1.0 2010-04-08 22:07:55 UTC 2025-11-18 23:06:59 UTC FDB008113 Maleic acid Maleic acid is an industrial raw material for the production of glyoxylic acid by ozonolysis. Maleic acid is an organic compound which is a dicarboxylic acid (molecule with two carboxyl groups). The molecule consists of an ethylene group flanked by two carboxylic acid groups. Maleic acid is the cis isomer of butenedioic acid, whereas fumaric acid is the trans isomer. The cis isomer is the less stable one of the two; the difference in heat of combustion is 22.7 kJ/mol. The physical properties of maleic acid are very different from that of fumaric acid. Maleic acid is soluble in water whereas fumaric acid is not and the melting point of maleic acid (130 - 131 degree centigrade) is also much lower than that of fumaric acid (287 degree centigrade). Both properties of maleic acid can be explained on account of the intramolecular hydrogen bonding that takes place at the expense of intermolecular interactions. Maleic acid is converted into maleic anhydride by dehydration, to malic acid by hydration, and to succinic acid by hydrogenation. It reacts with thionyl chloride or phosphorus pentachloride to give the maleic acid chloride (it is not possible to isolate the mono acid chloride). Maleic acid is a reactant in many Diels-Alder reactions. [HMDB]. Maleic acid is found in many foods, some of which are cocoa bean, lovage, roselle, and corn. (2Z)-2-Butenedioate (2Z)-2-Butenedioic acid (2Z)-But-2-enedioate (2Z)-But-2-enedioic acid (2Z)-Butene-2-dioate (2Z)-Butene-2-dioic acid (Z)-2-Butenedioate (Z)-2-Butenedioic acid (Z)-2-Butenedioic acid, 9CI (Z)-Butenedioate (Z)-Butenedioic acid 2-Butenedioate 2-Butenedioic acid cis-1,2-Ethylenedicarboxylate cis-1,2-Ethylenedicarboxylic acid cis-2-Butenedioate cis-2-Butenedioic acid cis-But-2-enedioate cis-But-2-enedioic acid cis-Butenedioate cis-Butenedioic acid cis-Ethylene-1,2-dicarboxylic acid H2Male Kyselina maleinova Maleate Maleinic acid Malenic acid Malezid cm Scotchbond multipurpose etchant Toxilate C4H4O4 116.0722 116.010958616 (2Z)-but-2-enedioic acid maleic acid 110-16-7 OC(=O)\C=C/C(O)=O InChI=1S/C4H4O4/c5-3(6)1-2-4(7)8/h1-2H,(H,5,6)(H,7,8)/b2-1- VZCYOOQTPOCHFL-UPHRSURJSA-N belongs to the class of organic compounds known as dicarboxylic acids and derivatives. These are organic compounds containing exactly two carboxylic acid groups. Dicarboxylic acids and derivatives Organic compounds Organic acids and derivatives Carboxylic acids and derivatives Dicarboxylic acids and derivatives Aliphatic acyclic compounds Carbonyl compounds Carboxylic acids Hydrocarbon derivatives Organic oxides Unsaturated fatty acids Aliphatic acyclic compound Carbonyl group Carboxylic acid Dicarboxylic acid or derivatives Fatty acid Fatty acyl Hydrocarbon derivative Organic oxide Organic oxygen compound Organooxygen compound Unsaturated