Record Information
Version1.0
Creation date2011-09-21 00:10:28 UTC
Update date2015-10-09 22:33:03 UTC
Primary IDFDB022221
Secondary Accession NumbersNot Available
Chemical Information
FooDB 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. Based on a literature review a small amount of articles have been published on Mesaconic acid.
CAS Number498-24-8
Structure
Thumb
Synonyms
SynonymSource
(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 acidHMDB
Citraconic acidHMDB
Citraconic acid, (e)-isomerHMDB
Citraconic acid, ammonium saltHMDB
Citraconic acid, calcium saltHMDB
Citraconic acid, sodium saltHMDB
Methylmaleic acidHMDB
MonomethylfumarateHMDB
(2E)-2-Methyl-2-butenedioateHMDB
(2E)-2-Methyl-2-butenedioic acidHMDB
(E)-Citraconatehmdb
(E)-Citraconic acidhmdb
Predicted 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
Chemical FormulaC5H6O4
IUPAC name(2E)-2-methylbut-2-enedioic acid
InChI IdentifierInChI=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
Isomeric SMILESC\C(=C/C(O)=O)C(O)=O
Average Molecular Weight130.0987
Monoisotopic Molecular Weight130.02660868
Classification
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
OntologyNo ontology term
Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionNot Available
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
GC-MSCitraconic acid, 2 TMS, GC-MS Spectrumsplash10-0002-1910000000-7b5cb889d8459c0edd01Spectrum
GC-MSCitraconic acid, 2 TMS, GC-MS Spectrumsplash10-00di-9500000000-b21cd4d2b489173d2933Spectrum
GC-MSCitraconic acid, 2 TMS, GC-MS Spectrumsplash10-053r-2940000000-4329a46b213ac4abcca9Spectrum
GC-MSCitraconic acid, non-derivatized, GC-MS Spectrumsplash10-0002-1910000000-7b5cb889d8459c0edd01Spectrum
GC-MSCitraconic acid, non-derivatized, GC-MS Spectrumsplash10-00di-9500000000-b21cd4d2b489173d2933Spectrum
GC-MSCitraconic acid, non-derivatized, GC-MS Spectrumsplash10-053r-2940000000-4329a46b213ac4abcca9Spectrum
Predicted GC-MSCitraconic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-01q3-9200000000-99f5b89fc0026d764b2bSpectrum
Predicted GC-MSCitraconic acid, 2 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-05g3-9540000000-ba938fe63ed9356955c6Spectrum
Predicted GC-MSCitraconic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSCitraconic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSCitraconic acid, TMS_1_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSCitraconic acid, TMS_1_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSCitraconic acid, TBDMS_1_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSCitraconic acid, TBDMS_1_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSCitraconic acid, TBDMS_2_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-000j-9400000000-e10edb30d7748a7adb052012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-00m0-9000000000-6ef60fd2abfbb5741bca2012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-0159-9000000000-e14ffb74e5a8298232a32012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negativesplash10-000i-9100000000-8749d95b95760456aeed2012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-000i-9100000000-8749d95b95760456aeed2017-09-14View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-5900000000-48835a534a81752d30852017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00kr-9100000000-dcbf0f65cbb6f9b6b5782017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000i-9000000000-632723c704c4db90a4b62017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004r-5900000000-4b2260c72d18030ec9122017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-002r-9500000000-1fd59395c864782b12b92017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-014u-9000000000-b6d65140f365dabf3b3a2017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-01p9-9400000000-ebf4634a042628bb8a442021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00ko-9000000000-e04449c635203c9d3da02021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9000000000-1b2c407328e3780e996e2021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-9000000000-ec20127c74818b1f634d2021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-9000000000-8867d7b163c801abd1852021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-014l-9000000000-55fcd5974652df6210542021-09-24View Spectrum
NMR
TypeDescriptionView
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, experimental)Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, experimental)Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)Spectrum
ChemSpider ID10289044
ChEMBL IDNot Available
KEGG Compound IDC01732
Pubchem Compound ID638129
Pubchem Substance IDNot Available
ChEBI ID16600
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB00749
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG ID38272
KNApSAcK IDNot Available
HET IDMEZ
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDMesaconic acid
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSshow
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference