664351-42-2

Basic information

• Product Name: [4,8]-2,3-cis-3,4-trans:2,3-trans-octa-O-benzyl-(-)-3-O-acetyl-(-)-epicatechin-(+)-catechin
• Synonyms: [4,8]-2,3-cis-3,4-trans:2,3-trans-octa-O-benzyl-(-)-3-O-acetyl-(-)-epicatechin-(+)-catechin
• CAS NO: 664351-42-2
• Molecular Weight: 1341.56
• Mol File: 664351-42-2.mol
• Article Data: 5

Chemical Properties

• CAS DataBase Reference: [4,8]-2,3-cis-3,4-trans:2,3-trans-octa-O-benzyl-(-)-3-O-acetyl-(-)-epicatechin-(+)-catechin(CAS DataBase Reference)
• NIST Chemistry Reference: [4,8]-2,3-cis-3,4-trans:2,3-trans-octa-O-benzyl-(-)-3-O-acetyl-(-)-epicatechin-(+)-catechin(664351-42-2)
• EPA Substance Registry System: [4,8]-2,3-cis-3,4-trans:2,3-trans-octa-O-benzyl-(-)-3-O-acetyl-(-)-epicatechin-(+)-catechin(664351-42-2)

Safety Data

• Hazardous Substances Data: 664351-42-2(Hazardous Substances Data)

Upstream product

• 1375486-52-4 C₄₇H₄₄O₉ 
• 20728-73-8 5,7,3',4'-tetra-O-benzyl-(+)-catechin 
• 1375486-50-2 C₄₇H₄₄O₈ 
• 1375486-51-3 C₄₈H₄₆O₈ 
• 1030624-94-2 3,4-cis-4-acetoxy-3-O-acetyl-4-4-dehydro-5,7,3',4'-tetra-O-benzyl-(-)-epicatechin 

Downstream Products

• 20315-25-7 procyanidin B₁ 
• 664351-43-3 5,7,3',4'-tetra-O-benzyl-(-)-epicatechin-(4β,8β)-[5,7,3',4'-tetra-O-benzyl-(+)-catechin] 

Relevant articles and documents

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.

Synthesis of procyanidins by stepwise- and self-condensation using 3,4-cis-4-acetoxy-3-O-acetyl-4-dehydro-5,7,3′,4′-tetra-O-ben zyl-(+)-catechin and (-)-epicatechin as a key building monomer

3,4-cis-4-Acetoxy-3-O-acetyl-4-dehydro-5,7,3′,4′-tetra-O-ben zyl-(+)-catechin (1a) or (-)-epicatechin (1b) reacted high regio- and stereo-selectively with 1.5 equiv of the 5,7,3′,4′-tetra-O-benzyloxyflavan-3-ol (4a or 4b) in the presence of 1 equiv of TMSOTf to give the corresponding procyanidins. On the other hand, the self-condensation of 1a in the presence of a catalytic amount of B(C6F5)3 afforded wide-range procyanidins from dimer to 15-mer like a biomass.

Synthetic studies of proanthocyanidins. Part 5.1 Highly stereoselective synthesis and inhibitory activity of Maillard reaction of 3,4-trans catechin and epicatechin dimers, procyanidin B1, B2, B3, B4 and their acetates

TMSOTf-catalyzed condensation of a potential electrophile with a nucleophile was achieved with a high level of 3,4-trans condensation, and we succeeded in the stereoselective synthesis of procyanidin B2 and its peracetate. Studies on the inhibitory activity of the Maillard reaction of four 3,4-trans series of catechin and epicatechin dimers, procyanidin B1, B2, B3 and B4, and their peracetates were also carried out.