6674-40-4

Basic information

• Product Name: 5-hydroxy-7-acetoxyflavone
• Synonyms: 5-hydroxy-7-acetoxyflavone;5-Hydroxy-4-oxo-2-phenyl-4H-chroMen-7-yl acetate;5-hydroxy-7-acetoxylsaccharidesavone
• CAS NO: 6674-40-4
• Molecular Formula: C₁₇H₁₂O₅
• Molecular Weight: 296
• EINECS: 200-258-5
• Mol File: 6674-40-4.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 510.2 °C at 760 mmHg
• Flash Point: 192.3 °C
• Appearance: /
• Density: 1.375 g/cm³
• Storage Temp.: 2-8°C
• CAS DataBase Reference: 5-hydroxy-7-acetoxyflavone(CAS DataBase Reference)
• NIST Chemistry Reference: 5-hydroxy-7-acetoxyflavone(6674-40-4)
• EPA Substance Registry System: 5-hydroxy-7-acetoxyflavone(6674-40-4)

Safety Data

• Hazardous Substances Data: 6674-40-4(Hazardous Substances Data)

Usage

General Description

5-Hydroxy-7-acetoxyflavone is a chemical compound belonging to the flavone class of flavonoids. It is a natural product found in various plant sources, including the traditional Chinese medicine Scutellaria baicalensis. 5-Hydroxy-7-acetoxyflavone has been studied for its potential bioactive properties, including antioxidant, anti-inflammatory, and anticancer activities. Its structure contains a hydroxyl group and an acetoxy group, which contribute to its biological effects. Research on 5-Hydroxy-7-acetoxyflavone continues to explore its potential therapeutic applications and mechanisms of action.

Upstream product

• 480-40-0 5,7-dihydroxy-2-phenyl-chromen-4-one 
• 108-24-7 acetic anhydride 

Downstream Products

• 1265223-26-4 7-acetoxy-5-methoxyflavone 
• 520-28-5 tectochrysine 
• 21392-57-4 Dimethyl-chrysin 
• 23296-91-5 5-acetoxy-7-methoxyflavone 
• 4431-47-4 5,8-dihydroxy-7-methoxyflavone 
• 29550-13-8 5,6-dihydroxy-7-methoxyflavone 
• 89971-03-9 7-methoxy-2-phenyl-4H-1-benzopyran-4,5,8-trione 
• 1265223-36-6 C₁₈H₁₄O₆ 
• 1265223-29-7 4,6-dimethoxy-1aphenyl-1aH-oxireno[2,3-b]chromen-7(7aH)-one 
• 119892-40-9 6-hydroxy-5,7-dimethoxyflavone 
• 89971-04-0 8-hydroxy-5,7-dimethoxyflavone 
• 1329-10-8 toringin 
• 539823-65-9 acetic acid 5-hydroxy-6,8-diiodo-4-oxo-2-phenyl-4H-chromen-7-yl ester 

Relevant articles and documents

Flavonoid-based inhibitors of the Phi-class glutathione transferase from black-grass to combat multiple herbicide resistance

The evolution and growth of multiple-herbicide resistance (MHR) in grass weeds continues to threaten global cereal production. While various processes can contribute to resistance, earlier work has identified the phi class glutathione-S-transferase (AmGSTF1) as a functional biomarker of MHR in black-grass (Alopecurus myosuroides). This study provides further insights into the role of AmGSTF1 in MHR using a combination of chemical and structural biology. Crystal structures of wild-type AmGSTF1, together with two specifically designed variants that allowed the co-crystal structure determination with glutathione and a glutathione adduct of the AmGSTF1 inhibitor 4-chloro-7-nitro-benzofurazan (NBD-Cl) were obtained. These studies demonstrated that the inhibitory activity of NBD-Cl was associated with the occlusion of the active site and the impediment of substrate binding. A search for other selective inhibitors of AmGSTF1, using ligand-fishing experiments, identified a number of flavonoids as potential ligands. Subsequent experiments using black-grass extracts discovered a specific flavonoid as a natural ligand of the recombinant enzyme. A series of related synthetic flavonoids was prepared and their binding to AmGSTF1 was investigated showing a high affinity for derivatives bearing a O-5-decyl-α-carboxylate. Molecular modelling based on high-resolution crystal structures allowed a binding pose to be defined which explained flavonoid binding specificity. Crucially, high binding affinity was linked to a reversal of the herbicide resistance phenotype in MHR black-grass. Collectively, these results present a nature-inspired new lead for the development of herbicide synergists to counteract MHR in weeds. This journal is

Anti-glycation, carbonyl trapping and anti-inflammatory activities of chrysin derivatives

The aim of this study was searching anti-glycation, carbonyl trapping and anti-inflammatory activities of chrysin derivatives. The inhibitory effect of chrysin on advanced glycation end-products (AGEs) was investigated by trapping methylglyoxal (MGO), and MGO-conjugated adducts of chrysin were analyzed using LC-MS/MS. The mono- or di-MGO-conjugated adducts of chrysin were present at 63.86 and 29.69% upon 48 h of incubation at a chrysin:MGO ratio of 1:10. The MGO adducted positions on chrysin were at carbon 6 or 6 & 8 in the A ring by classic aldol condensation. To provide applicable knowledge for developing chrysin derivatives as AGE inhibitors, we synthesized several O-alkyl or ester derivatives of chrysin and compared their AGE formation inhibitory, anti-inflammatory, and water solubility characteristics. The results showed that 5,7-di-O-acetylchrysin possessed higher AGE inhibitory and water solubility qualities than original chrysin, and retained the anti-inflammation activity. These results suggested that 5,7-di-O-acetylchrysin could be a potent functional food ingredient as an AGE inhibitor and anti-inflammatory agent, and promotes the development of the use of chrysin in functional foods.

Synthesis and anticancer effect of chrysin derivatives

A series of chrysin derivatives, prepared by alkylation, halogenation, nitration, methylation, acetylation and trifluoromethylation, were tested in vitro against human gastric adenocarcinoma cell line (SGC-7901) and colorectal adenocarcinoma (HT-29) cells. Among these derivatives of chrysin, 5,7-dimethoxy-8-iodochrysin 3 and 8-bromo-5-hydroxy-7-methoxychrysin 11 have the strongest activities against SGC-7901 and HT-29 cells, respectively. 5,7-Dihydroxy-8-nitrochrysin 12 were found to have strong activities against both SGC-7901 and HT-29 cells.