Record Information
Version1.0
Creation date2011-09-21 00:09:17 UTC
Update date2019-11-26 03:21:01 UTC
Primary IDFDB022155
Secondary Accession NumbersNot Available
Chemical Information
FooDB 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. Based on a literature review a significant number of articles have been published on Citraconic acid.
CAS Number498-23-7
Structure
Thumb
Synonyms
Predicted Properties
PropertyValueSource
Water Solubility15.9 g/LALOGPS
logP0.21ALOGPS
logP0.35ChemAxon
logS-0.91ALOGPS
pKa (Strongest Acidic)2.5ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area74.6 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity28.96 m³·mol⁻¹ChemAxon
Polarizability11.17 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC5H6O4
IUPAC name(2Z)-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
Disposition

Route of exposure:

Source:

Biological location:

Process

Naturally occurring process:

Role

Industrial application:

Biological role:

Physico-Chemical Properties
Physico-Chemical Properties - Experimental
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
GC-MS, 2 TMS, GC-MS Spectrumsplash10-053s-9830000000-9984d183d92e149a6ab4Spectrum
GC-MS, non-derivatized, GC-MS Spectrumsplash10-000i-9300000000-e6df22429c37d2a7f548Spectrum
GC-MS, non-derivatized, GC-MS Spectrumsplash10-053s-9830000000-9984d183d92e149a6ab4Spectrum
GC-MS, non-derivatized, GC-MS Spectrumsplash10-0002-1910000000-5eda2b2a1e8b0386b997Spectrum
Predicted GC-MS, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-01q3-9200000000-640fe5e61db043d72d25Spectrum
Predicted GC-MS, 2 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-05g3-9540000000-ba938fe63ed9356955c6Spectrum
Predicted GC-MS, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS, TMS_1_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS, TMS_1_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS, TBDMS_1_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS, TBDMS_1_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS, TBDMS_2_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Negative (Annotated)splash10-000i-9100000000-707e9072305131e101d92012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated)splash10-0006-9000000000-2a007e703ec5aa2df51a2012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Negative (Annotated)splash10-000f-9200000000-5095d8b00331302fe65f2012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-004i-2900000000-98ab39de610d4d7e428d2012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-000i-9000000000-1786e7db899e123443152012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negativesplash10-000i-9000000000-a1b543932fc2650209732012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negativesplash10-0006-9000000000-d5dc2c9fdcd47f64c4042012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negativesplash10-0006-9000000000-81b2f20752aef9eee2e92012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negativesplash10-000i-9200000000-ddad81eb9311ec64a8c72012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-004i-2900000000-98ab39de610d4d7e428d2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-000i-9000000000-1786e7db899e123443152017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-000i-9000000000-a1b543932fc2650209732017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0006-9000000000-d5dc2c9fdcd47f64c4042017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0006-9000000000-81b2f20752aef9eee2e92017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-000i-9200000000-ddad81eb9311ec64a8c72017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - n/a 9V, positivesplash10-001i-9000000000-243e35b5f07a2e9728512020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - QTOF 4V, positivesplash10-03di-1900000000-e8a9dc6bff676e7ead5a2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - QTOF 5V, positivesplash10-03di-1900000000-d2e84a4209df386737702020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - QTOF 7V, positivesplash10-03di-2900000000-214b108bacb2c899d8002020-07-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-01q9-4900000000-86e2b44f3c8ee5a18c482017-07-26View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-02g9-9200000000-6d6e041c039e8649caf32017-07-26View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00kf-9000000000-7eeaf466a984bad3e0c82017-07-26View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004r-6900000000-69d0c4409d2eb535ceeb2017-07-26View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-002r-9400000000-a67e18d9101e6c4863ec2017-07-26View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00ko-9100000000-6c212f68da0a408b4ea12017-07-26View Spectrum
NMR
TypeDescriptionView
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, experimental)Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)Spectrum
2D NMR[1H, 1H]-TOCSY. Unexported temporarily by An Chi on Oct 15, 2021 until json or nmrML file is generated. 2D NMR Spectrum (experimental)Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)Spectrum
ChemSpider ID553689
ChEMBL IDNot Available
KEGG Compound IDC02226
Pubchem Compound ID643798
Pubchem Substance IDNot Available
ChEBI ID17626
Phenol-Explorer IDNot Available
DrugBank IDDB04734
HMDB IDHMDB00634
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
Milk (Cow)Expected but not quantifiedNot Available25599412
AbiyuchExpected but not quantifiedNot AvailablePATHBANK
AcerolaExpected but not quantifiedNot AvailablePATHBANK
AcornExpected but not quantifiedNot AvailablePATHBANK
Acorn squashExpected but not quantifiedNot AvailablePATHBANK
Adzuki beanExpected but not quantifiedNot AvailablePATHBANK
AgaveExpected but not quantifiedNot AvailablePATHBANK
Alaska blueberryExpected but not quantifiedNot AvailablePATHBANK
Alaska wild rhubarbExpected but not quantifiedNot AvailablePATHBANK
Albizia gummiferaExpected but not quantifiedNot AvailablePATHBANK
Showing 1 to 10 of 544 entries
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