357194-03-7

Basic information

• Product Name: 2-(2,2-diphenylbenzo[d][1,3]dioxol-5-yl)-3,5,7-trihydroxy-4H-chroMen-4-one
• Synonyms: 2-(2,2-diphenylbenzo[d][1,3]dioxol-5-yl)-3,5,7-trihydroxy-4H-chroMen-4-one;2-(2,2-diphenyl-1,3-benzodioxol-5-yl)-3,5,7-trihydroxychromen-4-one
• CAS NO: 357194-03-7
• Molecular Formula: C₂₈H₁₈O₇
• Molecular Weight: 466.43832
• Mol File: 357194-03-7.mol
• Article Data: 31

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 2-(2,2-diphenylbenzo[d][1,3]dioxol-5-yl)-3,5,7-trihydroxy-4H-chroMen-4-one(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(2,2-diphenylbenzo[d][1,3]dioxol-5-yl)-3,5,7-trihydroxy-4H-chroMen-4-one(357194-03-7)
• EPA Substance Registry System: 2-(2,2-diphenylbenzo[d][1,3]dioxol-5-yl)-3,5,7-trihydroxy-4H-chroMen-4-one(357194-03-7)

Safety Data

• Hazardous Substances Data: 357194-03-7(Hazardous Substances Data)

Usage

Uses

2-(2,2-Diphenyl-1,3-benzodioxol-5-yl)-3,5,7-trihydroxy-4H-1-benzopyran-4-one is an related compound of the flavanoid Quercetin (Q509500) with inhibitory activity on lipopolysaccharide-induced activation of macrophage U937 cells.

Upstream product

• 2051-90-3 Dichlorodiphenylmethane 
• 117-39-5 quercetol 

Downstream Products

• 357194-11-7 2-(2,2-diphenyl-1,3-benzodioxol-5-yl)-3,5-dihydroxy-7-[tetra-O-acetyl-β-D-glucopyranosyloxy]-4H-1-benzopyran-4-one 
• 498548-17-7 3-(benzyloxy)-2-(2,2-diphenylbenzo[d][1,3]dioxol-5-yl)-5,7-dihydroxy-4H-chromen-4-one 
• 498548-14-4 2-(2,2-diphenylbenzo[1,3]dioxol-5-yl)-3,5,7-tribenzyloxy-4H-chromen-4-one 
• 1393953-78-0 3-(benzyloxy)-2-(2,2-diphenylbenzo[d][1,3]dioxol-5-yl)-5,7-dimethoxy-4H-chromen-4-one 
• 498548-19-9 3-(benzyloxy)-2-(2,2-diphenylbenzo[d][1,3]dioxol-5-yl)-5-hydroxy-7-methoxy-4H-chromen-4-one 
• 2068-02-2 2-(3,4-dihydroxyphenyl)-5-hydroxy-3,7-dimethoxychromen-4-one 

Relevant articles and documents

Quercetin-3-oleoyl derivatives as new GPR40 agonists: Molecular docking studies and functional evaluation

The G-protein-coupled receptor 40 (GPR40)is an attractive molecular target for the treatment of type 2 diabetes mellitus. Previously, based on the natural oleic acid substrate, an exogenous ligand for this receptor, named AV1, was synthesized. In this context, here we validated the activity of AV1 as a full agonist, while the corresponding catechol analogue, named AV2, was investigated for the first time. The ligand-protein interaction between this new molecule and the receptor was highlighted in the lower portion of the GPR40 groove that generally accommodates DC260126. The functional assays performed have demonstrated that AV2 is a suitable GPR40 partial agonist, showing a therapeutic potential and representing a useful tool in the management of type 2 diabetes.

New lipophenols prevent carbonyl and oxidative stresses involved in macular degeneration

Dry age-related macular degeneration and Stargardt disease undergo a known toxic mechanism caused by carbonyl and oxidative stresses (COS). This is responsible for accumulation in the retinal pigment epithelium (RPE) of A2E, a main toxic pyridinium bis-retinoid lipofuscin component. Previous studies have shown that carbonyl stress in retinal cells could be reduced by an alkyl-phloroglucinol-DHA conjugate (lipophenol). Here, we performed a rational design of different families of lipophenols to conserve anti-carbonyl stress activities and improve antioxidant properties. Five synthetic pathways leading to alkyl-(poly)phenol derivatives, with phloroglucinol, resveratrol, catechin and quercetin as the main backbone, linked to poly-unsaturated fatty acid, are presented. These lipophenols were evaluated in ARPE-19 cell line for their anti-COS properties and a structure-activity relationship study is proposed. Protection of ARPE-19 cells against A2E toxicity was assessed for the four best candidates. Finally, interesting anti-COS properties of the most promising quercetin lipophenol were confirmed in primary RPE cells.

Synthesis, characterization and antioxidant activity of quercetin derivatives

A series of quercetin derivatives were synthesized via Williamson etherification, Steglich esterification or Koenigs–Knorr glycosylation reaction at 3 and 7 position hydroxyl groups selectively. The structures of the synthesized compounds were characteriz