15485-80-0

Basic information

• Product Name: 4H-1-BENZOPYRAN-4-ONE
• Synonyms: 7-Hydroxy-4’-nitroisoflavone
• CAS NO: 15485-80-0
• Molecular Formula: C₁₅H₉NO₅
• Molecular Weight: 283.24
• Mol File: 15485-80-0.mol
• Article Data: 12

Chemical Properties

• Melting Point: 290-292℃
• Boiling Point: 530.788 °C at 760 mmHg
• Flash Point: 274.811 °C
• Appearance: Pale yellow/Powder
• Density: 1.494 g/cm³
• Vapor Pressure: 6.98E-12mmHg at 25°C
• Refractive Index: 1.692
• Storage Temp.: 2-8°C
• PKA: 6.68±0.20(Predicted)
• Water Solubility: Slightly soluble in water.
• CAS DataBase Reference: 4H-1-BENZOPYRAN-4-ONE(CAS DataBase Reference)
• NIST Chemistry Reference: 4H-1-BENZOPYRAN-4-ONE(15485-80-0)
• EPA Substance Registry System: 4H-1-BENZOPYRAN-4-ONE(15485-80-0)

Safety Data

• Hazardous Substances Data: 15485-80-0(Hazardous Substances Data)

Usage

Uses

7-Hydroxy-4'-nitroisoflavone is used in the synthesis of iso flavones, Synthesis of daidzin, soflavone amide derivatives.

InChI:InChI=1/C15H9NO5/c17-11-5-6-12-14(7-11)21-8-13(15(12)18)9-1-3-10(4-2-9)16(19)20/h1-8,17H

Upstream product

• 137522-86-2 7-hydroxy-3-(4-nitro-phenyl)-4-oxo-4H-chromene-2-carboxylic acid 
• 104-03-0 4-nitrobenzeneacetic acid 
• 15485-63-9 1-(2,4-dihydroxyphenyl)-2-(4-nitrophenyl)ethanone 
• 124-63-0 methanesulfonyl chloride 
• 108-46-3 recorcinol 
• 68-12-2 N,N-dimethyl-formamide 
• 15485-74-2 7-hydroxy-3-(4-nitro-phenyl)-4-oxo-4H-chromene-2-carboxylic acid ethyl ester 
• 555-21-5 4-Nitrophenylacetonitrile 
• 137522-88-4 7-Formyloxy-3-(4-nitrophenyl)-4H-1-benzopyran-4-one 
• 122-51-0 orthoformic acid triethyl ester 

Downstream Products

• 19816-54-7 7-methoxy-3-(4-nitrophenyl)-4H-1-benzopyran-4-one 
• 77316-78-0 7-hydroxy-3-(4-aminophenyl)-4H-benzopyran-4-one 
• 67523-11-9 4-[4-(4-nitro-phenyl)-isoxazol-5-yl]-benzene-1,3-diol 
• 486-66-8 daidzein 
• 3682-01-7 daidzein diacetate 
• 1426687-89-9 N-(4-(7-(3-hydroxy-3-methylbut-1-ynyl)-4-oxo-4H-chromen-3-yl)phenyl)methanesulfonamide 
• 1426688-21-2 N-(4-(4-oxo-7-((trimethylsilyl)ethynyl)-4H-chromen-3-yl)phenyl)methanesulfonamide 
• 1426688-28-9 N-(4-(7-((2-tert-butoxypyridin-4-yl)ethynyl)-4-oxo-4H-chromen-3-yl)phenyl)methanesulfonamide 
• 1426688-25-6 N-(4-(4-oxo-7-((2-oxo-1,2-dihydropyridin-4-yl)ethynyl)-4H-chromen-3-yl)phenyl)methanesulfonamide 
• 1426688-23-4 N-(4-(7-ethynyl-4-oxo-4H-chromen-3-yl)phenyl)methanesulfonamide 
• 1426687-85-5 3-(4-aminophenyl)-4-oxo-4H-chromen-7-yl trifluoromethanesulfonate 
• 1426687-87-7 3-(4-(methylsulfonamido)phenyl)-4-oxo-4H-chromen-7-yl trifluoromethanesulfonate 
• 1426687-83-3 3-(4-nitrophenyl)-4-oxo-4H-chromen-7-yl trifluoromethanesulfonate 

Relevant articles and documents

The synthesis and anti-inflammatory evaluation of 1,2,3-triazole linked isoflavone benzodiazepine hybrids

Copper catalyzed azide-alkyne cycloaddition was used for the first time to access a small series of eight novel 1,2,3-triazole linked isoflavone benzodiazepine hybrids. As part of this work, a previously unreported alkyne substituted pyrrolo[1,4]benzodiaz

Structure-guided design and synthesis of isoflavone analogs of GW4064 with potent lipid accumulation inhibitory activities

Our group has previously reported a series of isoflavone derivatives with antidyslipidemic activity. With this background, a series of isoflavone analogs of GW4064 were designed, synthesized and evaluated the lipid-lowering activity of analogs. As a result, most of compounds significantly reduced the lipid accumulation in 3T3-L1 adipocytes and four of them (10a, 11, 15c and 15d) showed stronger inhibitory than GW4064. The most potent compound 15d exhibited promising agonistic activity for FXR in a cell-based luciferase reporter assay. Meanwhile, 15d up-regulated FXR, SHP and BSEP gene expression and down-regulated the mRNA expression of lipogenesis gene SREBP-1c. Besides, an improved safety profile of 15d was also observed in a HepG2 cytotoxicity assay compared with GW4064. The obtained biological results were further confirmed by a molecular docking study showing that 15d fitted well in the binding pocket of FXR and interacted with some key residues simultaneously.

Synthesis and biological evaluation of isoflavone amide derivatives with antihyperlipidemic and preadipocyte antiproliferative activities

A series of isoflavone amides were designed with isoflavone in place of the scaffold of 2-arylbenzoxazole as cholesterol ester transfer protein (CETP) inhibitors. Twelve new compounds were synthesized, and their inhibitory activities of CETP and preadipocyte proliferation were assayed. The hypolipidemic potency of the most effective compound HY-2c was further tested in vivo by hamster. The results indicate that HY-2c exhibited favorable antihyperlipidemic and preadipocyte antiproliferative activities.