Hmdb loader
You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Human Metabolome Database.
Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:41:40 UTC
Update Date2021-10-13 06:14:17 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
1-Ethoxybutane-1,3-dioneChEBI
3-Ketobutyric acid ethyl esterChEBI
3-Oxobutanoic acid ethyl esterChEBI
3-Oxobutyric acid ethyl esterChEBI
Acetoacetic acid ethyl esterChEBI
Active acetyl acetateChEBI
Diacetic etherChEBI
Ethyl 3-oxidanylidenebutanoateChEBI
Ethyl 3-oxobutanoateChEBI
Ethyl 3-oxobutyrateChEBI
Ethyl acetyl acetateChEBI
Ethyl acetylacetateChEBI
Ethyl acetylacetonateChEBI
Ethyl beta-ketobutyrateChEBI
3-Ketobutyrate ethyl esterGenerator
3-Oxobutanoate ethyl esterGenerator
3-Oxobutyrate ethyl esterGenerator
Acetoacetate ethyl esterGenerator
Active acetyl acetic acidGenerator
Ethyl 3-oxidanylidenebutanoic acidGenerator
Ethyl 3-oxobutanoic acidGenerator
Ethyl 3-oxobutyric acidGenerator
Ethyl acetyl acetic acidGenerator
Ethyl acetylacetic acidGenerator
Ethyl acetylacetonic acidGenerator
Ethyl b-ketobutyrateGenerator
Ethyl b-ketobutyric acidGenerator
Ethyl beta-ketobutyric acidGenerator
Ethyl β-ketobutyrateGenerator
Ethyl β-ketobutyric acidGenerator
Ethyl acetoacetic acidGenerator
EAAHMDB
Ethyl 3-hydroxy-2-butenoateHMDB
FEMA 2415HMDB
Ethyl acetoacetate, 1,3-(14)C-labeledMeSH, HMDB
Ethyl acetoacetate, 2,4-(14)C-labeledMeSH, HMDB
Ethyl acetoacetate, 2-(14)C-labeledMeSH, HMDB
Ethyl acetoacetate, 1,2-(14)C-labeledMeSH, HMDB
Ethyl acetoacetate, 3-(14)C-labeledMeSH, HMDB
Ethyl acetoacetate, 14c4-labeledMeSH, HMDB
Ethyl acetoacetateKEGG
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
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 Descriptors
Ontology
Disposition

Biological location

Source

Route of exposure

Physical Properties
StateLiquid
Experimental Molecular Properties
PropertyValueReference
Melting Point-45 °CNot Available
Boiling Point180.00 to 181.00 °C. @ 760.00 mm HgThe Good Scents Company Information System
Water Solubility110 mg/mL at 17 °CNot Available
LogP0.25Not Available
Experimental Spectral PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility58.6 g/LALOGPS
logP10(0.19) g/LALOGPS
logP10(0.5) g/LChemAxon
logS10(-0.35) g/LALOGPS
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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Spectral Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+128.98831661259
DarkChem[M-H]-124.07131661259

Predicted Kovats Retention Indices

Not Available
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - Ethyl acetoacetate EI-B (Non-derivatized)splash10-0006-9000000000-c1d7540b51e68aae277f2017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Ethyl acetoacetate EI-B (Non-derivatized)splash10-0006-9000000000-f40d68840be65d2cc6bd2017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Ethyl acetoacetate EI-B (Non-derivatized)splash10-000f-9000000000-aad3ec5cf145a68918162017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Ethyl acetoacetate CI-B (Non-derivatized)splash10-000i-9200000000-d0f54fdbaded925d36192017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Ethyl acetoacetate EI-B (Non-derivatized)splash10-0006-9000000000-4a1188d69a9a3efd5ef82017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Ethyl acetoacetate EI-B (Non-derivatized)splash10-0006-9000000000-c1d7540b51e68aae277f2018-05-18HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Ethyl acetoacetate EI-B (Non-derivatized)splash10-0006-9000000000-f40d68840be65d2cc6bd2018-05-18HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Ethyl acetoacetate EI-B (Non-derivatized)splash10-000f-9000000000-aad3ec5cf145a68918162018-05-18HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Ethyl acetoacetate CI-B (Non-derivatized)splash10-000i-9200000000-d0f54fdbaded925d36192018-05-18HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Ethyl acetoacetate EI-B (Non-derivatized)splash10-0006-9000000000-4a1188d69a9a3efd5ef82018-05-18HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Ethyl acetoacetate EI-B (Non-derivatized)splash10-0006-9000000000-c1d7540b51e68aae277f2018-05-18HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Ethyl acetoacetate EI-B (Non-derivatized)splash10-0006-9000000000-f40d68840be65d2cc6bd2018-05-18HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Ethyl acetoacetate EI-B (Non-derivatized)splash10-000f-9000000000-aad3ec5cf145a68918162018-05-18HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Ethyl acetoacetate CI-B (Non-derivatized)splash10-000i-9200000000-d0f54fdbaded925d36192018-05-18HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Ethyl acetoacetate EI-B (Non-derivatized)splash10-0006-9000000000-4a1188d69a9a3efd5ef82018-05-18HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Ethyl acetoacetate EI-B (Non-derivatized)splash10-0006-9000000000-c1d7540b51e68aae277f2018-05-18HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Ethyl acetoacetate EI-B (Non-derivatized)splash10-0006-9000000000-f40d68840be65d2cc6bd2018-05-18HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Ethyl acetoacetate EI-B (Non-derivatized)splash10-000f-9000000000-aad3ec5cf145a68918162018-05-18HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Ethyl acetoacetate CI-B (Non-derivatized)splash10-000i-9200000000-d0f54fdbaded925d36192018-05-18HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Ethyl acetoacetate EI-B (Non-derivatized)splash10-0006-9000000000-4a1188d69a9a3efd5ef82018-05-18HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Ethyl acetoacetate GC-MS (Non-derivatized) - 70eV, Positivesplash10-004r-9100000000-39e60e7c126db56d47de2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Ethyl acetoacetate GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
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
FooDB IDFDB003241
KNApSAcK IDNot Available
Chemspider ID13865426
KEGG Compound IDC03500
BioCyc IDETHYL-ACETOACETATE
BiGG IDNot Available
Wikipedia LinkEthyl_acetoacetate
METLIN IDNot Available
PubChem Compound8868
PDB IDNot Available
ChEBI ID4893
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1001852
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.. .