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

Description

PROCYANIDINB5, also known as Procyanidin B5, is a bioactive metabolite derived from the leaves and stem bark of Quercus robur L. It is known for its antioxidant and antidiabetic properties, making it a valuable compound for various applications in the pharmaceutical and health industries.

Uses

Used in Pharmaceutical Applications:
PROCYANIDINB5 is used as an antioxidant agent for its ability to neutralize harmful free radicals in the body, which can contribute to cellular damage and various diseases. Its antioxidant properties make it a promising candidate for the development of treatments for conditions associated with oxidative stress.
Used in Antidiabetic Applications:
PROCYANIDINB5 is used as an antidiabetic agent for its potential to help regulate blood sugar levels and improve insulin sensitivity. This makes it a valuable compound for the development of treatments for diabetes and related metabolic disorders.
Used in Health Supplements:
Due to its antioxidant and antidiabetic properties, PROCYANIDINB5 can be used as an ingredient in health supplements and nutraceutical products to support overall health and well-being.
Used in Cosmetics:
The antioxidant properties of PROCYANIDINB5 may also make it a useful ingredient in the cosmetics industry, where it can be used to protect the skin from environmental damage and promote a more youthful appearance.

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

• 480-17-1 (+)-leucocyanidin 
• 154-23-4 catechin 
• 480-18-2 taxifolin 
• 480-17-1 2,3-trans-flavan-3,4-diol 
• 1438268-60-0 C₉₃H₁₅⁽²⁾H₆₃BrClO₁₂ 
• 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 
• 22970-70-3 (2R,3R,4S)-2,3-cis-3,4-trans-3',4',5,7-tetramethoxyflavan-3,4-diol 
• 490-46-0 (2R,3R)-2-(3,4-dihydroxyphenyl)-3,4-dihydro-1[2H]-benzopyran-3,5,7-triol 
• 35323-91-2 (+)-epicatechin 
• 101401-64-3 epicatechin-(4β->6)-epicatechin-(4β->6)-epicatechin 
• 100-53-8 phenylmethanethiol 
• 61540-96-3 C₁₅H₁₃O₆⁽¹⁺⁾ 
• 126671-46-3 epicatechin-(4β→6)-epicatechin-(4β→8)-epicatechin-(4β→6)-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.