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2-Hexanone (FDB008079)

Record Information
Version1.0
Creation date2010-04-08 22:07:54 UTC
Update date2019-11-26 03:02:03 UTC
Primary IDFDB008079
Secondary Accession NumbersNot Available
Chemical Information
FooDB Name2-Hexanone
DescriptionPresent in hop oil (Humulus lupulus), potato (Solanum tuberosum) and groundnuts (Arachis hypogaea) 2-Oxohexane is a volatile organic compound. 2-Oxohexane is occasionally found as a volatile component of normal human biofluids. 2-Oxohexane is an hexacarbon solvent; Hexan-2-one is the organic compound with the formula C4H9COCH3. This colorless to pale yellow liquid has a sharp odor. It is a ketone and often known either as MBK (methyl butyl ketone) or 2-hexanone. It dissolves very easily in water, and can evaporate easily into the air as a vapor. Hexan-2-one was used in the past in paint and paint thinner, to make other chemical substances, and to dissolve oils and waxes.; the neurotoxicity of hexacarbon solvents has become apparent and an extensive literature has already developed as a result of the clinical and epidemiological implications of the human disease. The main neurological disorders associated with chronic volatile substance are peripheral neuropathy, cerebellar disease, chronic encephalopathy and dementia. Apart from peripheral neuropathy, the clinical features are non-specific, evidence for solvent-related toxicity is in most cases circumstantial and there is no clear dose/response relationship. (PMID: 5556886, 6278344, 2550357). 2-Hexanone is found in many foods, some of which are nuts, cereals and cereal products, pepper (c. annuum), and cloves.
CAS Number591-78-6
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
Not AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility8.14 g/LALOGPS
logP1.45ALOGPS
logP1.7ChemAxon
logS-1.1ALOGPS
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 Count3ChemAxon
Refractivity30.02 m³·mol⁻¹ChemAxon
Polarizability12.26 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC6H12O
IUPAC namehexan-2-one
InChI IdentifierInChI=1S/C6H12O/c1-3-4-5-6(2)7/h3-5H2,1-2H3
InChI KeyQQZOPKMRPOGIEB-UHFFFAOYSA-N
Isomeric SMILESCCCCC(C)=O
Average Molecular Weight100.1589
Monoisotopic Molecular Weight100.088815006
Classification
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
Physiological effect

Health effect:

Disposition

Route of exposure:

Biological location:

Source:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateLiquid
Physical DescriptionNot Available
Mass CompositionC 71.95%; H 12.08%; O 15.97%DFC
Melting Point-55.5 oC
Boiling PointBp 127°DFC
Experimental Water Solubility17.2 mg/mL at 20 oCYALKOWSKY,SH & HE,Y (2003)
Experimental logP1.38HANSCH,C ET AL. (1995)
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
Densityd0 0.83DFC
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
EI-MSMass Spectrum (Electron Ionization)splash10-052f-9000000000-f15df0bf9af914ce3f162014-09-20View Spectrum
GC-MS2-Hexanone, non-derivatized, GC-MS Spectrumsplash10-052f-9000000000-b9a2ab16adfdd94ece2aSpectrum
GC-MS2-Hexanone, non-derivatized, GC-MS Spectrumsplash10-052f-9000000000-c9c9e98957d1fde0dce7Spectrum
GC-MS2-Hexanone, non-derivatized, GC-MS Spectrumsplash10-052f-9000000000-a8db7120c386c93d25ffSpectrum
GC-MS2-Hexanone, non-derivatized, GC-MS Spectrumsplash10-0006-9000000000-858b1e62ef5dfd041bafSpectrum
GC-MS2-Hexanone, non-derivatized, GC-MS Spectrumsplash10-052f-9000000000-e2acd59c62ae4caefc56Spectrum
GC-MS2-Hexanone, non-derivatized, GC-MS Spectrumsplash10-052f-9000000000-b9a2ab16adfdd94ece2aSpectrum
GC-MS2-Hexanone, non-derivatized, GC-MS Spectrumsplash10-052f-9000000000-c9c9e98957d1fde0dce7Spectrum
GC-MS2-Hexanone, non-derivatized, GC-MS Spectrumsplash10-052f-9000000000-a8db7120c386c93d25ffSpectrum
GC-MS2-Hexanone, non-derivatized, GC-MS Spectrumsplash10-0006-9000000000-858b1e62ef5dfd041bafSpectrum
GC-MS2-Hexanone, non-derivatized, GC-MS Spectrumsplash10-052f-9000000000-e2acd59c62ae4caefc56Spectrum
Predicted GC-MS2-Hexanone, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0006-9000000000-0884cf76c54fac458024Spectrum
Predicted GC-MS2-Hexanone, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - EI-B (HITACHI RMU-6M) , Positivesplash10-052f-9000000000-b9a2ab16adfdd94ece2a2012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - EI-B (HITACHI RMU-7M) , Positivesplash10-052f-9000000000-c9c9e98957d1fde0dce72012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - EI-B (HITACHI M-80B) , Positivesplash10-052f-9000000000-214c4efe96ae363515d52012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - EI-B (HP 5970) , Positivesplash10-0006-9000000000-858b1e62ef5dfd041baf2012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - EI-B (HITACHI RMU-6M) , Positivesplash10-052f-9000000000-e2acd59c62ae4caefc562012-08-31View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-9000000000-e69f92c1ea30b1c8b7582017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0002-9000000000-b2aac1a98aa5c3d5501e2017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a5c-9000000000-a65bc7e7cdfb70bec9db2017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-9000000000-658fe53778817eb823012021-09-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001l-9000000000-e907871a490af2e1ded72021-09-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9000000000-c861cd366a7a836ef1bd2021-09-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0ue9-8900000000-7f95c62c199ac18bb6172017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0f8c-9300000000-86d93f8a23031d7005162017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9000000000-52c2a4eb34b81253f5b02017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0536-9000000000-0559a7010081eca96a3d2021-09-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0006-9000000000-e97d6cc8af942e33a1982021-09-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9000000000-44563a4a9f48cfa3a8d92021-09-21View Spectrum
NMR
TypeDescriptionView
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, experimental)Spectrum
1D NMR13C NMR Spectrum (1D, 25.16 MHz, CDCl3, experimental)Spectrum
1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, experimental)Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, experimental)Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)Spectrum
ChemSpider ID11095
ChEMBL IDCHEMBL195861
KEGG Compound IDNot Available
Pubchem Compound ID11583
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB05842
CRC / DFC (Dictionary of Food Compounds) IDDBR31-C:DBR31-C
EAFUS IDNot Available
Dr. Duke IDHEXAN-2-ONE|2-HEXANONE
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet ID591-78-6
GoodScent IDrw1046671
SuperScent IDNot Available
Wikipedia ID2-Hexanone
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
Flavours
FlavorCitations
ether
  1. Arn, H, Acree TE. “Flavornet: A database of aroma compounds based on odor potency in natural products”. Developments in Food Science 40 (1998): 27. doi:10.1016/S0167-4501(98)80029-0
ethereal
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
Files
MSDSshow
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).