Ethyl-2-methylacetoacetate (ECMDB20553) (M2MDB001358)

IdentificationTaxonomyPhysical PropertiesBiological PropertiesSpectraConcentrationsLinksReferencesEnzymes (1)XML
Proteins (1)
Record Information
Version2.0
Creation Date2012-05-31 14:50:19 -0600
Update Date2015-06-03 17:20:17 -0600
Secondary Accession Numbers
  • ECMDB20553
Identification
Name:Ethyl-2-methylacetoacetate
DescriptionEthyl-2-methylacetoacetate belongs to the class of Fatty Acid Esters. These are carboxylic ester derivatives of a fatty acid. (inferred from compound structure)
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms:
  • 2-Methylacetoacetate ethyl ester
  • 2-Methylacetoacetic acid ethyl ester
  • Acetoacetate, 2-methyl-, ethyl ester
  • Acetoacetic acid, 2-methyl-, ethyl ester
  • Butanoate, 2-methyl-3-oxo-, ethyl ester
  • Butanoic acid, 2-methyl-3-oxo-, ethyl ester
  • Ethyl 2-acetylpropionate
  • Ethyl 2-acetylpropionic acid
  • Ethyl 2-methyl-3-oxobutanoate
  • Ethyl 2-methyl-3-oxobutanoic acid
  • Ethyl 2-methyl-3-oxobutyrate
  • Ethyl 2-methyl-3-oxobutyric acid
  • Ethyl 2-methylacetoacetate
  • Ethyl 2-methylacetoacetic acid
  • Ethyl ester of 2-methyl-3-oxobutanoate
  • Ethyl ester of 2-methyl-3-oxobutanoic acid
  • Ethyl methylacetoacetate
  • Ethyl methylacetoacetic acid
  • Ethyl-2-methylacetoacetic acid
Chemical Formula:C7H12O3
Weight:Average: 144.1684
Monoisotopic: 144.07864425
InChI Key:FNENWZWNOPCZGK-RXMQYKEDSA-N
InChI:InChI=1S/C7H12O3/c1-4-10-7(9)5(2)6(3)8/h5H,4H2,1-3H3/t5-/m1/s1
CAS number:609-14-3
IUPAC Name:ethyl (2R)-2-methyl-3-oxobutanoate
Traditional IUPAC Name:ethyl (2R)-2-methyl-3-oxobutanoate
SMILES:[H][C@@](C)(C(C)=O)C(=O)OCC
Chemical Taxonomy
Description 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
  • Fatty acid ester
  • Beta-keto acid
  • Fatty acyl
  • 1,3-dicarbonyl compound
  • Ketone
  • Carboxylic acid ester
  • Monocarboxylic acid or derivatives
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External DescriptorsNot Available
Physical Properties
State:Solid
Charge:0
Melting point:Boiling Pt : 187 °C
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility19.2 g/LALOGPS
logP0.69ALOGPS
logP1.04ChemAxon
logS-0.88ALOGPS
pKa (Strongest Acidic)11.5ChemAxon
pKa (Strongest Basic)-7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area43.37 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity36.63 m³·mol⁻¹ChemAxon
Polarizability15.28 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Cytoplasm
Reactions:
Hydrogen ion + Ethyl-2-methylacetoacetate + NADPH <> Ethyl-(2R)-methyl-(3S)-hydroxybutanoate + NADP
SMPDB Pathways:Not Available
KEGG Pathways:Not Available
EcoCyc Pathways:Not Available
Concentrations
Not Available
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-3900000000-257c42fbd25716a75550View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0002-9400000000-b3cf9474865601fe4fffView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-9000000000-b3c02ab448e12e9c7516View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-3900000000-dcbd0ada741da2f71689View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00di-9300000000-e2bf21ae91f68197f4c7View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0600-9000000000-d66ce6f968228216c4ebView in MoNA
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
References
References:
  • Keseler, I. M., Collado-Vides, J., Santos-Zavaleta, A., Peralta-Gil, M., Gama-Castro, S., Muniz-Rascado, L., Bonavides-Martinez, C., Paley, S., Krummenacker, M., Altman, T., Kaipa, P., Spaulding, A., Pacheco, J., Latendresse, M., Fulcher, C., Sarker, M., Shearer, A. G., Mackie, A., Paulsen, I., Gunsalus, R. P., Karp, P. D. (2011). "EcoCyc: a comprehensive database of Escherichia coli biology." Nucleic Acids Res 39:D583-D590. Pubmed: 21097882
  • van der Werf, M. J., Overkamp, K. M., Muilwijk, B., Coulier, L., Hankemeier, T. (2007). "Microbial metabolomics: toward a platform with full metabolome coverage." Anal Biochem 370:17-25. Pubmed: 17765195
  • Yurtsever D. (2007). Fatty acid methyl ester profiling of Enterococcus and Esherichia coli for microbial source tracking. M.sc. Thesis. Villanova University: U.S.A
Synthesis Reference:Not Available
Material Safety Data Sheet (MSDS)Not Available
External Links:
ResourceLink
CHEBI IDNot Available
HMDB IDNot Available
Pubchem Compound ID7017228
Kegg IDNot Available
ChemSpider ID5380222
Wikipedia IDNot Available
BioCyc IDETHYL-2-METHYLACETOACETATE
EcoCyc IDETHYL-2-METHYLACETOACETATE

Enzymes

Protein Details
1. 2,5-diketo-D-gluconic acid reductase A
General function:
Involved in oxidoreductase activity
Specific function:
Catalyzes the reduction of 2,5-diketo-D-gluconic acid (25DKG) to 2-keto-L-gulonic acid (2KLG). It is also capable of stereoselective -keto ester reductions on ethyl acetoacetate and other 2-substituted derivatives
Gene Name:
dkgA
Uniprot ID:
Q46857
Molecular weight:
31109
Reactions
2-dehydro-D-gluconate + NADP(+) = 2,5-didehydro-D-gluconate + NADPH.