12798-58-2

Basic information

• Product Name: CATECHIN-(4ALPHA->6)-CATECHIN
• Synonyms: PROCYANIDIN B6;CATECHIN-(4ALPHA->6)-CATECHIN;(2R)-2α-(3,4-Dihydroxyphenyl)-4α-[(2R)-2α-(3,4-dihydroxyphenyl)-3β,5,7-trihydroxy-3,4-dihydro-2H-1-benzopyran-6-yl]-3,4-dihydro-2H-1-benzopyran-3β,5,7-triol;(2R,2'R,3S,3'S,4α)-3,3',4,4'-Tetrahydro-2α,2'α-bis(3,4-dihydroxyphenyl)-4,6'-bi[2H-1-benzopyran]-3,3',5,5',7,7'-hexol;(2R,3S)-2-(3,4-Dihydroxyphenyl)-3,4-dihydro-6-[[(2R,3S)-2-(3,4-dihydroxyphenyl)-3,4-dihydro-3,5,7-trihydroxy-2H-1-benzopyran]-4α-yl]-2H-1-benzopyran-3,5,7-triol;(4→6)-Procyanidin B6
• CAS NO: 12798-58-2
• Molecular Formula: C₃₀H₂₆O₁₂
• Molecular Weight: 578.52
• Product Categories: Catechins & Tannins
• Mol File: 12798-58-2.mol
• Article Data: 10

Chemical Properties

• Appearance: /
• CAS DataBase Reference: CATECHIN-(4ALPHA->6)-CATECHIN(CAS DataBase Reference)
• NIST Chemistry Reference: CATECHIN-(4ALPHA->6)-CATECHIN(12798-58-2)
• EPA Substance Registry System: CATECHIN-(4ALPHA->6)-CATECHIN(12798-58-2)

Safety Data

• Hazardous Substances Data: 12798-58-2(Hazardous Substances Data)

Upstream product

• 480-17-1 2,3-trans-flavan-3,4-diol 
• 154-23-4 catechin 
• 1438268-60-0 C₉₃H₁₅⁽²⁾H₆₃BrClO₁₂ 
• 490-46-0 (2R,3R)-2-(3,4-dihydroxyphenyl)-3,4-dihydro-1[2H]-benzopyran-3,5,7-triol 
• 101401-64-3 epicatechin-(4β->6)-epicatechin-(4β->6)-epicatechin 
• 100-53-8 phenylmethanethiol 
• 480-18-2 taxifolin 
• 480-17-1 (+)-leucocyanidin 

Downstream Products

• 105487-44-3 (2R,3S,4S,2'R,3'R)-2,2'-Bis-(3,4-dimethoxy-phenyl)-5,7,5',7'-tetramethoxy-3,4,3',4'-tetrahydro-2H,2'H-[4,6']bichromenyl-3,3'-diol 

Relevant articles and documents

Regioselective synthesis of procyanidin B6, A 4-6-condensed (+)-catechin dimer, by intramolecular condensation

Proanthocyanidins, also known as condensed tannins or oligomeric flavonoids, are found in many edible plants and exhibit interesting biological activities. Herein, we report a new, simple method for the stereoselective synthesis of procyanidin B6, a (+)-catechin-(4-6)-(+)-catechin dimer, by Lewis acid-catalyzed intramolecular condensation. The 5-O-t-butyldimethylsilyl (TBDMS) group of 5,7,34-tetra-O-TBDMS-(+)-catechin was regioselectively removed using trifluoroacetic acid, leading to the “regio-controlled” synthesis of procyanidin B6. The 5-hydroxyl group of the 7,3,4-tri-O-TBDMS-(+)-catechin nucleophile and the 3-hydroxyl group of 5,7,3,4-tetra-O-benzylated-(+)-catechin electrophile were connected with an azelaic acid. The subsequent SnCl4-catalyzed intramolecular condensation proceeded smoothly to give the 4-6-condensed catechin dimer. This is the first report on the complete regioselective synthesis of a 4-6-connected oligomer without modifying the 8-position.

A seco-catechin cyclization approach to 4→6-linked catechin dimers

A viable route has been developed for the selective synthesis of the 4→6-linked catechin dimers, scarcely accessible from Nature and/or through synthesis. An acyclic nucleophilic catechin precursor (seco-catechin) was used for the regioselective union with an electrophilic catechin unit, and subsequent pyran cyclization gave the desired 4→6-linked dimers, i.e., procyanidin B6 and catechin-(4α→6)-gallocatechin. This journal is

Extensive High-Resolution Reverse 2D NMR Analysis for the Structural Elucidation of Procyanidin Oligomers

The structures of the procyanidin dimers catechin-(4α-8)-catechin and catechin-(4α-6)-catechin were proved by spectroscopic means.To distinguish between the two possible interflavonoid linkages, it is necessary to assign all the quaternary aromatic carbon signals.How these assignments can be made through two-dimensional NMR spectroscopy is described. - Keywords: 2D NMR 1H NMR 13C NMR Structural analysis Proanthocyanidins Catechin dimers Tannins