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4-Methyl-2-oxopentanoic acid (PC000232)

Record Information
Version1.0
Creation date2015-10-09 22:29:21 UTC
Update date2017-01-19 02:36:17 UTC
FoodComEx IDPC000232
FoodDB RecordFDB012607
Chemical Information
Name4-Methyl-2-oxopentanoic acid
DescriptionKetoleucine, also known as 2-oxoisocaproate or 2-oxoleucine, 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. Ketoleucine is an extremely weak basic (essentially neutral) compound (based on its pKa). Ketoleucine exists in all living species, ranging from bacteria to humans. Outside of the human body, Ketoleucine has been detected, but not quantified in, several different foods, such as oriental wheats, nances, corianders, quinces, and soursops. This could make ketoleucine a potential biomarker for the consumption of these foods. Ketoleucine is a potentially toxic compound. Ketoleucine, with regard to humans, has been found to be associated with several diseases such as eosinophilic esophagitis, periodontal probing depth, rheumatoid arthritis, and gout; ketoleucine has also been linked to the inborn metabolic disorder maple syrup urine disease.
CAS Number816-66-0
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
α-ketoisocaproic acidbiospider
2-keto-4-methyl-pentanoatebiospider
2-Keto-4-methylpentanoic acidbiospider
2-keto-4-Methylvaleratebiospider
2-keto-4-Methylvaleric acidbiospider
2-Ketoisocaproatebiospider
2-Ketoisocaproic acidbiospider
2-Oxo-4-methylpentanoatebiospider
2-Oxo-4-methylpentanoic acidbiospider
2-Oxo-4-methylvaleratebiospider
2-Oxo-4-methylvaleric acidbiospider
2-Oxoisocaproatebiospider
2-Oxoisocaproic aciddb_source
2-Oxoleucinebiospider
2K-4CH3-PENTANOATEbiospider
4-methyl-2-oxo-Valeratebiospider
4-methyl-2-oxo-Valeric acidbiospider
4-Methyl-2-oxopentanoatebiospider
4-Methyl-2-oxovalerateGenerator
4-methyl-2-oxovaleric acidbiospider
A-ketoisocaproatebiospider
A-ketoisocaproic acidbiospider
A-ketoisocapronatebiospider
A-ketoisocapronic acidbiospider
A-oxoisocaproatebiospider
A-oxoisocaproic acidbiospider
Alpha-keto-isocaproatebiospider
Alpha-keto-isocaproic acidbiospider
Alpha-ketoisocaproatebiospider
Alpha-ketoisocaproic acidbiospider
Alpha-ketoisocapronatebiospider
Alpha-ketoisocapronic acidbiospider
Alpha-oxoisocaproatebiospider
Alpha-oxoisocaproic acidbiospider
Isobutylglyoxylic aciddb_source
Isopropylpyruvic aciddb_source
Ketoisocaproatebiospider
Ketoisocaproic aciddb_source
Ketoleucinedb_source
KICAdb_source
Methyloxovaleratebiospider
Methyloxovaleric acidbiospider
Oxoisocaproatebiospider
Oxoisocaproic acidbiospider
Pentanoic acid, 4-methyl-2-oxo-biospider
α-ketoisocaproateGenerator
α-ketoisocaproic acidGenerator
Chemical FormulaC6H10O3
IUPAC name4-methyl-2-oxopentanoic acid
InChI IdentifierInChI=1S/C6H10O3/c1-4(2)3-5(7)6(8)9/h4H,3H2,1-2H3,(H,8,9)
InChI KeyBKAJNAXTPSGJCU-UHFFFAOYSA-N
Isomeric SMILESCC(C)CC(=O)C(O)=O
Average Molecular Weight130.1418
Monoisotopic Molecular Weight130.062994186
Chemical Taxonomy
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
  • Branched fatty acid
  • Methyl-branched fatty acid
  • Short-chain keto acid
  • Alpha-keto acid
  • Fatty acyl
  • Alpha-hydroxy ketone
  • Ketone
  • Carboxylic acid derivative
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Carbonyl group
  • Hydrocarbon derivative
  • Organic oxygen compound
  • Organooxygen compound
  • Organic oxide
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Physico-Chemical Properties - Experimental
PropertyValueReference
Experimental logPNot Available
Experimental Water SolubilityNot Available
Melting PointMp 10-11° (-1.5°)DFC
Foods of Origin
FoodContent Range AverageReference
FoodReference
Production Data
Production Methodcommercial
Production Method ReferenceNot Available
Production Method Reference FileNot Available
Quantity AvailableProduction upon request, up to 400 mg
Delivery TimeNot Available
Storage Formsolid
Storage Conditions-80°C
StabilityNot Available
PurityNot Available
Spectra
Spectral Data Upon RequestNot Available
Provider Information
Contact NameContact InstitutionContact Email
Rosa Vazquez Fresnovazquezf@ualberta.ca
Commercial Vendors
AKSci 2659AC