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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2012-09-11 17:40:28 UTC
Update Date2023-02-21 17:19:51 UTC
HMDB IDHMDB0031019
Secondary Accession Numbers
  • HMDB31019
Metabolite Identification
Common Name2-Dodecanone
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 ).
Structure
Data?1676999991
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 Weight184.3184
Monoisotopic Molecular Weight184.18271539
IUPAC Namedodecan-2-one
Traditional Namemethyl decyl ketone
CAS Registry Number6175-49-1
SMILES
CCCCCCCCCCC(C)=O
InChI Identifier
InChI=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
Ontology
Physiological effect
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point21 °CNot Available
Boiling Point245.00 to 246.00 °C. @ 760.00 mm HgThe Good Scents Company Information System
Water Solubility13.99 mg/L @ 25 °C (est)The Good Scents Company Information System
LogP4.544 (est)The Good Scents Company Information System
Experimental Chromatographic PropertiesNot Available
Predicted Molecular 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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+146.24731661259
DarkChem[M-H]-145.61431661259
DeepCCS[M+H]+152.82730932474
DeepCCS[M-H]-149.33230932474
DeepCCS[M-2H]-186.82730932474
DeepCCS[M+Na]+162.09830932474
AllCCS[M+H]+150.432859911
AllCCS[M+H-H2O]+146.632859911
AllCCS[M+NH4]+153.932859911
AllCCS[M+Na]+154.932859911
AllCCS[M-H]-151.732859911
AllCCS[M+Na-2H]-153.232859911
AllCCS[M+HCOO]-155.032859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
2-DodecanoneCCCCCCCCCCC(C)=O1692.5Standard polar33892256
2-DodecanoneCCCCCCCCCCC(C)=O1373.1Standard non polar33892256
2-DodecanoneCCCCCCCCCCC(C)=O1395.1Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
2-Dodecanone,1TMS,isomer #1CCCCCCCCCC=C(C)O[Si](C)(C)C1576.8Semi standard non polar33892256
2-Dodecanone,1TMS,isomer #1CCCCCCCCCC=C(C)O[Si](C)(C)C1540.7Standard non polar33892256
2-Dodecanone,1TMS,isomer #2C=C(CCCCCCCCCC)O[Si](C)(C)C1534.4Semi standard non polar33892256
2-Dodecanone,1TMS,isomer #2C=C(CCCCCCCCCC)O[Si](C)(C)C1545.3Standard non polar33892256
2-Dodecanone,1TBDMS,isomer #1CCCCCCCCCC=C(C)O[Si](C)(C)C(C)(C)C1798.9Semi standard non polar33892256
2-Dodecanone,1TBDMS,isomer #1CCCCCCCCCC=C(C)O[Si](C)(C)C(C)(C)C1719.5Standard non polar33892256
2-Dodecanone,1TBDMS,isomer #2C=C(CCCCCCCCCC)O[Si](C)(C)C(C)(C)C1754.4Semi standard non polar33892256
2-Dodecanone,1TBDMS,isomer #2C=C(CCCCCCCCCC)O[Si](C)(C)C(C)(C)C1722.1Standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - 2-Dodecanone EI-B (Non-derivatized)splash10-0a4l-9000000000-34e6acbca9cad7e871222017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 2-Dodecanone EI-B (Non-derivatized)splash10-0a4l-9000000000-34e6acbca9cad7e871222018-05-18HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 2-Dodecanone GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-9200000000-0353d00aa5e15385eb242017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 2-Dodecanone GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
MSMass Spectrum (Electron Ionization)splash10-0a4l-9000000000-3293f8f85d26475dec632015-03-01Not AvailableView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Dodecanone 10V, Positive-QTOFsplash10-00kr-0900000000-ab1933445b5a3d0421542015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Dodecanone 20V, Positive-QTOFsplash10-014r-5900000000-9126f214b8985aa865602015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Dodecanone 40V, Positive-QTOFsplash10-052f-9100000000-37d18b291c83e062574a2015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Dodecanone 10V, Negative-QTOFsplash10-001i-0900000000-cf9811fb05e5749853412015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Dodecanone 20V, Negative-QTOFsplash10-001i-2900000000-aa662eccf2d30e16197d2015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Dodecanone 40V, Negative-QTOFsplash10-0a4l-9300000000-d14edf445ec441bbc9e32015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Dodecanone 10V, Positive-QTOFsplash10-0a4i-9100000000-07ec12e8bad7e14309772021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Dodecanone 20V, Positive-QTOFsplash10-0a4i-9000000000-0c4798dac932e7b979e02021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Dodecanone 40V, Positive-QTOFsplash10-0a4l-9000000000-20a5578b404a8d3d5eb62021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Dodecanone 10V, Negative-QTOFsplash10-001i-0900000000-ca9602a541fe011da51a2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Dodecanone 20V, Negative-QTOFsplash10-001i-1900000000-b24721324e22c6311e7b2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Dodecanone 40V, Negative-QTOFsplash10-052f-9200000000-9d3d006469f91c6ac7412021-09-22Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView

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
  • Membrane
Biospecimen Locations
  • Feces
  • Saliva
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected and Quantified0-503440.423 nmol/g wet fecesChildren (1-13 years old)Not Specified
Normal
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Not SpecifiedNormal details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothCrohns disease details
FecesDetected and Quantified0-971941.307 nmol/g wet fecesChildren (1-13 years old)Not Specified
Treated celiac disease
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothUlcerative colitis details
Associated Disorders and Diseases
Disease References
Celiac disease
  1. 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. [PubMed:21970810 ]
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 ]
Ulcerative colitis
  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 IDFDB003012
KNApSAcK IDC00029455
Chemspider ID21153
KEGG Compound IDC14996
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound22556
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. 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. [PubMed:24421258 ]
  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. [PubMed:21970810 ]
  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. [PubMed:11757742 ]
  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. [PubMed:31240663 ]
  5. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .