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Methylacetoacetic acid (FDB021937)

Record Information
Version1.0
Creation date2011-09-21 00:05:31 UTC
Update date2015-10-09 22:28:24 UTC
Primary IDFDB021937
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameMethylacetoacetic acid
DescriptionMethylacetoacetic acid, also known as 3-oxo-butanoate or methyl acetylacetate, belongs to the class of organic compounds known as beta-keto acids and derivatives. These are organic compounds containing an aldehyde substituted with a keto group on the C3 carbon atom. Methylacetoacetic acid is a citrus, fresh, and fruity tasting compound. Methylacetoacetic acid has been detected, but not quantified in, a few different foods, such as anatidaes (Anatidae), chickens (Gallus gallus), and domestic pigs (Sus scrofa domestica). This could make methylacetoacetic acid a potential biomarker for the consumption of these foods. Based on a literature review a significant number of articles have been published on Methylacetoacetic acid.
CAS Number105-45-3
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
Not AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility137 g/LALOGPS
logP-0.29ALOGPS
logP0.14ChemAxon
logS0.07ALOGPS
pKa (Strongest Acidic)10.28ChemAxon
pKa (Strongest Basic)-7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area43.37 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity27.31 m³·mol⁻¹ChemAxon
Polarizability11.27 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC5H8O3
IUPAC namemethyl 3-oxobutanoate
InChI IdentifierInChI=1S/C5H8O3/c1-4(6)3-5(7)8-2/h3H2,1-2H3
InChI KeyWRQNANDWMGAFTP-UHFFFAOYSA-N
Isomeric SMILESCOC(=O)CC(C)=O
Average Molecular Weight116.1152
Monoisotopic Molecular Weight116.047344122
Classification
Description Belongs to the class of organic compounds known as beta-keto acids and derivatives. These are organic compounds containing an aldehyde substituted with a keto group on the C3 carbon atom.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassKeto acids and derivatives
Sub ClassBeta-keto acids and derivatives
Direct ParentBeta-keto acids and derivatives
Alternative Parents
Substituents
  • Beta-keto acid
  • Fatty acid ester
  • Fatty acid methyl ester
  • 1,3-dicarbonyl compound
  • Fatty acyl
  • Methyl ester
  • Carboxylic acid ester
  • Ketone
  • Monocarboxylic acid or derivatives
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Carbonyl group
  • Organooxygen compound
  • Hydrocarbon derivative
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Source:

Physico-Chemical Properties
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateLiquid
Physical DescriptionNot Available
Mass CompositionNot Available
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
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
GC-MSMethylacetoacetic acid, non-derivatized, GC-MS Spectrumsplash10-0006-9000000000-9801f4fde1f8c64f6bafSpectrum
GC-MSMethylacetoacetic acid, non-derivatized, GC-MS Spectrumsplash10-0006-9000000000-e4481e7d9e6ac8fc177bSpectrum
GC-MSMethylacetoacetic acid, non-derivatized, GC-MS Spectrumsplash10-0006-9000000000-f8789e71041e62cce331Spectrum
GC-MSMethylacetoacetic acid, non-derivatized, GC-MS Spectrumsplash10-0006-9100000000-65b70a114483f92cc1f4Spectrum
GC-MSMethylacetoacetic acid, non-derivatized, GC-MS Spectrumsplash10-00kr-9300000000-7a638e147c3997a85598Spectrum
GC-MSMethylacetoacetic acid, non-derivatized, GC-MS Spectrumsplash10-0006-9000000000-9801f4fde1f8c64f6bafSpectrum
GC-MSMethylacetoacetic acid, non-derivatized, GC-MS Spectrumsplash10-0006-9000000000-e4481e7d9e6ac8fc177bSpectrum
GC-MSMethylacetoacetic acid, non-derivatized, GC-MS Spectrumsplash10-0006-9000000000-f8789e71041e62cce331Spectrum
GC-MSMethylacetoacetic acid, non-derivatized, GC-MS Spectrumsplash10-0006-9100000000-65b70a114483f92cc1f4Spectrum
GC-MSMethylacetoacetic acid, non-derivatized, GC-MS Spectrumsplash10-00kr-9300000000-7a638e147c3997a85598Spectrum
Predicted GC-MSMethylacetoacetic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0006-9100000000-869c1574ff891034b665Spectrum
Predicted GC-MSMethylacetoacetic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSMethylacetoacetic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, N/A (Annotated)splash10-000l-9100000000-be1b334229aa020fc7e82012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, N/A (Annotated)splash10-0006-9000000000-e512bbad2ab7f1c253a72012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, N/A (Annotated)splash10-0006-9000000000-0627dffba19580aa6a7d2012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - EI-B (HITACHI RMU-7M) , Positivesplash10-0006-9000000000-6f423389be91a0d883a22012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - EI-B (HITACHI RMU-6M) , Positivesplash10-0006-9000000000-e4481e7d9e6ac8fc177b2012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - EI-B (JEOL JMS-D-3000) , Positivesplash10-0006-9000000000-970f150ada556d2324642012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - EI-B (HITACHI RMU-6M) , Positivesplash10-0006-9100000000-86a6dd485ea6cf9b06322012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - CI-B (HITACHI M-80) , Positivesplash10-00kr-9300000000-0d967b807194a0d4f1892012-08-31View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014r-9300000000-e5dc637782adee6c0e042017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014j-9100000000-3bc03bc80fc348b48f882017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-014u-9000000000-ed2c64d5d7629d00368e2017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-8900000000-26833f2c7b71af9eed1f2017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0aw9-9200000000-d2941bafc6ef6d37ea382017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a59-9000000000-765079c1255f5f8b29072017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-01bc-9400000000-ac614382ccd32f161a652021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-9000000000-f50f28ce0031ed1ca1af2021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9000000000-7ab0f1f6abf2d008ff8e2021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-9000000000-d66fe58106ad458e0f712021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0006-9000000000-0c548d0b4e3b334064ce2021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9000000000-87bbaed151efac0845912021-09-24View Spectrum
NMR
TypeDescriptionView
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, 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, 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, 1000 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)Spectrum
ChemSpider ID13874867
ChEMBL IDCHEMBL3186053
KEGG Compound IDNot Available
Pubchem Compound ID7757
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB00310
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 IDrw1014971
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
Flavours
FlavorCitations
fresh
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
fruity
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
citrus
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
green
  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