480-70-6

Basic information

• Product Name: AUREUSIDIN
• Synonyms: 4,6,3',4'-TETRAHYDROXYAURONE;AUREUSIDIN
• CAS NO: 480-70-6
• Molecular Formula: C₁₅H₁₀O₆
• Molecular Weight: 286.24
• Product Categories: Aurones
• Mol File: 480-70-6.mol
• Article Data: 13

Chemical Properties

• Melting Point: 295-295 °C (decomp)
• Boiling Point: 628.6°C at 760 mmHg
• Flash Point: 244.3°C
• Appearance: /
• Density: 1.708g/cm³
• Vapor Pressure: 2.14E-16mmHg at 25°C
• Refractive Index: 1.832
• Storage Temp.: -20°C Freezer, Under inert atmosphere
• Solubility: DMSO (Slightly), Methanol (Slightly)
• PKA: 6.04±0.20(Predicted)
• CAS DataBase Reference: AUREUSIDIN(CAS DataBase Reference)
• NIST Chemistry Reference: AUREUSIDIN(480-70-6)
• EPA Substance Registry System: AUREUSIDIN(480-70-6)

Safety Data

• Hazardous Substances Data: 480-70-6(Hazardous Substances Data)

Usage

InChI:InChI=1/C15H10O6/c16-8-5-11(19)14-12(6-8)21-13(15(14)20)4-7-1-2-9(17)10(18)3-7/h1-6,16-19H/b13-4-

Upstream product

• 3260-49-9 4,6-dihydroxybenzofuran-3(2H)-one 
• 139-85-5 3,4-dihydroxybenzaldehyde 
• 23053-69-2 (Z)-2-(3,4-dimethoxybenzylidene)-4,6-dimethoxybenzofuran-3(2H)-one 
• 108-73-6 3,5-dihydroxyphenol 
• 110865-03-7 2-chloro-1-(2,4,6-trihydroxyphenyl)ethan-1-one 
• 4225-35-8 4,6-dimethoxycoumaranone 
• 120-14-9 3,4-dimethoxy-benzaldehyde 
• 1202495-48-4 (2Z)-2-[3,4-bis(methoxymethoxy)benzylidene]-4,6-bis(methoxymethoxy)-1-benzofuran-3(2H)-one 
• 73692-51-0 2',3,4,4',6'-pentahydroxychalcone 
• 112772-60-8 3-(3,4-bis(methoxymethoxy)phenyl)-1-(2-hydroxy-4,6-bis(methoxymethoxy)phenyl)prop-2-en-1-one 
• 480-66-0 2,4,6-trihydroxyacetophenone 
• 65490-09-7 2'-hydroxy-4',6'-bis(methoxymethoxy)acetophenone 
• 6515-06-6 3,4-bis-methoxymethoxy-benzaldehyde 
• 6515-21-5 4-methoxymethoxy-benzaldehyde 

Downstream Products

• 57765-66-9 eriodictoyl dihydrochalcone 
• 65370-64-1 4,6-diacetoxy-2-((Z)-3,4-diacetoxy-benzylidene)-benzofuran-3-one 

Relevant articles and documents

Design, synthesis and biological activities of dihydroaurones

To widen aurones applicability in achromatic food and cosmetic applications, a series of dihydroaurones were designed to mimic natural aurones as well as synthetic aurones. Dihydroaurones have been synthesized from the corresponding aurones by hydrogenation. These dihydroaurones and their corresponding aurones were screened for antioxidant, anti-inflammatory and tyrosinase enzyme inhibitory activity. Synthesized dihydroaurones (3b-f) displayed superior antioxidant activity in superoxide free radical scavenging assay than the standard gallic acid. Dihydroaurones (3b-f) also exhibited significant tyrosinase enzyme inhibitory activity and two dihydroaurones (3h, 3j) showed promising 5-lipoxygenase inhibitory activity.

Aurones as new porcine pancreatic α-amylase inhibitors

Background: Aurones, (Z)-2-benzylidenebenzofuran-3-one derivatives, are naturally-occurring structural isomers of flavones, with promising pharmacological potential. Methods: In this study, the structural requirements for the inhibition of porcine pancreatic α-amylase by hydroxylated or methoxylated aurone derivatives were investigated by assessing their in vitro biological activities against porcine pancreatic α-amylase. Results: The structure-activity relationship of these inhibitors based on both in vitro and in silico findings showed that the hydrogen bonds between the OH groups of the A or B ring of (Z)-benzylidenebenzofuran-3-one derivatives and the catalytic residues of the binding site are crucial for their inhibitory activities. Conclusion: It seems that the OH groups in aurones inhibit α-amylase in a manner similar to that of OH groups in flavones and flavonols.

Aurones as histone deacetylase inhibitors: Identification of key features

In this study, a total of 22 flavonoids were tested for their HDAC inhibitory activity using fluorimetric and BRET-based assays. Four aurones were found to be active in both assays and showed IC50 values below 20 μM in the enzymatic assay. Molecular modelling revealed that the presence of hydroxyl groups was responsible for good compound orientation within the isoenzyme catalytic site and zinc chelation.