Maleic acid (CHEM003757)

Record Information
Version1.0
Creation Date2014-09-11 05:17:11 UTC
Update Date2026-05-14 18:07:24 UTC
Accession NumberCHEM003757
Identification
Common NameMaleic acid
ClassSmall Molecule
Description
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.
Contaminant Sources
  • Clean Air Act Chemicals
  • FooDB Chemicals
  • HMDB Contaminants - Feces
  • HMDB Contaminants - Urine
  • HPV EPA Chemicals
  • OECD HPV Chemicals
  • STOFF IDENT Compounds
  • T3DB toxins
  • ToxCast & Tox21 Chemicals
Contaminant Type
  • Food Toxin
  • Household Toxin
  • Industrial/Workplace Toxin
  • Metabolite
  • Natural Compound
  • Organic Compound
Chemical Structure
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(Z)-2-Butenedioic acidChEBI
(Z)-Butenedioic acidChEBI
cis-1,2-Ethylenedicarboxylic acidChEBI
cis-But-2-enedioic acidChEBI
cis-Butenedioic acidChEBI
H2MaleChEBI
Toxilic acidChEBI
MaleateKegg
(Z)-2-ButenedioateGenerator
(Z)-ButenedioateGenerator
cis-1,2-EthylenedicarboxylateGenerator
cis-But-2-enedioateGenerator
cis-ButenedioateGenerator
ToxilateGenerator
(2Z)-2-ButenedioateHMDB
(2Z)-2-Butenedioic acidHMDB
(2Z)-But-2-enedioateHMDB
(2Z)-But-2-enedioic acidHMDB
(2Z)-Butene-2-dioateHMDB
(2Z)-Butene-2-dioic acidHMDB
2-ButenedioateHMDB
2-Butenedioic acidHMDB
cis-2-ButenedioateHMDB
cis-2-Butenedioic acidHMDB
Kyselina maleinovaHMDB
MAEHMDB
Maleinic acidHMDB
Malenic acidHMDB
Malezid CMHMDB
Scotchbond multipurpose etchantHMDB
Maleic acid, disodium saltHMDB
Maleic acid, monocopper (2+) saltHMDB
Maleic acid, potassium saltHMDB
Maleic acid, sodium saltHMDB
Sodium maleateHMDB
Hydrogen maleateHMDB
Maleic acid, ammonium saltHMDB
Maleic acid, calcium saltHMDB
Maleic acid, iron saltHMDB
Maleic acid, neodymium saltHMDB
Maleic acid, dipotassium saltHMDB
Maleic acid, monoammonium saltHMDB
Maleic acid, monosodium saltHMDB
Chemical FormulaC4H4O4
Average Molecular Mass116.072 g/mol
Monoisotopic Mass116.011 g/mol
CAS Registry Number110-16-7
IUPAC Name(2Z)-but-2-enedioic acid
Traditional Namemaleic acid
SMILESOC(=O)\C=C/C(O)=O
InChI IdentifierInChI=1S/C4H4O4/c5-3(6)1-2-4(7)8/h1-2H,(H,5,6)(H,7,8)/b2-1-
InChI KeyVZCYOOQTPOCHFL-UPHRSURJSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as dicarboxylic acids and derivatives. These are organic compounds containing exactly two carboxylic acid groups.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassDicarboxylic acids and derivatives
Direct ParentDicarboxylic acids and derivatives
Alternative Parents
Substituents
  • Fatty acyl
  • Fatty acid
  • Unsaturated fatty acid
  • Dicarboxylic acid or derivatives
  • Carboxylic acid
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginEndogenous
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Membrane
Biofluid LocationsNot Available
Tissue Locations
  • Fibroblasts
  • Muscle
  • Neuron
  • Pancreas
  • Platelet
  • Prostate
  • Spleen
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateSolid
AppearanceWhite powder.
Experimental Properties
PropertyValue
Melting Point130.5°C
Boiling PointNot Available
Solubility4.41E+005 mg/L (at 25°C)
Predicted Properties
PropertyValueSource
Water Solubility24.1 g/LALOGPS
logP0.21ALOGPS
logP-0.041ChemAxon
logS-0.68ALOGPS
pKa (Strongest Acidic)3.05ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area74.6 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity24.61 m³·mol⁻¹ChemAxon
Polarizability9.19 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)No indication of carcinogenicity to humans (not listed by IARC).
Uses/SourcesThis is an endogenously produced metabolite found in the human body. It is used in metabolic reactions, catabolic reactions or waste generation.
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
External Links
DrugBank IDDB04299
HMDB IDHMDB0000176
FooDB IDFDB008113
Phenol Explorer IDNot Available
KNApSAcK IDC00007417
BiGG IDNot Available
BioCyc IDMALEATE
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkMaleic_acid
Chemspider ID392248
ChEBI ID18300
PubChem Compound ID444266
Kegg Compound IDC01384
YMDB IDNot Available
ECMDB IDECMDB21414
References
Synthesis Reference

