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Showing metabocard for Maleic acid (HMDB0000176)

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IdentificationTaxonomyOntologyPhysical propertiesSpectraBiological propertiesConcentrationsLinksReferencesXML
Record Information
Version4.0
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2020-04-22 23:28:50 UTC
HMDB IDHMDB0000176
Secondary Accession Numbers
  • HMDB00176
Metabolite Identification
Common NameMaleic acid
DescriptionMaleic 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.
Structure
Data?1582752115
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 saltMeSH
Maleic acid, monocopper (2+) saltMeSH
Maleic acid, potassium saltMeSH
Maleic acid, sodium saltMeSH
Sodium maleateMeSH
Hydrogen maleateMeSH
Maleic acid, ammonium saltMeSH
Maleic acid, calcium saltMeSH
Maleic acid, iron saltMeSH
Maleic acid, neodymium saltMeSH
Maleic acid, dipotassium saltMeSH
Maleic acid, monoammonium saltMeSH
Maleic acid, monosodium saltMeSH
Chemical FormulaC4H4O4
Average Molecular Weight116.0722
Monoisotopic Molecular Weight116.010958616
IUPAC Name(2Z)-but-2-enedioic acid
Traditional Namemaleic acid
CAS Registry Number110-16-7
SMILES
OC(=O)\C=C/C(O)=O
InChI Identifier
InChI=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
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Process

Naturally occurring process:

Role

Biological role:

Environmental role:

