Record Information
Version1.0
Creation date2010-04-08 22:05:43 UTC
Update date2018-05-29 00:37:35 UTC
Primary IDFDB003241
Secondary Accession Numbers
  • FDB003239
Chemical Information
FooDB NameEthyl 3-oxobutanoate
DescriptionThe organic compound ethyl acetoacetate (EAA) 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 and aminopyrine, and vitamin B1; as well as the manufacture of dyes, inks, lacquers, perfumes, plastics, and yellow paint pigments. Alone, it is used as a flavoring for food.
CAS Number141-97-9
Structure
Thumb
Synonyms
SynonymSource
Ethyl acetoacetateKegg
Ethyl acetoacetic acidGenerator
Ethyl 3-oxobutanoic acidGenerator
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-labeledHMDB
Ethyl acetoacetate, 2,4-(14)C-labeledHMDB
Ethyl acetoacetate, 2-(14)C-labeledHMDB
Ethyl acetoacetate, 1,2-(14)C-labeledHMDB
Ethyl acetoacetate, 3-(14)C-labeledHMDB
Ethyl acetoacetate, 14c4-labeledHMDB
Ethyl 3-oxobutanoateMeSH
3-Oxo-butyric acid ethyl esterbiospider
3-Oxobutanoic acid ethyl esterbiospider
Butanoic acid, 3-oxo-ethyl esterbiospider
Ethyl 3-oxobutyratebiospider
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
Chemical FormulaC6H10O3
IUPAC nameethyl 3-oxobutanoate
InChI IdentifierInChI=1S/C6H10O3/c1-3-9-6(8)4-5(2)7/h3-4H2,1-2H3
InChI KeyXYIBRDXRRQCHLP-UHFFFAOYSA-N
Isomeric SMILESCCOC(=O)CC(C)=O
Average Molecular Weight130.1418
Monoisotopic Molecular Weight130.062994186
Classification
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

Route of exposure:

Source:

Biological location:

Role

Industrial application:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateLiquid
Physical DescriptionNot Available
Mass CompositionC 55.37%; H 7.74%; O 36.88%DFC
Melting Point-45 oC
Boiling PointBp1 28.5°DFC
Experimental Water Solubility110 mg/mL at 17 oCYALKOWSKY,SH & DANNENFELSER,RM (1992)
Experimental logP0.25CATZ,P & FRIEND,D (1989)
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
Densityd20 1.03DFC
Refractive Indexn20D 1.4190DFC
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0006-9000000000-c1d7540b51e68aae277fView in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0006-9000000000-f40d68840be65d2cc6bdView in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-000f-9000000000-aad3ec5cf145a6891816View in MoNA
GC-MSGC-MS Spectrum - CI-B (Non-derivatized)splash10-000i-9200000000-d0f54fdbaded925d3619View in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0006-9000000000-4a1188d69a9a3efd5ef8View in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0006-9000000000-c1d7540b51e68aae277fView in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0006-9000000000-f40d68840be65d2cc6bdView in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-000f-9000000000-aad3ec5cf145a6891816View in MoNA
GC-MSGC-MS Spectrum - CI-B (Non-derivatized)splash10-000i-9200000000-d0f54fdbaded925d3619View in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0006-9000000000-4a1188d69a9a3efd5ef8View in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0006-9000000000-c1d7540b51e68aae277fView in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0006-9000000000-f40d68840be65d2cc6bdView in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-000f-9000000000-aad3ec5cf145a6891816View in MoNA
GC-MSGC-MS Spectrum - CI-B (Non-derivatized)splash10-000i-9200000000-d0f54fdbaded925d3619View in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0006-9000000000-4a1188d69a9a3efd5ef8View in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0006-9000000000-c1d7540b51e68aae277fView in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0006-9000000000-f40d68840be65d2cc6bdView in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-000f-9000000000-aad3ec5cf145a6891816View in MoNA
GC-MSGC-MS Spectrum - CI-B (Non-derivatized)splash10-000i-9200000000-d0f54fdbaded925d3619View in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0006-9000000000-4a1188d69a9a3efd5ef8View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-004r-9100000000-39e60e7c126db56d47deView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-01q9-4900000000-29f09f28b24891a22618View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-029i-9300000000-af778dca9727536ec993View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00kf-9000000000-3918640dd15245bebce9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0059-9800000000-0a07fb5054503628c784View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0569-9100000000-c332a02de02bb728d9dbView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a59-9000000000-3e3615c76305bc07ac7cView in MoNA
ChemSpider ID13865426
ChEMBL IDCHEMBL169176
KEGG Compound IDC03500
Pubchem Compound ID8868
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB31218
CRC / DFC (Dictionary of Food Compounds) IDCTW38-T:CTW41-P
EAFUS ID1135
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDEAC
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDrw1001851
SuperScent IDNot Available
Wikipedia IDEthyl_acetoacetate
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
Flavours
FlavorCitations
fresh
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
fruity
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
green
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
apple
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
fatty
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference