Record Information
Version1.0
Creation date2010-04-08 22:05:46 UTC
Update date2018-01-23 18:58:30 UTC
Primary IDFDB003359
Secondary Accession NumbersNot Available
Chemical Information
FooDB Name2-Oxobutanoic acid
DescriptionFlavour ingredient 2-Ketobutyric acid is a substance that is involved in the metabolism of many amino acids (glycine, methionine, valine, leucine, serine, threonine, isoleucine) as well as propanoate metabolism and C-5 branched dibasic acid metabolism. More specifically, alpha-ketobutyric acid is a product of the lysis of cystathionine. It is also one of the degradation products of threonine. It can be converted to propionyl-CoA (and subsequently methylmalonyl CoA, which can be converted to succinyl CoA, a citric acid cycle intermediate), and thus enter the citric acid cycle.; Alpha-ketobutyric acid is a product of the lysis of cystathionine.; It is also one of the degradation products of threonine. 2-Oxobutanoic acid is found in many foods, some of which are cloudberry, garden onion, blackcurrant, and chinese cabbage.
CAS Number600-18-0
Structure
Thumb
Synonyms
SynonymSource
2-Ketobutanoic acidChEBI
2-Oxobutyric acidChEBI
3-Methyl pyruvic acidChEBI
alpha-KetobutyrateChEBI
alpha-Ketobutyric acidChEBI
alpha-oxo-N-Butyric acidChEBI
2-OxobutyrateKegg
2-Oxobutanoic acidKegg
2-KetobutanoateGenerator
3-Methyl pyruvateGenerator
a-KetobutyrateGenerator
a-Ketobutyric acidGenerator
Α-ketobutyrateGenerator
Α-ketobutyric acidGenerator
a-oxo-N-ButyrateGenerator
a-oxo-N-Butyric acidGenerator
alpha-oxo-N-ButyrateGenerator
Α-oxo-N-butyrateGenerator
Α-oxo-N-butyric acidGenerator
2-OxobutanoateGenerator
2-KetobutyrateGenerator
2-oxo-ButanoateHMDB
2-oxo-Butanoic acidHMDB
2-oxo-ButyrateHMDB
2-oxo-Butyric acidHMDB
2-oxo-N-ButyrateHMDB
2-oxo-N-Butyric acidHMDB
3-MethylpyruvateHMDB
3-Methylpyruvic acidHMDB
a-Keto-N-butyrateHMDB
a-Keto-N-butyric acidHMDB
a-OxobutyrateHMDB
a-Oxobutyric acidHMDB
alpha-Keto-N-butyrateHMDB
alpha-Keto-N-butyric acidHMDB
alpha-Ketobutric acidHMDB
alpha-OxobutyrateHMDB
alpha-Oxobutyric acidHMDB
Methyl-pyruvateHMDB
Methyl-pyruvic acidHMDB
Propionyl-formateHMDB
Propionyl-formic acidHMDB
alpha-Ketobutyric acid, sodium saltHMDB
2-Ketobutyric acidChEBI
α-keto-n-butyric acidbiospider
α-ketobutric acidbiospider
α-ketobutyric acidbiospider
α-oxo-n-butyric acidbiospider
α-oxobutyratebiospider
α-oxobutyric acidbiospider
2-keto-butyratebiospider
2-ketobutyratebiospider
2-Oxo-Butanoatebiospider
2-Oxo-Butanoic acidbiospider
2-Oxo-n-butyratebiospider
2-Oxo-n-butyric acidbiospider
3-methyl pyruvic acidbiospider
A-keto-n-butyratebiospider
A-keto-n-butyric acidbiospider
A-ketobutyratebiospider
A-ketobutyric acidbiospider
A-oxo-n-butyratebiospider
A-oxo-n-butyric acidbiospider
A-oxobutyratebiospider
A-oxobutyric acidbiospider
Alpha-keto-n-butyratebiospider
Alpha-keto-n-butyric acidbiospider
Alpha-ketobutric acidbiospider
Alpha-ketobutyratebiospider
Alpha-ketobutyric acidbiospider
Alpha-ketobutyric acid, nabiospider
Alpha-oxo-n-butyratebiospider
Alpha-oxo-n-butyric acidbiospider
Alpha-oxobutyratebiospider
Alpha-oxobutyric acidbiospider
Butanoic acid, 2-oxo-biospider
Butanoic acid, 2-oxo- (9CI)biospider
Butyric acid, 2-oxo-biospider
Butyric acid, 2-oxo- (8CI)biospider
FEMA 3723db_source
Formic acid, propionyl-biospider
Ketobutyratebiospider
Oxobutyratebiospider
Propionylformic acidbiospider
Pyruvic acid, methyl-biospider
α-ketobutyrateGenerator
α-ketobutyric acidGenerator
α-oxo-N-butyrateGenerator
α-oxo-N-butyric acidGenerator
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
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
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
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
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)splash10-0gbj-1900000000-8daa299f5bc38a7f9b3eView in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)splash10-014s-1910000000-d01bcd7b41fdcc634eeaView in MoNA
GC-MSGC-MS Spectrum - GC-MS (1 MEOX; 1 TMS)splash10-000i-9200000000-3b3816ffee5771215904View in MoNA
GC-MSGC-MS Spectrum - GC-MS (1 MEOX; 1 TMS)splash10-000i-6910000000-5b264d5f7e53f3e80b12View in MoNA
GC-MSGC-MS Spectrum - GC-MS (2 TMS)splash10-001i-6950000000-db7f6a0f03a8cce59baeView in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0ftb-0920000000-a6c93d8761ef15f7f7d4View in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-014i-0920000000-406fe70e72dbd9c3f274View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0gbj-1900000000-8daa299f5bc38a7f9b3eView in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-014s-1910000000-d01bcd7b41fdcc634eeaView in MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-000i-9200000000-3b3816ffee5771215904View in MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-000i-6910000000-5b264d5f7e53f3e80b12View in MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-001i-6950000000-db7f6a0f03a8cce59baeView in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-000i-8900000000-97bab6630de4df095a7fView in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-000i-9200000000-0ebb2354fe3f935fe177View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a6r-9000000000-32269ef3ef778c482f99View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-0adi-9200000000-f92941e9f326d8ccf3e4View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Negative (Annotated)splash10-0pb9-9600000000-53ebb7164f74d7d92a4dView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated)splash10-0zfr-5900000000-1db864754705beb79b55View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Negative (Annotated)splash10-0udi-9800000000-5ba5b9ede5b1bc389b87View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negativesplash10-0udi-0900000000-bfdcad5bc3ed586bdedeView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-0udi-0900000000-bfdcad5bc3ed586bdedeView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0k9i-9400000000-0061f4635858d851f127View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4r-9100000000-b943445194fb5f8e3a0fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-9000000000-bc5920b9bd140be6b06dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-5900000000-f7dfb4554f0b9e1499c9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a59-9200000000-e54106ad5bf45a9f072cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9000000000-7bbba57578cf720974e3View in MoNA
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableView in JSpectraViewer
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
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