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Fumaric acid (FDB003291)

Record Information
Version1.0
Creation date2010-04-08 22:05:44 UTC
Update date2019-11-26 02:58:50 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
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
Not AvailableNot Available
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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
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
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Process

Naturally occurring process:

Role

Biological role:

Environmental role:

Industrial application:

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
EI-MS/GC-MS
TypeDescriptionSplash KeyView
EI-MSMass Spectrum (Electron Ionization)splash10-0092-9000000000-003dd2d9303272b2ebea2014-09-20View Spectrum
GC-MSfumarate, 2 TMS, GC-MS Spectrumsplash10-0002-2940000000-e988056514d4ce4acc27Spectrum
GC-MSfumarate, 2 TMS, GC-MS Spectrumsplash10-0002-2960000000-a5ebaf2bbade922838ecSpectrum
GC-MSfumarate, 2 TMS, GC-MS Spectrumsplash10-0002-2950000000-32afa4d45e0e72b174b4Spectrum
GC-MSfumarate, non-derivatized, GC-MS Spectrumsplash10-0002-0950000000-fe0f05c02c783d0b6f6bSpectrum
GC-MSfumarate, 2 TMS, GC-MS Spectrumsplash10-006t-9530000000-0fc03f31f09dc8dbf4c6Spectrum
GC-MSfumarate, 2 TMS, GC-MS Spectrumsplash10-0002-3690000000-75089756992cdbe841e3Spectrum
GC-MSfumarate, non-derivatized, GC-MS Spectrumsplash10-0002-9100000000-2cf649749b42cc0c610cSpectrum
GC-MSfumarate, non-derivatized, GC-MS Spectrumsplash10-0007-0890000000-b1c35cd55deb81254f66Spectrum
GC-MSfumarate, non-derivatized, GC-MS Spectrumsplash10-0002-2940000000-e988056514d4ce4acc27Spectrum
GC-MSfumarate, non-derivatized, GC-MS Spectrumsplash10-0002-2960000000-a5ebaf2bbade922838ecSpectrum
GC-MSfumarate, non-derivatized, GC-MS Spectrumsplash10-0002-2950000000-32afa4d45e0e72b174b4Spectrum
GC-MSfumarate, non-derivatized, GC-MS Spectrumsplash10-0002-0950000000-fe0f05c02c783d0b6f6bSpectrum
GC-MSfumarate, non-derivatized, GC-MS Spectrumsplash10-006t-9530000000-0fc03f31f09dc8dbf4c6Spectrum
GC-MSfumarate, non-derivatized, GC-MS Spectrumsplash10-0002-3690000000-75089756992cdbe841e3Spectrum
GC-MSfumarate, non-derivatized, GC-MS Spectrumsplash10-0002-0940000000-177fdb9168659029ffaaSpectrum
Predicted GC-MSfumarate, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-01ba-9200000000-52f88e04bac0ff8cdf17Spectrum
Predicted GC-MSfumarate, 2 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-00di-8920000000-06da44f348d0fe0358b3Spectrum
Predicted GC-MSfumarate, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSfumarate, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSfumarate, TMS_1_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSfumarate, TBDMS_1_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSfumarate, TBDMS_2_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Negative (Annotated)splash10-00di-9100000000-57f13cd433a6fe4bf0b32012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated)splash10-0229-9600000000-cd9e2979d0bb1e2a62f22012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Negative (Annotated)splash10-03k9-8900000000-dc50dbf8a50872383d542012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - EI-B (HITACHI RMU-6L) , Positivesplash10-0002-9100000000-b47e534bc82a6ed36e7c2012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - 10V, Negativesplash10-00di-9000000000-04b277f233e1bd56c9af2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 10V, Negativesplash10-03di-4900000000-99764eff7d7cb7bfaee32021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 35V, Negativesplash10-00di-9000000000-453b921a0aaf64cfd5582021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-0f6x-9000000000-cd7e7026d13bb5fe844b2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-00dj-9000000000-383c22a29e2769626c472021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-0ir3-9000000000-3013847e2e0f9bf18d292021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 30V, Negativesplash10-00di-9000000000-9cc4f29b523ed34dc0b62021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 15V, Negativesplash10-00di-9000000000-d9885a6093f38dd8b9fa2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 45V, Negativesplash10-00di-9000000000-46fdee94b5a787f1b81f2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 35V, Negativesplash10-03k9-8900000000-3ff0fb725ec9dffc36882021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 20V, Negativesplash10-014m-9000000000-394fd8f1b59c7befec9d2021-09-20View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014j-9800000000-dbf34563376daeb2901f2016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00xs-9200000000-113bf08cdc77707ed3ad2016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00fr-9000000000-f32d7ec65e8649bc2b0a2016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-2900000000-408d53a9fff7acc8ca232016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-6900000000-f149e9e5a34e27dd4d4e2016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0fxt-9000000000-cae5f71dc27daaf17d9e2016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-9000000000-3d34cd791255c022876a2021-09-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00di-9000000000-55a5c43ec34fdd2cb0a42021-09-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0uk9-9000000000-7c9639a65d534cd8ff972021-09-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000t-9000000000-c5eb63dc643f72e91ede2021-09-25View Spectrum
NMR
TypeDescriptionView
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, experimental)Spectrum
1D NMR13C NMR Spectrum (1D, 125 MHz, H2O, experimental)Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, DMSO-d6, experimental)Spectrum
1D NMR13C NMR Spectrum (1D, 22.53 MHz, DMSO-d6, experimental)Spectrum
1D NMR1H NMR Spectrum (1D, D2O, experimental)Spectrum
1D NMR13C NMR Spectrum (1D, D2O, 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
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 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
Food Biomarker OntologyNot Available
VMH IDNot Available
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.