Cannabis Compound Database: Showing Compound Card for Terpinolene (CDB000209)

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Identification Taxonomy Ontology Physical properties Spectra Protein target Pathways Concentrations Links References Show 2 proteins XML

Record Information

Version

1.0

Created at

2020-03-18 23:28:49 UTC

Updated at

2020-12-07 19:07:16 UTC

CannabisDB ID

CDB000209

Secondary Accession Numbers

Not Available

Cannabis Compound Identification

Common Name

Terpinolene

Description

Terpinolene (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

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
1,4(8)-p-Menthadiene	ChEBI
1-Methyl-4-(1-methylethylidene)-1-cyclohexene	ChEBI
1-Methyl-4-(1-methylethylidene)cyclohexene	ChEBI
4-Isopropylidene-1-methylcyclohexene	ChEBI
alpha-Terpinolene	ChEBI
Isoterpinene	ChEBI
Terpinolen	ChEBI
a-Terpinolene	Generator
Α-terpinolene	Generator
1,4(8)-Terpadiene	HMDB
1-Methyl-4-(1-methylethylidene)-cyclohexene	HMDB
1-Methyl-4-(1-methylethylidene)cyclohexene, 9ci	HMDB
1-Methyl-4-(propan-2-ylidene)cyclohexene	HMDB
1-Methyl-4-isopropylidene-1-cyclohexene	HMDB
4-Isopropylidene-1-methyl-cyclohexene	HMDB
alpha -Terpinolene	HMDB
Cyclohexene, 3-methyl-6-(1-methylethylidene)- (9ci)	HMDB
FEMA 3046	HMDB
p-Mentha-1,4(8)-diene	PhytoBank
Terpinolene	PhytoBank
delta-Terpinene	PhytoBank
δ-Terpinene	PhytoBank

Chemical Formula

C₁₀H₁₆

Average Molecular Weight

136.24

Monoisotopic Molecular Weight

136.1252

IUPAC Name

1-methyl-4-(propan-2-ylidene)cyclohex-1-ene

Traditional Name

terpinolene

CAS Registry Number

69073-38-7

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 Key

MOYAFQVGZZPNRA-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.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Monoterpenoids

Direct Parent

Menthane 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 Framework

Aliphatic homomonocyclic compounds

External Descriptors

p-menthadiene (CHEBI:9457 )
Menthane monoterpenoids (C06075 )
Menthane monoterpenoids (LMPR0102090062 )
a monoterpenoid (CPD-4890 )

Ontology

Disposition

Route of exposure:

Enteral:

Ingestion

Extracellular

Subcellular:

Biofluid and excreta:

Feces

Role

Industrial application:

Personal care products:

Perfuming agent

Pharmaceutical industry:

Household products:

Antifungal

Antimicrobial agent:

Antibacterial

Food and nutrition:

Flavoring agent

Biological role:

Physical Properties

State

Solid

Experimental Properties

Property	Value	Reference
Melting Point	< 25 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.0095 mg/mL at 23 °C	Not Available
logP	4.47	Not Available

Predicted Properties

Property	Value	Source
logP	3.82	ALOGPS
logP	3.12	ChemAxon
logS	-2	ALOGPS
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	0	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	0 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	47.29 m³·mol⁻¹	ChemAxon
Polarizability	17.76 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
EI-MS	Mass Spectrum (Electron Ionization)	splash10-0006-9400000000-2d00513ea08f32f70cc4	2014-09-20	View Spectrum
GC-MS	Terpinolene, non-derivatized, GC-MS Spectrum	splash10-009f-9400000000-68d00c428f3eca0ec8a8	Spectrum
GC-MS	Terpinolene, non-derivatized, GC-MS Spectrum	splash10-001l-9400000000-960c0e59a9b4fbc2f209	Spectrum
GC-MS	Terpinolene, non-derivatized, GC-MS Spectrum	splash10-009f-9400000000-68d00c428f3eca0ec8a8	Spectrum
GC-MS	Terpinolene, non-derivatized, GC-MS Spectrum	splash10-001l-9400000000-960c0e59a9b4fbc2f209	Spectrum
GC-MS	Terpinolene, non-derivatized, GC-MS Spectrum	splash10-0006-9500000000-3a9b5aafe573ed72e592	Spectrum
Predicted GC-MS	Terpinolene, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-006x-9300000000-9316ff5aec80ce021334	Spectrum
Predicted GC-MS	Terpinolene, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Terpinolene, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-000i-3900000000-b14825d366b8c8e2ab12	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-000j-9500000000-18b9e19b4b2f2fd07710	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-1000-9100000000-59a2560a612381b96a85	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-000i-0900000000-954e07bd601b6ad95425	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-000i-1900000000-e9d35affdc69e9aca942	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-014u-6900000000-e560043bc5cf9af10365	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-000b-9400000000-7485c8b1e120c014c1c4	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-055f-9100000000-1239888ed93266e025ce	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-00ou-9000000000-c37bc4fa72e3458af8e0	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-000i-0900000000-a013b4ae27f975ab5621	2021-09-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-000i-0900000000-a013b4ae27f975ab5621	2021-09-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-014l-8900000000-4cdb68ef9159fc3b02c7	2021-09-23	View Spectrum

