Record Information
Version1.0
Creation date2010-04-08 22:10:04 UTC
Update date2020-09-17 15:38:09 UTC
Primary IDFDB012250
Secondary Accession Numbers
  • FDB030441
Chemical Information
FooDB Name3-Methyl-2-oxobutanoic acid
Descriptionalpha-Ketoisovaleric acid, also known as a-keto-isovalerate or 3-methyl-2-oxobutanoate, 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. alpha-Ketoisovaleric acid is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. alpha-Ketoisovaleric acid exists in all living species, ranging from bacteria to humans. alpha-Ketoisovaleric acid is a fruity tasting compound. Outside of the human body, alpha-Ketoisovaleric acid has been detected, but not quantified in, several different foods, such as root vegetables, jerusalem artichokes, rapinis, chia, and cowpea. This could make alpha-ketoisovaleric acid a potential biomarker for the consumption of these foods. alpha-Ketoisovaleric acid is a potentially toxic compound. alpha-Ketoisovaleric acid, with regard to humans, has been found to be associated with the diseases such as colorectal cancer; alpha-ketoisovaleric acid has also been linked to the inborn metabolic disorder maple syrup urine disease. A 2-oxo monocarboxylic acid that is the 2-oxo derivative of isovaleric acid.
CAS Number759-05-7
Structure
Thumb
Synonyms
SynonymSource
2-keto-3-Methylbutyratebiospider
2-keto-3-Methylbutyric acidChEBI
2-KETO-ISOVALERATEbiospider
2-Ketoisovaleratebiospider
2-Ketoisovaleric acidbiospider
2-Ketoisvaleric acidHMDB
2-KetovalineChEBI
2-oxo-3-Methyl-butyrateHMDB
2-oxo-3-MethylbutanoateGenerator
2-Oxo-3-methylbutanoic acidbiospider
2-Oxo-3-methylbutyratebiospider
2-Oxo-3-methylbutyric acidbiospider
2-Oxoisopentanoic aciddb_source
2-OxoisovalerateGenerator
2-Oxoisovaleric acidbiospider
3-methyl-2-oxo-Butanoatebiospider
3-methyl-2-oxo-Butanoic acidbiospider
3-methyl-2-oxo-Butyratebiospider
3-methyl-2-oxo-Butyric acidbiospider
3-Methyl-2-oxobutanoateChEBI
3-Methyl-2-oxobutinoatebiospider
3-Methyl-2-oxobutinoic acidbiospider
3-Methyl-2-oxobutyratebiospider
3-Methyl-2-oxobutyric acidChEBI
A-keto-b-methylbutyratebiospider
A-keto-b-methylbutyric acidbiospider
A-keto-isovaleratebiospider
A-keto-isovaleric acidbiospider
A-ketoisovaleratebiospider
a-Ketoisovaleric aciddb_source
a-KetovalineGenerator
A-oxo-b-methylbutyratebiospider
A-oxo-b-methylbutyric acidbiospider
a-oxo-b-MethylbutyricacidGenerator
A-oxoisovaleratebiospider
A-oxoisovaleric acidbiospider
Alpha-keto-beta-methylbutyratebiospider
Alpha-keto-beta-methylbutyric acidbiospider
Alpha-keto-isovaleratebiospider
Alpha-keto-isovaleric acidbiospider
Alpha-keto-valinebiospider
Alpha-ketoisopentanoic acidbiospider
Alpha-ketoisovaleratebiospider
Alpha-ketoisovaleric acidbiospider
alpha-KetovalineChEBI
Alpha-oxo-beta-methylbutyratebiospider
Alpha-oxo-beta-methylbutyric acidbiospider
alpha-oxo-beta-MethylbutyricacidChEBI
Alpha-oxoisovaleratebiospider
Alpha-oxoisovaleric acidbiospider
Butanoic acid, 3-methyl-2-oxo-biospider
Dimethylpyruvatebiospider
Dimethylpyruvic aciddb_source
FEMA 3869db_source
Isopropylglyoxylatebiospider
Isopropylglyoxylic acidbiospider
Ketovalinedb_source
KIVbiospider
α-keto-isovalerateGenerator
α-keto-isovaleric acidGenerator
α-ketovalineGenerator
α-oxo-β-methylbutyricacidGenerator
α-oxoisovalerateGenerator
α-oxoisovaleric acidGenerator
Predicted PropertiesNot Available
Chemical FormulaC5H8O3
IUPAC name
InChI IdentifierInChI=1S/C5H8O3/c1-3(2)4(6)5(7)8/h3H,1-2H3,(H,7,8)
InChI KeyQHKABHOOEWYVLI-UHFFFAOYSA-N
Isomeric SMILESCC(C)C(=O)C(O)=O
Average Molecular Weight116.1152
Monoisotopic Molecular Weight116.047344122
Classification
ClassificationNot classified
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Process

Naturally occurring process:

Role

Indirect biological role:

Biological role:

Industrial application:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionC 51.72%; H 6.94%; O 41.34%DFC
Melting PointMp 31°DFC
Boiling PointBp 170.5°DFC
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-MSNot Available
MS/MSNot Available
NMRNot Available
ChemSpider ID48
ChEMBL IDCHEMBL146554
KEGG Compound IDC00141
Pubchem Compound ID49
Pubchem Substance IDNot Available
ChEBI ID16530
Phenol-Explorer IDNot Available
DrugBank IDDB04074
HMDB IDHMDB00019
CRC / DFC (Dictionary of Food Compounds) IDHFL26-U:HFL26-U
EAFUS ID2433
Dr. Duke IDNot Available
BIGG ID34011
KNApSAcK IDC00007623
HET IDKIV
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDrw1047091
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
Enzymes
NameGene NameUniProt ID
Branched-chain-amino-acid aminotransferase, cytosolicBCAT1P54687
Branched-chain-amino-acid aminotransferase, mitochondrialBCAT2O15382
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
Dihydrolipoyllysine-residue acetyltransferase component of pyruvate dehydrogenase complex, mitochondrialDLATP10515
Pathways
NameSMPDB LinkKEGG Link
Valine, Leucine and Isoleucine DegradationSMP00032 map00280
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
Flavours
FlavorCitations
fruity
  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