Back to Compounds

3-Oxobutanoic acid, 9CI (PC000544)

Record Information
Version1.0
Creation date2015-10-09 22:31:17 UTC
Update date2017-01-19 02:36:27 UTC
FoodComEx IDPC000544
FoodDB RecordFDB021801
Chemical Information
Name3-Oxobutanoic acid, 9CI
DescriptionIt is a weak organic acid and can be produced in the human liver under certain conditions of poor metabolism leading to excessive fatty acid breakdown (diabetes mellitus leading to diabetic ketoacidosis), it is then partially converted to acetone by decarboxylation and excreted either in urine or through respiration. Persistent mild hyperketonemia is a common finding in newborns. These compounds serve as an indispensable source of energy for extrahepatic tissues, especially the brain and lung of developing rats. Another important function of ketone bodies is to provide acetoacetyl-CoA and acetyl-CoA for synthesis of cholesterol, fatty acids, and complex lipids. During the early postnatal period, acetoacetate (AcAc) and beta-hydroxybutyrate are preferred over glucose as substrates for synthesis of phospholipids and sphingolipids in accord with requirements for brain growth and myelination. Thus, during the first 2 wk of postnatal development, when the accumulation of cholesterol and phospholipids accelerates, the proportion of ketone bodies incorporated into these lipids increases. On the other hand, an increased proportion of ketone bodies are utilized for cerebroside synthesis during the period of active myelination. In the lung, AcAc serves better than glucose as a precursor for the synthesis of lung phospholipids. The synthesized lipids, particularly dipalmityl phosphatidylcholine, are incorporated into surfactant, and thus have a potential role in supplying adequate surfactant lipids to maintain lung function during the early days of life. (PMID 3884391) The acid is also present in the metabolism of those undergoing starvation or prolonged physical exertion as part of gluconeogenesis. When ketone bodies are measured by way of urine concentration, acetoacetic acid, along with beta-hydroxybutyric acid or acetone, is what is detected. [HMDB]
CAS Number541-50-4
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
3-KetobutanoateGenerator
3-Ketobutanoic acidChEBI
3-KetobutyrateGenerator
3-Ketobutyric acidChEBI
3-OxobutyrateGenerator
3-Oxobutyric acidChEBI
AcetoacetateGenerator
Acetoacetic aciddb_source
Acetonecarboxylic aciddb_source
Acetylacetic aciddb_source
b-KetobutyrateGenerator
b-Ketobutyric acidGenerator
beta-KetobutyrateGenerator
beta-Ketobutyric acidChEBI
DiacetateHMDB
Diacetic aciddb_source
β-ketobutyrateGenerator
β-ketobutyric acidGenerator
Chemical FormulaC8H12O6
IUPAC name(2E)-3-hydroxybut-2-enoic acid; 3-oxobutanoic acid
InChI IdentifierInChI=1S/2C4H6O3/c2*1-3(5)2-4(6)7/h2H2,1H3,(H,6,7);2,5H,1H3,(H,6,7)/b;3-2+
InChI KeyUNNIHLXYGZEWRE-ZPYUXNTASA-N
Isomeric SMILESCC(=O)CC(O)=O.C\C(O)=C/C(O)=O
Average Molecular Weight204.1773
Monoisotopic Molecular Weight204.063388116
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
  • Short-chain keto acid
  • Hydroxy fatty acid
  • Beta-keto acid
  • Fatty acyl
  • Fatty acid
  • 1,3-dicarbonyl compound
  • Unsaturated fatty acid
  • Beta-hydroxy ketone
  • Vinylogous acid
  • Ketone
  • Monocarboxylic acid or derivatives
  • Enol
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic acyclic compound
Molecular FrameworkNot Available
External DescriptorsNot Available
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 60 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
Not Available