12798-57-1

Basic information

• Product Name: PROCYANIDINB5
• Synonyms: (2R,3R)-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 B5;4β,6'-Bi[(2R)-3,4-dihydro-2α-(3,4-dihydroxyphenyl)-2H-1-benzopyran-3α,5,7-triol];Epicatechin-(4β→6)-epicatechin
• CAS NO: 12798-57-1
• Molecular Formula: C₃₀H₂₆O₁₂
• Molecular Weight: 578.523
• Mol File: 12798-57-1.mol
• Article Data: 15

Chemical Properties

• Boiling Point: 1009.6°C at 760 mmHg
• Flash Point: 564.4°C
• Appearance: /
• Density: 1.705g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.803
• CAS DataBase Reference: PROCYANIDINB5(CAS DataBase Reference)
• NIST Chemistry Reference: PROCYANIDINB5(12798-57-1)
• EPA Substance Registry System: PROCYANIDINB5(12798-57-1)

Safety Data

• Hazardous Substances Data: 12798-57-1(Hazardous Substances Data)

Usage

Uses

Procyanidin B5 is a bioactive metabolite extracted from Quercus robur L. leaves/stem bark with antioxidant and antidiabetic properties.

InChI:InChI=1/C30H26O12/c31-13-7-19(36)24-23(8-13)42-30(12-2-4-16(33)18(35)6-12)28(40)26(24)25-20(37)10-22-14(27(25)39)9-21(38)29(41-22)11-1-3-15(32)17(34)5-11/h1-8,10,21,26,28-40H,9H2/t21-,26-,28-,29-,30-/m1/s1

Upstream product

• 1438268-60-0 C₉₃H₁₅⁽²⁾H₆₃BrClO₁₂ 
• 154-23-4 catechin 
• 480-18-2 taxifolin 
• 61540-96-3 C₁₅H₁₃O₆⁽¹⁺⁾ 
• 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 
• 480-17-1 2,3-trans-flavan-3,4-diol 
• 22970-70-3 (2R,3R,4S)-2,3-cis-3,4-trans-3',4',5,7-tetramethoxyflavan-3,4-diol 
• 86849-64-1 (2R,3R,4R)-2,3-cis-3,4-trans-3,3',4',5,7-pentahydroxy-4-<(2R,3S,4S)-2,3-cis-3,4-trans-3,3',4',5,7-pentahydroxy-4-phenylthioflavan-6-yl>flavan 
• 126671-46-3 epicatechin-(4β→6)-epicatechin-(4β→8)-epicatechin-(4β→6)-epicatechin 
• 480-17-1 (+)-leucocyanidin 
• 35323-91-2 (+)-epicatechin 

Downstream Products

• 37064-35-0 4β-benzylthioepicatechin 
• 490-46-0 (2R,3R)-2-(3,4-dihydroxyphenyl)-3,4-dihydro-1[2H]-benzopyran-3,5,7-triol 
• 65052-97-3 Acetic acid (2R,3R,4R,2'R,3'R)-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 
• 114569-31-2 proanthocyanidin A-6 
• 114569-32-3 proanthocyanidin A-7 
• 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 
• 105561-65-7 octa-O-methylprocyanidin B-5 

Relevant articles and documents

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.

Procyanidins from the roots of Fragaria vesca: Characterization and pharmacological approach

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Molecular Interaction between Salivary Proteins and Food Tannins

Polyphenols interaction with salivary proteins (SP) has been related with organoleptic features such as astringency. The aim of this work was to study the interaction between some human SP and tannins through two spectroscopic techniques, fluorescence quenching, and saturation transfer difference-nuclear magnetic resonance (STD-NMR). Generally, the results showed a significant interaction between SP and both condensed tannins and ellagitannins. Herein, STD-NMR proved to be a useful tool to map tannins' epitopes of binding, while fluorescence quenching allowed one to discriminate binding affinities. Ellagitannins showed the greatest binding constants values (KSV from 20.1 to 94.1 mM-1 KA from 0.7 to 8.3 mM-1) in comparison with procyanidins (KSV from 5.4 to 40.0 mM-1 KA from 1.1 to 2.7 mM-1). In fact, punicalagin was the tannin that demonstrated the highest affinity for all three SP. Regarding SP, P-B peptide was the one with higher affinity for ellagitannins. On the other hand, cystatins showed in general the lower KSV and KA values. In the case of condensed tannins, statherin was the SP with the highest affinity, contrasting with the other two SP. Altogether, these results are evidence that the distinct SP present in the oral cavity have different abilities to interact with food tannins class.

First regiocontrolled synthesis of procyanidin B6, a catechin dimer with rare connectivity: A halo-capping strategy for formation of 4,6-interflavan bonds

The first regiocontrolled synthesis of procyanidin B6, a dimer with a rare 4,6-interflavan linkage, is described. Regioselective linking was achieved by the halo-capping strategy followed by removal of all the benzyl protecting groups and the halo-caps by one-pot hydrogenolysis.