137550-06-2

Basic information

• Product Name: 5,7,3',4'-tetra-O-benzyl-4α-(5,7,3',4'-tetra-O-benzylcatechin)catechin
• Synonyms: 5,7,3',4'-tetra-O-benzyl-4α-(5,7,3',4'-tetra-O-benzylcatechin)catechin
• CAS NO: 137550-06-2
• Molecular Weight: 1299.53
• Mol File: 137550-06-2.mol
• Article Data: 9

Chemical Properties

• CAS DataBase Reference: 5,7,3',4'-tetra-O-benzyl-4α-(5,7,3',4'-tetra-O-benzylcatechin)catechin(CAS DataBase Reference)
• NIST Chemistry Reference: 5,7,3',4'-tetra-O-benzyl-4α-(5,7,3',4'-tetra-O-benzylcatechin)catechin(137550-06-2)
• EPA Substance Registry System: 5,7,3',4'-tetra-O-benzyl-4α-(5,7,3',4'-tetra-O-benzylcatechin)catechin(137550-06-2)

Safety Data

• Hazardous Substances Data: 137550-06-2(Hazardous Substances Data)

Upstream product

• 476312-06-8 [4,8']-2,3-trans-3,4-trans:2',3'-trans-octa-O-benzyl-3-O-acetyl-bi-(+)-catechin 
• 1217257-69-6 3’,4’,5,7-tetra-O-benzyl-4β-O-propargylcatechin 
• 20728-73-8 5,7,3',4'-tetra-O-benzyl-(+)-catechin 
• 137624-11-4 (2R,3S,4S)-5,7-Bis-benzyloxy-2-(3,4-bis-benzyloxy-phenyl)-chroman-3,4-diol 
• 664351-41-1 (2R,3S,4S)-3-acetoxy-5,7,3',4'-tetrabenzyloxy-4-(2-ethoxyethoxy)flavan 
• 294203-72-8 (2R,3S,4S)-5,7,3',4'-tetrabenzyloxy-4-methoxyflavan-3-ol 

Downstream Products

• 828249-33-8 [4,8’]-2,3-trans-3.4-trans:2’,3’-trans-octabenzyloxy-(+)-catechin-3-(tribenzyloxy)gall 
• 223387-33-5 [4,8’]-2,3-trans-3.4-trans:2’,3’-trans-Octabenzyloxy-bi-(+)-catechin-3,3”-di-(tribenzyloxy)gallate 
• 23567-23-9 procyanidin B₃ 

Relevant articles and documents

Synthesis of procyanidin B3 and its anti-inflammatory activity. the effect of 4-alkoxy group of catechin electrophile in the Yb(OTf)3-catalyzed condensation with catechin nucleophile

(Figure Presented) Yb(OTf)3-catalyzed equimolar condensation of the benzylated catechin with various 4-alkoxy catechin derivatives was studied. In particular, the reaction using 4-(2′′-ethoxyethoxy)flavan derivative gave good yield with excellent stereoselectivity. The condensed product was successfully converted to procyanidin B3 (1). The anti-inflammatory effect of procyanidin B3 (1) on 12-O-tetradecanoylphorbol-13-acetate (TPA)-induced inflammation of mouse ears was examined. The anti-inflammatory activity of 1 was stronger than that of indomethacin and glycyrrhetinic acid, the normally used anti-inflammatory agents.

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.

An efficient synthesis of procyanidins using equimolar condensation of catechin and/or epicatechin catalyzed by ytterbium triflate

Stereoselective synthesis of catechin and epicatechin dimers under intermolecular condensation of equimolar amount of catechin derivatives catalyzed by Yb(OTf)3. The coupled products were successfully converted to procyanidins B1, B2, B3, and B4, respectively. Procyanidins B1, B2, B3, and B4 could be used as standard compounds for identifying the polyphenols in natural source.