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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2023-02-21 17:15:01 UTC
HMDB IDHMDB0000634
Secondary Accession Numbers
  • HMDB00634
Metabolite Identification
Common NameCitraconic acid
DescriptionCitraconic acid, also known as 2-methylmaleate or methylmaleic 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. Citraconic acid is a dicarboxylic acid consisting of maleic acid having a methyl substituent at the 2-position. Citraconic acid exists as a white solid. It is the cis-isomer of mesaconic acid and is one of the pyrocitric acids formed upon the heating of citric acid. Citraconic acid has been detected in the urine of both normal and fasting individuals (PMID: 6778884 ). Citraconic acid is also elevated in the urine of individuals with methylmalonic acidaemia who have suffered ketotic attacks (PMID: 116077 ). Altered serum levels of citraconic acid have been detected in patients with primary biliary cholangitis (PMID: 28400566 ).
Structure
Thumb
Synonyms
Chemical FormulaC5H6O4
Average Molecular Weight130.0987
Monoisotopic Molecular Weight130.02660868
IUPAC Name(2Z)-2-methylbut-2-enedioic acid
Traditional Namecitraconic acid
CAS Registry Number498-23-7
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-IHWYPQMZSA-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
Physiological effectNot Available
Disposition
Biological locationRoute of exposureSource
Process
Role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point88 - 94 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility783 mg/mLNot Available
LogPNot AvailableNot Available
Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct TypeData SourceCCS Value (Å2)Reference
[M-H]-Not Available119.0http://allccs.zhulab.cn/database/detail?ID=AllCCS00002139
Predicted Molecular Properties
Predicted Chromatographic Properties
Spectra
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biospecimen Locations
  • Blood
  • Feces
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Colorectal cancer
details
Associated Disorders and Diseases
Disease References
Colorectal cancer
  1. Goedert JJ, Sampson JN, Moore SC, Xiao Q, Xiong X, Hayes RB, Ahn J, Shi J, Sinha R: Fecal metabolomics: assay performance and association with colorectal cancer. Carcinogenesis. 2014 Sep;35(9):2089-96. doi: 10.1093/carcin/bgu131. Epub 2014 Jul 18. [PubMed:25037050 ]
Associated OMIM IDs
DrugBank IDDB04734
Phenol Explorer Compound IDNot Available
FooDB IDFDB022155
KNApSAcK IDC00052049
Chemspider ID553689
KEGG Compound IDC02226
BioCyc ID2-METHYLMALEATE
BiGG IDNot Available
Wikipedia LinkCitraconic_acid
METLIN ID5607
PubChem Compound643798
PDB IDNot Available
ChEBI ID17626
Food Biomarker OntologyNot Available
VMH ID2MMALE
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceBerg, Rudolph G. Catalytic preparation of citraconic and itaconic acids. U.S. (1972), 5 pp.
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Duran M, Bruinvis L, Ketting D, Wadman SK: Deranged isoleucine metabolism during ketotic attacks in patients with methylmalonic acidaemia. J Inherit Metab Dis. 1978;1(3):105-7. [PubMed:116077 ]
  2. Liebich HM, Pickert A, Stierle U, Woll J: Gas chromatography-mass spectrometry of saturated and unsaturated dicarboxylic acids in urine. J Chromatogr. 1980 Oct 31;199:181-9. [PubMed:6778884 ]
  3. Stoltz JF, Nicolas A: Study of amino groups of the human platelet membrane. Acta Haematol. 1978;60(5):304-9. [PubMed:101016 ]
  4. Alelu-Paz R, Iturrieta-Zuazo I, Byne W, Haroutunian V, Garcia-Villanueva M, Rabano A, Garcia-Amado M, Prensa L, Gimenez-Amaya JM: A new antigen retrieval technique for human brain tissue. PLoS One. 2008;3(10):e3378. doi: 10.1371/journal.pone.0003378. Epub 2008 Oct 13. [PubMed:18852880 ]
  5. Hao J, Yang T, Zhou Y, Gao GY, Xing F, Peng Y, Tao YY, Liu CH: Serum Metabolomics Analysis Reveals a Distinct Metabolic Profile of Patients with Primary Biliary Cholangitis. Sci Rep. 2017 Apr 11;7(1):784. doi: 10.1038/s41598-017-00944-9. [PubMed:28400566 ]