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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:53:53 UTC
Update Date2022-03-07 02:53:36 UTC
HMDB IDHMDB0033129
Secondary Accession Numbers
  • HMDB33129
Metabolite Identification
Common Name3-Acetyl-4-hydroxy-6-methyl-2H-pyran-2-one
Description3-Acetyl-4-hydroxy-6-methyl-2H-pyran-2-one belongs to the class of organic compounds known as aryl alkyl ketones. These are ketones have the generic structure RC(=O)R', where R = aryl group and R'=alkyl group. 3-Acetyl-4-hydroxy-6-methyl-2H-pyran-2-one is an odorless tasting compound. Based on a literature review very few articles have been published on 3-Acetyl-4-hydroxy-6-methyl-2H-pyran-2-one.
Structure
Data?1563862356
Synonyms
ValueSource
Dehydracetic acidHMDB
Dehydroacetic acidHMDB
MethylacetopyrononeHMDB
DHASMeSH, HMDB
Dehydroacetic acid, potassium ion (1-)MeSH, HMDB
Dehydroacetic acid, sodium ion (1-)MeSH, HMDB
Dehydroacetic acid, zinc ion (1-)MeSH, HMDB
Dehydroacetic acid ion (1-)MeSH, HMDB
DHA-SMeSH, HMDB
Dehydroacetic acid, sodium monohydrate ion (1-)MeSH, HMDB
Dihydroxyacetone sulfateMeSH, HMDB
Sodium dehydroacetateMeSH, HMDB
DehydroacetateGenerator
Chemical FormulaC8H8O4
Average Molecular Weight168.1467
Monoisotopic Molecular Weight168.042258744
IUPAC Name3-acetyl-4-hydroxy-6-methyl-2H-pyran-2-one
Traditional Name3-acetyl-4-hydroxy-6-methylpyran-2-one
CAS Registry Number771-03-9
SMILES
CC(=O)C1=C(O)C=C(C)OC1=O
InChI Identifier
InChI=1S/C8H8O4/c1-4-3-6(10)7(5(2)9)8(11)12-4/h3,10H,1-2H3
InChI KeyPKLPQOJFHFGVBS-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as aryl alkyl ketones. These are ketones have the generic structure RC(=O)R', where R = aryl group and R'=alkyl group.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbonyl compounds
Direct ParentAryl alkyl ketones
Alternative Parents
Substituents
  • Aryl alkyl ketone
  • Pyranone
  • Pyran
  • Heteroaromatic compound
  • Vinylogous acid
  • Lactone
  • Oxacycle
  • Organoheterocyclic compound
  • Organic oxide
  • Hydrocarbon derivative
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Biological location

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point109 °CNot Available
Boiling Point352.00 to 353.00 °C. @ 760.00 mm Hg (est)The Good Scents Company Information System
Water Solubility817800 mg/L @ 25 °C (est)The Good Scents Company Information System
LogP0.221 (est)The Good Scents Company Information System
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility8.12 g/LALOGPS
logP0.08ALOGPS
logP0.47ChemAxon
logS-1.3ALOGPS
pKa (Strongest Acidic)6.49ChemAxon
pKa (Strongest Basic)-6.5ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area63.6 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity43.43 m³·mol⁻¹ChemAxon
Polarizability15.82 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+136.76731661259
DarkChem[M-H]-135.93131661259
DeepCCS[M+H]+132.84930932474
DeepCCS[M-H]-129.0230932474
DeepCCS[M-2H]-166.73330932474
DeepCCS[M+Na]+142.27230932474
AllCCS[M+H]+134.132859911
AllCCS[M+H-H2O]+129.632859911
AllCCS[M+NH4]+138.232859911
AllCCS[M+Na]+139.432859911
AllCCS[M-H]-132.132859911
AllCCS[M+Na-2H]-133.132859911
AllCCS[M+HCOO]-134.332859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
3-Acetyl-4-hydroxy-6-methyl-2H-pyran-2-oneCC(=O)C1=C(O)C=C(C)OC1=O1920.8Standard polar33892256
3-Acetyl-4-hydroxy-6-methyl-2H-pyran-2-oneCC(=O)C1=C(O)C=C(C)OC1=O1568.2Standard non polar33892256
3-Acetyl-4-hydroxy-6-methyl-2H-pyran-2-oneCC(=O)C1=C(O)C=C(C)OC1=O1329.7Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
3-Acetyl-4-hydroxy-6-methyl-2H-pyran-2-one,1TMS,isomer #1CC(=O)C1=C(O[Si](C)(C)C)C=C(C)OC1=O1588.0Semi standard non polar33892256
3-Acetyl-4-hydroxy-6-methyl-2H-pyran-2-one,1TBDMS,isomer #1CC(=O)C1=C(O[Si](C)(C)C(C)(C)C)C=C(C)OC1=O1840.5Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 3-Acetyl-4-hydroxy-6-methyl-2H-pyran-2-one GC-MS (Non-derivatized) - 70eV, Positivesplash10-0v03-5900000000-88feceb65a900415a7fe2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3-Acetyl-4-hydroxy-6-methyl-2H-pyran-2-one GC-MS (1 TMS) - 70eV, Positivesplash10-00fu-9750000000-35bd9230699a5ce09dbc2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3-Acetyl-4-hydroxy-6-methyl-2H-pyran-2-one 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 - 3-Acetyl-4-hydroxy-6-methyl-2H-pyran-2-one 10V, Positive-QTOFsplash10-014i-0900000000-fe08202ce08585250c132016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Acetyl-4-hydroxy-6-methyl-2H-pyran-2-one 20V, Positive-QTOFsplash10-014i-0900000000-bd5f45f8f94e766bd9d32016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Acetyl-4-hydroxy-6-methyl-2H-pyran-2-one 40V, Positive-QTOFsplash10-0pc9-4900000000-414640773faaabce25652016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Acetyl-4-hydroxy-6-methyl-2H-pyran-2-one 10V, Negative-QTOFsplash10-014i-0900000000-0087476b0935000afd8b2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Acetyl-4-hydroxy-6-methyl-2H-pyran-2-one 20V, Negative-QTOFsplash10-004i-2900000000-5c44a21e733f2784dd8d2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Acetyl-4-hydroxy-6-methyl-2H-pyran-2-one 40V, Negative-QTOFsplash10-001i-9500000000-dbca1de8be7e3b295f4e2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Acetyl-4-hydroxy-6-methyl-2H-pyran-2-one 10V, Positive-QTOFsplash10-014i-0900000000-647525daac9281f7e6012021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Acetyl-4-hydroxy-6-methyl-2H-pyran-2-one 20V, Positive-QTOFsplash10-016r-2900000000-af544e3828cc82d853912021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Acetyl-4-hydroxy-6-methyl-2H-pyran-2-one 40V, Positive-QTOFsplash10-0006-9000000000-0b60e0eff1ec85de185c2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Acetyl-4-hydroxy-6-methyl-2H-pyran-2-one 10V, Negative-QTOFsplash10-014i-0900000000-930f9ca2cc854ecca14e2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Acetyl-4-hydroxy-6-methyl-2H-pyran-2-one 20V, Negative-QTOFsplash10-016r-1900000000-02682960868c1120ad262021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Acetyl-4-hydroxy-6-methyl-2H-pyran-2-one 40V, Negative-QTOFsplash10-05mx-9000000000-06c4c7a773034883d2772021-09-24Wishart 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
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 IDFDB011130
KNApSAcK IDNot Available
Chemspider ID10486535
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound54678494
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1529191
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.. .