Record Information
Version1.0
Creation date2010-04-08 22:10:24 UTC
Update date2019-11-26 03:07:47 UTC
Primary IDFDB012876
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameAcetoxyacetone
DescriptionAcetoxyacetone belongs to the class of organic compounds known as alpha-acyloxy ketones. These are ketones that have an acyloxy substituent alpha to the carbonyl group. They have the general structure R4C(=O)OC(R2)(R3)C(R1)=O (R1=organyl, R4=H or organyl; R2,R3 = any atom). Acetoxyacetone is a buttery and fruity tasting compound. Acetoxyacetone has been detected, but not quantified in, pineapples (Ananas comosus). This could make acetoxyacetone a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on Acetoxyacetone.
CAS Number592-20-1
Structure
Thumb
Synonyms
SynonymSource
1-(Acetyloxy)-2-propanoneHMDB
1-Acetoxy-2-propanoneHMDB
1-Acetoxy-propan-2-oneHMDB
1-AcetoxyacetoneHMDB
1-Acetyloxy-propan-2-oneHMDB
1-Hydroxy-2-propanone acetateHMDB
2-Oxopropyl acetateHMDB
2-Propanone, 1-hydroxy-, acetateHMDB
2-Propanone, 1-hydroxy-, acetate (8ci)HMDB
ACETIC ACID,(2-oxopropyl) ester acetonylacetATEHMDB
Acetol acetateHMDB
Acetonyl acetateHMDB
Acetoxy-2-propanoneHMDB
AcetoxypropanoneHMDB
Acetylmethyl acetateHMDB
O-AcetylacetolHMDB
2-Oxopropyl acetic acidGenerator
2-Propanone, 1-(acetyloxy)-biospider
2-Propanone, 1-hydroxy-, acetate (8CI)biospider
ACETIC ACID,(2-OXOPROPYL) ESTER ACETONYLACETATEbiospider
acetoxy-2-propanonebiospider
Acetoxyacetonedb_source
O-acetylacetolbiospider
Predicted Properties
PropertyValueSource
Water Solubility149 g/LALOGPS
logP-0.27ALOGPS
logP-0.27ChemAxon
logS0.11ALOGPS
pKa (Strongest Acidic)17.51ChemAxon
pKa (Strongest Basic)-7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area43.37 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity27.05 m³·mol⁻¹ChemAxon
Polarizability11.36 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC5H8O3
IUPAC name2-oxopropyl acetate
InChI IdentifierInChI=1S/C5H8O3/c1-4(6)3-8-5(2)7/h3H2,1-2H3
InChI KeyDBERHVIZRVGDFO-UHFFFAOYSA-N
Isomeric SMILESCC(=O)COC(C)=O
Average Molecular Weight116.1152
Monoisotopic Molecular Weight116.047344122
Classification
Description Belongs to the class of organic compounds known as alpha-acyloxy ketones. These are ketones that have an acyloxy substituent alpha to the carbonyl group. They have the general structure R4C(=O)OC(R2)(R3)C(R1)=O (R1=organyl, R4=H or organyl; R2,R3 = any atom).
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbonyl compounds
Direct ParentAlpha-acyloxy ketones
Alternative Parents
Substituents
  • Alpha-acyloxy ketone
  • Ketone
  • Carboxylic acid ester
  • Monocarboxylic acid or derivatives
  • Carboxylic acid derivative
  • Organic oxide
  • Hydrocarbon derivative
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Role

Biological role:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionC 51.72%; H 6.94%; O 41.34%DFC
Melting PointNot Available
Boiling PointBp 172°DFC
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
Densityd1515 1.08DFC
Refractive Indexn11D 1.4197DFC
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
GC-MSAcetoxyacetone, non-derivatized, GC-MS Spectrumsplash10-0006-9000000000-081dd10fc4cec8f7a8d2Spectrum
GC-MSAcetoxyacetone, non-derivatized, GC-MS Spectrumsplash10-0006-9000000000-081dd10fc4cec8f7a8d2Spectrum
Predicted GC-MSAcetoxyacetone, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0006-9000000000-be74d7212b518aff1241Spectrum
Predicted GC-MSAcetoxyacetone, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-2900000000-5c4d2eea3d4901362999Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-016s-9500000000-f9bd2bd95ded46d57513Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0007-9000000000-7dca30a1ecbbc3524dd8Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-2900000000-df223813d335b54b3c19Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-01b9-7900000000-84c27d4b558cd2e8a35fSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0596-9000000000-aa982e016b815042bd5eSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-9000000000-9b28085e966959baa29bSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-052f-9000000000-cee02bbbce1163482e92Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9000000000-0077b79d645b83018202Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00xr-9600000000-9ce48973ba0bd39c76bdSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004j-9000000000-31a616f5ae0f5db9de35Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-006x-9000000000-bc267c34e8d1ebde5036Spectrum
NMRNot Available
ChemSpider ID11105
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound ID11593
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB34466
CRC / DFC (Dictionary of Food Compounds) IDHCS63-R:HMP84-B
EAFUS IDNot Available
Dr. Duke IDACETOXYACETONE
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDrw1053041
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
fruity
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
buttery
  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— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).