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Record Information
Version1.0
Creation Date2016-07-13 19:40:45 UTC
Update Date2021-04-30 20:57:57 UTC
LmdbLMDB00026
Secondary Accession NumbersNone
Metabolite Identification
Common NameAcetoacetic acid
DescriptionIt is a weak organic acid and can be produced in the animal 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.
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
Acetoacetic acid, calcium saltMeSH
Acetoacetic acid, lithium saltMeSH
Acetoacetic acid, sodium saltMeSH
OxobutyrateMeSH
Sodium acetoacetateMeSH
3-oxo-ButanoateHMDB
3-oxo-Butanoic acidHMDB
DiacetateHMDB
Diacetic acidHMDB
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
Ontology
StatusDetected and Quantified
OriginNot Available
BiofunctionNot Available
ApplicationNot Available
Cellular locationsNot Available
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot 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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
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-3940000000-008eb78d2ba3cfa053b4Spectrum
GC-MSGC-MS Spectrum - GC-MS (1 MEOX; 1 TMS)splash10-000i-9500000000-c3940e591f8aef9d6aacSpectrum
GC-MSGC-MS Spectrum - GC-MS (1 MEOX; 1 TMS)splash10-000i-9800000000-67a95675672c3f5447a7Spectrum
GC-MSGC-MS Spectrum - GC-MS (2 TMS)splash10-001i-4950000000-1778836b3908a79b814fSpectrum
GC-MSGC-MS Spectrum - GC-MS (2 TMS)splash10-001i-4950000000-4039bb48c98ec17b5c0cSpectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00kk-3940000000-008eb78d2ba3cfa053b4Spectrum
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-000i-9500000000-c3940e591f8aef9d6aacSpectrum
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-000i-9800000000-67a95675672c3f5447a7Spectrum
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-001i-4950000000-1778836b3908a79b814fSpectrum
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-001i-4950000000-4039bb48c98ec17b5c0cSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-9000000000-9f6c0d100736f4d183c9Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-0100-9600000000-470bf0676151478bca3eSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, N/A (Annotated)splash10-000i-9200000000-9b4ab7b6a41632cb125bSpectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, N/A (Annotated)splash10-0udi-6900000000-cfab9d4cdb56acafe8ccSpectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, N/A (Annotated)splash10-0pb9-9800000000-108aa5ef93455fb1ba28Spectrum
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-000i-9100000000-869e2338bbadb32272d4Spectrum
LC-MS/MSLC-MS/MS Spectrum - n/a 7V, negativesplash10-0a4i-9000000000-3f979a5a82ec557199d2Spectrum
LC-MS/MSLC-MS/MS Spectrum - 20V, Negativesplash10-000f-9000000000-2b35e5493fb76f714c22Spectrum
LC-MS/MSLC-MS/MS Spectrum - 10V, Negativesplash10-05fr-9000000000-d2734268ae2c1230e50fSpectrum
LC-MS/MSLC-MS/MS Spectrum - 40V, Negativesplash10-00di-9000000000-0d73b25163774c0d1eb1Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0f79-9400000000-081c4a1a05f5581a5ffbSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000l-9100000000-960a06fd90db43d3e0f6Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9000000000-bd091454ccc8f532b42eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0zfr-9700000000-b01f47bb6cd4f1043983Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-9100000000-d2649829e8a79045e73bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9000000000-1486ce68d51ba83ed499Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0pb9-9400000000-2f187d15e3b22b7629d9Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-9100000000-1e5e193606848f9d64b4Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4l-9000000000-73a6b61cfeb4b8ae9612Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-9000000000-de86214ccec455e1860bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0006-9000000000-42af30a03d7e2d4c22fcSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9000000000-6aa1f4078505fa3b0971Spectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableSpectrum
Biological Properties
Cellular LocationsNot Available
Biofluid Locations and Tissue Locations
  • Milk
  • Plasma
  • Ruminal Fluid
  • Serum
  • Urine
Concentrations
BiofluidStatusValueConditionSpeciesReferenceDetails
MilkDetected and Quantified4-14 uMNot AvailableBovine details
MilkDetected but not QuantifiedNot ApplicableNot AvailableBovine details
PlasmaDetected but not QuantifiedNot ApplicableNot AvailableBovine
    • Trabi M, Keller M...
details
PlasmaDetected but not QuantifiedNot ApplicableNot AvailableEquine
    • E. E. Escalona, J...
details
PlasmaDetected but not QuantifiedNot ApplicableNot AvailableBovine details
PlasmaDetected but not QuantifiedNot ApplicableNot AvailableBovine details
PlasmaDetected but not QuantifiedNot ApplicableNot AvailableBovine details
PlasmaDetected but not QuantifiedNot ApplicableNot AvailableBovine details
PlasmaDetected but not QuantifiedNot ApplicableNot AvailableEquine details
Ruminal FluidDetected and Quantified141 +/- 16 uMNot AvailableBovine details
Ruminal FluidDetected and Quantified70.8 +/- 6.9 uMNot AvailableBovine details
Ruminal FluidDetected and Quantified84.7 +/- 17 uMNot AvailableBovine details
Ruminal FluidDetected and Quantified564 +/- 56 uMNot AvailableCaprine details
Ruminal FluidDetected and Quantified48 +/- 17 uMNot AvailableBovine
    • Saleem F, Bouatra...
details
Ruminal FluidDetected and Quantified64 +/- 9 uMNot AvailableBovine
    • Saleem F, Bouatra...
