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Acetoacetic acid (FDB112157)

Record Information
Version1.0
Creation date2020-04-20 17:18:07 UTC
Update date2024-11-29 22:28:01 UTC
Primary IDFDB112157
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameAcetoacetic acid
DescriptionAcetoacetic acid, also known as 3-oxobutanoic acid or 3-oxobutyrate, 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 is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Acetoacetic acid exists in all living species, ranging from bacteria to humans. Acetoacetic acid is a potentially toxic compound. A 3-oxo monocarboxylic acid that is butyric acid bearing a 3-oxo substituent. Acetoacetic acid, with regard to humans, has been found to be associated with several diseases such as late-onset preeclampsia, crohn's disease, and schizophrenia; acetoacetic acid has also been linked to several inborn metabolic disorders including 2-ketoglutarate dehydrogenase complex deficiency and glucose transporter type 1 deficiency syndrome.
CAS NumberNot Available
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
SynonymSource
Not AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility240 g/LALOGPS
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
Chemical FormulaC4H6O3
IUPAC name3-oxobutanoic acid
InChI IdentifierInChI=1S/C4H6O3/c1-3(5)2-4(6)7/h2H2,1H3,(H,6,7)
InChI KeyWDJHALXBUFZDSR-UHFFFAOYSA-N
Isomeric SMILESCC(=O)CC(O)=O
Average Molecular Weight102.0886
Monoisotopic Molecular Weight102.031694058
Classification
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
OntologyNo ontology term
Physico-Chemical Properties
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionNot Available
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
GC-MSAcetoacetic acid, non-derivatized, GC-MS Spectrumsplash10-00kk-3940000000-008eb78d2ba3cfa053b4Spectrum
GC-MSAcetoacetic acid, 1 MEOX; 1 TMS, GC-MS Spectrumsplash10-000i-9500000000-c3940e591f8aef9d6aacSpectrum
GC-MSAcetoacetic acid, 1 MEOX; 1 TMS, GC-MS Spectrumsplash10-000i-9800000000-67a95675672c3f5447a7Spectrum
GC-MSAcetoacetic acid, 2 TMS, GC-MS Spectrumsplash10-001i-4950000000-1778836b3908a79b814fSpectrum
GC-MSAcetoacetic acid, 2 TMS, GC-MS Spectrumsplash10-001i-4950000000-4039bb48c98ec17b5c0cSpectrum
GC-MSAcetoacetic acid, non-derivatized, GC-MS Spectrumsplash10-00kk-3940000000-008eb78d2ba3cfa053b4Spectrum
GC-MSAcetoacetic acid, non-derivatized, GC-MS Spectrumsplash10-000i-9500000000-c3940e591f8aef9d6aacSpectrum
GC-MSAcetoacetic acid, non-derivatized, GC-MS Spectrumsplash10-000i-9800000000-67a95675672c3f5447a7Spectrum
GC-MSAcetoacetic acid, non-derivatized, GC-MS Spectrumsplash10-001i-4950000000-1778836b3908a79b814fSpectrum
GC-MSAcetoacetic acid, non-derivatized, GC-MS Spectrumsplash10-001i-4950000000-4039bb48c98ec17b5c0cSpectrum
Predicted GC-MSAcetoacetic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0006-9000000000-9f6c0d100736f4d183c9Spectrum
Predicted GC-MSAcetoacetic acid, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0100-9600000000-470bf0676151478bca3eSpectrum
Predicted GC-MSAcetoacetic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSAcetoacetic acid, TMS_1_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSAcetoacetic acid, TMS_1_3, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSAcetoacetic acid, TBDMS_1_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSAcetoacetic acid, TBDMS_1_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSAcetoacetic acid, TBDMS_1_3, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, N/A (Annotated)splash10-000i-9200000000-9b4ab7b6a41632cb125b2012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, N/A (Annotated)splash10-0udi-6900000000-cfab9d4cdb56acafe8cc2012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, N/A (Annotated)splash10-0pb9-9800000000-108aa5ef93455fb1ba282012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - , positivesplash10-000i-9100000000-869e2338bbadb32272d42017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - n/a 7V, negativesplash10-0a4i-9000000000-3f979a5a82ec557199d22020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - 20V, Negativesplash10-000f-9000000000-2b35e5493fb76f714c222021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 10V, Negativesplash10-05fr-9000000000-d2734268ae2c1230e50f2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 40V, Negativesplash10-00di-9000000000-0d73b25163774c0d1eb12021-09-20View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0f79-9400000000-081c4a1a05f5581a5ffb2016-09-14View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000l-9100000000-960a06fd90db43d3e0f62016-09-14View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9000000000-bd091454ccc8f532b42e2016-09-14View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0zfr-9700000000-b01f47bb6cd4f10439832016-09-14View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-9100000000-d2649829e8a79045e73b2016-09-14View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9000000000-1486ce68d51ba83ed4992016-09-14View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0pb9-9400000000-2f187d15e3b22b7629d92021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-9100000000-1e5e193606848f9d64b42021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4l-9000000000-73a6b61cfeb4b8ae96122021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-9000000000-de86214ccec455e1860b2021-09-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0006-9000000000-42af30a03d7e2d4c22fc2021-09-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9000000000-6aa1f4078505fa3b09712021-09-25View Spectrum
NMR
TypeDescriptionView
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, experimental)Spectrum
1D NMR13C NMR Spectrum (1D, 125 MHz, H2O, experimental)Spectrum
1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 400 MHz, H2O, experimental)Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)Spectrum
ChemSpider IDNot Available
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound IDNot Available
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDNot Available
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
EnzymesNot Available
Pathways
NameSMPDB LinkKEGG Link
Metabolism and Physiological Effects of β-Hydroxybutyric acidSMP0126987 Not Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference