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Propanedioic acid (FDB008117)

Record Information
Version1.0
Creation date2010-04-08 22:07:56 UTC
Update date2020-09-17 15:32:16 UTC
Primary IDFDB008117
Secondary Accession NumbersNot Available
Chemical Information
FooDB NamePropanedioic acid
DescriptionMalonic acid, also known as malonate or H2MALO, belongs to the class of organic compounds known as dicarboxylic acids and derivatives. These are organic compounds containing two carboxylic acid groups. Malonic acid is a very hydrophobic molecule, practically insoluble in water. Malonic acid exists in all living species, ranging from bacteria to humans. In humans, malonic acid is involved in fatty acid biosynthesis. Malonic acid has also been detected, but not quantified, in several different foods, such as red beetroots, corns, scarlet beans, common beets, and cow milks. Industrially, it is used in a number of manufacturing processes as a high value specialty chemical, including the electronics industry, flavors and fragrances industry, specialty solvents, polymer crosslinking, and pharmaceutical industry.
CAS Number141-82-2
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
SynonymSource
Not AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility197 g/LALOGPS
logP-0.6ALOGPS
logP-0.33ChemAxon
logS0.28ALOGPS
pKa (Strongest Acidic)2.43ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area74.6 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity18.99 m³·mol⁻¹ChemAxon
Polarizability8.13 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC3H4O4
IUPAC namepropanedioic acid
InChI IdentifierInChI=1S/C3H4O4/c4-2(5)1-3(6)7/h1H2,(H,4,5)(H,6,7)
InChI KeyOFOBLEOULBTSOW-UHFFFAOYSA-N
Isomeric SMILESOC(=O)CC(O)=O
Average Molecular Weight104.0615
Monoisotopic Molecular Weight104.010958616
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
  • 1,3-dicarbonyl compound
  • 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:

Role

Industrial application:

Biological role:

Physico-Chemical Properties
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionC 34.63%; H 3.87%; O 61.50%DFC
Melting PointMp 135.6°DFC
Boiling PointNot Available
Experimental Water Solubility763 mg/mL at 25 oCYALKOWSKY,SH & DANNENFELSER,RM (1992)
Experimental logP-0.81HANSCH,C ET AL. (1995)
Experimental pKapKa2 5.7 (25°,H2O)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)splash10-01ox-9000000000-dd4efef191376724d0f12015-03-01View Spectrum
GC-MSPropanedioic acid, 2 TMS, GC-MS Spectrumsplash10-0002-1900000000-a1463432c138c328557dSpectrum
GC-MSPropanedioic acid, non-derivatized, GC-MS Spectrumsplash10-0002-0900000000-5e58241137fee0ccc64aSpectrum
GC-MSPropanedioic acid, 2 TMS, GC-MS Spectrumsplash10-006t-9700000000-54976b3ce8f36ce0676dSpectrum
GC-MSPropanedioic acid, 2 TMS, GC-MS Spectrumsplash10-001i-4930000000-e7dbed4919870db8dabfSpectrum
GC-MSPropanedioic acid, 3 TMS, GC-MS Spectrumsplash10-05gl-1943000000-456e387fdf365bf0f8eeSpectrum
GC-MSPropanedioic acid, non-derivatized, GC-MS Spectrumsplash10-0006-9000000000-6c56a402111059603ba4Spectrum
GC-MSPropanedioic acid, non-derivatized, GC-MS Spectrumsplash10-0006-9000000000-f239df8fdd12e9a74445Spectrum
GC-MSPropanedioic acid, non-derivatized, GC-MS Spectrumsplash10-0006-9000000000-6865e83f0df5c9831619Spectrum
GC-MSPropanedioic acid, non-derivatized, GC-MS Spectrumsplash10-0002-0900000000-a768f0aae86e17a3a6baSpectrum
GC-MSPropanedioic acid, non-derivatized, GC-MS Spectrumsplash10-0002-1900000000-a1463432c138c328557dSpectrum
GC-MSPropanedioic acid, non-derivatized, GC-MS Spectrumsplash10-0002-0900000000-5e58241137fee0ccc64aSpectrum
GC-MSPropanedioic acid, non-derivatized, GC-MS Spectrumsplash10-006t-9700000000-54976b3ce8f36ce0676dSpectrum
GC-MSPropanedioic acid, non-derivatized, GC-MS Spectrumsplash10-05gl-1943000000-456e387fdf365bf0f8eeSpectrum
GC-MSPropanedioic acid, non-derivatized, GC-MS Spectrumsplash10-001i-4930000000-e7dbed4919870db8dabfSpectrum
GC-MSPropanedioic acid, non-derivatized, GC-MS Spectrumsplash10-0002-0900000000-a45cfb1e2683f8ad8c5cSpectrum
GC-MSPropanedioic acid, non-derivatized, GC-MS Spectrumsplash10-0002-0911000000-8b0d7393c5dc4462a756Spectrum
Predicted GC-MSPropanedioic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0zfu-9300000000-cbc239877c485e6dff65Spectrum
Predicted GC-MSPropanedioic acid, 2 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-00di-9410000000-c30e36ba8e95ef1c83beSpectrum
Predicted GC-MSPropanedioic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPropanedioic acid, TMS_1_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPropanedioic acid, TBDMS_1_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPropanedioic acid, TBDMS_2_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Negative (Annotated)splash10-0a4i-9100000000-c7a1704f8a38ca2d245a2012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated)splash10-0a4l-9100000000-9fa84f43f2e19b56035c2012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Negative (Annotated)splash10-052f-9100000000-8a21753b343cf5dabdcb2012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - EI-B (Unknown) , Positivesplash10-0006-9000000000-6c56a402111059603ba42012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - EI-B (HITACHI RMU-7M) , Positivesplash10-0006-9000000000-f239df8fdd12e9a744452012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-0udi-3900000000-e0a4c7e792cfd0e60cc32012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-0a4i-9000000000-4c03aa889e6a98ab532f2012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negativesplash10-0a4l-9000000000-b3d14c986f292bdcf4772012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negativesplash10-0006-9000000000-8e1041322f9acda4088a2012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negativesplash10-0006-9000000000-af4dccf21d68110099a12012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0udi-3900000000-e0a4c7e792cfd0e60cc32017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0a4i-9000000000-4c03aa889e6a98ab532f2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0a4l-9000000000-b3d14c986f292bdcf4772017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0006-9000000000-8e1041322f9acda4088a2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0006-9000000000-af4dccf21d68110099a12017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - , negativesplash10-0006-3900000000-2126168f67ddb43e544d2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - , positivesplash10-000i-9000000000-e9d5906655e37a471b892017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-9000000000-c742107695804ea678f12021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 40V, Negativesplash10-0006-9000000000-cb15cb8d630a4fbd07502021-09-20View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4r-7900000000-795ca313c7daaf448ede2016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0bti-9400000000-a6390568ef61fe1a284e2016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-01ox-9100000000-cc17364c6d52c2c208f32016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0zfr-6900000000-b1169abf90c9693f8e302016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-9300000000-cec6a47ea3eb4a95a9572016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9000000000-cffa3dea7855764ea8542016-09-12View Spectrum
NMR
TypeDescriptionView
1D NMR13C NMR Spectrum (1D, 125 MHz, H2O, experimental)Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, experimental)Spectrum
1D NMR1H NMR Spectrum (1D, 90 MHz, DMSO-d6, experimental)Spectrum
1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 400 MHz, H2O, experimental)Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, experimental)Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)Spectrum
ChemSpider ID844
ChEMBL IDCHEMBL7942
KEGG Compound IDC04025
Pubchem Compound ID867
Pubchem Substance IDNot Available
ChEBI ID30794
Phenol-Explorer IDNot Available
DrugBank IDDB02175
HMDB IDHMDB00691
CRC / DFC (Dictionary of Food Compounds) IDDCG89-D:DCG89-D
EAFUS IDNot Available
Dr. Duke IDMALONIC-ACID
BIGG IDNot Available
KNApSAcK IDC00001193
HET IDMLA
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDMalonic 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
irritantDUKE
Enzymes
NameGene NameUniProt ID
4-aminobutyrate aminotransferase, mitochondrialABATP80404
Proto-oncogene tyrosine-protein kinase SrcSRCP12931
Pathways
NameSMPDB LinkKEGG Link
Aspartate MetabolismSMP00067 map00250
Fatty Acid BiosynthesisSMP00456 Not Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
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.