Canmetcon
Record Information
Version1.0
Creation date2010-04-08 22:05:44 UTC
Update date2018-05-29 18:26:56 UTC
Primary IDFDB003291
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameFumaric acid
DescriptionProduced industrially by fermentation of Rhizopus nigricans, or manufactured by catalytic or thermal isomerisation of maleic anhydride or maleic acid. Used as an antioxidant, acidulant, leavening agent and flavouring agent in foods. Present in raw lean fish. Dietary supplement. Used in powdered products since fumaric acid is less hygroscopic than other acids. A precursor to L-malate in the Krebs tricarboxylic acid cycle. It is formed by the oxidation of succinate by succinate dehydrogenase (wikipedia). Fumaric acid is also found in garden tomato, papaya, wild celery, and star fruit.
CAS Number110-17-8
Structure
Thumb
Synonyms
SynonymSource
(2E)-2-Butenedioic acidChEBI
(e)-2-Butenedioic acidChEBI
e297ChEBI
FumarsaeureChEBI
trans-1,2-Ethylenedicarboxylic acidChEBI
trans-But-2-enedioic acidChEBI
trans-Butenedioic acidChEBI
(2E)-2-ButenedioateGenerator
(e)-2-ButenedioateGenerator
trans-1,2-EthylenedicarboxylateGenerator
trans-But-2-enedioateGenerator
trans-ButenedioateGenerator
FumarateGenerator
(2E)-But-2-enedioateHMDB
(2E)-But-2-enedioic acidHMDB
2-(e)-ButenedioateHMDB
2-(e)-Butenedioic acidHMDB
AllomaleateHMDB
Allomaleic acidHMDB
BoletateHMDB
Boletic acidHMDB
FC 33HMDB
LichenateHMDB
Lichenic acidHMDB
Sodium fumarateHMDB
trans-2-ButenedioateHMDB
trans-2-Butenedioic acidHMDB
FuramagHMDB
Ammonium fumarateHMDB
Magnesium fumarateHMDB
MafusolMeSH
(2e)-2-ButenedioateGenerator
(E)-2-Butenedioatebiospider
(E)-2-Butenedioic acid, 9CIdb_source
2-(E)-Butenedioatebiospider
2-(E)-Butenedioic acidbiospider
E297db_source
FEMA 2488db_source
Glaucic aciddb_source
Paramaleic aciddb_source
Toxilic acidbiospider
trans-Ethylene-1,2-dicarboxylic aciddb_source
Tumaric acidbiospider
Predicted Properties
PropertyValueSource
Water Solubility24.1 g/LALOGPS
logP0.21ALOGPS
logP-0.041ChemAxon
logS-0.68ALOGPS
pKa (Strongest Acidic)3.55ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area74.6 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity24.61 m³·mol⁻¹ChemAxon
Polarizability9.35 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC4H4O4
IUPAC name(2E)-but-2-enedioic acid
InChI IdentifierInChI=1S/C4H4O4/c5-3(6)1-2-4(7)8/h1-2H,(H,5,6)(H,7,8)/b2-1-
InChI KeyVZCYOOQTPOCHFL-UPHRSURJSA-N
Isomeric SMILESOC(=O)\C=C/C(O)=O
Average Molecular Weight116.0722
Monoisotopic Molecular Weight116.010958616
Classification
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
Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionC 41.39%; H 3.47%; O 55.14%DFC
Melting PointMp 300-302° (sealed tube)DFC
Boiling PointNot Available
Experimental Water Solubility7 mg/mL at 25 oCUS EPA (1981)
Experimental logP0.46HANSCH,C ET AL. (1995)
Experimental pKapKa 4.54 (25°)DFC
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (2 TMS)splash10-0002-2940000000-e988056514d4ce4acc27View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (2 TMS)splash10-0002-2960000000-a5ebaf2bbade922838ecView in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (2 TMS)splash10-0002-2950000000-32afa4d45e0e72b174b4View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)splash10-0002-0950000000-fe0f05c02c783d0b6f6bView in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (2 TMS)splash10-006t-9530000000-0fc03f31f09dc8dbf4c6View in MoNA
GC-MSGC-MS Spectrum - GC-MS (2 TMS)splash10-0002-3690000000-75089756992cdbe841e3View in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0002-9100000000-2cf649749b42cc0c610cView in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0007-0890000000-b1c35cd55deb81254f66View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0002-2940000000-e988056514d4ce4acc27View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0002-2960000000-a5ebaf2bbade922838ecView in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0002-2950000000-32afa4d45e0e72b174b4View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0002-0950000000-fe0f05c02c783d0b6f6bView in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-006t-9530000000-0fc03f31f09dc8dbf4c6View in MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-0002-3690000000-75089756992cdbe841e3View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0002-0940000000-177fdb9168659029ffaaView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-01ba-9200000000-52f88e04bac0ff8cdf17View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-00di-8920000000-06da44f348d0fe0358b3View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Negative (Annotated)splash10-00di-9100000000-57f13cd433a6fe4bf0b3View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated)splash10-0229-9600000000-cd9e2979d0bb1e2a62f2View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Negative (Annotated)splash10-03k9-8900000000-dc50dbf8a50872383d54View in MoNA
LC-MS/MSLC-MS/MS Spectrum - EI-B (HITACHI RMU-6L) , Positivesplash10-0002-9100000000-b47e534bc82a6ed36e7cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014j-9800000000-dbf34563376daeb2901fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00xs-9200000000-113bf08cdc77707ed3adView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00fr-9000000000-f32d7ec65e8649bc2b0aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-2900000000-408d53a9fff7acc8ca23View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-6900000000-f149e9e5a34e27dd4d4eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0fxt-9000000000-cae5f71dc27daaf17d9eView in MoNA
MSMass Spectrum (Electron Ionization)splash10-0092-9000000000-003dd2d9303272b2ebeaView in MoNA
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
2D NMR[1H,1H] 2D NMR SpectrumNot AvailableView in JSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableView in JSpectraViewer
ChemSpider ID10197150
ChEMBL IDCHEMBL503160
KEGG Compound IDC00122
Pubchem Compound ID444972
Pubchem Substance IDNot Available
ChEBI ID18012
Phenol-Explorer IDNot Available
DrugBank IDDB01677
HMDB IDHMDB00134
CRC / DFC (Dictionary of Food Compounds) IDCVQ85-P:CVQ85-P
EAFUS ID1403
Dr. Duke IDFUMARIC-ACID
BIGG ID33938
KNApSAcK IDC00001183
HET IDFUM
Flavornet IDNot Available
GoodScent IDrw1024321
SuperScent ID444972
Wikipedia IDFumaric 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 / Bioactivities
DescriptorIDDefinitionReference
acidulant64047 Any substance which is added to food to preserve or enhance its flavour and/or appearance.DUKE
anti dermatitic50177 A drug used to treat or prevent skin disorders or for the routine care of skin.DUKE
anti hepatocarcinogenic35610 A substance that inhibits or prevents the proliferation of neoplasms.DUKE
antioxidant22586 A substance that opposes oxidation or inhibits reactions brought about by dioxygen or peroxides. In European countries, E-numbers for permitted antioxidant food additives are from E 300 to E 324.DUKE
anti psoriac52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
antitumor35610 A substance that inhibits or prevents the proliferation of neoplasms.DUKE
flavor48318 A substance, extract, or preparation for diffusing or imparting an agreeable or attractive smell.DUKE
Enzymes
NameGene NameUniProt ID
Fumarate hydratase, mitochondrialFHP07954
Argininosuccinate lyaseASLP04424
Adenylosuccinate lyaseADSLP30566
Pathways
NameSMPDB LinkKEGG Link
Arginine and Proline MetabolismSMP00020 map00330
Aspartate MetabolismSMP00067 map00250
Citric Acid CycleSMP00057 map00020
Mitochondrial Electron Transport ChainSMP00355 map00190
Phenylalanine and Tyrosine MetabolismSMP00008 map00360
Tyrosine MetabolismSMP00006 map00350
Urea CycleSMP00059 map00330
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
Flavours
FlavorCitations
sour
  1. Dunkel, M. et al. SuperScent – a database of flavors and scents. Nucleic Acids Research 2008, doi:10.1093/nar/gkn695
odorless
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
Files
MSDSshow
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).
— Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.