Terpinolene (CHEM003883)

Record Information
Version1.0
Creation Date2014-09-11 05:22:50 UTC
Update Date2026-08-18 01:48:06 UTC
Accession NumberCHEM003883
Identification
Common NameTerpinolene
ClassSmall Molecule
Description
Terpinolene 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. Terpinolene has been shown to exhibit anti-fungal function (1).
Contaminant Sources
  • EAFUS Chemicals
  • FooDB Chemicals
  • HMDB Contaminants - Feces
  • HPV EPA Chemicals
  • STOFF IDENT Compounds
  • T3DB toxins
  • ToxCast & Tox21 Chemicals
Contaminant Type
  • Flavouring Agent
  • Food Toxin
  • Household Toxin
  • Metabolite
  • Natural Compound
  • Organic Compound
  • Plant Toxin
Chemical Structure
MOLSDFPDBSMILESInChI
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
p-Mentha-1,4(8)-dienePhytoBank
TerpinolenePhytoBank
delta-TerpinenePhytoBank
δ-TerpinenePhytoBank
Chemical FormulaC10H16
Average Molecular Mass136.238 g/mol
Monoisotopic Mass136.125 g/mol
CAS Registry Number586-62-9
IUPAC Name1-methyl-4-(propan-2-ylidene)cyclohex-1-ene
Traditional Nameterpinolene
SMILESCC(C)=C1CCC(C)=CC1
InChI IdentifierInChI=1S/C10H16/c1-8(2)10-6-4-9(3)5-7-10/h4H,5-7H2,1-3H3
InChI KeyMOYAFQVGZZPNRA-UHFFFAOYSA-N
Chemical Taxonomy
Description 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
  • P-menthane monoterpenoid
  • Monocyclic monoterpenoid
  • Branched unsaturated hydrocarbon
  • Cycloalkene
  • Cyclic olefin
  • Unsaturated aliphatic hydrocarbon
  • Unsaturated hydrocarbon
  • Olefin
  • Hydrocarbon
  • Aliphatic homomonocyclic compound
Molecular FrameworkAliphatic homomonocyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • Extracellular
  • Membrane
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateLiquid
AppearanceNot Available
Experimental Properties
PropertyValue
Melting Point< 25 °C
Boiling PointNot Available
Solubility0.0095 mg/mL at 23 °C
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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)No indication of carcinogenicity to humans (not listed by IARC).
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
External Links
DrugBank IDNot Available
HMDB IDHMDB0036994
FooDB IDFDB015966
Phenol Explorer IDNot Available
KNApSAcK IDC00000861
BiGG IDNot Available
BioCyc IDCPD-4890
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkTerpinene
Chemspider ID10979
ChEBI ID9457
PubChem Compound ID11463
Kegg Compound IDC06075
YMDB IDYMDB16083
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=22160253
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=22428252
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=22740904
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=23339024
5. 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.
6. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9.
7. 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.
8. 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.
9. Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621.
10. Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.
11. The lipid handbook with CD-ROM