37126-92-4

Basic information

• Product Name: 5,7,3',4',5'',7'',3''',4'''-octa-O-methylprocyanidin B-3
• Synonyms: 5,7,3',4',5'',7'',3''',4'''-octa-O-methylprocyanidin B-3
• CAS NO: 37126-92-4
• Molecular Weight: 690.744
• Mol File: 37126-92-4.mol
• Article Data: 5

Chemical Properties

• CAS DataBase Reference: 5,7,3',4',5'',7'',3''',4'''-octa-O-methylprocyanidin B-3(CAS DataBase Reference)
• NIST Chemistry Reference: 5,7,3',4',5'',7'',3''',4'''-octa-O-methylprocyanidin B-3(37126-92-4)
• EPA Substance Registry System: 5,7,3',4',5'',7'',3''',4'''-octa-O-methylprocyanidin B-3(37126-92-4)

Safety Data

• Hazardous Substances Data: 37126-92-4(Hazardous Substances Data)

Upstream product

• 186581-53-3 diazomethane 
• 23567-23-9 procyanidin B₃ 

Downstream Products

• 58065-35-3 (+)-catechin tetramethyl ether acetate 
• 51079-25-5 (2R,3S)-(+)-catechin 3',4',5,7-tetramethyl ether 
• 3888-39-9 octa-O-methyl-di-O-acetyl-bis-(+)-catechin 

Relevant articles and documents

FLAVAN-3-OL AND PROCYANIDIN GLYCOSIDES FROM QUERCUS MIYAGII

A chemical examination of the leaves and bark of Quercus miyagii has led to the isolation and characterization of two flavan-3-ol glycosides and two procyanidin rhamnosides in which the sugar residue is located at C-3. - Key Word Index: Quercus miyagii; Fagaceae; flavan-3-ol glycosides; procyanidin rhamnosides; catechin; tannin.

SYNTHESIS AND CHARACTERIZATION OF PROCYANIDIN DIMERS AS THEIR PERACETATES AND OCTAMETHYL ETHER DIACETATES

Key Word Index - Biomimetic synthesis; procyanidins B1-B8; 3,4-cis-biflavanoid; all--bi--(+)-catechin; 1H NMR parameters. Condensation of (2R,3S,4R or S)-leucocyanidin or the 5,7,3',4'-tetramethyl ether of (2R,3R,4S)-leucocyanidin with flavan-3-ols yielded dimeric flavanoids which were converted to their octamethyl ether diacetates, or the deca-acetates for the 2,3-trans-procyanidin series.Comparison is made of the 1H NMR spectra of the deca-acetate and octamethyl ether diacetate derivatives which lead to useful diagnostic shift parameters characteristic of their structures.Condensation afforded a novel biflavanoid with a 3,4-cis-configuration and a triflavanoid of 'mixed' stereochemistry.

Synthesis of Condensed Tannins. Part 4. A Direct Biomimetic Approach to - and -Biflavanoids

The generation of flavanyl-4-carbo-cations from flavan-3,4-diols and their condensation with nucleophilic flavan-3-ols to form - and -biflavanoids at ambient temperatures and mildly acidic aqueous conditions apparently simulates the initial step in condensed tannin formation in a number of natural sources.The stereospecificity (or stereoselectivity) of the reaction is conditioned mainly by the 2,3-cis or 2,3-trans stereochemistry of the parent flavan-3,4-diol, but also by the nuclephilicity of the flavan-3-ol, and its regiospecific (or regioselective) course by steric factors arising from variation in substitution of the receptive A-ring of the flavan-3-ol.