14756-22-0

Basic information

• Product Name: 2-(4-methoxyphenyl)-4H-benzo[h]chromen-4-one
• Synonyms: 14756-22-0; 4H-Naphtho(1,2-b)pyran-4-one, 2-(4-methoxyphenyl)-; 4'-Methoxy-7,8-benzoflavone; 4'-Methoxy-a-naphthoflavone
• CAS NO: 14756-22-0
• Molecular Formula: C₂₀H₁₄O₃
• Molecular Weight: 302.3234
• Mol File: 14756-22-0.mol
• Article Data: 10

Chemical Properties

• Boiling Point: 490.7°C at 760 mmHg
• Flash Point: 242.8°C
• Density: 1.273g/cm³
• Vapor Pressure: 8.97E-10mmHg at 25°C
• Refractive Index: 1.67
• CAS DataBase Reference: 2-(4-methoxyphenyl)-4H-benzo[h]chromen-4-one(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(4-methoxyphenyl)-4H-benzo[h]chromen-4-one(14756-22-0)
• EPA Substance Registry System: 2-(4-methoxyphenyl)-4H-benzo[h]chromen-4-one(14756-22-0)

Safety Data

• Hazardous Substances Data: 14756-22-0(Hazardous Substances Data)

Usage

Chemical class

benzo[h]chromen-4-one derivatives

Core structure

4H-benzo[h]chromen-4-one

Substituent

4-methoxyphenyl at the 2-position

Potential applications

medicinal chemistry, drug development, therapeutic properties

Unique structure

interesting target for pharmacological research

Possible uses

ligand in chemical synthesis, probe in chemical analysis

Upstream product

• 100-09-4 4-methoxybenzoic acid 
• 711-79-5 1-hydroxy-2-acetonaphthone 
• 123-11-5 4-methoxy-benzaldehyde 
• 135-19-3 β-naphthol 
• 90-15-3 α-naphthol 
• 1621629-41-1 C₂₀H₁₆O₄ 
• 125574-12-1 (E)-1-(1-hydroxynaphthalen-2-yl)-3-(4-methoxyphenyl)prop-2-en-1-one 
• 40649-75-0 2'-Hydroxy-4-methoxy-3',4'-benzochalkone 
• 100-07-2 4-methoxy-benzoyl chloride 
• 794-94-5 p-Methoxybenzoic anhydride 
• 370583-68-9 1-(1-hydroxy-[2]naphthyl)-3-(4-methoxy-phenyl)-propane-1,3-dione 

Downstream Products

• 98166-67-7 UCCF 355 
• 100-09-4 4-methoxybenzoic acid 

Relevant articles and documents

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Benzoflavone derivatives as potent antihyperuricemic agents

Two series of benzoflavone derivatives were rationally designed, synthesized and evaluated for their xanthine oxidase (XO) inhibitory potential. Among both series, eight compounds (NF-2, NF-4, NF-9, NF-12, NF-16, NF-25, NF-28, and NF-32) were found to exert significant XO inhibition with IC50 values lower than 10 μM. Enzyme kinetic studies revealed that the most potent benzoflavone derivatives (NF-4 and NF-28) are mixed type inhibitors of the XO enzyme. Molecular modeling studies were also performed to investigate the binding interactions of these molecules (NF-4 and NF-28) with the amino acid residues present in the active site of the enzyme. Docking results confirmed that their favorable binding conformations in the active site of XO can completely block the catalytic activity of the enzyme. Benzoflavone derivatives exhibiting potent XO enzyme inhibition also showed promising results in a hyperuricemic mice model when tested in vivo.

Application of α- and β-naphthoflavones as monooxygenase inhibitors of Absidia coerulea KCh 93, Syncephalastrum racemosum KCh 105 and Chaetomium sp. KCh 6651 in transformation of 17α-methyltestosterone

In this work, 17α-methyltestosterone was effectively hydroxylated by Absidia coerulea KCh 93, Syncephalastrum racemosum KCh 105 and Chaetomium sp. KCh 6651. A. coerulea KCh 93 afforded 6β-, 12β-, 7α-, 11α-, 15α-hydroxy derivatives with 44%, 29%, 6%, 5% and 9% yields, respectively. S. racemosum KCh 105 afforded 7α-, 15α- and 11α-hydroxy derivatives with yields of 45%, 19% and 17%, respectively. Chaetomium sp. KCh 6651 afforded 15α-, 11α-, 7α-, 6β-, 9α-, 14α-hydroxy and 6β,14α-dihydroxy derivatives with yields of 31%, 20%, 16%, 7%, 5%, 7% and 4%, respectively. 14α-Hydroxy and 6β,14α-dihydroxy derivatives were determined as new compounds. Effect of various sources of nitrogen and carbon in the media on biotransformations were tested, however did not affect the degree of substrate conversion or the composition of the products formed. The addition of α- or β-naphthoflavones inhibited 17α-methyltestosterone hydroxylation but did not change the percentage composition of the resulting products.