Record Information
Version1.0
Creation date2015-10-09 22:33:32 UTC
Update date2017-01-19 02:36:42 UTC
FoodComEx IDPC000946
FoodDB RecordFDB003362
Chemical Information
Name2-Oxohexanedioic acid
DescriptionOxoadipic acid, also known as 2-oxoadipate or a-ketoadipate, belongs to the class of organic compounds known as medium-chain keto acids and derivatives. These are keto acids with a 6 to 12 carbon atoms long side chain. Oxoadipic acid is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Oxoadipic acid exists in all living species, ranging from bacteria to humans. Within humans, oxoadipic acid participates in a number of enzymatic reactions. In particular, oxoadipic acid and L-glutamic acid can be biosynthesized from aminoadipic acid and oxoglutaric acid through its interaction with the enzyme kynurenine/alpha-aminoadipate aminotransferase, mitochondrial. In addition, oxoadipic acid can be converted into carbon dioxide through the action of the enzyme oxoglutarate dehydrogenase complex. In humans, oxoadipic acid is involved in the metabolic disorder called 2-aminoadipic 2-oxoadipic aciduria. Outside of the human body, Oxoadipic acid has been detected, but not quantified in, pulses. This could make oxoadipic acid a potential biomarker for the consumption of these foods. Oxoadipic acid is a potentially toxic compound. Oxoadipic acid, with regard to humans, has been linked to several inborn metabolic disorders including 2-aminoadipic aciduria, alpha-aminoadipic aciduria, and 2-ketoadipic acidemia. An oxo dicarboxylic acid that is adipic acid substituted by an oxo group at position 2.
CAS Number3184-35-8
Structure
Thumb
Synonyms
SynonymSource
2-keto-adipatebiospider
2-ketoadipatebiospider
2-Ketoadipic acidbiospider
2-Oxo-hexanedioatebiospider
2-Oxo-hexanedioic acidbiospider
2-oxoadipatebiospider
2-Oxoadipic aciddb_source
2-Oxohexanedioatebiospider
2-oxohexanedionic acidbiospider
2K-ADIPATEbiospider
A-ketoadipatebiospider
A-ketoadipic acidbiospider
A-oxoadipatebiospider
A-oxoadipic acidbiospider
Alpha-ketoadipatebiospider
Alpha-ketoadipic acidbiospider
Alpha-ketodipatebiospider
Alpha-oxoadipatebiospider
Alpha-oxoadipic acidbiospider
hexanedioic acid, 2-oxo-biospider
Hexanedioic acid, 2-oxo- (7CI,8CI,9CI)biospider
Oxoadipatebiospider
Chemical FormulaC6H8O5
IUPAC name2-oxohexanedioic acid
InChI IdentifierInChI=1S/C6H8O5/c7-4(6(10)11)2-1-3-5(8)9/h1-3H2,(H,8,9)(H,10,11)
InChI KeyFGSBNBBHOZHUBO-UHFFFAOYSA-N
Isomeric SMILESOC(=O)CCCC(=O)C(O)=O
Average Molecular Weight160.1247
Monoisotopic Molecular Weight160.037173366
Chemical Taxonomy
Description Belongs to the class of organic compounds known as medium-chain keto acids and derivatives. These are keto acids with a 6 to 12 carbon atoms long side chain.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassKeto acids and derivatives
Sub ClassMedium-chain keto acids and derivatives
Direct ParentMedium-chain keto acids and derivatives
Alternative Parents
Substituents
  • Medium-chain keto acid
  • Dicarboxylic acid or derivatives
  • Alpha-keto acid
  • Alpha-hydroxy ketone
  • Ketone
  • 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
PropertyValueReference
Experimental logPNot Available
Experimental Water SolubilityNot Available
Melting PointMp 127°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 10 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
MetaSci HMDB0000225
Sigma-Aldrich HMDB0000225