224644-18-2

Basic information

• Product Name: 4H-1-Benzopyran-4-one, 7-hydroxy-3-[(4-hydroxyphenyl)methyl]-
• CAS NO: 224644-18-2
• Molecular Formula: C16H12O4
• Molecular Weight: 268.269
• Mol File: 224644-18-2.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: 4H-1-Benzopyran-4-one, 7-hydroxy-3-[(4-hydroxyphenyl)methyl]-(CAS DataBase Reference)
• NIST Chemistry Reference: 4H-1-Benzopyran-4-one, 7-hydroxy-3-[(4-hydroxyphenyl)methyl]-(224644-18-2)
• EPA Substance Registry System: 4H-1-Benzopyran-4-one, 7-hydroxy-3-[(4-hydroxyphenyl)methyl]-(224644-18-2)

Safety Data

• Hazardous Substances Data: 224644-18-2(Hazardous Substances Data)

Upstream product

• 501-97-3 4-hydroxyphenylpropionic acid 
• 68-12-2 N,N-dimethyl-formamide 
• 108-46-3 recorcinol 
• 23130-26-9 davidigenin 
• 124-63-0 methanesulfonyl chloride 

Relevant articles and documents

A concise synthesis of polyhydroxydihydrochalcones and homoisoflavonoids

A general and single step synthesis of polyhydroxydihydrochalcones from the readily available phenols and dihydrocinnamic acids using BF 3·Et2O is described. The method allows the synthesis of a wide range of compounds with multiple phenolic hydroxyls and other substituents. These dihydrochalcones are converted into homoisoflavonoids by DMF/PCl5 and the methodology has been applied to the synthesis of naturally occurring phloretin and 5,7-dihydroxy-3-[(4-hydroxyphenyl)methyl]-4H- chromen-4-one. The antioxidant activity of dihydrochalcones and homoisoflavonoids was determined by superoxide free radical (NBT) and DPPH free radical scavenging methods. Polyhydroxydihydrochalcones 3c, 3f, 3g and homoisoflavonoids 4c, 4f, 4g displayed excellent antioxidant activity.

1-Benzopyran-4-one antioxidants as aldose reductase inhibitors

Starting from the inhibitory activity of the flavonoid Quercetin, a series of 4H-1-benzopyran-4-one derivatives was synthesized and tested for inhibition of aldose reductase, an enzyme involved in the appearance of diabetic complications. Some of the compounds obtained display inhibitory activity similar to that of Sorbinil but are more selective than Quercetin and Sorbinil with respect to the closely related enzyme, aldehyde reductase, and also possess antioxidant activity. Remarkably, these compounds possess higher pK(a) values than carboxylic acids, a characteristic which could make the pharmacokinetics of these compounds very interesting. Molecular modeling investigations on the structures of inhibitors bound at the active site of aldose reductase were performed in order to suggest how these new inhibitors might bind to the enzyme and also to interpret structure-activity relationships.