103430-01-9

Basic information

• Product Name: 5,7-dimethoxy-2-(3-methoxyphenyl)-4H-chromen-4-one
• Synonyms: 5,7-dimethoxy-2-(3-methoxyphenyl)-4H-chromen-4-one
• CAS NO: 103430-01-9
• Molecular Weight: 312.322
• Mol File: 103430-01-9.mol

Chemical Properties

• CAS DataBase Reference: 5,7-dimethoxy-2-(3-methoxyphenyl)-4H-chromen-4-one(CAS DataBase Reference)
• NIST Chemistry Reference: 5,7-dimethoxy-2-(3-methoxyphenyl)-4H-chromen-4-one(103430-01-9)
• EPA Substance Registry System: 5,7-dimethoxy-2-(3-methoxyphenyl)-4H-chromen-4-one(103430-01-9)

Safety Data

• Hazardous Substances Data: 103430-01-9(Hazardous Substances Data)

Upstream product

• 743430-86-6 2-(3-hydroxy-phenyl)-5,7-dimethoxy-chromen-4-one 
• 77-78-1 dimethyl sulfate 
• 90-24-4 2-hydroxy-4,6-dimethoxyacetophenone 
• 76554-68-2 2'-hydroxy-3,4',6'-trimethoxychalcone 
• 591-31-1 3-methoxy-benzaldehyde 
• 67837-36-9 2-chloro-5,7-dimethoxy-4H-chromen-4-one 
• 10365-98-7 3-methoxyphenylboronic acid 
• 500-99-2 3,5-dimethoxyphenol 
• 1255860-64-0 3’,5’-dimethoxyphenyl 3,3-dichloroacrylate 
• 64964-84-7 3,3-dichloro-1-(2’-hydroxy-4’,6’-dimethoxyphenyl)prop-2-en-1-one 
• 480-66-0 2,4,6-trihydroxyacetophenone 

Downstream Products

• 710338-99-1 5,3'-dihydroxy-7-methoxyflavone 
• 72472-92-5 5,7-dihydroxy-2-(3-hydroxyphenyl)-4H-chromen-4-one 
• 28973-32-2 5,7-dihydroxy-2-(3'-methoxyphenyl)chromone 

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

Unraveling the anti-influenza effect of flavonoids: Experimental validation of luteolin and its congeners as potent influenza endonuclease inhibitors

The biological effects of flavonoids on mammal cells are diverse, ranging from scavenging free radicals and anti-cancer activity to anti-influenza activity. Despite appreciable effort to understand the anti-influenza activity of flavonoids, there is no clear consensus about their precise mode-of-action at a cellular level. Here, we report the development and validation of a screening assay based on AlphaScreen technology and illustrate its application for determination of the inhibitory potency of a large set of polyols against PA N-terminal domain (PA-Nter) of influenza RNA-dependent RNA polymerase featuring endonuclease activity. The most potent inhibitors we identified were luteolin with an IC50 of 72 ± 2 nM and its 8-C-glucoside orientin with an IC50 of 43 ± 2 nM. Submicromolar inhibitors were also evaluated by an in vitro endonuclease activity assay using single-stranded DNA, and the results were in full agreement with data from the competitive AlphaScreen assay. Using X-ray crystallography, we analyzed structures of the PA-Nter in complex with luteolin at 2.0 ? resolution and quambalarine B at 2.5 ? resolution, which clearly revealed the binding pose of these polyols coordinated to two manganese ions in the endonuclease active site. Using two distinct assays along with the structural work, we have presumably identified and characterized the molecular mode-of-action of flavonoids in influenza-infected cells.

Modulation of human neutrophils' oxidative burst by flavonoids

Inflammation is a normal response towards tissue injury, but may become deleterious to the organism if uncontrolled. The overproduction of reactive species during the inflammatory process may cause or magnify the damage at inflammatory sites. Flavonoids have been suggested as therapeutic agents to avoid such damage, as these compounds exhibit anti-inflammatory activity, through the modulation of oxidative stress and signalling pathways. Both effects may attenuate neutrophils' activities at inflammatory sites. In this study,we investigated the structure/activity relationship of a series of flavonoids on the oxidative burst of human neutrophils in vitro, as a measure of its anti-inflammatory potential. Neutrophils were stimulated with phorbol-12-myristate-13-acetate, and fluorescence and chemiluminescence techniques were used to evaluate the generation of reactive oxygen species. All the tested flavonoids revealed the ability to modulate the neutrophil 's oxidative burst. From the obtained results, the pivotal role of the catechol group in the B-ringwas evidenced as well as the minor importance of the hydroxylations in the A-ring, which did not appear to be determinant for the activity, although clearly influencing the lipophilicity of the tested flavonoids. It is also clarified the importance of the methylation in the OH group at the B-ring catechol moiety. In conclusion, the obtained results uncover new possible strategies for the resolution of inflammatory processes, using flavonoids to modulate neutrophil's oxidative burst.

Selective and efficient oxidative modifications of flavonoids with 2-iodoxybenzoic acid (IBX)

2-Iodoxybenzoic acid (IBX), a mild and efficient hypervalent iodine oxidant, has been utilised in different reaction conditions to perform several efficient oxidative modifications of flavonoids. Fine-tuning of the reaction conditions allowed remarkably selective modifications of these compounds. At room temperature, IBX proved to be an excellent reagent for a highly regioselective aromatic hydroxylation of monohydroxylated flavanones and flavones, generating the corresponding catecholic derivatives showing high antioxidant activity. At 90 °C, IBX efficiently dehydrogenated a large panel of methoxylated flavanones to their corresponding flavones exhibiting anticancer activity. IBX polystyrene has also been utilised to increase the recovery of highly polar compounds. Following the first oxidation, the reagent was recovered and reused in several runs without loss of efficiency and selectivity. The first example of an application of IBX polystyrene in a dehydrogenation reaction has been described.