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Record Information
Version4.0
StatusDetected but not Quantified
Creation Date2012-09-11 22:14:15 UTC
Update Date2019-07-31 22:49:50 UTC
HMDB IDHMDB0036994
Secondary Accession Numbers
  • HMDB36994
Metabolite Identification
Common NameTerpinolene
DescriptionTerpinolene is found in allspice. Terpinolene is a constituent of many essential oils e.g. Citrus, Mentha, Juniperus, Myristica species Parsnip oil (Pastinaca sativa) is a major source (40-70%). Terpinolene is a flavouring ingredient
Structure
Data?1563862962
Synonyms
ValueSource
1,4(8)-P-MenthadieneChEBI
1-Methyl-4-(1-methylethylidene)-1-cyclohexeneChEBI
1-Methyl-4-(1-methylethylidene)cyclohexeneChEBI
4-Isopropylidene-1-methylcyclohexeneChEBI
alpha-TerpinoleneChEBI
IsoterpineneChEBI
TerpinolenChEBI
a-TerpinoleneGenerator
α-terpinoleneGenerator
1,4(8)-TerpadieneHMDB
1-Methyl-4-(1-methylethylidene)-cyclohexeneHMDB
1-Methyl-4-(1-methylethylidene)cyclohexene, 9ciHMDB
1-Methyl-4-(propan-2-ylidene)cyclohexeneHMDB
1-Methyl-4-isopropylidene-1-cyclohexeneHMDB
4-Isopropylidene-1-methyl-cyclohexeneHMDB
alpha -TerpinoleneHMDB
Cyclohexene, 3-methyl-6-(1-methylethylidene)- (9ci)HMDB
FEMA 3046HMDB
Chemical FormulaC10H16
Average Molecular Weight136.238
Monoisotopic Molecular Weight136.125200515
IUPAC Name1-methyl-4-(propan-2-ylidene)cyclohex-1-ene
Traditional Nameterpinolene
CAS Registry Number586-62-9
SMILES
CC(C)=C1CCC(C)=CC1
InChI Identifier
InChI=1S/C10H16/c1-8(2)10-6-4-9(3)5-7-10/h4H,5-7H2,1-3H3
InChI KeyMOYAFQVGZZPNRA-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as menthane monoterpenoids. These are monoterpenoids with a structure based on the o-, m-, or p-menthane backbone. P-menthane consists of the cyclohexane ring with a methyl group and a (2-methyl)-propyl group at the 1 and 4 ring position, respectively. The o- and m- menthanes are much rarer, and presumably arise by alkyl migration of p-menthanes.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassMonoterpenoids
Direct ParentMenthane monoterpenoids
Alternative Parents
Substituents
  • Menthane monoterpenoid
  • Monocyclic monoterpenoid
  • Cycloalkene
  • Cyclic olefin
  • Olefin
  • Hydrocarbon
  • Aliphatic homomonocyclic compound
Molecular FrameworkAliphatic homomonocyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Process

Naturally occurring process:

Role

Industrial application:

Biological role:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point< 25 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.0095 mg/mL at 23 °CNot Available
LogP4.47Not Available
Predicted Properties
PropertyValueSource
Water Solubility1.38 g/LALOGPS
logP3.82ALOGPS
logP3.12ChemAxon
logS-2ALOGPS
Physiological Charge0ChemAxon
Hydrogen Acceptor Count0ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area0 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity47.29 m³·mol⁻¹ChemAxon
Polarizability17.76 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-009f-9400000000-68d00c428f3eca0ec8a8JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-001l-9400000000-960c0e59a9b4fbc2f209JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-009f-9400000000-68d00c428f3eca0ec8a8JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-001l-9400000000-960c0e59a9b4fbc2f209JSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-006x-9300000000-9316ff5aec80ce021334JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-3900000000-b14825d366b8c8e2ab12JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000j-9500000000-18b9e19b4b2f2fd07710JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-1000-9100000000-59a2560a612381b96a85JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0900000000-954e07bd601b6ad95425JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-1900000000-e9d35affdc69e9aca942JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-014u-6900000000-e560043bc5cf9af10365JSpectraViewer | MoNA
MSMass Spectrum (Electron Ionization)splash10-0006-9400000000-2d00513ea08f32f70cc4JSpectraViewer | MoNA
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biospecimen Locations
  • Breath
  • Feces
Tissue LocationsNot 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 but not Quantified Adult (>18 years old)BothNormal details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BreathDetected but not Quantified Adult (>18 years old)BothAsthma details
FecesDetected but not Quantified Adult (>18 years old)Both
Nonalcoholic fatty liver disease (NAFLD)
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
Asthma
  1. Ibrahim B, Basanta M, Cadden P, Singh D, Douce D, Woodcock A, Fowler SJ: Non-invasive phenotyping using exhaled volatile organic compounds in asthma. Thorax. 2011 Sep;66(9):804-9. doi: 10.1136/thx.2010.156695. Epub 2011 Jul 11. [PubMed:21749985 ]
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 ]
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
FoodDB IDFDB015966
KNApSAcK IDC00000861
Chemspider ID10979
KEGG Compound IDC06075
BioCyc IDCPD-4890
BiGG IDNot Available
Wikipedia LinkTerpinene
METLIN IDNot Available
PubChem Compound11463
PDB IDNot Available
ChEBI ID9457
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Farooq A, Choudhary MI, Atta-ur-Rahman, Tahara S, Baser KH, Demirci F: Detoxification of terpinolene by plant pathogenic fungus Botrytis cinerea. Z Naturforsch C. 2002 Sep-Oct;57(9-10):863-6. [PubMed:12440725 ]
  2. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
  3. Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
  4. Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
  5. Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
  6. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .
  7. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.