223387-33-5

Basic information

• Product Name: 5,7,3',4'-tetra-O-benzyl-3-(3,4,5-tri-O-benzyl-galloyl)-epicatechin-(4β,8)-5,7,3',4'-tetra-O-benzyl-3-(3,4,5-tri-O-benzyl-galloyl)-epicatechin
• CAS NO: 223387-33-5
• Molecular Weight: 2144.49
• Mol File: 223387-33-5.mol
• Article Data: 8

Chemical Properties

• Density: 1.34±0.1 g/cm3(Predicted)
• CAS DataBase Reference: 5,7,3',4'-tetra-O-benzyl-3-(3,4,5-tri-O-benzyl-galloyl)-epicatechin-(4β,8)-5,7,3',4'-tetra-O-benzyl-3-(3,4,5-tri-O-benzyl-galloyl)-epicatechin(CAS DataBase Reference)
• NIST Chemistry Reference: 5,7,3',4'-tetra-O-benzyl-3-(3,4,5-tri-O-benzyl-galloyl)-epicatechin-(4β,8)-5,7,3',4'-tetra-O-benzyl-3-(3,4,5-tri-O-benzyl-galloyl)-epicatechin(223387-33-5)
• EPA Substance Registry System: 5,7,3',4'-tetra-O-benzyl-3-(3,4,5-tri-O-benzyl-galloyl)-epicatechin-(4β,8)-5,7,3',4'-tetra-O-benzyl-3-(3,4,5-tri-O-benzyl-galloyl)-epicatechin(223387-33-5)

Safety Data

• Hazardous Substances Data: 223387-33-5(Hazardous Substances Data)

Usage

Description

5,7,3',4'-tetra-O-benzyl-3-(3,4,5-tri-O-benzyl-galloyl)-epicatechin-(4β,8)-5,7,3',4'-tetra-O-benzyl-3-(3,4,5-tri-O-benzyl-galloyl)-epicatechin is a complex organic compound that belongs to the group of flavonoids. It is characterized by its unique structure, which includes multiple benzyl and galloyl groups attached to the epicatechin molecule. 5,7,3',4'-tetra-O-benzyl-3-(3,4,5-tri-O-benzyl-galloyl)-epicatechin-(4β,8)-5,7,3',4'-tetra-O-benzyl-3-(3,4,5-tri-O-benzyl-galloyl)-epicatechin serves as an intermediate in the synthesis of Procyanidin B2 3,3''-di-O-gallate, a compound with significant biological activities.

Uses

Used in Pharmaceutical Industry:
5,7,3',4'-tetra-O-benzyl-3-(3,4,5-tri-O-benzyl-galloyl)-epicatechin-(4β,8)-5,7,3',4'-tetra-O-benzyl-3-(3,4,5-tri-O-benzyl-galloyl)-epicatechin is used as an intermediate in the synthesis of Procyanidin B2 3,3''-di-O-gallate for its potential anticancer properties. Procyanidin B2 3,3''-di-O-gallate has been found to inhibit the growth of human prostate carcinoma cell lines, making it a promising candidate for the development of new cancer treatments.
Used in Research and Development:
5,7,3',4'-tetra-O-benzyl-3-(3,4,5-tri-O-benzyl-galloyl)-epicatechin-(4β,8)-5,7,3',4'-tetra-O-benzyl-3-(3,4,5-tri-O-benzyl-galloyl)-epicatechin is also used in research and development for studying the structure-activity relationships of flavonoids and their potential applications in various human cancer diseases. Understanding the properties and mechanisms of action of 5,7,3',4'-tetra-O-benzyl-3-(3,4,5-tri-O-benzyl-galloyl)-epicatechin-(4β,8)-5,7,3',4'-tetra-O-benzyl-3-(3,4,5-tri-O-benzyl-galloyl)-epicatechin can provide valuable insights into the development of novel therapeutic agents for cancer treatment.

Upstream product

• 1486-48-2 3,4,5-tribenzyloxybenzoic acid 
• 256236-30-3 (-)-(2R,3R)-5,7-bis(benzyloxy)-2-[3,4-bis(benzyloxy)phenyl]chroman-3-yl 3,4,5-tris(benzyloxy)benzoate 
• 828249-32-7 (2R,3S,4S)-5,7,3',4'-tetra-O-benzyl-4-(2''-ethoxyethoxy)flavan-3-yl (3'',4'',5''-tri-O-benzyl)gallate 
• 223387-28-8 5,7,3',4'-tetra-O-benzyl-(-)-epicatechin-(4β,8)-[5,7,3',4'-tetra-O-benzyl-(-)-epicatechin] 
• 1486-47-1 3,4,5-tris(benzyloxy)benzoyl chloride 
• 851775-46-7 (2R,3R,4S)-5,7,3',4'-tetra-O-benzyl-4-(2''-ethoxyethoxy)flavan-3-yl (3''',4''',5'''-tri-O-benzyl)gallate 
• 732298-13-4 (+)-(2R,3S)-5,7-bis(benzyloxy)-2-[3,4-bis(benzyloxy)phenyl]chroman-3-yl 3,4,5-tris(benzyloxy)benzoate 
• 137550-06-2 5,7,3',4'-tetra-O-benzyl-4α-(5,7,3',4'-tetra-O-benzylcatechin)catechin 

Relevant articles and documents

Synthesis of galloyl-substituted procyanidin B4 series, and their DPPH radical scavenging activity and DNA polymerase inhibitory activity

Synthesis of galloyl-substituted procyanidin B4 series, 3-O-gallate, 3″-O-gallate and 3,3″-di-O-gallate, is described. Condensationof the electrophile derived from (+)-catechin with the nucleophile derived from (-)-epicatechin the presence of TMSOTf as a

Processes for the preparation of protected-(+)-catechin and (-)-epicatechin monomers, for coupling the protected monomers with an activated, protected epicatechin monomer, and for the preparation of epicatechin-(4B,8)-epicatechin or -catechin dimers and their digallates

Improved processes for the preparation of tetra-O-benzyl protected catechin, for the coupling of the tetra-O-benzyl protected catechin or epicatechin with a C-4 activated, tetra-O-benzyl protected epicatechin for the galloylation of the epicatechin-(4β,8)-catechin or -epicatechin dimer-the dimer digallates, and for the deprotection (i.e., debenzylation) of the protected epicatechin dimers and protected epicatechin dimer digallates are disclosed.

Systematic synthesis of galloyl-substituted procyanidin B1 and B2, and their ability of DPPH radical scavenging activity and inhibitory activity of DNA polymerases

Six galloyl-substituted procyanidin B1 and B2, 3-O-gallate, 3″-O-gallate, and 3,3″-di-O-gallate, were systematically synthesized with the condensation method using TMSOTf as a catalyst. Their ability of DPPH radical scavenging activity and DNA polymerase inhibitory activity were also investigated. The results indicated that the galloyl group of these compounds is very important for both activities. 3,3″-Di-O-gallate dimers acted as strong inhibitor against DNA polymerase α and β, whereas the desgalloyl and monogalloyl compounds did not exhibit any appreciable inhibitory activity against the DNA polymerase β.