3374-46-7

Basic information

• Product Name: 2-(5-oxo-2-furylidene)acetic acid
• Synonyms: 2-(5-oxo-2-furylidene)acetic acid;cis-4-carboxymethylenebut-2-en-4-olide;cis-dienelactone
• CAS NO: 3374-46-7
• Molecular Formula: C₆H₄O₄
• Molecular Weight: 140.09
• Mol File: 3374-46-7.mol

Chemical Properties

• Boiling Point: 336.1°Cat760mmHg
• Flash Point: 151.4°C
• Appearance: /
• Density: 1.721g/cm³
• Vapor Pressure: 2.16E-05mmHg at 25°C
• Refractive Index: 1.722
• CAS DataBase Reference: 2-(5-oxo-2-furylidene)acetic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(5-oxo-2-furylidene)acetic acid(3374-46-7)
• EPA Substance Registry System: 2-(5-oxo-2-furylidene)acetic acid(3374-46-7)

Safety Data

• Hazardous Substances Data: 3374-46-7(Hazardous Substances Data)

Usage

Physical form

Yellow crystalline solid

Melting point

189-190°C

Derivative of

Furfural

Uses

Production of pharmaceuticals and agrochemicals, potential antioxidant and antimicrobial properties, building block in the synthesis of various organic compounds

Hazardous

Potentially hazardous substance, should be handled with care in a laboratory setting.

InChI:InChI=1/C6H4O4/c7-5(8)3-4-1-2-6(9)10-4/h1-3H,(H,7,8)/b4-3-

Upstream product

• 31571-51-4 4-oxo-hex-2t-enedioic acid 
• 13427-52-6 xylo-3-deoxy-hexaric acid 
• 55088-96-5 2-hydroxy-buta-1,3-diene-1,1,4t-tricarboxylic acid triethyl ester 
• 120-18-3 naphthalene-2-sulfonate 
• 56710-46-4 L-5,6-isopropylidene-gulono-1,4-lactone 
• 1128-23-0 L-gulono-1,4-lactone 
• 50-81-7 ascorbic acid 
• 74826-52-1 t-butyl (Z)-5-oxo-2,5-dihydrofuran-2-ylideneacetate 
• 74826-73-6 6-t-butyl 1-ethyl (Z)-4-oxohex-2-enedioate 
• 157762-78-2 (4R,5S)-5-chloromuconolactone 
• 74826-51-0 t-butyl(E,3aα,4β,7β,7aα)-3-oxo-1,3,3aβ,4α,7α,7aβ-hexahydro-4,7-epoxyisobenzofuran-1-ylideneacetate 
• 3374-46-7 (Z)-5-oxo-2,5-dihydrofuran-2-ylideneacetic acid 
• 2138-22-9 4-chloro-1,2-benzenediol 
• 102335-48-8 (-)-(4'S,5S)-5-(2,2-dimethyl-1,3-dioxolan-4-yl)-2(5H)-furanone 

Downstream Products

• 3374-46-7 (2E)-2-(5-oxo-2(5H)-furanylidene)acetic acid 
• 24740-88-3 3-keto-cis,cis-muconic acid 

Relevant articles and documents

Recombinant expression of a unique chloromuconolactone dehalogenase ClcF from Rhodococcus opacus 1CP and identification of catalytically relevant residues by mutational analysis

Chloromuconolactone dehalogenase ClcF plays a unique role in 3-chlorocatechol degradation by Rhodococcus opacus 1CP by compensating the inability of its chloromuconate cycloisomerase ClcB2 to dechlorinate the chemically stable cycloisomerization product (4R,5S)-5-chloromuconolactone (5CML). High sequence similarities showed relatedness of ClcF to muconolactone isomerases (MLIs, EC 5.3.3.4) of the 3-oxoadipate pathway. Although both enzyme types share the ability to dechlorinate 5CML, comparison of kcat/Km indicated a significant extent of specialization of ClcF for dechlorination. This assumption was substantiated by an almost complete inability of ClcF to convert (4S)-muconolactone and the exclusive formation of cis-dienelactone from 5CML. Mutational analysis of ClcF by means of variants E27D, E27Q, Y50A, N52A, and A89S indicated relevance of some highly conserved residues for substrate binding and catalysis. Based on the putative isomerization mechanism of MLI, evidence was provided for a role of E27 in initial proton abstraction as well as of Y50 and N52 in substrate binding. In case of N52 substrate binding is likely to occur to the carboxylic group of 5CML as indicated by a significant change of product specificity. Expression in Escherichia coli BL21-CP(DE)-RIL followed by a three-step purification procedure with heat treatment is a convenient strategy to obtain recombinant ClcF and variants thereof.

Synthesis of (E)- and (Z)-5-(bromomethylene)furan-2(5H)-one by bromodecarboxylation of (E)-2-(5-oxofuran-2(5H)-ylidene)acetic acid

(E)- and (Z)-5-(bromomethylene)furan-2(5H)-one have been prepared starting from the commercially available adduct between furan and maleic anhydride. A bromodecarboxylation reaction is a key step in the synthesis. The reaction gives the (E)- or (Z)-5-(bromomethylene)furan-2(5H)-one as the major product, dependent on the method used in the bromodecarboxylation. Copyright Taylor & Francis Group, LLC.

Oxygenative cleavage of catechols including protocatechuic acid with molecular oxygen in water catalysed by water-soluble non-heme iron(III) complexes in relevance to catechol dioxygenases

Catechol dioxygenase model oxygenations have been performed for the first time in water by using water-soluble nonheme iron(III) complexes, enabling the oxygenation of protocatechuic acid and other catechols.

Site-directed mutagenesis of dienelactone hydrolase produces dienelactone isomerase

Replacing the active site Cys-123 of dienelactone hydrolase with Ser completely changes the catalysis displayed by the protein, from hydrolysis of the substrate E- and Z-dienelactones to maleylacetate by the native enzyme, to interconversion of the substr

Vitamin-C- and isovitamin-C-derived chemistry. Part I. Synthesis of 2,3-dideoxy derivatives of the Ascorbinic acids.

5,6-O-Isopropylidene-L-gulono- and -D-mannono-1,4-lactones are converted into 2-(dimethylamino)-1,3-dioxolane derivatives on treatment with N,N-dimethylformamide dimethylacetal in chloroform with azeotropic removal of the methanol thus formed.Quaternisation of the products with iodomethane, followed by thermal decomposition yields the corresponding C(4)-substituted enantiomeric butenolides.Some aspects of the reactions, the characterisation of the products, and further transformation are described.

The Synthesis of 5-Oxo-2,5-dihydrofuran-2-ylideneacetic Acids

The 5-oxo-2,5-dihydrofuran-2-ylideneacetic acids (2a), (3a), (9a), (10a), (11a), (12a) and (13a) have been synthesized by a procedure which allows the unambiguous assignment of the stereochemistry about the double bond in each isomer.The method, of general application, enables the acids to be prepared from the corresponding t-butyl esters with acid without isomerization about the double bond.The t-butyl esters are available from the Wittig reaction between anhydrides and t-butoxycarbonylmethylenetriphenylphosphorane.Where mainly one isomer is produced in the Wittig reaction, isomerization to an easily separable mixture of the esters can be achieved.Aspects of the isomerization of enol-lactone esters (e.g.(2b)) are descibed