12798-59-3

Basic information

• Product Name: PROCYANIDIN B7
• Synonyms: PROCYANIDIN B7;(2R,2'R,3R,3'S,4β)-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,3R)-2-(3,4-dihydroxyphenyl)-3,4-dihydro-3,5,7-trihydroxy-2H-1-benzopyran]-4β-yl]-2H-1-benzopyran-3,5,7-triol;(4→6)-Procyanidin B7;2α,2'α-Bis(3,4-dihydroxyphenyl)-3,3',4,4'-tetrahydro-4β,6'-bi(2H-1-benzopyran)-3α,3'β,5,5',7,7'-hexaol
• CAS NO: 12798-59-3
• Molecular Formula: C₃₀H₂₆O₁₂
• Molecular Weight: 578.52
• Product Categories: Catechins & Tannins
• Mol File: 12798-59-3.mol
• Article Data: 14

Chemical Properties

• Appearance: /
• CAS DataBase Reference: PROCYANIDIN B7(CAS DataBase Reference)
• NIST Chemistry Reference: PROCYANIDIN B7(12798-59-3)
• EPA Substance Registry System: PROCYANIDIN B7(12798-59-3)

Safety Data

• Hazardous Substances Data: 12798-59-3(Hazardous Substances Data)

Upstream product

• 114637-80-8 C₆₀H₄₈O₂₄ 
• 100-53-8 phenylmethanethiol 
• 101401-64-3 epicatechin-(4β->6)-epicatechin-(4β->6)-epicatechin 
• 480-17-1 2,3-trans-flavan-3,4-diol 
• 490-46-0 (2R,3R)-2-(3,4-dihydroxyphenyl)-3,4-dihydro-1[2H]-benzopyran-3,5,7-triol 
• 154-23-4 catechin 
• 480-18-2 taxifolin 
• 480-17-1 (+)-leucocyanidin 
• 88191-48-4 5,7,3',4'-tetrahydroxyflavan-3-ol hydrate 
• 61540-96-3 C₁₅H₁₃O₆⁽¹⁺⁾ 
• 86849-67-4 (2R,3S,4S)-2,3-cis-3,4-trans-3,3',4',5,7-pentahydroxy-4-phenylthioflavan 
• 22970-70-3 (2R,3R,4S)-2,3-cis-3,4-trans-3',4',5,7-tetramethoxyflavan-3,4-diol 
• 1438268-60-0 C₉₃H₁₅⁽²⁾H₆₃BrClO₁₂ 

Downstream Products

• 37064-35-0 4β-benzylthioepicatechin 
• 128837-34-3 4α-Benzylthioepicatechin 
• 154-23-4 catechin 
• 65052-97-3 Acetic acid (2R,3R,4R,2'R,3'S)-5,7,3',5',7'-pentaacetoxy-2,2'-bis-(3,4-diacetoxy-phenyl)-3,4,3',4'-tetrahydro-2H,2'H-[4,6']bichromenyl-3-yl ester 
• 13306-05-3 cyanidin 
• 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

Preparation of dimeric procyanidins B1, B2, B5, and B7 from a polymeric procyanidin fraction of black chokeberry (Aronia melanocarpa)

A semisynthetic approach has been used for the preparative formation of dimeric procyanidins B1, B2, B5, and B7. As starting material for the semisynthesis, polymeric procyanidins from black chokeberry were applied. These polymers were found to consist almost exclusively of (-)-epicatechin units. Under acidic conditions the interflavanoid linkages of the polymeric procyanidins are cleaved and the liberated (-)-epicatechin can react with nucleophiles, such as (+)-catechin or (-)-epicatechin. In this way, the polymeric procyanidins are degraded while dimeric procyanidins are formed. During this reaction only dimeric procyanidins are formed that contain (-)-epicatechin in the upper unit, that is, B1 [(-)-EC-4β→8-(+)-C)], B2 [(-)-EC-4β→8-(-)-EC], B5 [(-)-EC-4β→6-(-)-EC], and B7 [(-)-EC-4β→6-(+)-C]. The reaction mixtures of the semisynthesis can be successfully fractionated with high-speed countercurrent chromatography (HSCCC), and it is possible to isolate pure procyanidins B1, B2, B5, and B7 on a preparative scale.