Its chemical formula is HO2CCH=CHCO2H. A butenedioic acid in which the double bond has cis- (Z)-configuration. However, conversion of the cis isomer into the trans isomer is possible by photolysis in the presence of a small amount of bromine. [6], Maleic acid is an industrial raw material for the production of glyoxylic acid by ozonolysis.[7]. CopyCopied, Validated by Experts, Validated by Users, Non-Validated, Removed by Users, Predicted data is generated using the ACD/Labs Percepta Platform - PhysChem Module, Predicted data is generated using the US Environmental Protection Agency’s EPISuite™, Click to predict properties on the Chemicalize site, For medical information relating to Covid-19, please consult the,, ACD/Labs Percepta Platform - PhysChem Module, US Environmental Protection Agency’s EPISuite™, Compounds with the same molecular formula, Search Google for structures with same skeleton. Maleic acid is also used as an adhesion promoter for different substrates, such as nylon and zinc coated metals e.g galvanized steel, in methyl methacrylate based adhesives. Get … Molecular Weight: 116.073 g/mol. Maleic acid esters are also called maleates, for instance dimethyl maleate. Kurt Lohbeck, Herbert Haferkorn, Werner Fuhrmann and Norbert Fedtke "Maleic and Fumaric Acids" in Ullmann's Encyclopedia of Industrial Chemistry, Wiley-VCH, Weinheim, 2000. Maleic acid, being electrophilic, participates as a dienophile in many Diels-Alder reactions. Maleic acid or cis-butenedioic acid is an organic compound that is a dicarboxylic acid, a molecule with two carboxyl groups. Maleic acid is more soluble in water than fumaric acid. The maleate ion is useful in biochemistry as an inhibitor of transaminase reactions. Cas Number: 110-16-7. Maleic acid or cis-butenedioic acid is an organic compound that is a dicarboxylic acid, a molecule with two carboxyl groups. [4], 22.7 kJ/mol higher than that of fumaric acid. Some bacteria produce the enzyme maleate isomerase, which is used by bacteria in nicotinate metabolism. In industry, maleic acid is derived by hydrolysis of maleic anhydride, the latter being produced by oxidation of benzene or butane. The isomerization is a popular topic in schools. The maleate ion is the ionized form of maleic acid. Maleic acid may be used to form acid addition salts with drugs to make them more stable, such as indacaterol maleate. CopyCopied, CSID:392248, (accessed 11:24, Nov 12, 2020) InChI=1S/C4H4O4/c5-3(6)1-2-4(7)8/h1-2H,(H,5,6)(H,7,8)/b2-1-, InChI=1/C4H4O4/c5-3(6)1-2-4(7)8/h1-2H,(H,5,6)(H,7,8)/b2-1-, Except where otherwise noted, data are given for materials in their, CRC Handbook of Chemistry and Physics, 73rd ed. Although not practised commercially, maleic acid can be converted into maleic anhydride by dehydration, to malic acid by hydration, and to succinic acid by hydrogenation (ethanol / palladium on carbon). Maleic acid is the cis-isomer of butenedioic acid, whereas fumaric acid is the trans-isomer. C(=C\C(=O)O)\C(=O)O CopyCopied, InChI=1S/C4H4O4/c5-3(6)1-2-4(7)8/h1-2H,(H,5,6)(H,7,8)/b2-1- Maleic acid | C4H4O4 | CID 444266 - structure, chemical names, physical and chemical properties, classification, patents, literature, biological activities, safety/hazards/toxicity information, supplier lists, and more. Maleic acid and fumaric acid do not spontaneously interconvert because rotation around a carbon carbon double bond is not energetically favourable. Maleic acid is the cis-isomer of butenedioic acid, whereas fumaric acid is the trans-isomer. Incompatible with strong oxidizingagents, bases. CopyCopied, VZCYOOQTPOCHFL-UPHRSURJSA-N In another method (used as a classroom demonstration), maleic acid is transformed into fumaric acid through the process of heating the maleic acid in hydrochloric acid solution. ; CRC Press: Boca Raton, Florida., 1993. Many drugs that contain amines are provided as the maleate acid salt, e.g. Its chemical formula is HO2CCH=CHCO2H. ORL-RAT LD50 708 mg kg-1, ORL-MUS LD50 2400 mg kg-1, P261-P280-P305+P351+P338-P304+P340-P405-P501a, WARNING: Irritates skin and eyes, harmful if swallowed. Stable. [8] Light converts elemental bromine into a bromine radical, which attacks the alkene in a radical addition reaction to a bromo-alkane radical; and now single bond rotation is possible. Combustible. Maleic acid. The major industrial use of maleic acid is its conversion to fumaric acid. The Merck Index: An Encyclopedia of Chemicals, Drugs, and Biologicals, Institute for Occupational Safety and Health, Maleic Anhydride, Maleic Acid, and Fumaric Acid, "A Refinement of the Crystal Structure of Maleic Acid", Calculator: Water and solute activities in aqueous maleic acid,, Pages using collapsible list with both background and text-align in titlestyle, Articles containing unverified chemical infoboxes, Creative Commons Attribution-ShareAlike License, This page was last edited on 23 April 2020, at 00:37. Maleic acid has a heat of combustion of -1,355 kJ/mol. A butenedioic acid in which the double bond has cis- (Z)-configuration.

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