details
Ruminal FluidDetected and Quantified68 +/- 9 uMNot AvailableBovine
    • Saleem F, Bouatra...
details
Ruminal FluidDetected and Quantified68 +/- 9 uMNot AvailableBovine
    • Saleem F, Bouatra...
details
Ruminal FluidDetected and Quantified78 +/- 15 uMNot AvailableBovine
    • Saleem F, Bouatra...
details
Ruminal FluidDetected and Quantified80 +/- 27 uMNot AvailableBovine
    • Saleem F, Bouatra...
details
Ruminal FluidDetected and Quantified64.1 uMNot AvailableBovine details
Ruminal FluidDetected and Quantified67.7 uMNot AvailableBovine details
Ruminal FluidDetected and Quantified77.9 uMNot AvailableBovine details
Ruminal FluidDetected and Quantified80.1 uMNot AvailableBovine details
Ruminal FluidDetected and Quantified47.1 uMNot AvailableBovine
    • Burim NA, Qendrim...
details
Ruminal FluidDetected and Quantified49.5 uMNot AvailableBovine
    • Burim NA, Qendrim...
details
Ruminal FluidDetected and Quantified54.1 uMNot AvailableBovine
    • Burim NA, Qendrim...
details
Ruminal FluidDetected and Quantified58 uMNot AvailableBovine
    • Burim NA, Qendrim...
details
SerumDetected and Quantified8.2206 +/- 3.004 uM
Normal
Ovine
    • Goldansaz et al.,...
details
SerumDetected and Quantified25.3298 +/- 15.9583 uM
Normal
Ovine
    • Goldansaz et al.,...
details
SerumDetected and Quantified36.3285 +/- 24.6503 uM
Normal
Ovine
    • Goldansaz et al.,...
details
SerumDetected and Quantified26.234 +/- 8.0583 uM
Normal
Ovine
    • Goldansaz et al.,...
details
SerumDetected and Quantified9.7659 +/- 4.9385 uM
Normal
Ovine
    • Goldansaz et al.,...
details
SerumDetected and Quantified7.67 +/- 3.09 uMNot AvailableOvine
    • Candidate serum m...
details
SerumDetected and Quantified25.0263 +/- 16.204 uM
Normal
Ovine
    • Goldansaz et al.,...
details
SerumDetected and Quantified20.0924 +/- 10.9962 uM
Normal
Ovine
    • Goldansaz et al.,...
details
SerumDetected and Quantified8.6432 +/- 2.9246 uM
Normal
Ovine
    • Goldansaz et al.,...
details
SerumDetected and Quantified18.5897 +/- 7.8661 uM
Normal
Ovine
    • Goldansaz et al.,...
details
SerumDetected and Quantified21.2791 +/- 13.185 uM
Normal
Ovine
    • Goldansaz et al.,...
details
SerumDetected and Quantified16.4646 +/- 3.7582 uM
Normal
Ovine
    • Goldansaz et al.,...
details
SerumDetected but not QuantifiedNot ApplicableNot AvailablePorcine details
SerumDetected but not QuantifiedNot ApplicableNot AvailableBovine details
SerumDetected but not QuantifiedNot ApplicableNot AvailableOvine details
SerumDetected and Quantified20.118 +/- 12.8336 uM
Normal
Ovine
    • Goldansaz et al.,...
details
SerumDetected and Quantified17.5074 +/- 10.0979 uM
Normal
Ovine
    • Goldansaz et al.,...
details
SerumDetected and Quantified48.1205 +/- 35.1489 uM
Normal
Ovine
    • Goldansaz et al.,...
details
SerumDetected and Quantified18.4463 +/- 4.8879 uM
Normal
Ovine
    • Goldansaz et al.,...
details
SerumDetected and Quantified9.2041 +/- 3.6766 uM
Normal
Ovine
    • Goldansaz et al.,...
details
SerumDetected and Quantified24.6698 +/- 18.0621 uM
Normal
Ovine
    • Goldansaz et al.,...
details
SerumDetected and Quantified18.055 +/- 8.1151 uM
Normal
Ovine
    • Goldansaz et al.,...
details
SerumDetected and Quantified47.4244 +/- 29.1011 uM
Normal
Ovine
    • Goldansaz et al.,...
details
SerumDetected and Quantified15.5044 +/- 5.2136 uM
Normal
Ovine
    • Goldansaz et al.,...
details
UrineDetected but not QuantifiedNot ApplicableNot AvailablePorcine
    • Federica Murgia, ...
details
UrineDetected but not QuantifiedNot ApplicableNot AvailableEquine
    • E. E. Escalona, J...
details
UrineDetected but not QuantifiedNot ApplicableNot AvailablePorcine details
UrineDetected but not QuantifiedNot ApplicableNot AvailableOvine details
UrineDetected but not QuantifiedNot ApplicableNot AvailableOvine details
DrugBank IDDB01762
HMDB IDHMDB0000060
FooDB IDFDB112157
Phenol Explorer IDNot Available
KNApSAcK IDC00007458
BiGG IDNot Available
BioCyc ID3-KETOBUTYRATE
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkAcetoacetic_acid
Chemspider ID94
ChEBI ID15344
PubChem Compound ID96
Kegg Compound IDC00164
YMDB IDYMDB16111
ECMDB IDECMDB00060
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Yeh YY, Sheehan PM: Preferential utilization of ketone bodies in the brain and lung of newborn rats. Fed Proc. 1985 Apr;44(7):2352-8. [3884391 ]