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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:41:40 UTC
Update Date2019-07-23 06:08:16 UTC
HMDB IDHMDB0031216
Secondary Accession Numbers
  • HMDB0031218
  • HMDB31216
  • HMDB31218
Metabolite Identification
Common NameEthyl acetoacetate
DescriptionEthyl acetoacetate (EAA) is found in coffee and coffee products as well as in strawberry and yellow passion fruit juice. Ethyl acetoacetate is a flavouring agent. The organic compound ethyl acetoacetate is the ethyl ester of acetoacetic acid. It is mainly used as a chemical intermediate in the production of a wide variety of compounds, such as amino acids, analgesics, antibiotics, antimalarial agents, antipyrine, aminopyrine, and vitamin B1, as well as in the manufacture of dyes, inks, lacquers, perfumes, plastics, and yellow paint pigments (Wikipedia).
Structure
Data?1563862096
Synonyms
ValueSource
Acetoacetic acid ethyl esterHMDB
Diacetic etherHMDB
EAAHMDB
Ethyl 3-hydroxy-2-butenoateHMDB
Ethyl acetyl acetateHMDB
Ethyl acetylacetateHMDB
Ethyl acetylacetonateHMDB
FEMA 2415HMDB
Ethyl acetoacetate, 1,3-(14)C-labeledMeSH
Ethyl acetoacetate, 2,4-(14)C-labeledMeSH
Ethyl acetoacetate, 2-(14)C-labeledMeSH
Ethyl 3-oxobutanoateMeSH
Ethyl acetoacetate, 1,2-(14)C-labeledMeSH
Ethyl acetoacetate, 3-(14)C-labeledMeSH
Ethyl acetoacetate, 14c4-labeledMeSH
Chemical FormulaC6H10O3
Average Molecular Weight130.1418
Monoisotopic Molecular Weight130.062994186
IUPAC Nameethyl 3-oxobutanoate
Traditional Nameethyl acetoacetate
CAS Registry Number141-97-9
SMILES
CCOC(=O)CC(C)=O
InChI Identifier
InChI=1S/C6H10O3/c1-3-9-6(8)4-5(2)7/h3-4H2,1-2H3
InChI KeyXYIBRDXRRQCHLP-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
  • 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 Descriptors
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Role

Industrial application:

Physical Properties
StateLiquid
Experimental Properties
PropertyValueReference
Melting Point-45 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility110 mg/mL at 17 °CNot Available
LogP0.25Not Available
Predicted Properties
PropertyValueSource
Water Solubility58.6 g/LALOGPS
logP0.19ALOGPS
logP0.5ChemAxon
logS-0.35ALOGPS
pKa (Strongest Acidic)9.93ChemAxon
pKa (Strongest Basic)-7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area43.37 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity32.06 m³·mol⁻¹ChemAxon
Polarizability13.2 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0006-9000000000-c1d7540b51e68aae277fJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0006-9000000000-f40d68840be65d2cc6bdJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-000f-9000000000-aad3ec5cf145a6891816JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - CI-B (Non-derivatized)splash10-000i-9200000000-d0f54fdbaded925d3619JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0006-9000000000-4a1188d69a9a3efd5ef8JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0006-9000000000-c1d7540b51e68aae277fJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0006-9000000000-f40d68840be65d2cc6bdJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-000f-9000000000-aad3ec5cf145a6891816JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - CI-B (Non-derivatized)splash10-000i-9200000000-d0f54fdbaded925d3619JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0006-9000000000-4a1188d69a9a3efd5ef8JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0006-9000000000-c1d7540b51e68aae277fJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0006-9000000000-f40d68840be65d2cc6bdJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-000f-9000000000-aad3ec5cf145a6891816JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - CI-B (Non-derivatized)splash10-000i-9200000000-d0f54fdbaded925d3619JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0006-9000000000-4a1188d69a9a3efd5ef8JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0006-9000000000-c1d7540b51e68aae277fJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0006-9000000000-f40d68840be65d2cc6bdJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-000f-9000000000-aad3ec5cf145a6891816JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - CI-B (Non-derivatized)splash10-000i-9200000000-d0f54fdbaded925d3619JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0006-9000000000-4a1188d69a9a3efd5ef8JSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-004r-9100000000-39e60e7c126db56d47deJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-01q9-4900000000-29f09f28b24891a22618JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-029i-9300000000-af778dca9727536ec993JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00kf-9000000000-3918640dd15245bebce9JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0059-9800000000-0a07fb5054503628c784JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0569-9100000000-c332a02de02bb728d9dbJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a59-9000000000-3e3615c76305bc07ac7cJSpectraViewer | MoNA
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
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 IDFDB003241
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDC03500
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkEthyl acetoacetate
METLIN IDNot Available
PubChem Compound8868
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .