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Record Information
Version1.0
Creation Date2016-09-30 22:19:07 UTC
Update Date2019-02-05 20:35:44 UTC
MCDB ID BMDB00060
Secondary Accession NumbersNone
Metabolite Identification
Common NameAcetoacetic acid
DescriptionAcetoacetic acid, also known as 3-oxobutyrate or 3-oxobutanoic 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. Acetoacetic acid exists as a solid, very hydrophobic, practically insoluble (in water), and relatively neutral molecule. Acetoacetic acid exists in all living species, ranging from bacteria to humans. Acetoacetic acid is a potentially toxic compound. Acetoacetic acid has been found to be associated with several diseases known as ketoacidosis, irritable bowel syndrome, anoxia, and diabetes mellitus type 2; also acetoacetic acid has been linked to the inborn metabolic disorders including glucose transporter type 1 deficiency syndrome.
Structure
Thumb
Synonyms
ValueSource
3-Ketobutanoic acidChEBI
3-Ketobutyric acidChEBI
3-Oxobutanoic acidChEBI
3-Oxobutyric acidChEBI
beta-Ketobutyric acidChEBI
3-KetobutanoateGenerator
3-KetobutyrateGenerator
3-OxobutanoateGenerator
3-OxobutyrateGenerator
b-KetobutyrateGenerator
b-Ketobutyric acidGenerator
beta-KetobutyrateGenerator
Β-ketobutyrateGenerator
Β-ketobutyric acidGenerator
AcetoacetateGenerator
3-oxo-ButanoateHMDB
3-oxo-Butanoic acidHMDB
DiacetateHMDB
Diacetic acidHMDB
Acetoacetic acid, sodium saltHMDB
Acetoacetic acid, calcium saltHMDB
Acetoacetic acid, lithium saltHMDB
OxobutyrateHMDB
Sodium acetoacetateHMDB
Chemical FormulaC4H6O3
Average Molecular Weight102.0886
Monoisotopic Molecular Weight102.031694058
IUPAC Name3-oxobutanoic acid
Traditional Nameacetoacetic acid
CAS Registry Number541-50-4
SMILES
CC(=O)CC(O)=O
InChI Identifier
InChI=1S/C4H6O3/c1-3(5)2-4(6)7/h2H2,1H3,(H,6,7)
InChI KeyWDJHALXBUFZDSR-UHFFFAOYSA-N
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
  • Beta-keto acid
  • 1,3-dicarbonyl compound
  • Beta-hydroxy ketone
  • Ketone
  • Monocarboxylic acid or derivatives
  • 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
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point36.5 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility1000 mg/mL at 20 °CNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP-0.47ALOGPS
logP-0.0015ChemAxon
logS0.37ALOGPS
pKa (Strongest Acidic)4.02ChemAxon
pKa (Strongest Basic)-7.5ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area54.37 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity22.54 m³·mol⁻¹ChemAxon
Polarizability9.18 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)splash10-00kk-3940000000-008eb78d2ba3cfa053b4JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-MS (1 MEOX; 1 TMS)splash10-000i-9500000000-c3940e591f8aef9d6aacJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-MS (1 MEOX; 1 TMS)splash10-000i-9800000000-67a95675672c3f5447a7JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-MS (2 TMS)splash10-001i-4950000000-1778836b3908a79b814fJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-MS (2 TMS)splash10-001i-4950000000-4039bb48c98ec17b5c0cJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00kk-3940000000-008eb78d2ba3cfa053b4JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-000i-9500000000-c3940e591f8aef9d6aacJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-000i-9800000000-67a95675672c3f5447a7JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-001i-4950000000-1778836b3908a79b814fJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-001i-4950000000-4039bb48c98ec17b5c0cJSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-9000000000-9f6c0d100736f4d183c9JSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-0100-9600000000-470bf0676151478bca3eJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, N/A (Annotated)splash10-000i-9200000000-9b4ab7b6a41632cb125bJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, N/A (Annotated)splash10-0udi-6900000000-cfab9d4cdb56acafe8ccJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, N/A (Annotated)splash10-0pb9-9800000000-108aa5ef93455fb1ba28JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-000i-9100000000-869e2338bbadb32272d4JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0f79-9400000000-081c4a1a05f5581a5ffbJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000l-9100000000-960a06fd90db43d3e0f6JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9000000000-bd091454ccc8f532b42eJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0zfr-9700000000-b01f47bb6cd4f1043983JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-9100000000-d2649829e8a79045e73bJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9000000000-1486ce68d51ba83ed499JSpectraViewer | MoNA
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableJSpectraViewer
Concentrations
StatusValueReferenceDetails
Detected and Quantified40 +/- 2 uM details
Detected and Quantified4 - 14 uM details
HMDB IDHMDB0000060
DrugBank IDDB01762
Phenol Explorer Compound IDNot Available
FoodDB IDFDB021801
KNApSAcK IDC00007458
Chemspider ID94
KEGG Compound IDC00164
BioCyc ID3-KETOBUTYRATE
BiGG ID1485291
Wikipedia LinkAcetoacetic_acid
METLIN ID276
PubChem Compound96
PDB IDNot Available
ChEBI ID15344
References
Synthesis ReferenceLopez-Soriano, F. J.; Argiles, J. M. A simple method for the preparation of acetoacetate. Analytical Letters (1985), 18(B5), 589-92.
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Enjalbert F, Nicot MC, Bayourthe C, Moncoulon R: Ketone bodies in milk and blood of dairy cows: relationship between concentrations and utilization for detection of subclinical ketosis. J Dairy Sci. 2001 Mar;84(3):583-9. doi: 10.3168/jds.S0022-0302(01)74511-0. [PubMed:11286410 ]
  2. Klein MS, Buttchereit N, Miemczyk SP, Immervoll AK, Louis C, Wiedemann S, Junge W, Thaller G, Oefner PJ, Gronwald W: NMR metabolomic analysis of dairy cows reveals milk glycerophosphocholine to phosphocholine ratio as prognostic biomarker for risk of ketosis. J Proteome Res. 2012 Feb 3;11(2):1373-81. doi: 10.1021/pr201017n. Epub 2011 Dec 9. [PubMed:22098372 ]
  3. Lu J, Antunes Fernandes E, Paez Cano AE, Vinitwatanakhun J, Boeren S, van Hooijdonk T, van Knegsel A, Vervoort J, Hettinga KA: Changes in milk proteome and metabolome associated with dry period length, energy balance, and lactation stage in postparturient dairy cows. J Proteome Res. 2013 Jul 5;12(7):3288-96. doi: 10.1021/pr4001306. Epub 2013 Jun 5. [PubMed:23738862 ]
  4. Antunes-Fernandes EC, van Gastelen S, Dijkstra J, Hettinga KA, Vervoort J: Milk metabolome relates enteric methane emission to milk synthesis and energy metabolism pathways. J Dairy Sci. 2016 Aug;99(8):6251-6262. doi: 10.3168/jds.2015-10248. Epub 2016 May 26. [PubMed:27236769 ]