58942-16-8

Basic information

• Product Name: 4H-1-Benzopyran-4-one, 3,5,6,7-tetrahydroxy-2-(4-methoxyphenyl)-
• CAS NO: 58942-16-8
• Molecular Formula: C16H12O7
• Molecular Weight: 316.267
• Mol File: 58942-16-8.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: 4H-1-Benzopyran-4-one, 3,5,6,7-tetrahydroxy-2-(4-methoxyphenyl)-(CAS DataBase Reference)
• NIST Chemistry Reference: 4H-1-Benzopyran-4-one, 3,5,6,7-tetrahydroxy-2-(4-methoxyphenyl)-(58942-16-8)
• EPA Substance Registry System: 4H-1-Benzopyran-4-one, 3,5,6,7-tetrahydroxy-2-(4-methoxyphenyl)-(58942-16-8)

Safety Data

• Hazardous Substances Data: 58942-16-8(Hazardous Substances Data)

Upstream product

• 170234-78-3 1-(6-Hydroxy-2,4-dimethoxy-3-methoxymethoxy-phenyl)-3-(4-methoxy-phenyl)-propane-1,3-dione 
• 170234-68-1 3-Hydroxy-5,7-dimethoxy-6-methoxymethoxy-2-(4-methoxy-phenyl)-chromen-4-one 
• 170234-85-2 5,7-Dimethoxy-6-methoxymethoxy-2-(4-methoxy-phenyl)-chromen-4-one 
• 104481-00-7 1-(6-hydroxy-2,4-dimethoxy-3-methoxymethoxyphenyl)-ethanone 
• 6962-57-8 3,6-dihydroxy-2,4-dimethoxyacetophenone 
• 6938-19-8 6-hydroxy-5,7-dimethoxy-2-(4-methoxyphenyl)-4H-chromen-4-one 
• 170234-57-8 3,6-Dihydroxy-5,7-dimethoxy-2-(4-methoxy-phenyl)-chromen-4-one 

Relevant articles and documents

Studies of the selective O-alkylation and dealkylation of flavonoids. XVIII. A convenient method for synthesizing 3,5,6,7-tetrahydroxyflavones

In the demethylation of 6-hydroxy-3,4',7-trimethoxy-5-(tosyloxy)flavone with anhydrous aluminum bromide, the 5-tosyloxyl group was eliminated with bromination to give 8-bromo-3,6,7-trihydroxy-4'-methoxyflavone as the main product. When anhydrous aluminum chloride was used in the demethylation of the acetate, the 5-tosyloxyl group was cleaved prior to the demethylation to give 5,6,7-trihydroxy-3,4'-dimethoxyflavone. Demethylation of 6-hydroxy-4',5,7-trimethoxy-3-(tosyloxy)flavone and its acetate with the bromide or chloride afforded the 5,6,7-trihydroxyflavone without the cleavage of the 3-tosyloxyl group, but was not suitable for the general synthesis of the 3,5,6,7-tetrahydroxyflavones because of the difficulty in removing the protecting group. Consequently, it was found that the direct demethylation of 3,6-dihydroxy-5,7-dimethoxyflavones with anhydrous aluminum chloride-sodium iodide in acetonitrile was the most useful general method for synthesizing 3,5,6,7-tetrahydroxyflavones. Additionally, the reported structures of two natural flavones were revised.