223387-28-8

Basic information

• Product Name: 5,7,3',4'-tetra-O-benzyl-(-)-epicatechin-(4β,8)-[5,7,3',4'-tetra-O-benzyl-(-)-epicatechin]
• Synonyms: 5,7,3',4'-tetra-O-benzyl-(-)-epicatechin-(4β,8)-[5,7,3',4'-tetra-O-benzyl-(-)-epicatechin]
• CAS NO: 223387-28-8
• Molecular Weight: 1299.53
• Mol File: 223387-28-8.mol
• Article Data: 12

Chemical Properties

• Density: 1.262±0.06 g/cm3(Predicted)
• CAS DataBase Reference: 5,7,3',4'-tetra-O-benzyl-(-)-epicatechin-(4β,8)-[5,7,3',4'-tetra-O-benzyl-(-)-epicatechin](CAS DataBase Reference)
• NIST Chemistry Reference: 5,7,3',4'-tetra-O-benzyl-(-)-epicatechin-(4β,8)-[5,7,3',4'-tetra-O-benzyl-(-)-epicatechin](223387-28-8)
• EPA Substance Registry System: 5,7,3',4'-tetra-O-benzyl-(-)-epicatechin-(4β,8)-[5,7,3',4'-tetra-O-benzyl-(-)-epicatechin](223387-28-8)

Safety Data

• Hazardous Substances Data: 223387-28-8(Hazardous Substances Data)

Usage

Description

5,7,3',4'-tetra-O-benzyl-(-)-epicatechin-(4β,8)-[5,7,3',4'-tetra-O-benzyl-(-)-epicatechin] is a complex organic compound that serves as an intermediate in the synthesis of Procyanidin B2 3,3''-Di-O-gallate (P755825). It belongs to the flavonoid group of compounds and is characterized by its unique structure with multiple benzyl groups attached to specific hydroxyl groups.

Uses

Used in Pharmaceutical Industry:
5,7,3',4'-tetra-O-benzyl-(-)-epicatechin-(4β,8)-[5,7,3',4'-tetra-O-benzyl-(-)-epicatechin] is used as an intermediate in the synthesis of Procyanidin B2 3,3''-Di-O-gallate, which is an important compound with significant biological activities. Its primary application is in the development of treatments for various human cancer diseases, particularly prostate carcinoma.
5,7,3',4'-tetra-O-benzyl-(-)-epicatechin-(4β,8)-[5,7,3',4'-tetra-O-benzyl-(-)-epicatechin]'s activity results in the inhibition of growth in human prostate carcinoma cell lines, making it a promising candidate for cancer research and therapeutic development. The benzyl groups in its structure may also contribute to its stability and potential interactions with biological targets, further enhancing its utility in pharmaceutical applications.

Upstream product

• 477565-90-5 bis(3-O-acetyl-5,7,3',4'-tetra-O-benzyl)epicatechin 4β,8-dimer 
• 87292-49-7 5,7,3',4'-tetra-O-benzylepicatechin 
• 664351-39-7 (2R,3R,4S)-5,7,3',4'-tetrabenzyloxy-4-(2''-ethoxyethoxy)flavan-3-ol 
• 223387-51-7 (2R,3S,4S)-5,7,3',4'-tetrabenzyloxy-4-(2-hydroxyethyloxy)flavan-3-ol 
• 223387-26-6 3’,4’,5,7-tetra-O-benzyl-4β-(2-hydroxyethyloxy)epicatechin 
• 154-23-4 catechin 
• 87292-54-4 (+)-(2R)-5,7-bis(benzyloxy)-2-[3,4-bis(benzyloxy)phenyl]chroman-3-one 
• 20728-73-8 5,7,3',4'-tetra-O-benzyl-(+)-catechin 
• 100-39-0 benzyl bromide 
• 478796-20-2 (2R,3S,4S)-5,7,3',4'-tetrabenzyloxy-4-(2-ethoxyethoxy)flavan-3-ol 
• 256236-25-6 5,7,3',4'-tetra-O-benzyl-4β-(2-hydroxyethoxy)epicatechin 

Downstream Products

• 79907-44-1 procyanidin B₂-3,3'-di-O-gallate 
• 223387-30-2 [4,8:4'',8'']-2,3-cis-3,4-trans: 2'',3''-cis-3'',4''-trans: 2'''',3''''-cis-dodeca-O-benzyl-tri-(-)-epicatechin 
• 223387-33-5 5,7,3',4'-tetra-O-benzyl-3-O-(3,4,5-tri-O-benzylgalloyl)-(-)-epicatechin-(4β,8β)-[5,7,3',4'-tetra-O-benzyl-3-O-(3,4,5-tri-O-benzylgalloyl)-(-)-epicatechin] 
• 1403746-93-9 C₁₃₁H₁₁₂O₁₉ 
• 477565-84-7 tris(5,7,3',4'-tetra-O-benzyl)epicatechin 4β,6:4β,8-trimer 
• 477565-90-5 bis(3-O-acetyl-5,7,3',4'-tetra-O-benzyl)epicatechin 4β,8-dimer 

Relevant articles and documents

Concise Synthesis of Cinnamtannin A2 from Dimeric Epicatechin Electrophile and Nucleophile Prepared by Zn(OTf)2-Mediated Self-Condensation

The synthesis of cinnamtannin A2 from dimeric epicatechin nucleophile and electrophile was accomplished. Dimeric epicatechin nucleophile was prepared directly by reduction of the C-4′′ 1-ethoxy-?ethoxy group of the electrophile which was previously synthe

Total synthesis of 14C-labeled procyanidin B2

During the last decades, many in vitro and in vivo studies have shown the beneficial effects on health of procyanidins. However, their absorption and metabolism is still not fully understood and some aspects are still controversial. In order to have a clearer picture of the metabolism of procyanidins, the use of labelled compounds is essential. In this context, the enantioselective synthesis of 14C-radiolabelled procyanidin B2 was developed in our laboratories. It was achieved in fourteen 'hot' steps, involving as key steps the Sharpless dihydroxylation of an elaborated alkene, a stereoselective intramolecular cyclization to benzylated (+)-catechin and the condensation of two (-)-epicatechin units. 11 mCi of protected procyanidin B2 were obtained from 524 mCi of potassium [14C]cyanide. Copyright

First total synthesis of14C-labeled procyanidin B2 - A milestone toward understanding cocoa polyphenol metabolism

The idea that foods consumed for pure pleasure could provide health benefits received much recognition in the recent years. Among these foods, cocoa and dark chocolate are particularly rich in procyanidins, one of the major dietary families of polyphenols. We developed the first asymmetric total synthesis of procyanidin B2 and applied it to the preparation of a regioselectively radiolabeled 14C-analogue, which will be used to strengthen our knowledge on the metabolism of procyanidins. Wiley-VCH Verlag GmbH & Co. KGaA, 2008.