fatty acid butenedioic acid Solid logp 0.21 ALOGPS logs -0.68 ALOGPS solubility 2.41e+01 g/l ALOGPS logp -0.041 ChemAxon pka_strongest_acidic 3.05 ChemAxon iupac (2Z)-but-2-enedioic acid ChemAxon average_mass 116.0722 ChemAxon mono_mass 116.010958616 ChemAxon smiles OC(=O)\C=C/C(O)=O ChemAxon formula C4H4O4 ChemAxon inchi InChI=1S/C4H4O4/c5-3(6)1-2-4(7)8/h1-2H,(H,5,6)(H,7,8)/b2-1- ChemAxon inchikey VZCYOOQTPOCHFL-UPHRSURJSA-N ChemAxon polar_surface_area 74.6 ChemAxon refractivity 24.61 ChemAxon polarizability 9.19 ChemAxon rotatable_bond_count 2 ChemAxon acceptor_count 4 ChemAxon donor_count 2 ChemAxon physiological_charge -2 ChemAxon formal_charge 0 ChemAxon Specdb::NmrTwoD 984 Specdb::NmrTwoD 1188 Specdb::CMs 415 Specdb::CMs 1036 Specdb::CMs 8094 Specdb::CMs 27693 Specdb::CMs 29705 Specdb::CMs 30138 Specdb::CMs 30617 Specdb::CMs 31050 Specdb::CMs 31936 Specdb::CMs 37339 Specdb::CMs 131405 Specdb::CMs 139139 Specdb::CMs 1052786 Specdb::CMs 1052788 Specdb::CMs 1052789 Specdb::NmrOneD 1144 Specdb::NmrOneD 142710 Specdb::NmrOneD 142711 Specdb::NmrOneD 142712 Specdb::NmrOneD 142713 Specdb::NmrOneD 142714 Specdb::NmrOneD 142715 Specdb::NmrOneD 142716 Specdb::NmrOneD 142717 Specdb::NmrOneD 142718 Specdb::NmrOneD 142719 Specdb::NmrOneD 142720 Specdb::NmrOneD 142721 Specdb::NmrOneD 142722 Specdb::NmrOneD 142723 Specdb::NmrOneD 142724 Specdb::NmrOneD 142725 Specdb::NmrOneD 142726 Specdb::NmrOneD 142727 Specdb::NmrOneD 142728 Specdb::NmrOneD 142729 Specdb::MsMs 280 Specdb::MsMs 281 Specdb::MsMs 282 Specdb::MsMs 3343 Specdb::MsMs 3344 Specdb::MsMs 3345 Specdb::MsMs 3346 Specdb::MsMs 3347 Specdb::MsMs 3348 Specdb::MsMs 3350 Specdb::MsMs 257739 Specdb::MsMs 257740 Specdb::MsMs 257741 Specdb::MsMs 277677 Specdb::MsMs 277678 Specdb::MsMs 277679 Specdb::MsMs 438089 Specdb::MsMs 438090 Specdb::MsMs 438091 Specdb::MsMs 438092 Specdb::MsMs 438093 Specdb::MsMs 439264 Specdb::MsMs 2252760 Specdb::MsMs 2254773 Specdb::MsMs 2255783 HMDB00176 MAE #<Reference:0x000055ce3189d690> #<Reference:0x000055ce3189d4d8> #<Reference:0x000055ce3189d320> #<Reference:0x000055ce3189d168> #<Reference:0x000055ce3189cfb0> #<Reference:0x000055ce3189cdf8> #<Reference:0x000055ce3189cc40> #<Reference:0x000055ce3189ca88> #<Reference:0x000055ce3189c8d0> #<Reference:0x000055ce3189c718> #<Reference:0x000055ce3189c560> #<Reference:0x000055ce3189c3a8> #<Reference:0x000055ce3189c1f0> #<Reference:0x000055ce3189c038> #<Reference:0x000055ce3193be30> #<Reference:0x000055ce3193bc78> #<Reference:0x000055ce3193bac0> #<Reference:0x000055ce3193b908> #<Reference:0x000055ce3193b750> #<Reference:0x000055ce3193b598> Beer Type 2 specific 0.0 0.0 0.0 mg/100 g Cocoa bean Type 1 specific Theobroma cacao 3641 Corn Type 1 specific Zea mays 4577 Lovage Type 1 specific Levisticum officinale 48042 Roselle Type 1 specific Hibiscus sabdariffa 183260 Sour cherry Type 1 specific Prunus cerasus 140311