20728-74-9

Upstream product

• 16198-01-9 (+)-pentaacetylcatechin 
• 100-44-7 benzyl chloride 
• 108-24-7 acetic anhydride 
• 20728-73-8 5,7,3',4'-tetra-O-benzyl-(+)-catechin 
• 100-39-0 benzyl bromide 
• 154-23-4 catechin 
• 3396-11-0 cesium acetate 
• 92052-29-4 2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl trichloroacetimidate 

Downstream Products

• 917567-15-8 3-acetoxy-5,7,3',4'-tetra-O-benzyl-8-formylcatechin 
• 1590438-50-8 C₇₀H₆₂O₁₈ 
• 20728-73-8 5,7,3',4'-tetra-O-benzyl-(+)-catechin 

Relevant academic research and scientific papers

Enhanced radical scavenging activity of a procyanidin B3 analogue comprised of a dimer of planar catechin

Proanthocyanidins are oligomers of catechins that exhibit potent antioxidative activity and inhibit binding of oxidized low-density lipoprotein (OxLDL) to the lectin-like oxidized LDL receptor (LOX-1), which is involved in the onset and development of arteriosclerosis. Previous attempts aimed at developing proanthocyanidin derivatives with more potent antioxidative activity and stronger inhibition for LOX-1 demonstrated the synthesis of a novel proanthocyanidin derivative (1), in which the geometry of one catechin molecule in procyanidin B3 was constrained to a planar orientation. The radical scavenging activity of 1 was 1.9-fold higher than that of procyanidin B3. Herein, we synthesized another procyanidin B3 analogue (2), in which the geometries of both catechin molecules in the dimer were constrained to planar orientations. The radical scavenging activity of 2 was 1.5-fold higher than that of 1, suggesting that 2 may be a more effective candidate than 1 as a therapeutic agent to reduce oxidative stress induced in arteriosclerosis or related cerebrovascular disease.

Synthesis and antioxidant activity of a procyanidin B3 analogue

Proanthocyanidin, an oligomer of catechin, is a natural antioxidant and a potent inhibitor of lectin-like oxidized LDL receptor-1, which is involved in the pathogenesis of arteriosclerosis. We synthesized proanthocyanidin analogue 1, in which the geometry of one catechin molecule in procyanidin B3, a dimer of (+)-catechin, is constrained to be planar. The antioxidant activities of the compounds were evaluated in terms of their capacities to scavenge galvinoxyl radicals, and results demonstrate that while procyanidin was 3.8 times more potent than (+)-catechin, the radical scavenging activity of proanthocyanidin analogue 1 was further increased to 1.9 times that of procyanidin B3. This newly designed proanthocyanidin analogue 1 may be a promising lead compound for the treatment of arteriosclerosis and related cerebrovascular diseases.

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.

Hydroxylation of ring A of flavan-3-ols: Influence of the ring A substitution pattern on the oxidative rearrangement of 6-hydroxyflavan-3-ols

A general procedure for the oxidation of catechin derivatives is described, leading to the introduction of a new hydroxyl group at C-6. This procedure has been used for the synthesis of a number of 6-hydroxy flavan-3-ols, including elephantorrhizol, a natural flavan-3-ol exhibiting a fully substituted A ring. The substitution at C-8, albeit of poor influence on the course of this oxidation reaction, has been demonstrated to be preponderant for the further spontaneous oxidation and rearrangement of 6-hydroxy-flavan-3-ols into p-benzoquinones. The whole procedure allows the preparation of 6-alkyl substituted benzoquinones derived from catechin. Georg Thieme Verlag Stuttgart.

Novel and efficient synthesis of cyanidin 3-O-β-D-glucoside from (+)-catechin via a flav-3-en-3-ol as a key intermediate

A novel and efficient synthesis of cyanidin 3-O-β-D-glucoside (1) was accomplished the first time by a biomimetic oxidation route. From (+)-catechin, 3-OH was glucosylated, and the 4-position of the nucleus was then oxidized and dehydrated to give the 5,7

O-Benzylation of phloroglucinol via phloroglucinol triacetate

O-Benzylation of phloroglucinol, which was difficult due to C-benzylation, was successfully carried out by a method using phloroglucinol triacetate as an intermediate.