Industrial application:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point130.5 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility441 mg/mL at 25 °CNot Available
LogP-0.48SANGSTER (1994)
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
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)splash10-0002-0900000000-170a9d63d0cb31451c1dSpectrum
GC-MSGC-MS Spectrum - GC-MS (2 TMS)splash10-001j-5940000000-59e85bafafc1675e24adSpectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0uxs-9000000000-d768b92d45a58ec32ec7Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-004i-9000000000-617284552377852c7c46Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0002-0910000000-15f30f525d5ea74dc9d4Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0002-0900000000-170a9d63d0cb31451c1dSpectrum
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-001j-5940000000-59e85bafafc1675e24adSpectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0002-0900000000-4b46518e6c4f0c6724f2Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-01ba-9200000000-52f88e04bac0ff8cdf17Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-00di-8920000000-06da44f348d0fe0358b3Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Negative (Annotated)splash10-00di-9200000000-77d8b2c7abcec2e3d5a1Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated)splash10-00di-9200000000-8d8a8b14a723e0363227Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Negative (Annotated)splash10-0229-9700000000-061b31801a2ae4703fc5Spectrum
LC-MS/MSLC-MS/MS Spectrum - EI-B (HITACHI RMU-6L) , Positivesplash10-0uxs-9000000000-d768b92d45a58ec32ec7Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-03di-2900000000-6bbe33cf398e663af0fcSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-00di-9100000000-550ee9efb3babd781bcaSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negativesplash10-00di-9000000000-18e922c569242e2111e7Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negativesplash10-00di-9000000000-f344fe84d76f2bf06f91Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negativesplash10-00fu-9000000000-6f90988f5d68f87b52d2Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negativesplash10-00di-9400000000-99bc7f4db87479b4122aSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-03di-2900000000-6bbe33cf398e663af0fcSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-00di-9100000000-550ee9efb3babd781bcaSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-00di-9000000000-18e922c569242e2111e7Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-00di-9000000000-f344fe84d76f2bf06f91Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-00fu-9000000000-6f90988f5d68f87b52d2Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-00di-9400000000-99bc7f4db87479b4122aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014j-9800000000-dbf34563376daeb2901fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00xs-9200000000-113bf08cdc77707ed3adSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00fr-9000000000-f32d7ec65e8649bc2b0aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-2900000000-408d53a9fff7acc8ca23Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-6900000000-f149e9e5a34e27dd4d4eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0fxt-9000000000-cae5f71dc27daaf17d9eSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
2D NMR[1H,1H] 2D NMR SpectrumNot AvailableSpectrum
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableSpectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Membrane
Biospecimen Locations
  • Blood
  • Feces
  • Urine
Tissue Locations
  • Fibroblasts
  • Neuron
  • Pancreas
  • Platelet
  • Prostate
  • Skeletal Muscle
  • Spleen
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not Quantified Not AvailableNot Available
Normal
    		 details
    FecesDetected but not Quantified Adult (>18 years old)Both
    Normal    		 details
    FecesDetected but not Quantified Adult (>18 years old)Both
    Normal    		 details
    FecesDetected but not Quantified Not SpecifiedNot Specified
    Normal    		 details
    UrineDetected and Quantified5.447 +/- 6.8 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
    Normal
      • Mordechai, Hien, ...
    		 details
    UrineDetected and Quantified10.4 umol/mmol creatinineNewborn (0-30 days old)BothNormal details
    UrineDetected and Quantified10.7 umol/mmol creatinineInfant (0-1 year old)BothNormal details
    UrineDetected and Quantified0.7 umol/mmol creatinineChildren (1-13 years old)BothNormal details
    UrineDetected and Quantified0.1 umol/mmol creatinineChildren (1-13 years old)BothNormal details
    UrineDetected and Quantified0.5 umol/mmol creatinineAdult (>18 years old)BothNormal details
    UrineDetected and Quantified0.4 (0.3-0.5) umol/mmol creatinineAdult (>18 years old)Both
    Normal    		 details
    UrineDetected and Quantified10.7 umol/mmol creatinineAdult (>18 years old)Not SpecifiedNormal details
    UrineDetected and Quantified0.1 umol/mmol creatinineNot SpecifiedNot SpecifiedNormal details
    Abnormal Concentrations
    BiospecimenStatusValueAgeSexConditionReferenceDetails
    UrineDetected and Quantified1.585 +/- 1.123 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
    Eosinophilic esophagitis
      • Mordechai, Hien, ...
    		 details
    Associated Disorders and Diseases
    Disease References
    Eosinophilic esophagitis
    1. (). Mordechai, Hien, and David S. Wishart. .
    Associated OMIM IDs
    DrugBank IDDB04299
    Phenol Explorer Compound IDNot Available
    FooDB IDFDB008113
    KNApSAcK IDC00007417
    Chemspider IDNot Available
    KEGG Compound IDC01384
    BioCyc IDMALEATE
    BiGG IDNot Available
    Wikipedia LinkMaleic_acid
    METLIN IDNot Available
    PubChem Compound444266
    PDB IDNot Available
    ChEBI ID18300
    Food Biomarker OntologyNot Available
    VMH IDNot Available
    References
    Synthesis ReferenceDethloff, Christian; Barbarino, Sergio. Process temperature optimization in the manufacture of maleic acid by the hydrolysis of maleic anhydride. Eur. Pat. Appl. (1998), 7 pp.
    Material Safety Data Sheet (MSDS)Download (PDF)
    General References
    1. Kotikoski H, Oksala O, Vapaatalo H, Aine E: Aqueous humour flow after a single oral dose of isosorbide-5-mononitrate in healthy volunteers. Acta Ophthalmol Scand. 2003 Aug;81(4):355-60. [PubMed:12859262 ]
    2. 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. [PubMed:1495787 ]
    3. Klose T, Welzel PB, Werner C: Protein adsorption from flowing solutions on pure and maleic acid copolymer modified glass particles. Colloids Surf B Biointerfaces. 2006 Aug 1;51(1):1-9. Epub 2006 May 17. [PubMed:16797943 ]
    4. Renner L, Pompe T, Salchert K, Werner C: Dynamic alterations of fibronectin layers on copolymer substrates with graded physicochemical characteristics. Langmuir. 2004 Mar 30;20(7):2928-33. [PubMed:15835174 ]
    5. Gong Z, Lv Y, Huang Y, Zhang Z: Determination of ergometrine maleate by fluorescence detection. Luminescence. 2005 May-Jun;20(3):124-8. [PubMed:15924314 ]
    6. Goes MF, Sinhoreti MA, Consani S, Silva MA: Morphological effect of the type, concentration and etching time of acid solutions on enamel and dentin surfaces. Braz Dent J. 1998;9(1):3-10. [PubMed:9835798 ]
    7. Guneral F, Bachmann C: Age-related reference values for urinary organic acids in a healthy Turkish pediatric population. Clin Chem. 1994 Jun;40(6):862-6. [PubMed:8087979 ]
    8. Gallagher RM: Menstrual migraine and intermittent ergonovine therapy. Headache. 1989 Jun;29(6):366-7. [PubMed:2759844 ]
    9. Seki T, Wakabayashi M, Nakagawa T, Imamura M, Tamai T, Nishimura A, Yamashiki N, Okamura A, Inoue K: Hepatic infarction following percutaneous ethanol injection therapy for hepatocellular carcinoma. Eur J Gastroenterol Hepatol. 1998 Nov;10(11):915-8. [PubMed:9872612 ]
    10. Snider BJ, Moss JL, Revilla FJ, Lee CS, Wheeler VC, Macdonald ME, Choi DW: Neocortical neurons cultured from mice with expanded CAG repeats in the huntingtin gene: unaltered vulnerability to excitotoxins and other insults. Neuroscience. 2003;120(3):617-25. [PubMed:12895502 ]
    11. Lavit M, Saivin S, Boudra H, Michel F, Martin A, Cahiez G, Labaune JP, Chomard JM, Houin G: Determination of trimebutine and desmethyl-trimebutine in human plasma by HPLC. Arzneimittelforschung. 2000 Jul;50(7):640-4. [PubMed:10965422 ]
    12. Strasser G, Grabner G: The influence of long-term treatment with timolol on human tear lysozyme albumin content. Graefes Arch Clin Exp Ophthalmol. 1982;218(2):93-5. [PubMed:7075967 ]
    13. Glazunova OO, Korepanova EA, Efimov VS, Smirnov AI, Vladimirov YuA: A synthetic polycation, a copolymer of 1-vinyl-3-methylimidazole iodide with maleic acid diethyl ester, increases passive ionic permeability in erythrocyte membranes modified by fatty acids. Membr Cell Biol. 1998;12(3):401-9. [PubMed:10024972 ]
    14. 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. [PubMed:10522050 ]
    15. 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. [PubMed:10635272 ]
    16. 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. [PubMed:16778650 ]
    17. 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. [PubMed:16043230 ]
    18. 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. [PubMed:7905382 ]
    19. 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. [PubMed:12450709 ]
    20. 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. [PubMed:12009699 ]