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Record Information
Version1.0
Creation Date2016-09-30 22:19:07 UTC
Update Date2020-03-18 18:13:14 UTC
MCDB ID BMDB0000060
Secondary Accession Numbers
  • BMDB00060
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 NameNot Available
Traditional NameNot Available
CAS Registry Number541-50-4
SMILESNot Available
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 PropertiesNot Available
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 but not QuantifiedNot Applicable 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 ]