Record Information
Version1.0
Created at2020-03-18 23:28:49 UTC
Updated at2020-12-07 19:07:16 UTC
CannabisDB IDCDB000209
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common NameTerpinolene
DescriptionTerpinolene (TPO), also known as alpha-terpinolene or isoterpinene, 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. Thus, terpinolene is considered to be an isoprenoid lipid molecule. Terpinolene is a very hydrophobic monoterpenoid, practically insoluble in water, and relatively neutral. Monoterpenoids are terpenes that contain 10 carbon atoms and are comprised of two isoprene units. The biosynthesis of monoterpenes in plants is known to occur mainly through the methyl-eritritol-phosphate (MEP) pathway in the plastids (PMID: 7640522 ). Geranyl diphosphate (GPP) is a key intermediate in the biosynthesis of cyclic monoterpenes. GPP undergoes several cyclization reactions to yield a diverse number of cyclic arrangements. Terpinolene is one of the constituents of turpentine and an isomer of terpinene. It appears colourless to pale yellow liquid. Alpha-terpinolene has been identified as an abundant monoterpene in the essential oil of Cannabis sativa plants (PMID: 6991645 ). There are more than 140 known terpenes in cannabis and the combination of these terepenoids produces the skunky, fruity odor characteristic of C. savita. Although common in cannabis cultivars, terpinolene is typically found in relatively low amounts. On the other hand, the concentration of terpinolene can be has high as 30% of the essential oil. It is thought that terpinolene offers a mildly sedative effect and can reduce anxiety (PMID: 28826544 ). In particular, terpinolene is a central nervous system depressant that has been shown to induce drowsiness (PMID: 23339024 ). Terpinolene has been demonstrated to prevent LDL oxidation and is of potential interest in the treatment of atherogenesis and coronary artery disease (PMID: 28826544 ). Terpinolene exhibits antifungal and larvicidal properties (PMID: 28826544 ). Terpinolene is also an effective anti-microbial agent, particularly against E coli and Staphylococcus bacteria (PMID: 16402540 ). Terpinolene is also employed as a fragrence ingredient in lotions, insect repellents (similar to other terpenes), perfumes, and soaps. Terpinolene is also a constituent of many other essential oils e. g. Citrus, Mentha, Juniperus, Myristica species. Parsnip oil (Pastinaca sativa) in particular, is a major source (40-70%). Terpinolene is a sweet, citrus, and fresh tasting compound. It produces a floral, woody or herbal aroma reminiscent of pine needles. In addition to being found in various plant essential oils, terpinolene is found in a few different foods and spices, such as allspice, apples, sage, rosemary, parsnips, nutmegs, and wild carrots and in a lower concentration in sweet bay, star anises, turmerics, apricots, cumins, evergreen blackberries, red bell peppers, and caraway.
Structure
Thumb
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 Weight136.24
Monoisotopic Molecular Weight136.1252
IUPAC Name1-methyl-4-(propan-2-ylidene)cyclohex-1-ene
Traditional Nameterpinolene
CAS Registry Number69073-38-7
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
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
Ontology
Disposition

Route of exposure:

Source:

Biological location:

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
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
EI-MS/GC-MS
TypeDescriptionSplash KeyView
EI-MSMass Spectrum (Electron Ionization)splash10-0006-9400000000-2d00513ea08f32f70cc4Spectrum
GC-MSTerpinolene, non-derivatized, GC-MS Spectrumsplash10-009f-9400000000-68d00c428f3eca0ec8a8Spectrum
GC-MSTerpinolene, non-derivatized, GC-MS Spectrumsplash10-001l-9400000000-960c0e59a9b4fbc2f209Spectrum
GC-MSTerpinolene, non-derivatized, GC-MS Spectrumsplash10-009f-9400000000-68d00c428f3eca0ec8a8Spectrum
GC-MSTerpinolene, non-derivatized, GC-MS Spectrumsplash10-001l-9400000000-960c0e59a9b4fbc2f209Spectrum
GC-MSTerpinolene, non-derivatized, GC-MS Spectrumsplash10-0006-9500000000-3a9b5aafe573ed72e592Spectrum
Predicted GC-MSTerpinolene, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-006x-9300000000-9316ff5aec80ce021334Spectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-3900000000-b14825d366b8c8e2ab12Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000j-9500000000-18b9e19b4b2f2fd07710Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-1000-9100000000-59a2560a612381b96a85Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0900000000-954e07bd601b6ad95425Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-1900000000-e9d35affdc69e9aca942Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-014u-6900000000-e560043bc5cf9af10365Spectrum
NMR
TypeDescriptionView
1D NMR1H NMR SpectrumSpectrum
1D NMR13C NMR SpectrumSpectrum
Pathways
Pathways
Protein Targets
EnzymesNot Available
TransportersNot Available
Metal BindingsNot Available
Receptors
Protein NameGene NameLocusUniprot IDDetails
Taste receptor type 1 member 3TAS1R31p36.33Q7RTX0 details
Taste receptor type 1 member 2TAS1R21p36.13Q8TE23 details
Transcriptional FactorsNot Available
Concentrations Data
Cannabis CultivarStatusValueReferenceDetails
Blue DreamDetected and Quantified3.633 mg/g dry wt details
Blue DreamDetected and Quantified4.533 mg/g dry wt details
Blue DreamDetected and Quantified7.325 mg/g dry wt details
Blue DreamDetected and Quantified7.404 mg/g dry wt details
Chemdawg #4Detected and Quantified0.055 mg/g dry wt details
Chemdawg #4Detected and Quantified0.067 mg/g dry wt details
Dairy QueenDetected and Quantified2.43 mg/g dry wt details
Dark Shadow HazeDetected and Quantified3.634 mg/g dry wt details
Golden SageDetected and Quantified6.051 mg/g dry wt details
Grizzly KushDetected and Quantified5.144 mg/g dry wt details
HemlockDetected and Quantified3.182 mg/g dry wt details
JabberwockyDetected and Quantified0.073 mg/g dry wt details
JabberwockyDetected and Quantified0.117 mg/g dry wt details
Jack HererDetected and Quantified8.3 +/- 3 mg/g dry wt details
Kandy KushDetected and Quantified0.056 mg/g dry wt details
Lemon SherbetDetected and Quantified2.21 mg/g dry wt details
Lemon SkunkDetected and Quantified0.07 mg/g dry wt details
Lemon SkunkDetected and Quantified3.012 mg/g dry wt details
Liberty HazeDetected and Quantified0.102 mg/g dry wt details
LohanDetected and Quantified1.368 mg/g dry wt details
Platinum DelightDetected and Quantified0.078 mg/g dry wt details
Rosetta StoneDetected and Quantified0.068 mg/g dry wt details
Sensi StarDetected and Quantified1.89 mg/g dry wt
    • Jiamin Zheng, Yil...
details
Sensi Star (Pure Indica)Detected and Quantified2.24 +/- 0.09 mg/g dry wt
    • Jiamin Zheng, Yil...
details
The SauceDetected and Quantified0.129 mg/g dry wt details
TrainwreckDetected and Quantified9.6 +/- 4.8 mg/g dry wt details
White WidowDetected and Quantified3.86 mg/g dry wt details
HMDB IDHMDB0036994
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
General References
  1. Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. [PubMed:6991645 ]
  2. McGarvey DJ, Croteau R: Terpenoid metabolism. Plant Cell. 1995 Jul;7(7):1015-26. doi: 10.1105/tpc.7.7.1015. [PubMed:7640522 ]
  3. Russo EB, Marcu J: Cannabis Pharmacology: The Usual Suspects and a Few Promising Leads. Adv Pharmacol. 2017;80:67-134. doi: 10.1016/bs.apha.2017.03.004. Epub 2017 Jun 5. [PubMed:28826544 ]
  4. Ito K, Ito M: The sedative effect of inhaled terpinolene in mice and its structure-activity relationships. J Nat Med. 2013 Oct;67(4):833-7. doi: 10.1007/s11418-012-0732-1. Epub 2013 Jan 22. [PubMed:23339024 ]
  5. Eftekhar F, Yousefzadi M, Azizian D, Sonboli A, Salehi P: Essential oil composition and antimicrobial activity of Diplotaenia damavandica. Z Naturforsch C J Biosci. 2005 Nov-Dec;60(11-12):821-5. doi: 10.1515/znc-2005-11-1202. [PubMed:16402540 ]