16692-52-7

Basic information

• Product Name: 2-(4-Methoxyphenyl)-3,5,7-trimethoxy-4H-1-benzopyran-4-one
• Synonyms: 2-(4-Methoxyphenyl)-3,5,7-trimethoxy-4H-1-benzopyran-4-one;Tetramethylkaempferol
• CAS NO: 16692-52-7
• Molecular Formula: C₁₉H₁₈O₆
• Molecular Weight: 342.34
• Mol File: 16692-52-7.mol
• Article Data: 14

Chemical Properties

• Melting Point: 114-116 °C
• Boiling Point: 540.6±50.0 °C(Predicted)
• Appearance: /
• Density: 1.29±0.1 g/cm3(Predicted)
• CAS DataBase Reference: 2-(4-Methoxyphenyl)-3,5,7-trimethoxy-4H-1-benzopyran-4-one(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(4-Methoxyphenyl)-3,5,7-trimethoxy-4H-1-benzopyran-4-one(16692-52-7)
• EPA Substance Registry System: 2-(4-Methoxyphenyl)-3,5,7-trimethoxy-4H-1-benzopyran-4-one(16692-52-7)

Safety Data

• Hazardous Substances Data: 16692-52-7(Hazardous Substances Data)

Usage

Description

2-(4-Methoxyphenyl)-3,5,7-trimethoxy-4H-1-benzopyran-4-one is a complex chemical compound belonging to the benzopyran-4-one class. It features a highly substituted structure with three methoxy groups and one methoxyphenyl group. Known for its potential biological activities, this compound has been studied for its antioxidant, anti-inflammatory, and anticancer properties, making it a valuable target for research in medicine and drug development.

Uses

Used in Pharmaceutical Industry:
2-(4-Methoxyphenyl)-3,5,7-trimethoxy-4H-1-benzopyran-4-one is used as a pharmaceutical agent for its potential antioxidant, anti-inflammatory, and anticancer properties. Its unique structure and pharmacological properties make it a promising candidate for the development of new drugs to treat various diseases and conditions.
Used in Cosmetic Industry:
In the cosmetic industry, 2-(4-Methoxyphenyl)-3,5,7-trimethoxy-4H-1-benzopyran-4-one is used as an active ingredient for its antioxidant and anti-inflammatory properties. It can be incorporated into skincare products to provide benefits such as reducing inflammation, promoting skin health, and protecting the skin from oxidative stress.
Used in Research and Development:
2-(4-Methoxyphenyl)-3,5,7-trimethoxy-4H-1-benzopyran-4-one is used as a research compound for studying its biological activities and potential applications in medicine and drug development. Its unique structure and pharmacological properties make it an interesting target for further investigation and exploration of its therapeutic potential.

Upstream product

• 59259-80-2 3,5,7-trimethoxy-4'-hydroxyflavonol 
• 77-78-1 dimethyl sulfate 
• 3301-49-3 kumatakenin 
• 186581-53-3 diazomethane 
• 491-54-3 4'-O-methylkaempferol 
• 94103-36-3 (2E)-1-(2,4,6-trimethoxyphenyl)-3-(4-methoxyphenyl)-2-propen-1-one 
• 34446-64-5 (E)-3-(4-methoxyphenyl)propenoyl chloride 
• 5128-44-9 5-hydroxy-7-methoxy-2-(4-methoxyphenyl)-4H-chromen-4-one 
• 5631-70-9 4',5,7-trimethoxyflavone 
• 520-18-3 kaempferol 
• 74-88-4 methyl iodide 
• 1385651-99-9 [2-(2-methoxyacetyl)-3,5-dimethoxy]-phenyl 4-methoxybenzoate 
• 1385652-16-3 1-(2-hydroxy-4,6-dimethoxyphenyl)-2-methoxy-3-(4-methoxyphenyl)-1,3-propanedione 
• 500-99-2 3,5-dimethoxyphenol 

Downstream Products

• 15486-34-7 5-hydroxy-3,4',7-trimethoxyflavone 
• 15486-33-6 4',7,-di-O-methylkaempferol 
• 1098-92-6 kaempferol 5,7,4'-trimethyl ether 
• 1467042-67-6 5,7-dimethoxy-2-(4-methoxyphenyl)-3-(prop-2-yn-1-yloxy)-4H-chromen-4-one 

Relevant articles and documents

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Pharmacokinetics and Metabolites of 12 Bioactive Polymethoxyflavones in Rat Plasma

Polymethoxyflavones (PMFs) are a subgroup of flavonoids possessing various health benefits. 3,5,7,4′-Tetramethoxyflavone (1), 5,6,7,4′-tetramethylflavone (2), 3,7,3′,4′-tetramethoxyflavone (3), 5,7,3′,4′-tetramethoxyflavone (4), 5-hydroxy-3,7,2′,4′-tetramethoxyflavone (5), 3,5,7,2′,4′-pentamethoxyflavone (6), 5-hydroxy-3,7,3′,4′-tetramethoxyflavone (7), 3-hydroxy-5,7,3′,4′-tetramethylflavone (8), 3,5,7,3′,4′-pentamethoxyflavone (9), 5-hydroxy-3,7,3′,4′,5′-pentamethoxyflavone (10), 3-hydroxy-5,7,3′,4′,5′-pentamethoxyflavone (11), and 3,5,7,3′,4′,5′-hexamethoxylflavone (12) were 12 bioactive and available PMFs. The aim of this study was to investigate the pharmacokinetic, metabolite, and antitumor activities as well as the structure-pharmacokinetic-antitumor activity relationships of these 12 PMFs to facilitate further studies of their medicinal potentials. The cytotoxicity of PMFs with a hydroxy group toward HeLa, A549, HepG2, and HCT116 cancer cell lines was generally significantly more potent than that of PMFs without a hydroxy group. Compounds 5, 7, 8, 10, and 11 were all undetectable in rat plasma, while compounds 1-4, 6, 9, and 12 were detectable. Both the number and position of hydroxy and methoxy groups played an important role in modulating PMF pharmacokinetics and metabolites.

Correlation study on methoxylation pattern of flavonoids and their heme-targeted antiplasmodial activity

A library of 33 polymethoxylated flavones (PMF) was evaluated for heme-binding affinity by biomimetic MS assay and in vitro antiplasmodial activity on two strains of P. falciparum. Stability of heme adducts was discussed using the dissociation voltage at 50% (DV50). No correlation was observed between the methoxylation pattern and the antiparasitic activity, either for the 3D7 chloroquine-sensitive or for the W2 chloroquine-resistant P. falciparum strains. However, in each PMF family an increased DV50 was observed for the derivatives methoxylated in position 5. Measurement of intra-erythrocytic hemozoin formation of selected derivatives was performed and hemozoin concentration was inversely correlated with heme-binding affinity. Kaempferol showed no influence on hemozoin formation, reinforcing the hypothesis that this compound may exert in vitro antiplasmodial activity mostly through other pathways. Pentamethoxyquercetin has simultaneously demonstrated a significant biological activity and a strong interaction with heme, suggesting that inhibition of hemozoin formation is totally or partially responsible for its antiparasitic effect.