71005-52-2

Basic information

• Product Name: (2Z)-2-(4-hydroxybenzylidene)-6-methoxy-1-benzofuran-3(2H)-one
• Synonyms: (2Z)-2-(4-hydroxybenzylidene)-6-methoxy-1-benzofuran-3(2H)-one
• CAS NO: 71005-52-2
• Molecular Formula: C₁₆H₁₂O₄
• Molecular Weight: 268.26408
• Mol File: 71005-52-2.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: (2Z)-2-(4-hydroxybenzylidene)-6-methoxy-1-benzofuran-3(2H)-one(CAS DataBase Reference)
• NIST Chemistry Reference: (2Z)-2-(4-hydroxybenzylidene)-6-methoxy-1-benzofuran-3(2H)-one(71005-52-2)
• EPA Substance Registry System: (2Z)-2-(4-hydroxybenzylidene)-6-methoxy-1-benzofuran-3(2H)-one(71005-52-2)

Safety Data

• Hazardous Substances Data: 71005-52-2(Hazardous Substances Data)

Upstream product

• 63529-06-6 4,2'-dihydroxy-4'-methoxy-trans-chalcone 
• 6272-26-0 6-hydroxybenzofuran-3-one 
• 15832-09-4 6-methoxy-3-coumaranone 
• 123-08-0 4-hydroxy-benzaldehyde 
• 108-46-3 recorcinol 
• 2491-39-6 2-bromo-2',4'-dihydroxyoacetophenone 

Downstream Products

• 77412-34-1 2-(4-hydroxybenzyl)-6-methoxybenzofuran-3(2H)-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.

"On water" synthesis of aurones: First synthesis of 4,5,3',4',5'-pentamethoxy-6-hydroxyaurone from Smilax riparia

A simple and green method for the synthesis of aurones by condensation of benzofuranone with aromatic aldehyde in neat water has been developed. The main advantages of this protocol include good yields, absence of catalyst, reagent, organic solvent, work-up and chromatographic purification. 4,5,3',4',5'-Pentamethoxy-6-hydroxyaurone, isolated from Smilax riparia was synthesized for the first time from 3-benzyloxy-4,5-dimethoxybenzaldehyde in five steps. {figure presented}.

Blood-brain barrier permeable anticholinesterase aurones: Synthesis, structure-activity relationship, and drug-like properties

A series of novel aurones bearing amine and carbamate functionalities at various positions (rings A and/or B) of the scaffold was synthesized and evaluated for their acetylcholinesterase and butyrylcholinesterase inhibitory activities. Structure-activity relationship study disclosed several potent submicromolar acetylcholinesterase inhibitors (AChEIs) particularly aurones bearing piperidine and pyrrolidine moieties at ring A or ring B. Bulky groups particularly methoxyls, and carbamate to a lesser extent, at either rings were also prominently featured in these AChEI aurones as exemplified by the trimethoxyaurone 4-3. The active aurones exhibited a lower butyrylcholinesterase inhibition. A 3g€2-chloroaurone 6-3 originally designed to improve the metabolic stability of the scaffold was the most potent of the series. Molecular docking simulations showed these AChEI aurones to adopt favourable binding modes within the active site gorge of the Torpedo californica AChE (TcAChE) including an unusual chlorine-π interaction by the chlorine of 6-3 to establish additional bondings to hydrophobic residues of TcAChE. Evaluation of the potent aurones for their blood-brain barrier (BBB) permeability and metabolic stability using PAMPA-BBB assay and in vitro rat liver microsomes (RLM) identified 4-3 as an aurone with an optimal combination of high passive BBB permeability and moderate CYP450 metabolic stability. LC-MS identification of a mono-hydroxylated metabolite found in the RLM incubation of 4-3 provided an impetus for further improvement of the compound. Thus, 4-3, discovered within this present series is a promising, drug-like lead for the development of the aurones as potential multipotent agents for Alzheimer's disease.

Synthesis of aurones and their inhibitory effects on nitric oxide and PGE2 productions in LPS-induced RAW 264.7 cells

Sulfuretin is one of major constituents of Rhus verniciflua that exerts anti-inflammatory activities. Some of aurones were synthesized as sulfuretin derivatives and evaluated for their abilities to inhibit NO and PGE2 production in LPS-induced RAW 264.7 cells in order to reveal the relationship. Of the aurones synthesized in the present study, 2h and 2i, which possess C-6 hydroxyl group in A-ring and methoxy substituents in B-ring, more potently inhibited NO and PGE2 production and were less cytotoxic than sulfuretin.

OXYGENATION OF 4-HYDROXYCHALCONES CATALYSED BY PEROXIDASE AND BY LIGHT

Peroxidase or light catalysed oxygenation of 2',4-dihydroxy-4'-methoxychalcone produced two labile initial products characterized as stereoisomers of 4'-hydroxy-6-methoxy-2-(α-hydroperoxybenzyl)coumaranone.By analogy, the products from similar oxygenation reactions of 2',4,4'-trihydroxychalcone previously studied are now considered to be hydroperoxy-benzylcoumaranones rather than dioxetanes. - Keywords: Oxygenation; photooxygenation; peroxidase; 4-hydroxychalcones; 2',4-dihydroxy-4'-methoxychalcone.