| Common Name |
Methylacetoacetic acid
| Description |
Methylacetoacetic 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 |
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
| Synonyms |
| Value |
Source |
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 Formlia |
C5H8O3
| Average Molecliar Weight |
116.1152
| Monoisotopic Molecliar Weight |
116.047344122
| IUPAC Name |
methyl 3-oxobutanoate
| Traditional Name |
methyl acetoacetate
| CAS Registry Number |
105-45-3
| SMILES |
COC(=O)CC(C)=O
| InChI Identifier |
InChI=1S/C5H8O3/c1-4(6)3-5(7)8-2/h3H2,1-2H3
| InChI Key |
WRQNANDWMGAFTP-UHFFFAOYSA-N
| Chemical Taxonomy |
| Description |
This compound belongs to the class of chemical entities known as beta-keto acids and derivatives. These are organic compounds containing an aldehyde substituted with a keto group on the C3 carbon atom.
| Kingdom |
Chemical entities
| Super Class |
Organic compounds
| Class |
Organic acids and derivatives
| Sub Class |
Keto acids and derivatives
| Direct Parent |
Beta-keto acids and derivatives
| Alternative Parents |
Fatty acid methyl esters
1,3-dicarbonyl compounds
Methyl esters
Ketones
Monocarboxylic acids and derivatives
Organic oxides
Hydrocarbon derivatives
| 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
| Molecliar Framework |
Aliphatic acyclic compounds
| External Descriptors |
Not Available
| Ontology |
| Status |
Expected but not Quantified
| Origin |
Endogenous
| Biofunction |
Not Available
| Application |
Not Available
| Cellliar locations |
Not Available
| Physical Properties |
| State |
Liquid
| Experimental Properties |
| Property |
Value |
Reference |
Melting Point-80 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility500.0 mg/mLNot Available
LogPNot AvailableNot Available
| Predicted Properties |
| Property |
Value |
Source |
Water Solubility137.0 mg/mLALOGPS
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 Å2ChemAxon
Rotatable Bond Count3ChemAxon
Refractivity27.31 m3·mol-1ChemAxon
Polarizability11.27 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rlie of FiveYesChemAxon
Ghose FilterYesChemAxon
Vebers RlieYesChemAxon
MDDR-like RlieYesChemAxon
| Spectra |
| Spectra |
| Spectrum Type |
Description |
Splash Key |
|
| LC-MS/MS |
LC-MS/MS Spectrum – Quattro_QQQ 10V, N/A (Annotated)splash10-000l-9100000000-be1b334229aa020fc7e8View in MoNA
| LC-MS/MS |
LC-MS/MS Spectrum – Quattro_QQQ 25V, N/A (Annotated)splash10-0006-9000000000-e512bbad2ab7f1c253a7View in MoNA
| LC-MS/MS |
LC-MS/MS Spectrum – Quattro_QQQ 40V, N/A (Annotated)splash10-0006-9000000000-0627dffba19580aa6a7dView in MoNA
| LC-MS/MS |
LC-MS/MS Spectrum – EI-B (HITACHI RMU-7M) , Positivesplash10-0006-9000000000-6f423389be91a0d883a2View in MoNA
| LC-MS/MS |
LC-MS/MS Spectrum – EI-B (HITACHI RMU-6M) , Positivesplash10-0006-9000000000-e4481e7d9e6ac8fc177bView in MoNA
| LC-MS/MS |
LC-MS/MS Spectrum – EI-B (JEOL JMS-D-3000) , Positivesplash10-0006-9000000000-970f150ada556d232464View in MoNA
| LC-MS/MS |
LC-MS/MS Spectrum – EI-B (HITACHI RMU-6M) , Positivesplash10-0006-9100000000-86a6dd485ea6cf9b0632View in MoNA
| LC-MS/MS |
LC-MS/MS Spectrum – CI-B (HITACHI M-80) , Positivesplash10-00kr-9300000000-0d967b807194a0d4f189View in MoNA
| 1D NMR |
1H NMR SpectrumNot Available
| 2D NMR |
[1H,13C] 2D NMR SpectrumNot Available
| Biological Properties |
| Cellliar Locations |
Not Available
| Biofluid Locations |
Not Available
| Tissue Location |
Not Available
| Pathways |
Not Available
| Normal Concentrations |
| Not Available |
| Abnormal Concentrations |
|
Not Available
| Associated Disorders and Diseases |
| Disease References |
None
| Associated OMIM IDs |
None
| External Links |
| DrugBank ID |
Not Available
| DrugBank Metabolite ID |
Not Available
| Phenol Explorer Compound ID |
Not Available
| Phenol Explorer Metabolite ID |
Not Available
| FoodDB ID |
FDB021937
| KNApSAcK ID |
Not Available
| Chemspider ID |
13874867
| KEGG Compound ID |
Not Available
| BioCyc ID |
Not Available
| BiGG ID |
Not Available
| Wikipedia Link |
Not Available
| NuGOwiki Link |
HMDB00310
| Metagene Link |
HMDB00310
| METLIN ID |
5299
| PubChem Compound |
7757
| PDB ID |
Not Available
| ChEBI ID |
Not Available
Product: BAY1125976
References |
| Synthesis Reference |
Chan, 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 |
- 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 ]
- 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 ]
- 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 ]
|
PMID: 24624468