487-24-1

Basic information

• Product Name: 7-HYDROXY-4'-METHOXYFLAVONE
• Synonyms: 7-HYDROXY-4'-METHOXYFLAVONE;7-HYDROXY-4-METHOXYFLAVONE;7-hydroxy-2-(4-methoxyphenyl)-4h-1-benzopyran-4-on;7-hydroxy-2-(4-methoxyphenyl)-4h-1-benzopyran-4-one;7-hydroxy-4’-methoxy-flavon;c.i.75570;PRATOL;7-hydroxy-2-(4-methoxyphenyl)-4-benzopyrone
• CAS NO: 487-24-1
• Molecular Formula: C₁₆H₁₂O₄
• Molecular Weight: 268.26
• EINECS: 207-653-2
• Product Categories: Di-substituted Flavones
• Mol File: 487-24-1.mol
• Article Data: 29

Chemical Properties

• Melting Point: 263-264°C
• Boiling Point: 479.4°Cat760mmHg
• Flash Point: 183.4°C
• Appearance: /
• Density: 1.329g/cm³
• Vapor Pressure: 8.17E-10mmHg at 25°C
• Refractive Index: 1.641
• CAS DataBase Reference: 7-HYDROXY-4'-METHOXYFLAVONE(CAS DataBase Reference)
• NIST Chemistry Reference: 7-HYDROXY-4'-METHOXYFLAVONE(487-24-1)
• EPA Substance Registry System: 7-HYDROXY-4'-METHOXYFLAVONE(487-24-1)

Safety Data

• Hazardous Substances Data: 487-24-1(Hazardous Substances Data)

Usage

InChI:InChI=1/C16H12O4/c1-19-12-5-2-10(3-6-12)15-9-14(18)13-7-4-11(17)8-16(13)20-15/h2-9,17H,1H3

Upstream product

• 13351-10-5 2',4'-dihydroxy-4-methoxychalcone 
• 108-46-3 recorcinol 
• 2881-83-6 ethyl 4-methoxybenzoylacetate 
• 81674-91-1 1-(2,4-dihydroxyphenyl)-3-(4-methoxyphenyl)-prop-2-en-1-one 
• 89-84-9 2',4'-dihydroxy-4-acetophenone 
• 123-11-5 4-methoxy-benzaldehyde 
• 100-09-4 4-methoxybenzoic acid 
• 75808-79-6 1-(2',4'-dihydroxyphenyl)-3-(4''-methoxyphenyl)-propane-1,3-dione 
• 67881-34-9 2',4'-bis(4-methoxybenzoyloxy)acetophenone 
• 102664-14-2 1-[2-hydroxy-4-(4-methoxy-benzoyloxy)-phenyl]-3-(4-methoxy-phenyl)-propane-1,3-dione 
• 109471-14-9 (2E)-1-[2-hydroxy-4-(methoxymethoxy)phenyl]-3-(4-methoxyphenyl)prop-2-en-1-one 
• 65490-08-6 2-hydroxy-4-(methoxymethoxy)acetophenone 
• 109471-14-9 2'-hydroxy-4'-(methoxymethoxy)-4-methoxychalcone 
• 25015-92-3 2-chloro-1-(2,4-dihydroxyphenyl)ethanone 

Downstream Products

• 20931-20-8 7-hydroxy-2-(4-methoxy-phenyl)-4-phenyl-chromenylium; chloride 
• 486-66-8 daidzein 
• 42345-42-6 7-hydroxy-2-(4-methoxy-phenyl)-4-oxo-4H-chromene-8-carbaldehyde 
• 1489103-10-7 2-(4-methoxyphenyl)-7-(3-(4-(3-((1,2,3,4-tetrahydroacridin-9-yl)amino)propyl)piperazin-1-yl)propoxy)-4H-chromen-4-one 
• 1489101-77-0 7-(3-bromopropoxy)-2-(4-methoxyphenyl)-4H-chromen-4-one 

Relevant articles and documents

Synthesis of ring-A hydroxylated flavones by sodium hydroxide-catalyzed cyclization of 1,3-diketones in water

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Scope and Applications of 2,3-Oxidative Aryl Rearrangements for the Synthesis of Isoflavone Natural Products

The reaction of flavanones with hypervalent iodine reagents was investigated with a view to the synthesis of naturally occurring isoflavones. In contrast to several previous reports in the literature, we did not observe the formation of any benzofurans via a ring contraction pathway, but could isolate only isoflavones, resulting from an oxidative 2,3-aryl rearrangement, and flavones, resulting from an oxidation of the flavanones. Although the 2,3-oxidative rearrangement allows a synthetically useful approach toward some isoflavone natural products due to the convenient accessibility of the required starting materials, the overall synthetic utility and generality of the reaction appear to be more limited than previous literature reports suggest.

Design, synthesis and apoptosis inducing activity of nonsteroidal flavone-methanesulfonate derivatives on MCF-7 cell line as potential sulfatase inhibitor

In recent years, focusing on new potent anticancer agents with selective activity is one of the greatest challenges in cancer therapy. Breast cancer is the most common cancer and the main cause of cancer deaths in women. The sulfatase enzyme plays an important role in converting the sulfated steroids into non-sulfate steroid hormones, which increases the growth and development of many hormone-dependent cancers, such as breast cancer. In this regard, structure-based optimization was conducted to design novel flavone-sulfonates pharmacophore as a new steroid sulfatase inhibitor. In the present work, the conventional methods for the synthesis of 4-oxo-2-phenyl-4H-chromen-7-yl methanesulfonate derivatives were reported. Their cytotoxicity was evaluated with MTT assay against a breast cancer cell line (MCF-7). The apoptosis inducing activity of the most cytotoxic compound 3c with an IC50 value of 0.615 μM was evaluated in comparison to docetaxel in the presence of estradiol which is a crucial growth factor to survive the cancerous cells. The results of double staining Annexin V-FITC/PI analysis suggested that the cytotoxic activity of this compound 3c in MCF-7 cells occurs via apoptosis. Molecular docking studies were conducted to clarify the inhibition mode of the most promising compound (3c) over the sulfatase (1P49) binding site. The analysis revealed the role of hydrogen bond interaction with Gly181 and hydrophobic interactions through the 1P49 active site in the ligand-receptor complex as significant descriptors to rationalize the potential inhibition activity. [Figure not available: see fulltext.]