1592-68-3

Basic information

• Product Name: 4H-1-Benzopyran-4-one, 2-[3,4-bis(phenylmethoxy)phenyl]-5-methoxy-3,7-bis(phenylmethoxy)-
• CAS NO: 1592-68-3
• Molecular Formula: C44H36O7
• Molecular Weight: 676.766
• Mol File: 1592-68-3.mol
• Article Data: 5

Chemical Properties

• CAS DataBase Reference: 4H-1-Benzopyran-4-one, 2-[3,4-bis(phenylmethoxy)phenyl]-5-methoxy-3,7-bis(phenylmethoxy)-(CAS DataBase Reference)
• NIST Chemistry Reference: 4H-1-Benzopyran-4-one, 2-[3,4-bis(phenylmethoxy)phenyl]-5-methoxy-3,7-bis(phenylmethoxy)-(1592-68-3)
• EPA Substance Registry System: 4H-1-Benzopyran-4-one, 2-[3,4-bis(phenylmethoxy)phenyl]-5-methoxy-3,7-bis(phenylmethoxy)-(1592-68-3)

Safety Data

• Hazardous Substances Data: 1592-68-3(Hazardous Substances Data)

Upstream product

• 100-39-0 benzyl bromide 
• 13157-90-9 2-[3,4-bis(phenylmethoxy)phenyl]-3,5,7-tris(phenylmethoxy)chromen-4-one 
• 117-39-5 quercetol 
• 1486-63-1 3,7-bis(benzyloxy)-2-[3,4-bis(benzyloxy)phenyl]-5-hydroxy-4H-1-benzopyran-4-one 
• 77-78-1 dimethyl sulfate 
• 74-88-4 methyl iodide 

Downstream Products

• 529-51-1 5-O-methylquercetin 

Relevant articles and documents

Natural and Synthetic Flavonoids as Potent Mycobacterium tuberculosis UGM Inhibitors

This study reports a novel class of inhibitors of uridine 5′-diphosphate (UDP) galactopyranose mutase (UGM) derived from a screening of natural products. This enzyme is an essential biocatalyst involved in the cell wall biosynthesis of Mycobacterium tuberculosis. Flavonoids are potent inhibitors of UGM. The synthesis of novel methylated flavonoids allowed a structure–activity relationship analysis to be performed and which functional groups and structural elements were required for UGM inhibition could be determined. The binding mode of one of the best inhibitors was found to be noncompetitive. Docking simulations indicated that this molecule was likely to bind UGM in its open conformation, in a cavity recently identified as a “druggable” pocket. Importantly, two of the best inhibitors of the M. tuberculosis UGM displayed moderate activity against whole M. tuberculosis cells. This study reports the first natural products that act as inhibitor of UGM. Given the importance of natural products in medicinal chemistry, these results create new opportunities for the discovery of new antitubercular agents.

Effects of Functional Groups and Sugar Composition of Quercetin Derivatives on Their Radical Scavenging Properties

Quercetin derivatives are widespread in the plant kingdom and exhibit various biological actions. The aim of this study was to investigate the structure-activity relationships of quercetin derivatives, with a focus on the influence of functional groups and sugar composition on their antioxidant capacity. A series of quercetin derivatives were therefore prepared and assessed for their DPPH radical scavenging properties. Isoquercetin O-gallates were more potent radical scavengers than quercetin. The systematic analysis highlights the importance of the distribution of hydroxy substituents in isoquercetin O-gallates to their potency.

Hemisynthesis of all the O-monomethylated analogues of quercetin including the major metabolites, through selective protection of phenolic functions

A new methodology for the hemisynthesis of all the five O-monomethylated analogues of quercetin (3′-O-methylquercetin (isorhamnetin), 4′-O-methylquercetin (tamarixetin), 3-O-methylquercetin, 5-O-methylquercetin (azaleatin) and 7-O-methylquercetin (rhamnetin)) through sequential protection of the different phenolic functions of quercetin is reported.