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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2012-09-11 17:42:10 UTC
Update Date2022-03-07 02:52:54 UTC
HMDB IDHMDB0031294
Secondary Accession Numbers
  • HMDB31294
Metabolite Identification
Common Name2-Octanone
Description2-Octanone, also known as octan-2-one or fema 2802, belongs to the class of organic compounds known as ketones. These are organic compounds in which a carbonyl group is bonded to two carbon atoms R2C=O (neither R may be a hydrogen atom). Ketones that have one or more alpha-hydrogen atoms undergo keto-enol tautomerization, the tautomer being an enol. Thus, 2-octanone is considered to be an oxygenated hydrocarbon lipid molecule. 2-Octanone is a very hydrophobic molecule, practically insoluble in water, and relatively neutral. 2-Octanone is a bitter, earthy, and gasoline tasting compound. 2-Octanone has been detected, but not quantified, in several different foods, such as tortilla chips, cloves, tea, corns, and pomes. This could make 2-octanone a potential biomarker for the consumption of these foods. A methyl ketone that is octane substituted by an oxo group at position 2.
Structure
Data?1563862106
Synonyms
ValueSource
N-Hexyl methyl ketoneChEBI
Hexyl methyl ketoneMeSH
Octan-2-oneChEMBL, HMDB
FEMA 2802HMDB
2-OctanoneMeSH
Chemical FormulaC8H16O
Average Molecular Weight128.212
Monoisotopic Molecular Weight128.120115134
IUPAC Nameoctan-2-one
Traditional Name2-octanone
CAS Registry Number111-13-7
SMILES
CCCCCCC(C)=O
InChI Identifier
InChI=1S/C8H16O/c1-3-4-5-6-7-8(2)9/h3-7H2,1-2H3
InChI KeyZPVFWPFBNIEHGJ-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as ketones. These are organic compounds in which a carbonyl group is bonded to two carbon atoms R2C=O (neither R may be a hydrogen atom). Ketones that have one or more alpha-hydrogen atoms undergo keto-enol tautomerization, the tautomer being an enol.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbonyl compounds
Direct ParentKetones
Alternative Parents
Substituents
  • Ketone
  • Organic oxide
  • Hydrocarbon derivative
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Disposition

Biological location

Source

Physical Properties
StateLiquid
Experimental Molecular Properties
PropertyValueReference
Melting Point-16 °CNot Available
Boiling Point173.00 to 175.00 °C. @ 760.00 mm HgThe Good Scents Company Information System
Water Solubility0.9 mg/mL at 20 °CNot Available
LogP2.37Not Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.72 g/LALOGPS
logP2.54ALOGPS
logP2.59ChemAxon
logS-2.2ALOGPS
pKa (Strongest Acidic)19.64ChemAxon
pKa (Strongest Basic)-7.3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area17.07 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity39.23 m³·mol⁻¹ChemAxon
Polarizability16.37 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]+129.90731661259
DarkChem[M-H]-126.81531661259
DeepCCS[M+H]+139.56730932474
DeepCCS[M-H]-137.46630932474
DeepCCS[M-2H]-173.48930932474
DeepCCS[M+Na]+148.35330932474
AllCCS[M+H]+132.332859911
AllCCS[M+H-H2O]+128.132859911
AllCCS[M+NH4]+136.232859911
AllCCS[M+Na]+137.432859911
AllCCS[M-H]-135.032859911
AllCCS[M+Na-2H]-137.732859911
AllCCS[M+HCOO]-140.832859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
2-OctanoneCCCCCCC(C)=O1276.4Standard polar33892256
2-OctanoneCCCCCCC(C)=O963.3Standard non polar33892256
2-OctanoneCCCCCCC(C)=O989.9Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
2-Octanone,1TMS,isomer #1CCCCCC=C(C)O[Si](C)(C)C1184.5Semi standard non polar33892256
2-Octanone,1TMS,isomer #1CCCCCC=C(C)O[Si](C)(C)C1145.9Standard non polar33892256
2-Octanone,1TMS,isomer #2C=C(CCCCCC)O[Si](C)(C)C1147.4Semi standard non polar33892256
2-Octanone,1TMS,isomer #2C=C(CCCCCC)O[Si](C)(C)C1151.1Standard non polar33892256
2-Octanone,1TBDMS,isomer #1CCCCCC=C(C)O[Si](C)(C)C(C)(C)C1400.2Semi standard non polar33892256
2-Octanone,1TBDMS,isomer #1CCCCCC=C(C)O[Si](C)(C)C(C)(C)C1342.9Standard non polar33892256
2-Octanone,1TBDMS,isomer #2C=C(CCCCCC)O[Si](C)(C)C(C)(C)C1357.5Semi standard non polar33892256
2-Octanone,1TBDMS,isomer #2C=C(CCCCCC)O[Si](C)(C)C(C)(C)C1342.9Standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - 2-Octanone EI-B (Non-derivatized)splash10-0a4l-9000000000-eb76e1a919e8ba73aebc2017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 2-Octanone EI-B (Non-derivatized)splash10-052f-9000000000-0c79f07e8e0b16f54caa2017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 2-Octanone EI-B (Non-derivatized)splash10-052f-9000000000-e8eee7d65060bf23e4f72017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 2-Octanone EI-B (Non-derivatized)splash10-0a4i-9000000000-1a27068f4efa2d8111ac2017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 2-Octanone EI-B (Non-derivatized)splash10-0a4l-9000000000-eb76e1a919e8ba73aebc2018-05-18HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 2-Octanone EI-B (Non-derivatized)splash10-052f-9000000000-0c79f07e8e0b16f54caa2018-05-18HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 2-Octanone EI-B (Non-derivatized)splash10-052f-9000000000-e8eee7d65060bf23e4f72018-05-18HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 2-Octanone EI-B (Non-derivatized)splash10-0a4i-9000000000-1a27068f4efa2d8111ac2018-05-18HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 2-Octanone GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-9000000000-4eaf5573633227d6579a2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 2-Octanone GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
MSMass Spectrum (Electron Ionization)splash10-052f-9000000000-52b01ebb1c5b2d3316c72015-03-01Not AvailableView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Octanone 10V, Positive-QTOFsplash10-01t9-1900000000-8a73689a15a142fe9d542016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Octanone 20V, Positive-QTOFsplash10-03fr-7900000000-2d48af0e24a02dc25eb02016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Octanone 40V, Positive-QTOFsplash10-0006-9000000000-8e8c8c5781d90ef01dc82016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Octanone 10V, Negative-QTOFsplash10-004i-0900000000-cf42078e94987c04b9012016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Octanone 20V, Negative-QTOFsplash10-004i-4900000000-9a6ffd82ab0a457f79fe2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Octanone 40V, Negative-QTOFsplash10-0a4i-9200000000-2bf2f5b30ac35d9185112016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Octanone 10V, Negative-QTOFsplash10-004i-0900000000-e8448bc978ba2df6edde2021-09-21Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Octanone 20V, Negative-QTOFsplash10-004i-2900000000-5595e054396126f6abb02021-09-21Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Octanone 40V, Negative-QTOFsplash10-052f-9000000000-507b09a57f62a6ceb31b2021-09-21Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Octanone 10V, Positive-QTOFsplash10-0aor-9000000000-b87fc221c68734225d792021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Octanone 20V, Positive-QTOFsplash10-0a4l-9000000000-0165058ceb44f636e0402021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Octanone 40V, Positive-QTOFsplash10-052f-9000000000-a228c73b6b89754b37f12021-09-25Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
Biospecimen Locations
  • Feces
  • Saliva
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Not SpecifiedNormal details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Campylobacter jejuni infection
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Clostridium difficile infection
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Ulcerative Colitis
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothCrohns disease details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothUlcerative colitis details
Associated Disorders and Diseases
Disease References
Ulcerative colitis
  1. Garner CE, Smith S, de Lacy Costello B, White P, Spencer R, Probert CS, Ratcliffe NM: Volatile organic compounds from feces and their potential for diagnosis of gastrointestinal disease. FASEB J. 2007 Jun;21(8):1675-88. Epub 2007 Feb 21. [PubMed:17314143 ]
  2. Ahmed I, Greenwood R, Costello B, Ratcliffe N, Probert CS: Investigation of faecal volatile organic metabolites as novel diagnostic biomarkers in inflammatory bowel disease. Aliment Pharmacol Ther. 2016 Mar;43(5):596-611. doi: 10.1111/apt.13522. Epub 2016 Jan 25. [PubMed:26806034 ]
Crohn's disease
  1. Ahmed I, Greenwood R, Costello B, Ratcliffe N, Probert CS: Investigation of faecal volatile organic metabolites as novel diagnostic biomarkers in inflammatory bowel disease. Aliment Pharmacol Ther. 2016 Mar;43(5):596-611. doi: 10.1111/apt.13522. Epub 2016 Jan 25. [PubMed:26806034 ]
Associated OMIM IDs
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB003344
KNApSAcK IDNot Available
Chemspider ID7802
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkOctanone
METLIN IDNot Available
PubChem Compound8093
PDB IDNot Available
ChEBI ID87434
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1001751
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.. .