2-Dodecanone (CHEM013059)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-19 04:07:00 UTC
Update Date2016-11-09 01:14:43 UTC
Accession NumberCHEM013059
Identification
Common Name2-Dodecanone
ClassSmall Molecule
Description2-Dodecanone, also known as dodecan-2-one or dodecanone-(2) is a 12-carbon long-chain aliphatic molecule that 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. 2-Dodecanone is also considered to be a long-chain methyl ketone. 2-Dodecanone is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. It has a low melting point of just 19 oC. 2-Dodecanone has a citrus, floral, or fruity aroma which is contrasted with a fatty taste. 2-Dodecanone has been found in the volatile components of human feces (PMID: 21970810) and saliva (PMID: 24421258). It has also been linked celiac disease in children (PMID: 21970810). Outside of the human body, 2-dodecanone has been found at levels of up to 1.8 mg/kg in blue cheese, milk and cocoa and up to 2700 mg/kg in hop oil (Humulus lupulus). It has also been detected, but not quantified in, several other oils, such as laurel leaf oil, rue oil (Ruta graveolens) and tomato leaves and trichomes (PMID: 11757742). This could make 2-dodecanone a potential biomarker for the consumption of these foods. 2-Dodecanone is a natural insecticide and exhibits strong insecticidal properties to several insect species including Tribolium castaneum (LD50 = 5.21 ug/adult), Lasioderma serricorne (LD50 = 2.54 ug/adult) and Liposcelis bostrychophila (LD50 = 23.41 ug/cm2) in contact assays (PMID: 31240663).
Contaminant Sources
  • FooDB Chemicals
  • HMDB Contaminants - Feces
  • HPV EPA Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
12-(2,3-Dihydroxycyclopentyl)-2-dodecanoneHMDB
2,3-Epoxypropyl methanesulphonateHMDB
Decyl methyl ketoneHMDB
Dodecan-2-oneHMDB
Dodecanone-(2)HMDB
Methyl decyl ketoneHMDB
N-Decyl methyl ketoneHMDB
Chemical FormulaC12H24O
Average Molecular Mass184.318 g/mol
Monoisotopic Mass184.183 g/mol
CAS Registry Number6175-49-1
IUPAC Namedodecan-2-one
Traditional Namemethyl decyl ketone
SMILESCCCCCCCCCCC(C)=O
InChI IdentifierInChI=1S/C12H24O/c1-3-4-5-6-7-8-9-10-11-12(2)13/h3-11H2,1-2H3
InChI KeyLSKONYYRONEBKA-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
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.0026 g/LALOGPS
logP4.74ALOGPS
logP4.36ChemAxon
logS-4.8ALOGPS
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 Count9ChemAxon
Refractivity57.63 m³·mol⁻¹ChemAxon
Polarizability24.77 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0a4l-9000000000-34e6acbca9cad7e87122Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0a4l-9000000000-34e6acbca9cad7e87122Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-9200000000-0353d00aa5e15385eb24Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00kr-0900000000-ab1933445b5a3d042154Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014r-5900000000-9126f214b8985aa86560Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-052f-9100000000-37d18b291c83e062574aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-0900000000-cf9811fb05e574985341Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-2900000000-aa662eccf2d30e16197dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4l-9300000000-d14edf445ec441bbc9e3Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-9100000000-07ec12e8bad7e1430977Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-9000000000-0c4798dac932e7b979e0Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4l-9000000000-20a5578b404a8d3d5eb6Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-0900000000-ca9602a541fe011da51aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-1900000000-b24721324e22c6311e7bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-052f-9200000000-9d3d006469f91c6ac741Spectrum
MSMass Spectrum (Electron Ionization)splash10-0a4l-9000000000-3293f8f85d26475dec63Spectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB0031019
FooDB IDFDB003012
Phenol Explorer IDNot Available
KNApSAcK IDC00029455
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID21153
ChEBI IDNot Available
PubChem Compound ID22556
Kegg Compound IDC14996
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. de Lacy Costello B, Amann A, Al-Kateb H, Flynn C, Filipiak W, Khalid T, Osborne D, Ratcliffe NM: A review of the volatiles from the healthy human body. J Breath Res. 2014 Mar;8(1):014001. doi: 10.1088/1752-7155/8/1/014001. Epub 2014 Jan 13.
2. Di Cagno R, De Angelis M, De Pasquale I, Ndagijimana M, Vernocchi P, Ricciuti P, Gagliardi F, Laghi L, Crecchio C, Guerzoni ME, Gobbetti M, Francavilla R: Duodenal and faecal microbiota of celiac children: molecular, phenotype and metabolome characterization. BMC Microbiol. 2011 Oct 4;11:219. doi: 10.1186/1471-2180-11-219.
3. Antonious GF: Production and quantification of methyl ketones in wild tomato accessions. J Environ Sci Health B. 2001 Nov;36(6):835-48. doi: 10.1081/PFC-100107416.
4. Wang Y, Zhang LT, Feng YX, Guo SS, Pang X, Zhang D, Geng ZF, Du SS: Insecticidal and repellent efficacy against stored-product insects of oxygenated monoterpenes and 2-dodecanone of the essential oil from Zanthoxylum planispinum var. dintanensis. Environ Sci Pollut Res Int. 2019 Aug;26(24):24988-24997. doi: 10.1007/s11356-019-05765-z. Epub 2019 Jun 26.
5. Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.