihydroxy-4''-methoxybenzoate

theaflavin-3-gallate

theaflavin-3-gallate

procyanidin B₄ 3'-O-gallate

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.