Record Information
Version1.0
Creation date2010-04-08 22:11:45 UTC
Update date2015-07-20 23:16:12 UTC
Primary IDFDB015274
Secondary Accession NumbersNot Available
Chemical Information
FooDB Name2-Methylpropyl 3-oxobutanoate
Description2-Methylpropyl 3-oxobutanoate, also known as acetoacetic acid, isobutyl ester or ACIB, 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. 2-Methylpropyl 3-oxobutanoate is an extremely weak basic (essentially neutral) compound (based on its pKa). 2-Methylpropyl 3-oxobutanoate is a sweet, brandy, and fruity tasting compound.
CAS Number7779-75-1
Structure
Thumb
Synonyms
SynonymSource
2-Methylpropyl 3-oxobutanoic acidGenerator
Acetoacetic acid, isobutyl esterHMDB
ACIBHMDB
Butanoic acid, 3-oxo-, 2-methylpropyl esterHMDB
FEMA 2177HMDB
Isobutyl 3-oxobutanoateHMDB
Isobutyl acetoacetateHMDB
2-Methylpropyl 3-oxobutanoatedb_source
Butanoic Acid, 3-oxo-, 2-methylpropyl Esterbiospider
Predicted Properties
PropertyValueSource
Water Solubility5.22 g/LALOGPS
logP0.99ALOGPS
logP1.39ChemAxon
logS-1.5ALOGPS
pKa (Strongest Acidic)9.93ChemAxon
pKa (Strongest Basic)-7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area43.37 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity41.05 m³·mol⁻¹ChemAxon
Polarizability17.05 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC8H14O3
IUPAC name2-methylpropyl 3-oxobutanoate
InChI IdentifierInChI=1S/C8H14O3/c1-6(2)5-11-8(10)4-7(3)9/h6H,4-5H2,1-3H3
InChI KeyZYXNLVMBIHVDRH-UHFFFAOYSA-N
Isomeric SMILESCC(C)COC(=O)CC(C)=O
Average Molecular Weight158.195
Monoisotopic Molecular Weight158.094294314
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 DescriptorsNot Available
Ontology
Disposition

Source:

Role

Industrial application:

Biological role:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionC 60.74%; H 8.92%; O 30.34%DFC
Melting PointNot Available
Boiling PointBp11 84.5°DFC
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
Densityd25 0.97DFC
Refractive Indexn25D 1.4219DFC
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-9000000000-1651f073cbf032c123e0JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-8900000000-8d22b72300ba62429628JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-9100000000-b13aadf248760f14a6e0JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-9000000000-7d24f841eadc50502513JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a59-8900000000-9554d900bd23e9773f18JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a59-9400000000-650e600e3fa08377b358JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a59-9000000000-1074f050fca1907fe572JSpectraViewer
ChemSpider ID21105926
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound ID522677
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB36395
CRC / DFC (Dictionary of Food Compounds) IDDFR99-E:JYY47-N
EAFUS ID1855
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDrw1013091
SuperScent IDNot Available
Wikipedia IDNot Available
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
sweet
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
wine
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
brandy
  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.
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference