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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-11 18:27:16 UTC
Update Date2019-07-23 06:14:06 UTC
HMDB IDHMDB0033698
Secondary Accession Numbers
  • HMDB33698
Metabolite Identification
Common NameAcetoin acetate
DescriptionAcetoin acetate, also known as fema 3526, 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). Acetoin acetate is an extremely weak basic (essentially neutral) compound (based on its pKa). Acetoin acetate is a sweet, buttery, and creamy tasting compound. Outside of the human body, acetoin acetate has been detected, but not quantified in, a few different foods, such as alcoholic beverages, cocoa and cocoa products, and fruits. This could make acetoin acetate a potential biomarker for the consumption of these foods.
Structure
Data?1563862446
Synonyms
ValueSource
Acetoin acetic acidGenerator
2-Acetoxy-3-butanoneHMDB
2-Butanon-3-ol, acetateHMDB
2-Ketobutan-3-yl acetateHMDB
3-(Acetyloxy)-2-butanoneHMDB
3-Acetoxy-2-butanoneHMDB
3-oxo-2-Butyl acetateHMDB
FEMA 3526HMDB
3-Oxobutan-2-yl acetic acidGenerator
Chemical FormulaC6H10O3
Average Molecular Weight130.1418
Monoisotopic Molecular Weight130.062994186
IUPAC Name3-oxobutan-2-yl acetate
Traditional Name3-oxobutan-2-yl acetate
CAS Registry Number4906-24-5
SMILES
CC(OC(C)=O)C(C)=O
InChI Identifier
InChI=1S/C6H10O3/c1-4(7)5(2)9-6(3)8/h5H,1-3H3
InChI KeyZKPTYCJWRHHBOW-UHFFFAOYSA-N
Chemical Taxonomy
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

Industrial application:

Biological role:

Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility58.7 g/LALOGPS
logP0.19ALOGPS
logP0.3ChemAxon
logS-0.35ALOGPS
pKa (Strongest Acidic)17.63ChemAxon
pKa (Strongest Basic)-7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area43.37 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity31.54 m³·mol⁻¹ChemAxon
Polarizability13.02 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0006-9000000000-e7ac49abd7363a6c2ff9Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0006-9000000000-e7ac49abd7363a6c2ff9Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-9000000000-0cb5acd665431e37d1e4Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-01x9-9700000000-44a3d578b4cfb8344142Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0h99-9100000000-af1bacb02f3c148ba22dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0fk9-9000000000-f01d31d37b643621ca6fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0570-9600000000-ffb0d80cd438e8a3088bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4r-9100000000-76ac94891263941d8d61Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9000000000-915d80e05a156301a8f6Spectrum
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 IDFDB011808
KNApSAcK IDNot Available
Chemspider ID454676
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound521246
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB ID
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .