29106-51-2

Basic information

• Product Name: CATECHIN-(4ALPHA->8)-EPICATECHIN
• Synonyms: PROCYANIDIN B-4;CATECHIN-(4ALPHA->8)-EPICATECHIN;PROCYANIDINDIMERB4;(+)-Catechin-(4α-8)-(-)-epicatechin;(2R,2'R)-2α-(3,4-Dihydroxyphenyl)-2'α-(3,4-dihydroxyphenyl)-4α,8'-bichroman-3β,3'α,5,5',7,7'-hexol;(2R,2'R,3S,3'R,4S)-2,2'-Bis(3,4-dihydroxyphenyl)-4,8'-bichroman-3,3',5,5',7,7'-hexol;(2R,2'R,3S,3'R,4α)-3,3',4,4'-Tetrahydro-2α,2'α-bis(3,4-dihydroxyphenyl)-4,8'-bi[2H-1-benzopyran]-3,3',5,5',7,7'-hexol;Proanthocyanidin B4
• CAS NO: 29106-51-2
• Molecular Formula: C₃₀H₂₆O₁₂
• Molecular Weight: 578.52
• Product Categories: Catechins & Tannins;Flavonoids
• Mol File: 29106-51-2.mol
• Article Data: 16

Chemical Properties

• Melting Point: 178-180 °C (decomp)
• Boiling Point: 955.3°Cat760mmHg
• Flash Point: 531.6°C
• Appearance: /
• Density: 1.705g/cm³
• PKA: 9.29±0.60(Predicted)
• CAS DataBase Reference: CATECHIN-(4ALPHA->8)-EPICATECHIN(CAS DataBase Reference)
• NIST Chemistry Reference: CATECHIN-(4ALPHA->8)-EPICATECHIN(29106-51-2)
• EPA Substance Registry System: CATECHIN-(4ALPHA->8)-EPICATECHIN(29106-51-2)

Safety Data

• Hazardous Substances Data: 29106-51-2(Hazardous Substances Data)

Usage

Description

CATECHIN-(4ALPHA->8)-EPICATECHIN, also known as Procyanidin B4, is a bioactive flavonoid and a proanthocyanidin derived from grape seed extracts. It is characterized by its ability to reduce inflammation, oxidative stress, and restore tight junction barrier function in caco-2 colon cells.

Uses

Used in Pharmaceutical Applications:
CATECHIN-(4ALPHA->8)-EPICATECHIN is used as an anti-inflammatory and antioxidant agent for its ability to reduce inflammation and oxidative stress, which can contribute to various health issues.
Used in Gastrointestinal Health:
CATECHIN-(4ALPHA->8)-EPICATECHIN is used as a tight junction barrier function restorer for its ability to restore the tight junction barrier function in caco-2 colon cells, which can help maintain gastrointestinal health.
Used in Nutritional Supplements:
CATECHIN-(4ALPHA->8)-EPICATECHIN is used as an ingredient in nutritional supplements for its potential health benefits, including anti-inflammatory and antioxidant properties.
Used in Food Industry:
CATECHIN-(4ALPHA->8)-EPICATECHIN is used as a natural additive for its antioxidant properties, which can help extend the shelf life of various food products and protect them from oxidative damage.
Used in Cosmetics:
CATECHIN-(4ALPHA->8)-EPICATECHIN is used as an ingredient in cosmetics for its potential skin health benefits, including anti-inflammatory and antioxidant effects.

Upstream product

• 115648-76-5 catechin-(4α->8)-epicatechin-(4β->S)-benzylthioether 
• 698998-85-5 4-benzylthioether of catechin 
• 490-46-0 (2R,3R)-2-(3,4-dihydroxyphenyl)-3,4-dihydro-1[2H]-benzopyran-3,5,7-triol 
• 664351-48-8 [4,8']-2,3-trans-3,4-trans:2',3'-cis-octa-O-benzyl-3-O-acetyl-(+)-catechin-(-)-epicatechin 
• 480-18-2 taxifolin 
• 223387-51-7 (2R,3S,4S)-5,7,3',4'-tetrabenzyloxy-4-(2-hydroxyethyloxy)flavan-3-ol 
• 154-23-4 catechin 
• 256236-21-2 5,7,3',4'-tetra-O-benzyl-8-bromocatechin 
• 87292-49-7 5,7,3',4'-tetra-O-benzylepicatechin 
• 20728-73-8 5,7,3',4'-tetra-O-benzyl-(+)-catechin 
• 923565-00-8 3’,4’,5,7-tetra-O-benzyl-4β-(2-hydroxyethyloxy)-8-bromocatechin 
• 923565-05-3 3',4',5,7-tetra-O-benzyl-8-bromocatechin-4α,8-(3',4',5,7-tetra-O-benzylepicatechin) 
• 100-53-8 phenylmethanethiol 
• 195145-79-0 [4,8']-2,3-trans-3,4-trans:2',3'-cis-octa-O-benzyl-(+)-catechin-(-)-epicatechin 

Downstream Products

• 698998-85-5 4-benzylthioether of catechin 
• 154-23-4 catechin 
• 126786-48-9 Catechin-(4alpha-8)-epigallocatechin-3-gallate 
• 490-46-0 (2R,3R)-2-(3,4-dihydroxyphenyl)-3,4-dihydro-1[2H]-benzopyran-3,5,7-triol 
• 195145-79-0 [4,8']-2,3-trans-3,4-trans:2',3'-cis-octa-O-benzyl-(+)-catechin-(-)-epicatechin 
• 725223-71-2 catechin-(4,8)-malvidin-3-O-glucoside 
• 21179-23-7 catechin-(4α->8)-epicatechin decaacetate 
• 154-23-4 (-)-catechin 
• 35323-91-2 (+)-epicatechin 
• 37064-33-8 procyanidin octamethyl ether 

Relevant articles and documents

Hemisynthesis and structural characterization of flavanol-(4,8)-vitisins by mass spectrometry

Vitisins constitute the major group of pyranoanthocyanins naturally occurring in red wines. Regarding their chemical structure, only carboxypyranoanthocyanins have been detected and quantified in red wines, but no vitisin with substitutions in the carbons of the A ring has been identified. However, considering the chemical reactions that take place in red wine, the existence of flavan-3-ol-(4,6/8)-vitisins is expected. This paper reports for the first time the structural identification of catechin-vitisin A and catechin-vitisin B based on their mass data and fragmentation patterns. This work also provides some chromatographic and visible spectroscopic features of these pigments and documents the existence of both in red table wines. Moreover, it is also proposed that Cat-Vit A pigments arise from the cycloaddition of pyruvic acid to an anthocyanin moiety of a flavanolanthocyanin adduct rather than by direct nucleophilic attack of a vitisin A on the carbocation C4 of catechin.

Synthesis of procyanidin B1, B2, and B4 and their anti-inflammatory activity: The effect of 4-alkoxy group of catechin and/or epicatechin electrophiles for condensation

Abstract: Procyanidin B1, B2, and B3 were synthesized based on a Yb(OTf)3 catalyzed equimolar condensation using methoxy and/or 4-(2-ethoxyethoxy) drivatives as electrophiles. The anti-inflammatory effect of synthetic procyanidin B1, B2, and B4 on 12-O-tetradecanoylphorbol-13-acetate (TPA)-induced inflammation of mouse ears was examined. Procyanidin B1, B2, B 4 suppressed TPA-induced inflammation of mouse ears by 48%, 34%, and 29%, respectively, at a dose of 200 μg. Their activities are stronger than those of indomethacin and glycyrrhetinic acid, the normally used antiinflammatory agent.

An efficient synthesis of procyanidins. Rare earth metal Lewis acid catalyzed equimolar condensation of catechin and epicatechin

Stereoselective synthesis of catechin and epicatechin dimers under intermolecular condensation is achieved by an equimolar amount of coupling catalyzed by Yb(OTf)3. The coupled products were successfully converted to procyanidin B1, B2, B3, and B4.