You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Human Metabolome Database.
Record Information
Version4.0
StatusDetected and Quantified
Creation Date2012-09-11 18:28:10 UTC
Update Date2018-05-20 18:54:40 UTC
HMDB IDHMDB0033713
Secondary Accession Numbers
  • HMDB33713
Metabolite Identification
Common Name2-Undecanone
Description2-Undecanone is found in cloves. 2-Undecanone is found in palm kernel oil and soya bean oil. 2-Undecanone is an important constituent of rue oil (Ruta graveolens) and found in many other essential oils. Also found in black currant buds, raspberry, black berry peach and other fruits. 2-Undecanone is used in flavourings 2-Undecanone is a ketone, also known as methyl nonyl ketone (MNK). It is soluble in ethanol, benzene, chloroform, and acetone, but its large carbon chain renders it insoluble in water. Like most methyl ketones, 2-undecanone undergoes a haloform reaction when in the presence of a base. For example, the reaction between 2-undecanone and sodium hypochlorite yields sodium decanoate, chloroform, and sodium hydroxide. 2-Undecanone, also known as methyl nonyl ketone and IBI-246, is an oily organic liquid manufactured synthetically, but which can also be extracted from oil of rue. It is found naturally in bananas, cloves, ginger, guava, strawberries, and wild-grown tomatoes. 2-Undecanone is used in the perfumery and flavoring industries, but because of its strong odor it is primarily used as an insect repellent or animal repellent. Typically, 1 2% concentrations of 2-undecanone are found in dog and cat repellents in the form of a liquid, aerosol spray, or gel.
Structure
Thumb
Synonyms
ValueSource
2-HendecanoneChEBI
Methyl nonyl ketoneChEBI
Rue ketoneChEBI
2-OxoundecaneHMDB
EnodylHMDB
FEMA 3093HMDB
Ketone, methyl nonylHMDB
LuparoneHMDB
Methyl N-nonyl ketoneHMDB
Methyl-N-nonylketoneHMDB
MethylnonylketoneHMDB
MGK Dog AMP MNKHMDB
Nonyl methyl ketoneHMDB
Undecan-2-oneHMDB
UndecanoneHMDB
Undecanone-(2)HMDB
BioUDMeSH
Chemical FormulaC11H22O
Average Molecular Weight170.2918
Monoisotopic Molecular Weight170.167065326
IUPAC Nameundecan-2-one
Traditional Nameundecan-2-one
CAS Registry Number112-12-9
SMILES
CCCCCCCCCC(C)=O
InChI Identifier
InChI=1S/C11H22O/c1-3-4-5-6-7-8-9-10-11(2)12/h3-10H2,1-2H3
InChI KeyKYWIYKKSMDLRDC-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound 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

Route of exposure:

Source:

Biological location:

Role

Industrial application:

Biological role:

Physical Properties
StateLiquid
Experimental Properties
PropertyValueReference
Melting Point15 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogP4.09Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.012 g/LALOGPS
logP4.25ALOGPS
logP3.92ChemAxon
logS-4.2ALOGPS
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 Count8ChemAxon
Refractivity53.03 m³·mol⁻¹ChemAxon
Polarizability22.66 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0a4l-9000000000-0b50ecd5a4e139569f95View in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0a4l-9000000000-0b50ecd5a4e139569f95View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-9100000000-52e32fb9de1c96bff48bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0fk9-0900000000-8fcf8019b6b437d7957cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0uk9-5900000000-c6f21e9a0d45a2555d70View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-052f-9100000000-3a81d8fd09c96d9c283eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0900000000-8eaba4a1b4a022676078View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-2900000000-4bd3f9e6cbf9a7cee068View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9300000000-ec90bdc81ba971e09058View in MoNA
MSMass Spectrum (Electron Ionization)splash10-0a4l-9000000000-3a214702b6cbf60221e0View in MoNA
Biological Properties
Cellular Locations
  • Membrane
Biospecimen Locations
  • Feces
  • Saliva
Tissue LocationNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not Quantified Adult (>18 years old)Both
Normal
details
FecesDetected but not Quantified Adult (>18 years old)Both
Normal
details
FecesDetected and Quantified0-841.693 nmol/g wet fecesChildren (1-13 years old)Not Specified
Normal
details
FecesDetected but not Quantified Adult (>18 years old)BothNormal details
SalivaDetected but not Quantified Adult (>18 years old)Not SpecifiedNormal details
SalivaDetected but not Quantified Adult (>18 years old)BothNormal details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not Quantified Adult (>18 years old)Both
Nonalcoholic fatty liver disease (NAFLD)
details
FecesDetected and Quantified0-11059.448 nmol/g wet fecesChildren (1-13 years old)Not Specified
Treated celiac disease
details
FecesDetected but not Quantified Adult (>18 years old)BothCrohns disease details
FecesDetected but not Quantified Adult (>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 ]
Nonalcoholic fatty liver disease
  1. Raman M, Ahmed I, Gillevet PM, Probert CS, Ratcliffe NM, Smith S, Greenwood R, Sikaroodi M, Lam V, Crotty P, Bailey J, Myers RP, Rioux KP: Fecal microbiome and volatile organic compound metabolome in obese humans with nonalcoholic fatty liver disease. Clin Gastroenterol Hepatol. 2013 Jul;11(7):868-75.e1-3. doi: 10.1016/j.cgh.2013.02.015. Epub 2013 Feb 27. [PubMed:23454028 ]
Associated OMIM IDs
DrugBank IDDB08688
Phenol Explorer Compound IDNot Available
FoodDB IDFDB011831
KNApSAcK IDC00030758
Chemspider ID7871
KEGG Compound IDC01875
BioCyc ID2-UNDECANONE
BiGG IDNot Available
Wikipedia Link2-Undecanone
METLIN IDNot Available
PubChem Compound8163
PDB IDUOC
ChEBI ID17700
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.. .