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2-Oxobutanoic acid (FDB003359)

Record Information
Version1.0
Creation date2010-04-08 22:05:46 UTC
Update date2020-09-17 15:38:09 UTC
Primary IDFDB003359
Secondary Accession NumbersNot Available
Chemical Information
FooDB Name2-Oxobutanoic acid
Description2-Ketobutyric acid, also known as alpha-ketobutyrate or 2-oxobutyrate, belongs to the class of organic compounds known as short-chain keto acids and derivatives. These are keto acids with an alkyl chain the contains less than 6 carbon atoms. 2-Ketobutyric acid is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. 2-Ketobutyric acid exists in all living species, ranging from bacteria to humans. Within humans, 2-ketobutyric acid participates in a number of enzymatic reactions. In particular, 2-ketobutyric acid can be biosynthesized from L-threonine; which is mediated by the enzyme L-serine dehydratase/l-threonine deaminase. In addition, 2-ketobutyric acid and coenzyme A can be converted into propionyl-CoA; which is mediated by the enzyme branched-chain alpha-keto dehydrogenase complex. In humans, 2-ketobutyric acid is involved in threonine and 2-oxobutanoate degradation. Outside of the human body, 2-Ketobutyric acid has been detected, but not quantified in, several different foods, such as black crowberries, lima beans, lettuces, oxheart cabbages, and grass pea. This could make 2-ketobutyric acid a potential biomarker for the consumption of these foods. A 2-oxo monocarboxylic acid that is the 2-oxo derivative of butanoic acid.
CAS Number600-18-0
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
Not AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility79.2 g/LALOGPS
logP0.07ALOGPS
logP0.77ChemAxon
logS-0.11ALOGPS
pKa (Strongest Acidic)3.19ChemAxon
pKa (Strongest Basic)-9.7ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area54.37 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity22.62 m³·mol⁻¹ChemAxon
Polarizability9.2 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC4H6O3
IUPAC name2-oxobutanoic acid
InChI IdentifierInChI=1S/C4H6O3/c1-2-3(5)4(6)7/h2H2,1H3,(H,6,7)
InChI KeyTYEYBOSBBBHJIV-UHFFFAOYSA-N
Isomeric SMILESCCC(=O)C(O)=O
Average Molecular Weight102.0886
Monoisotopic Molecular Weight102.031694058
Classification
Description Belongs to the class of organic compounds known as short-chain keto acids and derivatives. These are keto acids with an alkyl chain the contains less than 6 carbon atoms.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassKeto acids and derivatives
Sub ClassShort-chain keto acids and derivatives
Direct ParentShort-chain keto acids and derivatives
Alternative Parents
Substituents
  • Short-chain keto acid
  • Alpha-keto acid
  • Alpha-hydroxy ketone
  • Ketone
  • Monocarboxylic 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
OntologyNo ontology term
Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionC 47.06%; H 5.92%; O 47.02%DFC
Melting PointMp 31-32°DFC
Boiling PointBp12 66°DFC
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKapKa1 2.5 (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
GC-MS2-Oxobutanoic acid, non-derivatized, GC-MS Spectrumsplash10-0gbj-1900000000-8daa299f5bc38a7f9b3eSpectrum
GC-MS2-Oxobutanoic acid, non-derivatized, GC-MS Spectrumsplash10-014s-1910000000-d01bcd7b41fdcc634eeaSpectrum
GC-MS2-Oxobutanoic acid, 1 MEOX; 1 TMS, GC-MS Spectrumsplash10-000i-9200000000-3b3816ffee5771215904Spectrum
GC-MS2-Oxobutanoic acid, 1 MEOX; 1 TMS, GC-MS Spectrumsplash10-000i-6910000000-5b264d5f7e53f3e80b12Spectrum
GC-MS2-Oxobutanoic acid, 2 TMS, GC-MS Spectrumsplash10-001i-6950000000-db7f6a0f03a8cce59baeSpectrum
GC-MS2-Oxobutanoic acid, non-derivatized, GC-MS Spectrumsplash10-0ftb-0920000000-a6c93d8761ef15f7f7d4Spectrum
GC-MS2-Oxobutanoic acid, non-derivatized, GC-MS Spectrumsplash10-014i-0920000000-406fe70e72dbd9c3f274Spectrum
GC-MS2-Oxobutanoic acid, non-derivatized, GC-MS Spectrumsplash10-0gbj-1900000000-8daa299f5bc38a7f9b3eSpectrum
GC-MS2-Oxobutanoic acid, non-derivatized, GC-MS Spectrumsplash10-014s-1910000000-d01bcd7b41fdcc634eeaSpectrum
GC-MS2-Oxobutanoic acid, non-derivatized, GC-MS Spectrumsplash10-000i-9200000000-3b3816ffee5771215904Spectrum
GC-MS2-Oxobutanoic acid, non-derivatized, GC-MS Spectrumsplash10-000i-6910000000-5b264d5f7e53f3e80b12Spectrum
GC-MS2-Oxobutanoic acid, non-derivatized, GC-MS Spectrumsplash10-001i-6950000000-db7f6a0f03a8cce59baeSpectrum
GC-MS2-Oxobutanoic acid, non-derivatized, GC-MS Spectrumsplash10-000i-8900000000-97bab6630de4df095a7fSpectrum
GC-MS2-Oxobutanoic acid, non-derivatized, GC-MS Spectrumsplash10-000i-9200000000-0ebb2354fe3f935fe177Spectrum
Predicted GC-MS2-Oxobutanoic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0a6r-9000000000-32269ef3ef778c482f99Spectrum