Yasuhisha Fukumoto, Noboru Moriyama, Takashi Itoi, “Maleic acid copolymer, production thereof and scale-preventing agent containing the same.” U.S. Patent US4589995, issued August, 1933.

MSDSLink
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=10952545
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=11386868
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=22770225
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=9591280
5. Dethloff, Christian; Barbarino, Sergio. Process temperature optimization in the manufacture of maleic acid by the hydrolysis of maleic anhydride. Eur. Pat. Appl. (1998), 7 pp.
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7. Herreras JM, Pastor JC, Calonge M, Asensio VM: Ocular surface alteration after long-term treatment with an antiglaucomatous drug. Ophthalmology. 1992 Jul;99(7):1082-8.
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19. Yoshida H, Onda M, Tajiri T, Uchida E, Arima Y, Mamada Y, Yamamoto K, Kaneko M, Terada Y, Kumazaki T: Experience with intraarterial infusion of styrene maleic acid neocarzinostatin (SMANCS)-lipiodol in pancreatic cancer. Hepatogastroenterology. 1999 Jul-Aug;46(28):2612-5.
20. Benderli Y, Gokce K, Buyukgokcesu S: In vitro shear bond strength of adhesive to normal and fluoridated enamel under various contaminated conditions. Quintessence Int. 1999 Aug;30(8):570-5.
21. Liu Y, Yanai R, Lu Y, Hirano S, Sagara T, Nishida T: Effects of antiglaucoma drugs on collagen gel contraction mediated by human corneal fibroblasts. J Glaucoma. 2006 Jun;15(3):255-9.
22. Dorr J, Roth K, Zurbuchen U, Deisz R, Bechmann I, Lehmann TN, Meier S, Nitsch R, Zipp F: Tumor-necrosis-factor-related apoptosis-inducing-ligand (TRAIL)-mediated death of neurons in living human brain tissue is inhibited by flupirtine-maleate. J Neuroimmunol. 2005 Oct;167(1-2):204-9.
23. Turcan RG, Hillbeck D, Hartley TE, Gilbert PJ, Coe RA, Troke JA, Vose CW: Disposition of [14C]velnacrine maleate in rats, dogs, and humans. Drug Metab Dispos. 1993 Nov-Dec;21(6):1037-47.
24. Chen CN, Huang GF, Guo MK, Lin CP: An in vitro study on restoring bond strength of a GIC to saliva contaminated enamel under unrinse condition. J Dent. 2002 Jul-Aug;30(5-6):189-94.
25. Daykin CA, Foxall PJ, Connor SC, Lindon JC, Nicholson JK: The comparison of plasma deproteinization methods for the detection of low-molecular-weight metabolites by (1)H nuclear magnetic resonance spectroscopy. Anal Biochem. 2002 May 15;304(2):220-30.
26. van der Werf MJ, van den Tweel WJ, Hartmans S: Screening for microorganisms producing D-malate from maleate. Appl Environ Microbiol. 1992 Sep;58(9):2854-60. doi: 10.1128/aem.58.9.2854-2860.1992.