223387-30-2

Basic information

• Product Name: [4,8:4'',8'']-2,3-cis-3,4-trans: 2'',3''-cis-3'',4''-trans: 2'''',3''''-cis-dodeca-O-benzyl-tri-(-)-epicatechin
• Synonyms: [4,8:4'',8'']-2,3-cis-3,4-trans: 2'',3''-cis-3'',4''-trans: 2'''',3''''-cis-dodeca-O-benzyl-tri-(-)-epicatechin
• CAS NO: 223387-30-2
• Molecular Weight: 1948.28
• Mol File: 223387-30-2.mol
• Article Data: 7

Chemical Properties

• CAS DataBase Reference: [4,8:4'',8'']-2,3-cis-3,4-trans: 2'',3''-cis-3'',4''-trans: 2'''',3''''-cis-dodeca-O-benzyl-tri-(-)-epicatechin(CAS DataBase Reference)
• NIST Chemistry Reference: [4,8:4'',8'']-2,3-cis-3,4-trans: 2'',3''-cis-3'',4''-trans: 2'''',3''''-cis-dodeca-O-benzyl-tri-(-)-epicatechin(223387-30-2)
• EPA Substance Registry System: [4,8:4'',8'']-2,3-cis-3,4-trans: 2'',3''-cis-3'',4''-trans: 2'''',3''''-cis-dodeca-O-benzyl-tri-(-)-epicatechin(223387-30-2)

Safety Data

• Hazardous Substances Data: 223387-30-2(Hazardous Substances Data)

Upstream product

• 1403746-93-9 C₁₃₁H₁₁₂O₁₉ 
• 87292-49-7 5,7,3',4'-tetra-O-benzylepicatechin 
• 223387-51-7 (2R,3S,4S)-5,7,3',4'-tetrabenzyloxy-4-(2-hydroxyethyloxy)flavan-3-ol 
• 256236-25-6 5,7,3',4'-tetra-O-benzyl-4β-(2-hydroxyethoxy)epicatechin 
• 223387-28-8 5,7,3',4'-tetra-O-benzyl-(-)-epicatechin-(4β,8)-[5,7,3',4'-tetra-O-benzyl-(-)-epicatechin] 
• 664351-39-7 (2R,3R,4S)-5,7,3',4'-tetrabenzyloxy-4-(2''-ethoxyethoxy)flavan-3-ol 

Downstream Products

• 37064-30-5 procyanidin C₁ 

Relevant articles and documents

Systematic synthesis of four epicatechin series procyanidin trimers and their inhibitory activity on the Maillard reaction and antioxidant activity

A systematic synthesis of four natural epicatechin series procyanidin trimers {[4,8:4″,8″]-2,3-cis-3,4-trans: 2″,3″-cis- 3″,4″-trans: 2′?,3′?-trans-(-)-epi- catechin-(-)-epicatechin-(+)-catechin, [4,8:4″,8″]-2,3-cis-3,4- trans: 2″,3″-cis-3″,4″-trans: 2′?, 3′?-cis-tri-(-)-epicatechin: procyanidin C1, [4,8:4″, 8″]-2,3-cis-3,4-trans: 2″,3″-trans-3″,4″-trans: 2′?,3′?-trans-(-)-epicatechin-(+)-catechin-(+) -catechin: procyanidin C4, and [4,8:4″,8″]-2,3-cis-3,4-trans: 2″,3″-trans-3″,4″-trans: 2′?, 3′?-cis-(-)-epicatechin-(+)-catechin-(-)-epicatechin} is described. Condensation of (2R,3R,4S)-5,7,3′4′-tetra-O-benzyl-4-(2″- ethoxyethyloxy)flavan derived from (-)-epicatechin as an electrophile with the dimeric nucleophiles in the presence of TMSOTf followed by deprotection yielded trimers. Inhibitory activities on the Maillard reaction and antioxidant activity on lipid peroxide of the synthesized oligomers were also investigated.

Selective synthesis of epicatechin dimers by zinc(II) triflate mediated self-condensation

Epicatechin dimers were synthesized by zinc(II) triflate mediated self-condensation reactions of epicatechin monomer derivatives. One synthesized dimer was successfully converted into procyanidin C1.

Compositions and methods of use of dimer digallates

The invention relates to compositions, such as pharmaceuticals, foods, food additives, or dietary supplements, containing dimer digallates, and methods of use thereof, for prophylactic or therapeutic treatment of a human or a veterinary animal to treat or prevent NO-responsive health conditions, treat hypertension, cardiovascular disease, coronary artery disease, diabetes, cognitive dysfunction or disorder and/or vascular circulation disorders, prevent or reduce the risk of heart attack, stroke, congestive heart failure and/or kidney failure, or to improve blood flow, for example renal blood flow. The composition may optionally contain an additional NO modulating agent and/or a vascular-protective or therapeutic agent, or may be administered in combination with such an agent.