Predicted GC-MS2-Oxobutanoic acid, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0adi-9200000000-f92941e9f326d8ccf3e4Spectrum
Predicted GC-MS2-Oxobutanoic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS2-Oxobutanoic acid, TMS_1_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS2-Oxobutanoic acid, TBDMS_1_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS2-Oxobutanoic acid, TBDMS_1_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Negative (Annotated)splash10-0pb9-9600000000-53ebb7164f74d7d92a4d2012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated)splash10-0zfr-5900000000-1db864754705beb79b552012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Negative (Annotated)splash10-0udi-9800000000-5ba5b9ede5b1bc389b872012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negativesplash10-0udi-0900000000-bfdcad5bc3ed586bdede2012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-0udi-0900000000-bfdcad5bc3ed586bdede2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - QqQ 4V, positivesplash10-0pb9-9600000000-b10635fbec5572d4d0842020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - QqQ 8V, positivesplash10-0a4i-9100000000-4c5e7d24dca6677e15702020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - QqQ 12V, positivesplash10-0a4i-9000000000-ded44cfcbe7960954fdf2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - QqQ 16V, positivesplash10-0a4i-9000000000-1b350be7438b08f1946a2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - QqQ 20V, positivesplash10-056r-9000000000-172a175b8b9ebfd5529f2020-07-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0k9i-9400000000-0061f4635858d851f1272015-05-27View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4r-9100000000-b943445194fb5f8e3a0f2015-05-27View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-9000000000-bc5920b9bd140be6b06d2015-05-27View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-5900000000-f7dfb4554f0b9e1499c92015-05-27View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a59-9200000000-e54106ad5bf45a9f072c2015-05-27View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9000000000-7bbba57578cf720974e32015-05-27View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-9000000000-ca1ed9c5aadcbdabc2a32021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-9000000000-aced8e004436190f07b72021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-9000000000-a3d7ddf227bd6aa91a542021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0pb9-9700000000-503296025148ec3143832021-09-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-9000000000-933b567955b5de5b17442021-09-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9000000000-7d9db52021fefc87a8552021-09-25View Spectrum
NMR
TypeDescriptionView
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, experimental)Spectrum
1D NMR1H NMR Spectrum (1D, D2O, experimental)Spectrum
1D NMR13C NMR Spectrum (1D, D2O, experimental)Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)Spectrum
ChemSpider ID57
ChEMBL IDCHEMBL171246
KEGG Compound IDC00109
Pubchem Compound ID58
Pubchem Substance IDNot Available
ChEBI ID16763
Phenol-Explorer IDNot Available
DrugBank IDDB04553
HMDB IDHMDB00005
CRC / DFC (Dictionary of Food Compounds) IDCWG39-N:CWG39-N
EAFUS ID1963
Dr. Duke IDNot Available
BIGG ID33889
KNApSAcK IDC00019675
HET ID2KT
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDrw1037661
SuperScent IDNot Available
Wikipedia IDAlpha-ketobutyric_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 / BioactivitiesNot Available
Enzymes
NameGene NameUniProt ID
Cystathionine gamma-lyaseCTHP32929
Pyruvate dehydrogenase E1 component subunit beta, mitochondrialPDHBP11177
Pyruvate dehydrogenase E1 component subunit alpha, somatic form, mitochondrialPDHA1P08559
Pyruvate dehydrogenase E1 component subunit alpha, testis-specific form, mitochondrialPDHA2P29803
2-oxoisovalerate dehydrogenase subunit beta, mitochondrialBCKDHBP21953
2-oxoglutarate dehydrogenase, mitochondrialOGDHQ02218
L-serine dehydratase/L-threonine deaminaseSDSP20132
[3-methyl-2-oxobutanoate dehydrogenase [lipoamide]] kinase, mitochondrialBCKDKO14874
Serine dehydratase-likeSDSLQ96GA7
2-oxoglutarate dehydrogenase-like, mitochondrialOGDHLQ9ULD0
Pathways
NameSMPDB LinkKEGG Link
Glycine and Serine MetabolismSMP00004 map00260
Homocysteine DegradationSMP00455 Not Available
Methionine MetabolismSMP00033 map00270
Threonine and 2-Oxobutanoate DegradationSMP00452 Not Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
Flavours
FlavorCitations
sweet
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
brown
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
caramel
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
creamy
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
lactonic
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference