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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2021-09-07 16:31:55 UTC
HMDB IDHMDB0000749
Secondary Accession Numbers
  • HMDB00749
Metabolite Identification
Common NameMesaconic acid
DescriptionMesaconic acid, also known as 2-methylfumarate or citronic acid, belongs to the class of organic compounds known as methyl-branched fatty acids. These are fatty acids with an acyl chain that has a methyl branch. Usually, they are saturated and contain only one or more methyl group. However, branches other than methyl may be present. Mesaconic acid is a dicarboxylic butenoic acid, with a methyl group in position 2 and the double bound between carbons 2 and 3. Mesaconic acid was first studied for its physical properties in 1874 by Jacobus van ‘t Hoff (https://web.archive.org/web/20051117102410/http://dbhs.wvusd.k12.ca.us/webdocs/Chem-History/Van%27t-Hoff-1874.html). It is now known to be involved in the biosynthesis of vitamin B12 and it is also a competitor inhibitor of the reduction of fumarate.
Structure
Data?1582752154
Synonyms
ValueSource
(e)-2-Methyl-2-butenedioic acidChEBI
(e)-Citraconic acidChEBI
2-Methylfumaric acidChEBI
Citronic acidChEBI
Methylfumaric acidChEBI
trans-1-Propene-1,2-dicarboxylic acidChEBI
trans-2-Methyl-2-butenedioic acidChEBI
2-MethylfumarateKegg
(e)-2-Methyl-2-butenedioateGenerator
(e)-CitraconateGenerator
CitronateGenerator
MethylfumarateGenerator
trans-1-Propene-1,2-dicarboxylateGenerator
trans-2-Methyl-2-butenedioateGenerator
MesaconateGenerator
(Z)-2-Methyl-2-butenedioic acidMeSH
Citraconic acidMeSH
Citraconic acid, (e)-isomerMeSH
Citraconic acid, ammonium saltMeSH
Citraconic acid, calcium saltMeSH
Citraconic acid, sodium saltMeSH
Methylmaleic acidMeSH
MonomethylfumarateMeSH
(2E)-2-Methyl-2-butenedioateHMDB
(2E)-2-Methyl-2-butenedioic acidHMDB
Chemical FormulaC5H6O4
Average Molecular Weight130.0987
Monoisotopic Molecular Weight130.02660868
IUPAC Name(2E)-2-methylbut-2-enedioic acid
Traditional Namemesaconic acid
CAS Registry Number498-24-8
SMILES
C\C(=C/C(O)=O)C(O)=O
InChI Identifier
InChI=1S/C5H6O4/c1-3(5(8)9)2-4(6)7/h2H,1H3,(H,6,7)(H,8,9)/b3-2+
InChI KeyHNEGQIOMVPPMNR-NSCUHMNNSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as methyl-branched fatty acids. These are fatty acids with an acyl chain that has a methyl branch. Usually, they are saturated and contain only one or more methyl group. However, branches other than methyl may be present.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassFatty acids and conjugates
Direct ParentMethyl-branched fatty acids
Alternative Parents
Substituents
  • Methyl-branched fatty acid
  • Unsaturated fatty acid
  • Dicarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • 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

Industrial application:

Biological role:

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point200 - 202 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility26.3 mg/mL at 18 °CNot Available
LogPNot AvailableNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility15.9 g/LALOGPS
logP0.21ALOGPS
logP0.35ChemAxon
logS-0.91ALOGPS
pKa (Strongest Acidic)3.72ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area74.6 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity28.96 m³·mol⁻¹ChemAxon
Polarizability11.24 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Spectral Properties

Collision Cross Sections

NameAdductTypeData SourceValueReference
DarkChem[M+H]+PredictedNot Available129.08731661259
DarkChem[M-H]-PredictedNot Available122.35631661259
AllCCS[M+H]+PredictedNot Available130.26332859911
AllCCS[M-H]-PredictedNot Available123.73632859911

Retention Indices

Underivatized

Not Available

Derivatized

DerivativeValueReference
Mesaconic acid,1TMS,#11324.8182https://arxiv.org/abs/1905.12712
Mesaconic acid,1TMS,#21326.743https://arxiv.org/abs/1905.12712
Mesaconic acid,2TMS,#11388.2233https://arxiv.org/abs/1905.12712
Mesaconic acid,1TBDMS,#11567.9457https://arxiv.org/abs/1905.12712
Mesaconic acid,1TBDMS,#21567.0879https://arxiv.org/abs/1905.12712
Mesaconic acid,2TBDMS,#11802.1334https://arxiv.org/abs/1905.12712
Spectra

GC-MS

Spectrum TypeDescriptionSplash KeyDeposition DateView
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (2 TMS)splash10-0002-1910000000-7b5cb889d8459c0edd012014-06-16View Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (2 TMS)splash10-00di-9500000000-b21cd4d2b489173d29332014-06-16View Spectrum
GC-MSGC-MS Spectrum - GC-MS (2 TMS)splash10-053r-2940000000-4329a46b213ac4abcca92014-06-16View Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0002-1910000000-7b5cb889d8459c0edd012017-09-12View Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00di-9500000000-b21cd4d2b489173d29332017-09-12View Spectrum
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-053r-2940000000-4329a46b213ac4abcca92017-09-12View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-01q3-9200000000-99f5b89fc0026d764b2b2017-09-01View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-05g3-9540000000-ba938fe63ed9356955c62017-10-06View Spectrum

LC-MS/MS

Spectrum TypeDescriptionSplash KeyDeposition DateView
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-000j-9400000000-e10edb30d7748a7adb052012-07-24View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-00m0-9000000000-6ef60fd2abfbb5741bca2012-07-24View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-0159-9000000000-e14ffb74e5a8298232a32012-07-24View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negativesplash10-000i-9100000000-8749d95b95760456aeed2012-08-31View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-000i-9100000000-8749d95b95760456aeed2017-09-14View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-5900000000-48835a534a81752d30852017-09-01View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00kr-9100000000-dcbf0f65cbb6f9b6b5782017-09-01View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000i-9000000000-632723c704c4db90a4b62017-09-01View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004r-5900000000-4b2260c72d18030ec9122017-09-01View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-002r-9500000000-1fd59395c864782b12b92017-09-01View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-014u-9000000000-b6d65140f365dabf3b3a2017-09-01View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-01p9-9400000000-ebf4634a042628bb8a442021-09-08View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00ko-9000000000-e04449c635203c9d3da02021-09-08View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9000000000-1b2c407328e3780e996e2021-09-08View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-9000000000-ec20127c74818b1f634d2021-09-08View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-9000000000-8867d7b163c801abd1852021-09-08View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-014l-9000000000-55fcd5974652df6210542021-09-08View Spectrum

NMR

Spectrum TypeDescriptionDeposition DateView
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, experimental)2012-12-04View Spectrum
2D NMR[1H, 13C] NMR Spectrum (2D, 600 MHz, H2O, predicted)2012-12-05View Spectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
  • Mitochondria
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB022221
KNApSAcK IDC00051539
Chemspider ID10289044
KEGG Compound IDC01732
BioCyc IDNot Available
BiGG ID38272
Wikipedia LinkMesaconic_acid
METLIN ID4130
PubChem Compound638129
PDB IDMEZ
ChEBI ID16600
Food Biomarker OntologyNot Available
VMH IDMESCON
MarkerDB IDNot Available
References
Synthesis ReferenceShriner, R. L.; Ford, S. G.; Roll, L. J. Mesaconic acid. Organic Syntheses (1931), XI 74-5.
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Truscott RJ, Malegan D, McCairns E, Burke D, Hick L, Sims P, Halpern B, Tanaka K, Sweetman L, Nyhan WL, Hammond J, Bumack C, Haan EA, Danks DM: New metabolites in isovaleric acidemia. Clin Chim Acta. 1981 Mar 5;110(2-3):187-203. [PubMed:6452974 ]