66585-05-5

Basic information

• Product Name: 4H-1-Benzopyran-4-one,3-hydroxy-2-phenyl-,radicalion(1+)(9CI)
• Synonyms: 4H-1-Benzopyran-4-one,3-hydroxy-2-phenyl-,radicalion(1+)(9CI)
• CAS NO: 66585-05-5
• Molecular Formula: C15H10O3
• Molecular Weight: 238.24
• Product Categories: FLAVONE
• Mol File: 66585-05-5.mol
• Article Data: 58

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 4H-1-Benzopyran-4-one,3-hydroxy-2-phenyl-,radicalion(1+)(9CI)(CAS DataBase Reference)
• NIST Chemistry Reference: 4H-1-Benzopyran-4-one,3-hydroxy-2-phenyl-,radicalion(1+)(9CI)(66585-05-5)
• EPA Substance Registry System: 4H-1-Benzopyran-4-one,3-hydroxy-2-phenyl-,radicalion(1+)(9CI)(66585-05-5)

Safety Data

• Hazardous Substances Data: 66585-05-5(Hazardous Substances Data)

Upstream product

• 577-85-5 3-hydroxyflavone 
• 100-52-7 benzaldehyde 
• 582-24-1 1-phenyl-2-hydroxyethanone 
• 118-93-4 o-hydroxyacetophenone 
• 19334-31-7 2-(3-phenylprop-2-enoyl)phenyl methanesulfonate 
• 1300709-21-0 C₁₅H₉BF₂O₃ 
• 1382310-08-8 2-phenyl-3-(prop-2-yn-1-yloxy)-4H-chromen-4-one 
• 76323-09-6 2,5-dihydroxydibenzyloxymethane 
• 1332744-73-6 allyl 4-oxo-2-phenyl-4H-chromen-3-yl carbonate 
• 1332744-70-3 benzyl 4-oxo-2-phenyl-4H-chromen-3-yl carbonate 
• 152459-36-4 3-(benzyloxy)-2-phenyl-4H-chromen-4-one 
• 120450-93-3 ethyl 4-oxo-2-phenyl-4H-chromen-3-yl carbonate 
• 1214-47-7 1-(2-hydroxyphenyl)-3-phenylprop-2-en-1-one 
• 67139-31-5 trans-3-mesyloxyflavanone 

Downstream Products

• 114050-93-0 3-(4-bromo-butoxy)-2-phenyl-chromen-4-one 
• 881184-17-4 flavon-3-yl N,N,N',N'-tetraethyldiamidophosphite 
• 32889-71-7 3-hydroxy-3-phenyl-1,2 indiandione 
• 70460-60-5 2-phenyl-chroman-3,4-dione 

Relevant articles and documents

Oxygenolysis of a series of copper(ii)-flavonolate adducts varying the electronic factors on supporting ligands as a mimic of quercetin 2,4-dioxygenase-like activity

Four copper(ii)-flavonolate compounds of type [Cu(LR)(fla)] {where LR = 2-(p-R-benzyl(dipyridin-2-ylmethyl)amino)acetate; R = -OMe (1), -H (2), -Cl (3) and -NO2 (4)} have been developed as a structural and functional enzyme-substrate (ES) model of the Cu2+-containing quercetin 2,4-dioxygenase enzyme. The ES model complexes 1-4 are synthesized by reacting 3-hydroxyflavone in the presence of a base with the respective acetate-bound copper(ii) complexes, [Cu(LR)(OAc)]. In the presence of dioxygen the ES model complexes undergo enzyme-type oxygenolysis of flavonolate (dioxygenase type bond cleavage reaction) at 80 °C in DMF. The reactivity shows a substituent group dependent order as -OMe (1) > -H (2) > -Cl (3) > ?NO2 (4). Experimental and theoretical studies suggest a single-electron transfer (SET) from flavonolate to dioxygen, rather than valence tautomerism {[CuII(fla?)] ? [CuI(fla˙)]}, to generate the reactive flavonoxy radical (fla˙) that reacts further with the superoxide radical to bring about the oxygenative ring opening reaction. The SET pathway has been further verified by studying the dioxygenation reaction with a redox-inactive Zn2+ complex, [Zn(LOMe)(fla)] (5).

Synthesis, inverse docking-assisted identification and in vitro biological characterization of Flavonol-based analogs of fisetin as c-Kit, CDK2 and mTOR inhibitors against melanoma and non-melanoma skin cancers

Due to hurdles, including resistance, adverse effects, and poor bioavailability, among others linked with existing therapies, there is an urgent unmet need to devise new, safe, and more effective treatment modalities for skin cancers. Herein, a series of flavonol-based derivatives of fisetin, a plant-based flavonoid identified as an anti-tumorigenic agent targeting the mammalian targets of rapamycin (mTOR)-regulated pathways, were synthesized and fully characterized. New potential inhibitors of receptor tyrosine kinases (c-KITs), cyclin-dependent kinase-2 (CDK2), and mTOR, representing attractive therapeutic targets for melanoma and non-melanoma skin cancers (NMSCs) treatment, were identified using inverse-docking, in vitro kinase activity and various cell-based anticancer screening assays. Eleven compounds exhibited significant inhibitory activities greater than the parent molecule against four human skin cancer cell lines, including melanoma (A375 and SK-Mel-28) and NMSCs (A431 and UWBCC1), with IC50 values ranging from 0.12 to 15 μM. Seven compounds were identified as potentially potent single, dual or multi-kinase c-KITs, CDK2, and mTOR kinase inhibitors after inverse-docking and screening against twelve known cancer targets, followed by kinase activity profiling. Moreover, the potent compound F20, and the multi-kinase F9 and F17 targeted compounds, markedly decreased scratch wound closure, colony formation, and heightened expression levels of key cancer-promoting pathway molecular targets c-Kit, CDK2, and mTOR. In addition, these compounds downregulated Bcl-2 levels and upregulated Bax and cleaved caspase-3/7/8 and PARP levels, thus inducing apoptosis of A375 and A431 cells in a dose-dependent manner. Overall, compounds F20, F9 and F17, were identified as promising c-Kit, CDK2 and mTOR inhibitors, worthy of further investigation as therapeutics, or as adjuvants to standard therapies for the control of melanoma and NMSCs.

COMPOSITION FOR IMPROVING RESPIRATORY HEALTH CONTINUOUSLY EXPOSED TO PARTICULATE MATTER ATMOSPHERE

An aspect of the present disclosure relates to a composition for improving respiratory health exposed to particulate matter, which contains a green tea extract, a green tea polysaccharide and a green tea flavonol as active ingredients. The composition provided in an aspect of the present disclosure can improve respiratory health damaged by exposure to particulate matter by enhancing the effect of preventing adsorption of particulate matter to bronchial epithelial cells and activating the cilia of bronchial epithelial cells. The composition provided in an aspect of the present disclosure may decrease blood heavy metal level.