51196-37-3

Basic information

• Product Name: 3,4-cis-(+)-catechin-(4β->8)-(+)-catechin
• Synonyms: 3,4-cis-(+)-catechin-(4β->8)-(+)-catechin
• CAS NO: 51196-37-3
• Molecular Weight: 578.529
• Mol File: 51196-37-3.mol

Chemical Properties

• CAS DataBase Reference: 3,4-cis-(+)-catechin-(4β->8)-(+)-catechin(CAS DataBase Reference)
• NIST Chemistry Reference: 3,4-cis-(+)-catechin-(4β->8)-(+)-catechin(51196-37-3)
• EPA Substance Registry System: 3,4-cis-(+)-catechin-(4β->8)-(+)-catechin(51196-37-3)

Safety Data

• Hazardous Substances Data: 51196-37-3(Hazardous Substances Data)

Upstream product

• 923565-04-2 3’,4’,5,7-tetra-O-benzyl-8-bromocatechin-(4α8)-3’,4’,5,7-tetra-O-benzylcatechin 
• 20728-73-8 5,7,3',4'-tetra-O-benzyl-(+)-catechin 
• 596829-29-7 (2R,3S)-5,7,3',4'-tetrabenzykloxy-flavan-3-yl (2R,3S,4S)-5,7,3',4'-tetrabenzyloxy-4-ethoxyethoxy-flavan-3-yl glutarate 
• 596829-27-5 C₉₀H₇₆O₁₄ 
• 137624-12-5 5,7,3',4'-tetra-O-benzyl-4β-(5,7,3',4'-tetra-O-benzylcatechin)catechin 
• 154-23-4 catechin 
• 480-18-2 taxifolin 
• 480-17-1 2,3-trans-flavan-3,4-diol 

Downstream Products

• 88079-93-0 [4,8]-2,3-trans-3,4-cis:2,3-trans-deca-O-acetyl-bi-(+)-catechin 

Relevant articles and documents

From the gold-catalysed benzylation of arenes to the regio- and stereoselective synthesis of procyanidins dimers

This work reports on a new intermolecular C-C coupling reaction between electron rich arenes and benzylic alcohols or ethers, catalysed by gold(III) salts, or other catalysts such as gold(I) and iron (III), and its application to the regio- and stereoselective synthesis of procyanidins dimers B1 and B3.

Stereoselection of 3,4-cis and 3,4-trans catechin and catechin condensation under intramolecular coupling method

A high level of stereoselection between 3,4-cis and 3,4-trans catechin-catechin condensation under intramolecular coupling method has been realized by changing the diester linker between the nucleophile and the electrophile. The azelaic acid linker gave exclusively 3,4-trans catechin-catechin dimer, whereas glutaric acid linker gave 3,4-cis catechin-catechin dimer as the sole product.

Synthetic studies of proanthocyanidins. Part 3: Stereoselective 3,4-cis catechin and catechin condensation by TMSOTf-catalyzed intramolecular coupling method

TMSOTf-catalyzed intramolecular condensation for catechin and epicatechin units are described. A potential electrophile and a nucleophile were connected with diester linkers and TMSOTf-catalyzed condensation was examined. In comparison with intermolecular

Synthetic studies of proanthocyanidins. Part 2: Stereoselective gram-scale synthesis of procyanidin-B3

A stereoselective synthesis of procyanidin-B3, a condensed catechin dimer, is described. Condensation of benzylated catechin with various 4-O-alkylated flavan-3,4-diol derivatives as an electrophile in the presence of a Lewis acid led to protected procyanidin-B3 and its diastereomer. In particular, the reaction using (2R,3S,4S)-3-acetoxy-5,7,3′,4′-tetrabenzyloxy-4-(2″- ethoxyethoxy)flavan as an electrophile in the presence of TMSOTf at -78°C afforded octa-O-benzylated procyanidin-B3 with high levels of stereoselectivity and in excellent isolation yields. Furthermore, we succeeded in a stereoselective gram-scale synthesis of protected procyanidin-B3.

Deuterium labeled procyanidin syntheses

Deuterium-labeled procyanidins have been prepared by hemisynthesis from taxifolin in order to investigate their metabolism in human. The structures of the desired deuterated natural compounds B3 10D (R1 = D, R2 = H) and B4 13D (R1 = D, R2 = H) were proven by spectroscopic and physical properties means, including 2H NMR spectrum. By-products with unatural absolute configuration at some centers were also formed along the process and were characterised.

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 and Conformation of Procyanidin Diastereoisomers

The four theoretically possible diastereoisomeric 4->8 linked procyanidin dimers with two 2,3-cis-flavanoid units, epicatechin-(4β->8)-epicatechin (6), epicatechin-(4β->8)-ent-epicatechin (8), ent-epicatechin-(4α->8)-epicatechin (7), and ent-epicatechin-(4α->8)-ent-epicatechin (2), have been synthesized together with the 2,3-trans diastereoisomers catechin-(4α->8)-catechin (14) and catechin-(4α->8)-ent-catechin (15).The preferred rotamer conformations of the deca-acetate derivatives of (6), (8), (14), and (15) in chloroform were deduced from their 13C n.m.r. and high-field 1H n.m.r. spectra.The 1H n.m.r. spectra of the preferred conformers of the pairs of acetate derivatives of (6) and (15), and (8) and (14), were qualitatively similar as the relative configuration about the interflavanoid bond of one pair has a meso-relationship to the other.