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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:44:15 UTC
Update Date2022-03-07 02:53:02 UTC
HMDB IDHMDB0031593
Secondary Accession Numbers
  • HMDB31593
Metabolite Identification
Common Name5-Methyl-2,3-hexanedione
Description5-Methyl-2,3-hexanedione belongs to the class of organic compounds known as alpha-diketones. These are organic compounds containing two ketone groups on two adjacent carbon atoms. 5-Methyl-2,3-hexanedione is a sweet, brown, and butter tasting compound. 5-Methyl-2,3-hexanedione has been detected, but not quantified in, several different foods, such as arabica coffees (Coffea arabica), coffee and coffee products, potatos (Solanum tuberosum), and robusta coffees (Coffea canephora). This could make 5-methyl-2,3-hexanedione a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on 5-Methyl-2,3-hexanedione.
Structure
Data?1563862145
Synonyms
ValueSource
2-Methylhexa-4,5-dioneHMDB
5-Methylhexane-2,3-dioneHMDB
Acetyl isopentanoylHMDB
Acetyl isovalerylHMDB
AcetylisopentanoylHMDB
AcetylisovalerylHMDB
FEMA 3190HMDB
Isobutyl methyl diketoneHMDB
IsobutylmethylglyoxalHMDB
Chemical FormulaC7H12O2
Average Molecular Weight128.169
Monoisotopic Molecular Weight128.083729628
IUPAC Name5-methylhexane-2,3-dione
Traditional Name2,3-hexanedione, 5-methyl-
CAS Registry Number13706-86-0
SMILES
CC(C)CC(=O)C(C)=O
InChI Identifier
InChI=1S/C7H12O2/c1-5(2)4-7(9)6(3)8/h5H,4H2,1-3H3
InChI KeyPQCLJXVUAWLNSV-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as alpha-diketones. These are organic compounds containing two ketone groups on two adjacent carbon atoms.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbonyl compounds
Direct ParentAlpha-diketones
Alternative Parents
Substituents
  • Alpha-diketone
  • Organic oxide
  • Hydrocarbon derivative
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Biological location

Source

Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility6.61 g/LALOGPS
logP1.27ALOGPS
logP1.83ChemAxon
logS-1.3ALOGPS
pKa (Strongest Acidic)16.25ChemAxon
pKa (Strongest Basic)-8.4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area34.14 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity35.32 m³·mol⁻¹ChemAxon
Polarizability14.01 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+129.88831661259
DarkChem[M-H]-125.25231661259
DeepCCS[M+H]+137.10530932474
DeepCCS[M-H]-134.87730932474
DeepCCS[M-2H]-171.24230932474
DeepCCS[M+Na]+145.96930932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
5-Methyl-2,3-hexanedioneCC(C)CC(=O)C(C)=O1149.1Standard polar33892256
5-Methyl-2,3-hexanedioneCC(C)CC(=O)C(C)=O804.6Standard non polar33892256
5-Methyl-2,3-hexanedioneCC(C)CC(=O)C(C)=O853.7Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
5-Methyl-2,3-hexanedione,1TMS,isomer #1CC(=O)C(=CC(C)C)O[Si](C)(C)C1117.3Semi standard non polar33892256
5-Methyl-2,3-hexanedione,1TMS,isomer #1CC(=O)C(=CC(C)C)O[Si](C)(C)C1076.5Standard non polar33892256
5-Methyl-2,3-hexanedione,1TMS,isomer #2C=C(O[Si](C)(C)C)C(=O)CC(C)C1145.1Semi standard non polar33892256
5-Methyl-2,3-hexanedione,1TMS,isomer #2C=C(O[Si](C)(C)C)C(=O)CC(C)C1100.9Standard non polar33892256
5-Methyl-2,3-hexanedione,2TMS,isomer #1C=C(O[Si](C)(C)C)C(=CC(C)C)O[Si](C)(C)C1263.2Semi standard non polar33892256
5-Methyl-2,3-hexanedione,2TMS,isomer #1C=C(O[Si](C)(C)C)C(=CC(C)C)O[Si](C)(C)C1261.6Standard non polar33892256
5-Methyl-2,3-hexanedione,1TBDMS,isomer #1CC(=O)C(=CC(C)C)O[Si](C)(C)C(C)(C)C1356.4Semi standard non polar33892256
5-Methyl-2,3-hexanedione,1TBDMS,isomer #1CC(=O)C(=CC(C)C)O[Si](C)(C)C(C)(C)C1288.3Standard non polar33892256
5-Methyl-2,3-hexanedione,1TBDMS,isomer #2C=C(O[Si](C)(C)C(C)(C)C)C(=O)CC(C)C1355.2Semi standard non polar33892256
5-Methyl-2,3-hexanedione,1TBDMS,isomer #2C=C(O[Si](C)(C)C(C)(C)C)C(=O)CC(C)C1281.7Standard non polar33892256
5-Methyl-2,3-hexanedione,2TBDMS,isomer #1C=C(O[Si](C)(C)C(C)(C)C)C(=CC(C)C)O[Si](C)(C)C(C)(C)C1693.5Semi standard non polar33892256
5-Methyl-2,3-hexanedione,2TBDMS,isomer #1C=C(O[Si](C)(C)C(C)(C)C)C(=CC(C)C)O[Si](C)(C)C(C)(C)C1664.5Standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 5-Methyl-2,3-hexanedione GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-9000000000-95394dc7f793985476c52017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 5-Methyl-2,3-hexanedione 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 - 5-Methyl-2,3-hexanedione 10V, Positive-QTOFsplash10-01t9-3900000000-5e05e379ff4bb7ad56f82016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-Methyl-2,3-hexanedione 20V, Positive-QTOFsplash10-0btc-9400000000-2fc37f8e6a8b9c2fd9952016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-Methyl-2,3-hexanedione 40V, Positive-QTOFsplash10-0a4i-9000000000-8449854a9e24fc33506f2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-Methyl-2,3-hexanedione 10V, Negative-QTOFsplash10-004i-2900000000-f76a0fc23c35bbf490ba2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-Methyl-2,3-hexanedione 20V, Negative-QTOFsplash10-003i-9400000000-e0e4abb2a6212927d0a92016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-Methyl-2,3-hexanedione 40V, Negative-QTOFsplash10-05u6-9100000000-9dc212ff65cb65fdca632016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-Methyl-2,3-hexanedione 10V, Positive-QTOFsplash10-000f-9000000000-be00c8c4f145ec4957702021-09-21Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-Methyl-2,3-hexanedione 20V, Positive-QTOFsplash10-0006-9000000000-4c884380c32d7999bfcd2021-09-21Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-Methyl-2,3-hexanedione 40V, Positive-QTOFsplash10-0006-9000000000-2cf92c9ae73e11664fcb2021-09-21Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-Methyl-2,3-hexanedione 10V, Negative-QTOFsplash10-004r-7900000000-fb962e2c9d27f797c84e2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-Methyl-2,3-hexanedione 20V, Negative-QTOFsplash10-0006-9000000000-f2f93da260ee7b7c4bee2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-Methyl-2,3-hexanedione 40V, Negative-QTOFsplash10-0006-9000000000-e763a48d243c151a72662021-09-25Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-30Wishart 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 IDFDB008223
KNApSAcK IDNot Available
Chemspider ID24415
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound26204
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
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.. .