177344-55-7

Basic information

• Product Name: 2-Propen-1-one, 1-(2,5-dihydroxyphenyl)-3-(4-hydroxyphenyl)-, (2E)-
• CAS NO: 177344-55-7
• Molecular Formula: C15H12O4
• Molecular Weight: 256.258
• Mol File: 177344-55-7.mol
• Article Data: 5

Chemical Properties

• CAS DataBase Reference: 2-Propen-1-one, 1-(2,5-dihydroxyphenyl)-3-(4-hydroxyphenyl)-, (2E)-(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Propen-1-one, 1-(2,5-dihydroxyphenyl)-3-(4-hydroxyphenyl)-, (2E)-(177344-55-7)
• EPA Substance Registry System: 2-Propen-1-one, 1-(2,5-dihydroxyphenyl)-3-(4-hydroxyphenyl)-, (2E)-(177344-55-7)

Safety Data

• Hazardous Substances Data: 177344-55-7(Hazardous Substances Data)

Upstream product

• 6515-21-5 4-methoxymethoxy-benzaldehyde 
• 100-52-7 benzaldehyde 
• 123-08-0 4-hydroxy-benzaldehyde 
• 490-78-8 2,5-Dihydroxyacetophenone 
• 3557-22-0 1-(2-hydroxy-5-((tetrahydro-2H-pyran-2-yl)oxy)phenyl)ethan-1-one 
• 74189-56-3 4-(tetrahydropyran-2-yloxy)benzaldehyde 
• 64-17-5 ethanol 

Downstream Products

• 943768-30-7 4',6-diacetoxyflavan-4-one 
• 943768-32-9 4',6-diacetoxyflav-3-ene 
• 61429-75-2 6-hydroxy-2-(4-hydroxyphenyl)chroman-4-one 
• 63046-09-3 6,4'-dihydroxyflavone 

Relevant articles and documents

Acid catalyzed stereoselective rearrangement and dimerization of flavenes: synthesis of dependensin

Appropriately substituted flavenes undergo stereoselective rearrangement and dimerization when treated with methanolic hydrochloric acid to give benzopyranobenzopyrans. A rationale for the rearrangement is proposed. This synthetic methodology has been used for a high yield synthesis of the natural product dependensin.

Synthesis and PPAR-γ ligand-binding activity of the new series of 2′-hydroxychalcone and thiazolidinedione derivatives

Fifteen chalcones and three thiazolidinedione (TZD) chalcones were prepared to evaluate their peroxisome proliferator-activated receptor-γ (PPAR-γ) ligand-binding activities. Among the three TZDs, one compound possessed PPAR-γ transactivation potential, while the others showed antagonistic activity against PPAR-γ transactivation. Among the chalcones, compound 5 was the most potent, and structure-activity relationship studies indicated that a methoxyl group in position C-4 and hydroxyl group in position C-4′ or 5′ in chalcone plays a key role in determining the potency of PPAR-γ activation.

Synthesis and description of chalcone-like compounds, inhibitors of aldose reductase

A series of hydroxy- and hydroxy-methoxychalcones was synthesized and the inhibitory activity and selectivity of the compounds towards bovine lens aldose reductase (AR) were tested. All the compounds display affinity for AR. The most active proved to be 1-(2,4-dihydroxyphenyl)-3-(4-hydroxyphenyl)propen-1-one (isoliquiritigenin, IC50= 7.60 μM). The selectivity of this compound was also tested, its inhibitory activity being assayed against glutathione reductase and sorbitol dehydrogenase.