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3-Methyl-2-oxopentanoic acid (PC000402)

Record Information
Version1.0
Creation date2015-10-09 22:30:27 UTC
Update date2017-01-19 02:36:22 UTC
FoodComEx IDPC000402
FoodDB RecordFDB021447
Chemical Information
Name3-Methyl-2-oxopentanoic acid
Description3-Methyl-2-oxovaleric acid, also known as 3-methyl-2-oxopentanoate or α-keto-β-methyl-N-valeric acid, 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. 3-Methyl-2-oxovaleric acid is an extremely weak basic (essentially neutral) compound (based on its pKa). 3-Methyl-2-oxovaleric acid exists in all living organisms, ranging from bacteria to humans. Outside of the human body, 3-Methyl-2-oxovaleric acid has been detected, but not quantified in, several different foods, such as alcoholic beverages, asparagus, cocoa and cocoa products, green vegetables, and milk and milk products. This could make 3-methyl-2-oxovaleric acid a potential biomarker for the consumption of these foods. An alpha-keto acid analogue and metabolite of isoleucine in man, animals and bacteria. 3-Methyl-2-oxovaleric acid is a potentially toxic compound. A 2-oxo monocarboxylic acid that is valeric acid carrying oxo- and methyl substituents at C-2 and C-3, respectively. 3-Methyl-2-oxovaleric acid, with regard to humans, has been found to be associated with several diseases such as colorectal cancer, prosthesis/missing teeth, attachment loss, and missing teeth; 3-methyl-2-oxovaleric acid has also been linked to the inborn metabolic disorder maple syrup urine disease. Used as a clinical marker for maple syrup urine disease (MSUD).
CAS Number1460-34-0
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
(3R)-3-Methyl-2-oxopentanoateHMDB
(3R)-3-Methyl-2-oxopentanoic acidHMDB
(R)-3-Methyl-2-oxopentanoateHMDB
(R)-3-Methyl-2-oxopentanoic acidHMDB
(S)-3-Methyl-2-oxopentanoateHMDB
(S)-3-Methyl-2-oxopentanoic acidHMDB
2-keto-3-MethylvalerateHMDB
2-keto-3-Methylvaleric acidHMDB
2-Oxo-3-methyl-n-valeratebiospider
2-Oxo-3-methyl-n-valeric acidbiospider
2-Oxo-3-methylpentanoatebiospider
2-Oxo-3-methylpentanoic acidbiospider
2-Oxo-3-methylvaleratebiospider
2-Oxo-3-methylvaleric acidbiospider
2-Oxoisoleucinebiospider
2-oxokolavenatebiospider
2-oxokolavenic acidbiospider
3-Ethyl-3-methylpyruvateGenerator
3-Ethyl-3-methylpyruvic acidChEBI
3-methyl-2-oxo-pentanoatebiospider
3-methyl-2-oxo-pentanoic acidbiospider
3-methyl-2-oxo-Valeratebiospider
3-methyl-2-oxo-Valeric acidbiospider
3-Methyl-2-oxopentanoatebiospider
3-Methyl-2-oxopentanoic acidbiospider
3-Methyl-2-oxovaleratebiospider
3-Methyl-2-oxovalericbiospider
3-Methyl-2-oxovaleric acidChEBI
3-Methyl-2-oxovaleric acid, 8CIdb_source
A-keto-b-methyl-n-valeratebiospider
A-keto-b-methyl-n-valeric acidbiospider
A-keto-b-methylvaleratebiospider
A-keto-b-methylvaleric acidbiospider
A-oxo-b-methyl-n-valeratebiospider
A-oxo-b-methyl-n-valeric acidbiospider
A-oxo-b-methylvaleratebiospider
A-oxo-b-methylvaleric acidbiospider
Alpha-keto-beta-methyl-n-valeratebiospider
Alpha-keto-beta-methyl-n-valeric acidbiospider
Alpha-keto-beta-methylvaleratebiospider
Alpha-keto-beta-methylvaleric acidbiospider
Alpha-oxo-beta-methyl-n-valeratebiospider
Alpha-oxo-beta-methyl-n-valeric acidbiospider
Alpha-oxo-beta-methylvaleratebiospider
Alpha-oxo-beta-methylvaleric acidbiospider
FEMA 3870db_source
Ketoisoleucinedb_source
α-keto-β-methyl-N-valerateGenerator
α-keto-β-methyl-N-valeric acidGenerator
α-keto-β-methylvalerateGenerator
α-keto-β-methylvaleric acidGenerator
α-oxo-β-methyl-N-valerateGenerator
α-oxo-β-methyl-N-valeric acidGenerator
α-oxo-β-methylvalerateGenerator
α-oxo-β-methylvaleric acidGenerator
Chemical FormulaC6H10O3
IUPAC name3-methyl-2-oxopentanoic acid
InChI IdentifierInChI=1S/C6H10O3/c1-3-4(2)5(7)6(8)9/h4H,3H2,1-2H3,(H,8,9)
InChI KeyJVQYSWDUAOAHFM-UHFFFAOYSA-N
Isomeric SMILESCCC(C)C(=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 PointNot Available
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 200 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 6099AL