76288-41-0

Basic information

• Product Name: 1,3-Propanedione, 1-(2-hydroxy-4,6-dimethoxyphenyl)-3-(4-methoxyphenyl)-
• CAS NO: 76288-41-0
• Molecular Formula: C18H18O6
• Molecular Weight: 330.337
• Mol File: 76288-41-0.mol
• Article Data: 8

Chemical Properties

• CAS DataBase Reference: 1,3-Propanedione, 1-(2-hydroxy-4,6-dimethoxyphenyl)-3-(4-methoxyphenyl)-(CAS DataBase Reference)
• NIST Chemistry Reference: 1,3-Propanedione, 1-(2-hydroxy-4,6-dimethoxyphenyl)-3-(4-methoxyphenyl)-(76288-41-0)
• EPA Substance Registry System: 1,3-Propanedione, 1-(2-hydroxy-4,6-dimethoxyphenyl)-3-(4-methoxyphenyl)-(76288-41-0)

Safety Data

• Hazardous Substances Data: 76288-41-0(Hazardous Substances Data)

Upstream product

• 90-24-4 2-hydroxy-4,6-dimethoxyacetophenone 
• 94-30-4 ethyl 4-methoxybenzoate 
• 100-07-2 4-methoxy-benzoyl chloride 
• 83171-42-0 4,6-dimethoxy-2-(4'-methoxybenzoyloxy)acetophenone 

Downstream Products

• 5631-70-9 4',5,7-trimethoxyflavone 
• 50848-67-4 6-iodo-5,7,4'-trimethoxyflavone 
• 49620-13-5 robustaflavone 
• 28442-04-8 robustaflavone hexamethyl ether 
• 5128-44-9 5-hydroxy-7-methoxy-2-(4-methoxyphenyl)-4H-chromen-4-one 
• 674367-99-8 5-[5,7-dimethoxy-2-(4-methoxy-phenyl)-4-oxo-4H-chromen-6-yl]-7-methyl-2-phenyl-5,8-dihydro-[1,2,4]triazolo[1,2-a]pyridazine-1,3-dione 
• 674367-92-1 5,7-Dimethoxy-2-(4-methoxy-phenyl)-6-((E)-3-methyl-buta-1,3-dienyl)-chromen-4-one 
• 76288-50-1 4',5-dihydroxy-8-C-prenyl-6'',6''-dimethyl-4'',5''-dihydropyrano<2'',3'':7,6>flavone 
• 76288-54-5 4',7-di-O-prenylapigenin 
• 76288-47-6 6′′,6′′-dimethyl-4′′,5′′-dihydropyrano[2′′,3′′:7,6]apigenin 
• 76288-49-8 4',5-dihydroxy-6'',6''-dimethyl-5''-C-prenyl-4'',5''-dihydropyrano<2'',3'':7,8>flavone 
• 76288-44-3 5-Hydroxy-2-(4-hydroxy-phenyl)-8,8-dimethyl-7,8-dihydro-6H-pyrano[3,2-g]chromen-4-one 
• 520-36-5 5,7-dihydroxy-2-(4-hydroxyphenyl)-4H-1-benzopyran-4-one 
• 70872-32-1 6,8-di-C-prenylapigenin 

Relevant articles and documents

TWO DIBENZOYLMETHANES FROM THE FROND EXUDATE OF NOTHOLAENA SPECIES

Fronds of various ferns in the genus notholaena produce an exudate which consists mostly of flavonoid aglycones.In some species we found small amounts of two dibenzoylmethanes or β-diketones.These have been identified by spectroscopic methods.Both, 2',β,4-trihydroxy-4',6'-dimethoxychalcone and 2',β-dihydroxy-4',6',4-trimethoxychalcone, are novel natural products.The structures have been confirmed by synthesis of the latter compound. Key words: Notholaena; Pteridaceae; frond exudates; β-diketones; 2',β,4-trihydroxy-4',6'-dimethoxychalcone; 2',β-dihydroxy-4',6',4-trimethoxychalcone; 2',4'-dihydroxy-4',6'-dimethoxydibenzoylmethane, 2'-hydroxy-4',6',4-trimethoxydebenzoylmethane.

Synthesis and preliminary biological evaluation of chrysin derivatives as potential anticancer drugs

A series of chrysin derivatives were prepared from 2-hydroxyacetophenone, 2,4-dihydroxyacetophenone, 2,4,6-trihydroxy- acetophenone, using modified Baker-Venkataraman transformation. Their anticancer activities in vitro were evaluated by the standard MTT method. The results of biological test showed that some of chrysin derivatives showed stronger anticancer activity than 5-fluorouracil.

Total synthesis of robustaflavone, a potential anti-hepatitis B agent

Robustaflavone, a naturally occurring compound, is an inhibitor of hepatitis B virus replication in vitro. Robustaflavone is a biflavanoid composed of two units of apigenin (5,7,4'-trihydroxyflavone) joined via a biaryl linkage between the 6-position of one unit and the 3'-position of the other (I6,II3'-biapigenin). The natural material was isolated from the seed- kernels of Rhus succedanea. To provide ready access to sufficient quantities of material for continued biological studies, as well as to provide a general route for the preparation of structural analogues, a total synthesis of robustaflavone was pursued. The total synthesis was approached by constructing apigenin ethers containing functionalities at the 6- and 3'- positions which could be cross-coupled using transition metal catalysis. Key steps of the synthesis included development of a regioselective iodination of an apigenin derivative at the 6-position. Also key was the formation of an apigenin 3'-boronate using a palladium-catalyzed exchange of the corresponding 3'-iodide with a diboron reagent. Finally, identification of appropriate reaction conditions for Suzuki coupling to form the sterically congested 6-3''' biaryl bond of robustaflavone provided access to the desired biflavanoid system. This work represents the first total synthesis of robustaflavone.