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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2017-12-07 01:16:02 UTC
HMDB IDHMDB0000310
Secondary Accession Numbers
  • HMDB00310
Metabolite Identification
Common NameMethylacetoacetic acid
DescriptionMethylacetoacetic acid has been identified in the urine of patients with an inherited deficiency of propionyl-CoA carboxylase (PMID 630060 ), and after isoleucine loading in the diagnosis of 2-methylacetoacetyl-CoA thiolase deficiency. (PMID 1861461 ).
Structure
Thumb
Synonyms
ValueSource
1-Methoxybutane-1,3-dioneHMDB
3-oxo-ButanoateHMDB
3-oxo-Butanoic acidHMDB
3-oxo-Butanoic acid methyl esterHMDB
3-OxobutanoateHMDB
3-Oxobutanoic acidHMDB
3-Oxobutanoic acid methyl esterHMDB
3-Oxobutyric acid methyl esterHMDB
Acetoacetate methyl esterHMDB
Acetoacetic acid methyl esterHMDB
Acetoacetic methyl esterHMDB
Methyl 3-oxobutanoateHMDB
Methyl 3-oxobutanoic acidHMDB
Methyl 3-oxobutyrateHMDB
Methyl acetoacetateHMDB
Methyl acetylacetateHMDB
Methyl acetylacetonateHMDB
Chemical FormulaC5H8O3
Average Molecular Weight116.1152
Monoisotopic Molecular Weight116.047344122
IUPAC Namemethyl 3-oxobutanoate
Traditional Namemethyl acetoacetate
CAS Registry Number105-45-3
SMILES
COC(=O)CC(C)=O
InChI Identifier
InChI=1S/C5H8O3/c1-4(6)3-5(7)8-2/h3H2,1-2H3
InChI KeyWRQNANDWMGAFTP-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as beta-keto acids and derivatives. These are organic compounds containing an aldehyde substituted with a keto group on the C3 carbon atom.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassKeto acids and derivatives
Sub ClassBeta-keto acids and derivatives
Direct ParentBeta-keto acids and derivatives
Alternative Parents
Substituents
  • Beta-keto acid
  • Fatty acid ester
  • Fatty acid methyl ester
  • 1,3-dicarbonyl compound
  • Fatty acyl
  • Methyl ester
  • Carboxylic acid ester
  • Ketone
  • Monocarboxylic acid or derivatives
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Carbonyl group
  • Organooxygen compound
  • Hydrocarbon derivative
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Source:

Physical Properties
StateLiquid
Experimental Properties
PropertyValueReference
Melting Point-80 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility500 mg/mLNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility137 g/LALOGPS
logP-0.29ALOGPS
logP0.14ChemAxon
logS0.07ALOGPS
pKa (Strongest Acidic)10.28ChemAxon
pKa (Strongest Basic)-7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area43.37 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity27.31 m³·mol⁻¹ChemAxon
Polarizability11.27 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0006-9000000000-9801f4fde1f8c64f6bafView in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0006-9000000000-e4481e7d9e6ac8fc177bView in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0006-9000000000-f8789e71041e62cce331View in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0006-9100000000-65b70a114483f92cc1f4View in MoNA
GC-MSGC-MS Spectrum - CI-B (Non-derivatized)splash10-00kr-9300000000-7a638e147c3997a85598View in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0006-9000000000-9801f4fde1f8c64f6bafView in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0006-9000000000-e4481e7d9e6ac8fc177bView in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0006-9000000000-f8789e71041e62cce331View in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0006-9100000000-65b70a114483f92cc1f4View in MoNA
GC-MSGC-MS Spectrum - CI-B (Non-derivatized)splash10-00kr-9300000000-7a638e147c3997a85598View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-9100000000-869c1574ff891034b665View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, N/A (Annotated)splash10-000l-9100000000-be1b334229aa020fc7e8View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, N/A (Annotated)splash10-0006-9000000000-e512bbad2ab7f1c253a7View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, N/A (Annotated)splash10-0006-9000000000-0627dffba19580aa6a7dView in MoNA
LC-MS/MSLC-MS/MS Spectrum - EI-B (HITACHI RMU-7M) , Positivesplash10-0006-9000000000-6f423389be91a0d883a2View in MoNA
LC-MS/MSLC-MS/MS Spectrum - EI-B (HITACHI RMU-6M) , Positivesplash10-0006-9000000000-e4481e7d9e6ac8fc177bView in MoNA
LC-MS/MSLC-MS/MS Spectrum - EI-B (JEOL JMS-D-3000) , Positivesplash10-0006-9000000000-970f150ada556d232464View in MoNA
LC-MS/MSLC-MS/MS Spectrum - EI-B (HITACHI RMU-6M) , Positivesplash10-0006-9100000000-86a6dd485ea6cf9b0632View in MoNA
LC-MS/MSLC-MS/MS Spectrum - CI-B (HITACHI M-80) , Positivesplash10-00kr-9300000000-0d967b807194a0d4f189View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014r-9300000000-e5dc637782adee6c0e04View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014j-9100000000-3bc03bc80fc348b48f88View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-014u-9000000000-ed2c64d5d7629d00368eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-8900000000-26833f2c7b71af9eed1fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0aw9-9200000000-d2941bafc6ef6d37ea38View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a59-9000000000-765079c1255f5f8b2907View in MoNA
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableView in JSpectraViewer
Biological Properties
Cellular LocationsNot Available
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB021937
KNApSAcK IDNot Available
Chemspider ID13874867
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN ID5299
PubChem Compound7757
PDB IDNot Available
ChEBI IDNot Available
References
Synthesis ReferenceChan, Tak-Hang; Brownbridge, Peter. Reaction of electrophiles with 1,3-bis(trimethylsiloxy)-1-methoxybuta-1,3-diene, a dianion equivalent of methyl acetoacetate. Journal of the Chemical Society, Chemical Communications (1979), (13), 578-9.
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Robinson BH, Sherwood WG, Taylor J, Balfe JW, Mamer OA: Acetoacetyl CoA thiolase deficiency: a cause of severe ketoacidosis in infancy simulating salicylism. J Pediatr. 1979 Aug;95(2):228-33. [PubMed:36452 ]
  2. Aramaki S, Lehotay D, Sweetman L, Nyhan WL, Winter SC, Middleton B: Urinary excretion of 2-methylacetoacetate, 2-methyl-3-hydroxybutyrate and tiglylglycine after isoleucine loading in the diagnosis of 2-methylacetoacetyl-CoA thiolase deficiency. J Inherit Metab Dis. 1991;14(1):63-74. [PubMed:1861461 ]
  3. Sweetman L, Weyler W, Nyhan WL, de Cespedes C, Loria AR, Estrada Y: Abnormal metabolites of isoleucine in a patient with propionyl-CoA carboxylase deficiency. Biomed Mass Spectrom. 1978 Mar;5(3):198-207. [PubMed:630060 ]