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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 18:27:16 UTC
Update Date2023-02-21 17:23:31 UTC
HMDB IDHMDB0033698
Secondary Accession Numbers
  • HMDB33698
Metabolite Identification
Common NameAcetoin acetate
DescriptionAcetoin acetate 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 a sweet, buttery, and creamy tasting compound. Acetoin acetate has been detected, but not quantified in, several different foods, such as alcoholic beverages, cocoa and cocoa products, cocoa beans (Theobroma cacao), and fruits. This could make acetoin acetate a potential biomarker for the consumption of these foods. Based on a literature review a significant number of articles have been published on Acetoin acetate.
Structure
Data?1677000211
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
Physiological effect
Disposition
ProcessNot Available
Role
Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling Point74.00 to 75.00 °C. @ 20.00 mm HgThe Good Scents Company Information System
Water Solubility0 slightlyThe Good Scents Company Information System
LogP0.680 (est)The Good Scents Company Information System
Experimental Chromatographic PropertiesNot Available
Predicted Molecular 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
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+129.47231661259
DarkChem[M-H]-123.06231661259
DeepCCS[M+H]+128.27630932474
DeepCCS[M-H]-126.02930932474
DeepCCS[M-2H]-162.3630932474
DeepCCS[M+Na]+136.95630932474
AllCCS[M+H]+131.032859911
AllCCS[M+H-H2O]+126.932859911
AllCCS[M+NH4]+134.832859911
AllCCS[M+Na]+135.932859911
AllCCS[M-H]-128.132859911
AllCCS[M+Na-2H]-131.032859911
AllCCS[M+HCOO]-134.132859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Acetoin acetateCC(OC(C)=O)C(C)=O1271.5Standard polar33892256
Acetoin acetateCC(OC(C)=O)C(C)=O809.9Standard non polar33892256
Acetoin acetateCC(OC(C)=O)C(C)=O890.1Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Acetoin acetate,1TMS,isomer #1CC(=O)OC(C)=C(C)O[Si](C)(C)C1124.3Semi standard non polar33892256
Acetoin acetate,1TMS,isomer #1CC(=O)OC(C)=C(C)O[Si](C)(C)C1129.5Standard non polar33892256
Acetoin acetate,1TMS,isomer #2C=C(O[Si](C)(C)C)C(C)OC(C)=O1038.8Semi standard non polar33892256
Acetoin acetate,1TMS,isomer #2C=C(O[Si](C)(C)C)C(C)OC(C)=O1073.5Standard non polar33892256
Acetoin acetate,1TBDMS,isomer #1CC(=O)OC(C)=C(C)O[Si](C)(C)C(C)(C)C1324.0Semi standard non polar33892256
Acetoin acetate,1TBDMS,isomer #1CC(=O)OC(C)=C(C)O[Si](C)(C)C(C)(C)C1341.9Standard non polar33892256
Acetoin acetate,1TBDMS,isomer #2C=C(O[Si](C)(C)C(C)(C)C)C(C)OC(C)=O1250.0Semi standard non polar33892256
Acetoin acetate,1TBDMS,isomer #2C=C(O[Si](C)(C)C(C)(C)C)C(C)OC(C)=O1283.3Standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - Acetoin acetate EI-B (Non-derivatized)splash10-0006-9000000000-e7ac49abd7363a6c2ff92017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Acetoin acetate EI-B (Non-derivatized)splash10-0006-9000000000-e7ac49abd7363a6c2ff92018-05-18HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Acetoin acetate GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-9000000000-0cb5acd665431e37d1e42017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Acetoin acetate GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Acetoin acetate 10V, Positive-QTOFsplash10-01x9-9700000000-44a3d578b4cfb83441422016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Acetoin acetate 20V, Positive-QTOFsplash10-0h99-9100000000-af1bacb02f3c148ba22d2016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Acetoin acetate 40V, Positive-QTOFsplash10-0fk9-9000000000-f01d31d37b643621ca6f2016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Acetoin acetate 10V, Negative-QTOFsplash10-0570-9600000000-ffb0d80cd438e8a3088b2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Acetoin acetate 20V, Negative-QTOFsplash10-0a4r-9100000000-76ac94891263941d8d612016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Acetoin acetate 40V, Negative-QTOFsplash10-0a4i-9000000000-915d80e05a156301a8f62016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Acetoin acetate 10V, Negative-QTOFsplash10-0a4r-9000000000-2d05de6fc16fb0aaba592021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Acetoin acetate 20V, Negative-QTOFsplash10-0a4i-9000000000-b62977f32ee5dcfb3a162021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Acetoin acetate 40V, Negative-QTOFsplash10-0a4i-9000000000-9e2bab7e30574fd7ec652021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Acetoin acetate 10V, Positive-QTOFsplash10-00dl-9000000000-5af9adb4c1ef6f1d7a602021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Acetoin acetate 20V, Positive-QTOFsplash10-0006-9000000000-cf7748127e0cc9a22d282021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Acetoin acetate 40V, Positive-QTOFsplash10-0006-9000000000-492cd06c14ee7be1db8f2021-09-24Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum

IR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)2023-02-04FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)2023-02-04FELIX 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 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 IDNot Available
Good Scents IDrw1036691
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.. .