23053-69-2

Basic information

• Product Name: 4,6,3',4'-tetramethoxyaurone
• Synonyms: 4,6,3',4'-tetramethoxyaurone
• CAS NO: 23053-69-2
• Molecular Weight: 342.348
• Mol File: 23053-69-2.mol

Chemical Properties

• CAS DataBase Reference: 4,6,3',4'-tetramethoxyaurone(CAS DataBase Reference)
• NIST Chemistry Reference: 4,6,3',4'-tetramethoxyaurone(23053-69-2)
• EPA Substance Registry System: 4,6,3',4'-tetramethoxyaurone(23053-69-2)

Safety Data

• Hazardous Substances Data: 23053-69-2(Hazardous Substances Data)

Upstream product

• 114021-60-2 2'-hydroxy-3,4,4',6'-tetramethoxychalcone 
• 7722-84-1 dihydrogen peroxide 
• 1008105-86-9 (Z)-2-(3,4-dimethoxybenzylidene)-4,6-dimethoxy-2,3-dihydrobenzofuran-3-ol 
• 10496-67-0 3-(3,4-dimethoxyphenyl)-1-(2-hydroxy-4,6-dimethoxyphenyl)prop-2-en-1-one 
• 76650-20-9 1-(2,4,6-trimethoxyphenyl)-3-(3,4-dimethoxyphenyl)propenone 
• 832-58-6 1-(2,4,6-trimethoxyphenyl)ethanone 
• 120-14-9 3,4-dimethoxy-benzaldehyde 
• 110865-03-7 2-chloro-1-(2,4,6-trihydroxyphenyl)ethan-1-one 
• 3260-49-9 4,6-dihydroxybenzofuran-3(2H)-one 
• 108-73-6 3,5-dihydroxyphenol 
• 1064710-43-5 3-(3',4'-dimethoxyphenyl)-1-(2-hydroxy-4,6-dimethoxyphenyl)prop-2-yn-1-one 
• 103040-51-3 2-chloro-1-(2-hydroxy-4,6-dimethoxyphenyl)ethanone 
• 54987-77-8 3.4.4'.6'-tetramethoxy-2'-acetoxy-trans-chalcone 
• 94757-83-2 2-(3,4-dimethoxy-benzyl)-2,4,6-trimethoxy-benzofuran-3-one 

Downstream Products

• 480-70-6 aureusidin 
• 480-70-6 4,6,3',4'-tetrahydroxyaurone 

Relevant articles and documents

Hydroxyaurone derivative as well as preparation method and application thereof

The invention relates to a hydroxyaurone derivative as well as a preparation method and application thereof. A monomeric compound aurone separated from Kunlun chrysanthemum in Xinjiang is used as a mother nucleus compound, hydroxyl is introduced into auro

Discovery of naturally occurring aurones that are potent allosteric inhibitors of hepatitis C virus RNA-dependent RNA polymerase

We have identified naturally occurring 2-benzylidenebenzofuran-3-ones (aurones) as new templates for non-nucleoside hepatitis C virus (HCV) RNA-dependent RNA polymerase (RdRp) inhibitors. The aurone target site, identified by site-directed mutagenesis, is located in thumb pocket I of HCV RdRp. The RdRp inhibitory activity of 42 aurones was rationally explored in an enzyme assay. Molecular docking studies were used to determine how aurones bind to HCV RdRp and to predict their range of inhibitory activity. Seven aurone derivatives were found to have potent inhibitory effects on HCV RdRp, with IC50 below 5 μM and excellent selectivity index (inhibition activity versus cellular cytotoxicity). The most active aurone analogue was (Z)-2-((1-butyl-1H-indol-3-yl)methylene)-4,6-dihydroxybenzofuran-3(2H)-one (compound 51), with an IC50 of 2.2 μM. Their potent RdRp inhibitory activity and their low toxicity make these molecules attractive candidates as direct-acting anti-HCV agents.

Versatile and expeditious synthesis of aurones via AuI-catalyzed cyclization

(Chemical Equation Presented) Aurones are conveniently formed in a three-step procedure including a goldI-catalyzed cyclization of 2-(1-hydroxyprop-2-ynyl)phenols as a highly regio- and stereoselective key step. A wide diversity of derivatives can be obtained starting from substituted salicylaldehydes. Synthesis of natural 4,6,3′,4′-tetramethoxyaurone and structure revision of two natural products (dalmaisione D and 4′-chloroaurone) were achieved.

Reactions of carbanions with 1,3-benzodioxin-4-ones: Facile routes to flavones, aurones, and acyl phloroglucinols

Two 1,3-benzodioxin-4-ones react with enolates, acetylides and aryllithium reagents to afford adducts that were converted into flavones, aurones, and an acyl phloroglucinol. Georg Thieme Verlag Stuttgart.

Synthesis and insect antifeedant activity of aurones against spodoptera litura larvae

A series of aurones were prepared from various phenols via phenoxy acetic acids and coumaranones and evaluated for insect antifeedant activity against the common cutworm (Spodoptera litura). The naturally occurring aurone was most active at an ED50 of 0.12 μmol/cm2. The synthetic precursor, coumaranones, showed that the introduction of methoxyl and methyl groups to the benzene ring increased insect antifeedant activity. Similarly, the tested aurones showed that the introduction of methoxyl group to the A and/or B rings increased the insect antifeedant activity, but 4,5,6- and 3 ,4 ,5 -trisubstituted compounds did not show this activity in this test. The hydroxylation of aurones in the B ring should be disadvantageous for insect antifeedant activity against S. litura. Although the melting points did not correlate well with the insect antifeedant activity, compounds that were nearly inactive had high melting points. A significant correlation was noted between biological activity (pED50) and a hydrogen-bonding parameter calculated from the Rf value obtained from SiOH thin-layer chromatography and a lipophilicity parameter (log k) calculated from the retention time in ODS high-performance liquid chromatography. The respective correlation coefficients (r) were -0.83 and -0.70. The introduction of alkoxy and alkyl groups along with adequate hydrogen bonding seems to contribute to the antifeedant activity of the compounds tested.

Preparation of 4,6,3',4'-tetrasubstituted aurones via aluminium oxide-catalyzed condensation

4,6,3',4'-Tetrasubstituted aurones were prepared by a protection- deprotection route with an alumina-catalyzed condensation of 3(2H)-benzofuranones with substituted aldehydes as the key step. Aureusidin (6) was obtained by demethylation of 4,6,3',4'-tetramethoxyaurone (5), a natural product from Cyperus capitatus. 4,6,3',4'-Tetrabenzyloxyaurone (9) was converted in a one hydrogenation-deprotection step to dihydroaureusidin (10).

Scope of mercuric acetate oxidation of chalcones and the antibacterial activity of resulting aurones

Mercuric acetate provides a convenient reagent for oxidative cyclization of 2′-hydroxychalcones resulting in stereospecific formation of Z-aurones. Thirteen aurones have been synthesised with varying substituents for studying the scope of the reaction. The antibacterial activity of these products has been studied against Staphylococcus aureus and Escherichia coli.

An environmentally benign synthesis of aurones and flavones from 2′-acetoxychalcones using n-tetrabutylammonium tribromide

A wide variety of aurones (3a-f) can be prepared exclusively from 2′-acetoxychalcones (1a-f) in high yields in two steps, by bromination using n-tetrabutylammonium tribromide (TBATB) in the presence of CaCO3 in CH2Cl2-MeOH (5:2) at 0-5°C followed by cyclization of the brominated products 2a-f on treating with 0.2 M ethanolic KOH solution at 0-5°C, respectively. In contrast various flavone derivatives 6a-f can be obtained exclusively from compounds 1a-f in fairly good yields, by brominating with the same reagent in CH2Cl2, followed by dehydrobromination and finally cyclization on treating with 0.1 M NaOMe solution.

Carbon-13 Nmr Spectroscopy of Methoxy- and Acetoxyaurones

The 13C nmr chemical shifts of methoxy and acetoxyaurones are reported.The signals are assigned on the basis of substituent effects and comaprison with structurally related compounds.Assignments are also verified by Sford.

Dye-sensitized Photoconversion of Chalkones into Aurones

Dye-sensitized photooxygenation of 2'-hydroxy-4',6',3,4-tetramethoxychalkone yields 4,6,3',4'-tetramethoxyaurone.It is the first report of photochemical conversion of chalkones into aurones.Besides this, methylation of chelated hydroxyl is also being reported for the first time from this reaction.