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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2012-09-11 17:42:09 UTC
Update Date2023-02-21 17:20:16 UTC
HMDB IDHMDB0031293
Secondary Accession Numbers
  • HMDB31293
Metabolite Identification
Common Name2,3-Octanedione
Description2,3-Octanedione belongs to the class of organic compounds known as alpha-diketones. These are organic compounds containing two ketone groups on two adjacent carbon atoms. 2,3-Octanedione is a broccoli, buttery, and cooked tasting compound. 2,3-Octanedione has been detected, but not quantified in, several different foods, such as evergreen blackberries (Rubus laciniatus), arabica coffees (Coffea arabica), blackberries (Rubus), rosemaries (Rosmarinus officinalis), and robusta coffees (Coffea canephora). This could make 2,3-octanedione a potential biomarker for the consumption of these foods. Based on a literature review a significant number of articles have been published on 2,3-Octanedione.
Structure
Data?1677000016
Synonyms
ValueSource
2,3-DioxooctaneHMDB
2,3-OctadioneHMDB
2,3-OctandioneHMDB
Methyl pentyl diketoneHMDB
Chemical FormulaC8H14O2
Average Molecular Weight142.1956
Monoisotopic Molecular Weight142.099379692
IUPAC Nameoctane-2,3-dione
Traditional Nameoctane-2,3-dione
CAS Registry Number585-25-1
SMILES
CCCCCC(=O)C(C)=O
InChI Identifier
InChI=1S/C8H14O2/c1-3-4-5-6-8(10)7(2)9/h3-6H2,1-2H3
InChI KeyXCBBNTFYSLADTO-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
Physiological effect
Disposition
ProcessNot Available
Role
Physical Properties
StateLiquid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling Point169.00 to 170.00 °C. @ 760.00 mm HgThe Good Scents Company Information System
Water Solubility23840 mg/L @ 25 °C (est)The Good Scents Company Information System
LogP0.698 (est)The Good Scents Company Information System
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility2.1 g/LALOGPS
logP2.31ALOGPS
logP2.43ChemAxon
logS-1.8ALOGPS
pKa (Strongest Acidic)16.22ChemAxon
pKa (Strongest Basic)-8.4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area34.14 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity39.97 m³·mol⁻¹ChemAxon
Polarizability16.28 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]+133.13231661259
DarkChem[M-H]-130.8831661259
DeepCCS[M+H]+138.32630932474
DeepCCS[M-H]-135.64330932474
DeepCCS[M-2H]-172.54830932474
DeepCCS[M+Na]+147.40430932474
AllCCS[M+H]+134.532859911
AllCCS[M+H-H2O]+130.432859911
AllCCS[M+NH4]+138.432859911
AllCCS[M+Na]+139.532859911
AllCCS[M-H]-134.632859911
AllCCS[M+Na-2H]-136.832859911
AllCCS[M+HCOO]-139.432859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
2,3-OctanedioneCCCCCC(=O)C(C)=O1337.6Standard polar33892256
2,3-OctanedioneCCCCCC(=O)C(C)=O934.6Standard non polar33892256
2,3-OctanedioneCCCCCC(=O)C(C)=O979.7Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
2,3-Octanedione,1TMS,isomer #1CCCCC=C(O[Si](C)(C)C)C(C)=O1266.4Semi standard non polar33892256
2,3-Octanedione,1TMS,isomer #1CCCCC=C(O[Si](C)(C)C)C(C)=O1210.5Standard non polar33892256
2,3-Octanedione,1TMS,isomer #2C=C(O[Si](C)(C)C)C(=O)CCCCC1264.4Semi standard non polar33892256
2,3-Octanedione,1TMS,isomer #2C=C(O[Si](C)(C)C)C(=O)CCCCC1222.3Standard non polar33892256
2,3-Octanedione,2TMS,isomer #1C=C(O[Si](C)(C)C)C(=CCCCC)O[Si](C)(C)C1409.3Semi standard non polar33892256
2,3-Octanedione,2TMS,isomer #1C=C(O[Si](C)(C)C)C(=CCCCC)O[Si](C)(C)C1367.8Standard non polar33892256
2,3-Octanedione,1TBDMS,isomer #1CCCCC=C(O[Si](C)(C)C(C)(C)C)C(C)=O1509.4Semi standard non polar33892256
2,3-Octanedione,1TBDMS,isomer #1CCCCC=C(O[Si](C)(C)C(C)(C)C)C(C)=O1419.9Standard non polar33892256
2,3-Octanedione,1TBDMS,isomer #2C=C(O[Si](C)(C)C(C)(C)C)C(=O)CCCCC1463.8Semi standard non polar33892256
2,3-Octanedione,1TBDMS,isomer #2C=C(O[Si](C)(C)C(C)(C)C)C(=O)CCCCC1405.9Standard non polar33892256
2,3-Octanedione,2TBDMS,isomer #1C=C(O[Si](C)(C)C(C)(C)C)C(=CCCCC)O[Si](C)(C)C(C)(C)C1856.5Semi standard non polar33892256
2,3-Octanedione,2TBDMS,isomer #1C=C(O[Si](C)(C)C(C)(C)C)C(=CCCCC)O[Si](C)(C)C(C)(C)C1748.6Standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 2,3-Octanedione GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-9000000000-64da66dfa75c6c26bb112017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 2,3-Octanedione GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 2,3-Octanedione 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 - 2,3-Octanedione 10V, Positive-QTOFsplash10-002f-1900000000-80095b918c7f36c7c5e72015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2,3-Octanedione 20V, Positive-QTOFsplash10-05i3-9500000000-3f95e1391470d0d177bb2015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2,3-Octanedione 40V, Positive-QTOFsplash10-052f-9000000000-2773cbabfa18d25aba062015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2,3-Octanedione 10V, Negative-QTOFsplash10-0006-1900000000-8a5c60aef76fbd632ad42015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2,3-Octanedione 20V, Negative-QTOFsplash10-0005-9400000000-facdc257ab1efc088b072015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2,3-Octanedione 40V, Negative-QTOFsplash10-00rf-9100000000-436f7735623dfb3b53302015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2,3-Octanedione 10V, Positive-QTOFsplash10-009y-9200000000-7f119b97cd3a2ea5b0dc2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2,3-Octanedione 20V, Positive-QTOFsplash10-006x-9000000000-3939c078bd1e95fd02632021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2,3-Octanedione 40V, Positive-QTOFsplash10-0006-9000000000-597374cc7b3cde0324252021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2,3-Octanedione 10V, Negative-QTOFsplash10-0006-6900000000-40ec4ecf97d76555cd6c2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2,3-Octanedione 20V, Negative-QTOFsplash10-0006-9000000000-0e08a0dd1a3578683efe2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2,3-Octanedione 40V, Negative-QTOFsplash10-0006-9000000000-7bcd74a858701b6b8ad72021-09-25Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum

IR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)2023-02-03FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)2023-02-03FELIX labView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
Biospecimen Locations
  • Saliva
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Not SpecifiedNormal details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB003341
KNApSAcK IDNot Available
Chemspider ID10965
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound11449
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1569281
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.. .