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

Description

2-(2,2-diphenylbenzo[d][1,3]dioxol-5-yl)-3,5,7-trihydroxy-4H-chroMen-4-one is a complex organic compound that is structurally related to the flavonoid Quercetin. It is characterized by its unique molecular structure, which includes a benzodioxole ring and multiple hydroxyl groups. 2-(2,2-diphenylbenzo[d][1,3]dioxol-5-yl)-3,5,7-trihydroxy-4H-chroMen-4-one has demonstrated biological activity, particularly in the inhibition of lipopolysaccharide-induced activation in macrophage cells.

Uses

Used in Pharmaceutical Applications:
2-(2,2-diphenylbenzo[d][1,3]dioxol-5-yl)-3,5,7-trihydroxy-4H-chroMen-4-one is used as a bioactive compound for its inhibitory effects on lipopolysaccharide-induced activation of macrophage U937 cells. This property suggests potential applications in the development of anti-inflammatory or immunomodulatory drugs, as modulation of macrophage activation can be crucial in treating various inflammatory conditions and immune disorders.
Used in Research and Development:
In the field of scientific research, 2-(2,2-diphenylbenzo[d][1,3]dioxol-5-yl)-3,5,7-trihydroxy-4H-chroMen-4-one serves as a valuable compound for studying the mechanisms of macrophage activation and the role of flavonoids in immune response regulation. Its structural similarity to Quercetin may also provide insights into the structure-activity relationships of related compounds and guide the design of novel therapeutic agents.
Used in Drug Delivery Systems:
Similar to gallotannin, 2-(2,2-diphenylbenzo[d][1,3]dioxol-5-yl)-3,5,7-trihydroxy-4H-chroMen-4-one could potentially be incorporated into drug delivery systems to enhance its bioavailability and therapeutic efficacy. By employing various organic and metallic nanoparticles as carriers, the compound's delivery, solubility, and stability could be improved, allowing for more effective targeting of specific cell types and tissues.
Used in Anticancer Applications:
While the provided materials do not explicitly mention anticancer properties for this compound, its structural similarity to Quercetin, a known anticancer agent, suggests that it may have potential applications in cancer research and treatment. Further investigation into its effects on cancer cell lines and signaling pathways could reveal its utility as an anticancer agent or as a component of combination therapies.

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 
• 96375-15-4 2-(2,2-diphenylbenzo[d][1,3]dioxol-5-yl)-5-hydroxy-3,7-dimethoxy-4H-chromen-4-one 
• 477244-18-1 2-(2,2-diphenylbenzo[1,3]dioxol-5-yl)-3-(2,3,4,6-tetra-O-acetyl)-β-D-glucopyranosyloxy-5,7-dihydroxy-4H-chromen-4-one 
• 742062-20-0 2-(2,2-diphenylbenzo[d][1,3]dioxol-5-yl)-5,7-dihydroxy-3-(2,3,4,6-tetraacetyl-β-D-galactopyranosyl)-4H-chromen-4-one 
• 742062-22-2 Acetic acid (2S,3R,4S,5S)-4,5-diacetoxy-2-[2-(2,2-diphenyl-benzo[1,3]dioxol-5-yl)-5,7-dihydroxy-4-oxo-4H-chromen-3-yloxy]-tetrahydro-pyran-3-yl ester 
• 742062-21-1 Acetic acid (2S,3R,4S,5R)-4,5-diacetoxy-2-[2-(2,2-diphenyl-benzo[1,3]dioxol-5-yl)-5,7-dihydroxy-4-oxo-4H-chromen-3-yloxy]-tetrahydro-pyran-3-yl ester 
• 918309-41-8 2-(2,2-diphenylbenzo[d][1,3]dioxol-5-yl)-5-hydroxy-3,7-di(2,3,4,6-tetraacetyl-β-D-galactopyranosyl)-4H-chromen-4-one 
• 1197215-49-8 2-(2,2-diphenylbenzo[d][1,3]dioxol-5-yl)-5-hydroxy-3,7-bis(methoxymethoxy)-4H-chromen-4-one 
• 1197215-50-1 2-(3,4-dihydroxyphenyl)-5-hydroxy-3,7-bis(methoxymethoxy)-4H-chromen-4-one 
• 1197215-51-2 5-hydroxy-2-(3-hydroxy-4-methoxyphenyl)-3,7-bis(methoxymethoxy)-4H-chromen-4-one 
• 1393953-70-2 3,7-bis(benzyloxy)-2-(2,2-diphenylbenzo[d][1,3]dioxol-5-yl)-5-methoxy-4H-chromen-4-one 
• 529-51-1 5-O-methylquercetin 
• 529-40-8 ombuin 
• 552-54-5 rhamnazin 

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