50634-02-1

Basic information

• Product Name: 4H-1-Benzopyran-4-one, 3-benzoyl-5-hydroxy-2-phenyl-
• CAS NO: 50634-02-1
• Molecular Formula: C22H14O4
• Molecular Weight: 342.351
• Mol File: 50634-02-1.mol
• Article Data: 5

Chemical Properties

• CAS DataBase Reference: 4H-1-Benzopyran-4-one, 3-benzoyl-5-hydroxy-2-phenyl-(CAS DataBase Reference)
• NIST Chemistry Reference: 4H-1-Benzopyran-4-one, 3-benzoyl-5-hydroxy-2-phenyl-(50634-02-1)
• EPA Substance Registry System: 4H-1-Benzopyran-4-one, 3-benzoyl-5-hydroxy-2-phenyl-(50634-02-1)

Safety Data

• Hazardous Substances Data: 50634-02-1(Hazardous Substances Data)

Upstream product

• 40296-16-0 2',6'-dibenzoyloxyacetophenone 
• 699-83-2 2,6-dihydroxylacetophenone 
• 93-97-0 benzoic acid anhydride 
• 108-88-3 toluene 
• 98-88-4 benzoyl chloride 
• 859054-43-6 2-benzoyl-1-(2,6-dihydroxy-phenyl)-3-phenyl-propane-1,3-dione 

Downstream Products

• 108012-98-2 5-hydroxy-6,8-dinitro-2-phenyl-chromen-4-one 
• 107572-71-4 5-acetoxy-8-nitro-2-phenyl-chromen-4-one 
• 92424-81-2 5-hydroxy-8-nitro-2-phenyl-chromen-4-one 
• 548-58-3 primetin 
• 502916-27-0 3-benzoyl-5-benzyloxyflavone 
• 491-78-1 5-Hydroxyflavone 

Relevant articles and documents

An Efficient One-Pot Synthesis and Anticancer Activity of 4'-Substituted Flavonoids

A number of 4'-substituted (R = H, Me, Cl, F) flavone derivatives is synthesized from 2-hydroxyacetophenones using the modified Baker–Venkataraman reaction. Compound [3-(4-fluorobenzoyl)-5- hydroxy-4'-fluoroflavone] was synthesized for the first time with the yield of 12%. Antiproliferative assays indicate that the synthesized flavones with F substituent at the 4' position demonstrate higher activity than the other flavone derivatives, particularly against HeLa and MCF-7 with the IC50 9.5 and 2.7 μM, respectively.

Baker-venkataraman rearrangement under microwave irradiation: A new strategy for the synthesis of 3-aroyl-5-hydroxyflavones

Microwave irradiation selectively induces the Baker-Venkataraman rearrangement of 2′,6′-diaroyloxyacetophenones to give 3-aroyl-5-hydroxyflavones, in a very short reaction time. Under classical heating conditions these reactions afforded 5-hydroxyflavones

3-Aroyl-5-hydroxyflavones: Synthesis and mechanistic studies by mass spectrometry

The synthesis and mass spectra of three 3-aroyl-5-hydroxflavones are reported. The interpretation of the mechanistic pathways for the fragmentation of the metastable molecular ions of these compounds was achieved through the analysis of their mass-analysed ion kinetic energy (MIKE) spectra and of the B2/E spectra of a few fragment ions. Labelling of the hydroxyl proton with deuterium and the analysis of the MIKE spectra of a model compound with chlorine atoms in the 2',6'- and 2',6'-positions led to a mechanism for the losses of OH. and HCO. which involves hydrogen migration from the 2'- or 6'-position to the 6-carbonyl oxygen atom. A mechanism for the loss of a neutral molecule of anisole from the molecular ion of the 3-aroyl-5-hydroxyflavone with a methoxyl group in the 4'- and 4'-positions is also suggested. For the flavones with hydrogen or chlorine substituents at these positions, loss of a phenyl (or chlorophenyl) radical occurs instead.