NMR

Type	Description	View
1D NMR	¹H NMR Spectrum (1D, CDCl₃, experimental)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, CDCl₃, experimental)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Spectrum

Pathways

Not Available

Protein Targets

Enzymes

Not Available

Transporters

Not Available

Metal Bindings

Not Available

Receptors

Protein Name	Gene Name	Locus	Uniprot ID	Details
Taste receptor type 1 member 3	TAS1R3	1p36.33	Q7RTX0	details
Taste receptor type 1 member 2	TAS1R2	1p36.13	Q8TE23	details

Transcriptional Factors

Not Available

Concentrations Data

Cannabis Cultivar	Status	Value	Reference	Details
Blue Dream	Detected and Quantified	3.633 mg/g dry wt	PMID: 30036388	details
Blue Dream	Detected and Quantified	4.533 mg/g dry wt	PMID: 30036388	details
Blue Dream	Detected and Quantified	7.325 mg/g dry wt	PMID: 30036388	details
Blue Dream	Detected and Quantified	7.404 mg/g dry wt	PMID: 30036388	details
Chemdawg #4	Detected and Quantified	0.055 mg/g dry wt	PMID: 30036388	details
Chemdawg #4	Detected and Quantified	0.067 mg/g dry wt	PMID: 30036388	details
Dairy Queen	Detected and Quantified	2.43 mg/g dry wt	PMID: 30036388	details
Dark Shadow Haze	Detected and Quantified	3.634 mg/g dry wt	PMID: 30036388	details
Golden Sage	Detected and Quantified	6.051 mg/g dry wt	PMID: 30036388	details
Grizzly Kush	Detected and Quantified	5.144 mg/g dry wt	PMID: 30036388	details
Hemlock	Detected and Quantified	3.182 mg/g dry wt	PMID: 30036388	details
Jabberwocky	Detected and Quantified	0.073 mg/g dry wt	PMID: 30036388	details
Jabberwocky	Detected and Quantified	0.117 mg/g dry wt	PMID: 30036388	details
Jack Herer	Detected and Quantified	8.3 +/- 3 mg/g dry wt	PMID: 28861503	details
Kandy Kush	Detected and Quantified	0.056 mg/g dry wt	PMID: 30036388	details
Lemon Sherbet	Detected and Quantified	2.21 mg/g dry wt	PMID: 30036388	details
Lemon Skunk	Detected and Quantified	0.07 mg/g dry wt	PMID: 30036388	details
Lemon Skunk	Detected and Quantified	3.012 mg/g dry wt	PMID: 30036388	details
Liberty Haze	Detected and Quantified	0.102 mg/g dry wt	PMID: 30036388	details
Lohan	Detected and Quantified	1.368 mg/g dry wt	PMID: 30036388	details
Platinum Delight	Detected and Quantified	0.078 mg/g dry wt	PMID: 30036388	details
Rosetta Stone	Detected and Quantified	0.068 mg/g dry wt	PMID: 30036388	details
Sensi Star	Detected and Quantified	1.89 mg/g dry wt	David S. Wishart,...	details
Sensi Star (Pure Indica)	Detected and Quantified	2.24 +/- 0.09 mg/g dry wt	David S. Wishart,...	details
The Sauce	Detected and Quantified	0.129 mg/g dry wt	PMID: 30036388	details
Trainwreck	Detected and Quantified	9.6 +/- 4.8 mg/g dry wt	PMID: 28861503	details
White Widow	Detected and Quantified	3.86 mg/g dry wt	PMID: 30036388	details

External Links

HMDB ID

HMDB0036994

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Not Available

Wikipedia Link

Terpinene

METLIN ID

Not Available

PubChem Compound

11463

PDB ID

Not Available

ChEBI ID

9457

References

General References

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 ]
McGarvey DJ, Croteau R: Terpenoid metabolism. Plant Cell. 1995 Jul;7(7):1015-26. doi: 10.1105/tpc.7.7.1015. [PubMed:7640522 ]
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 ]
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 ]
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 ]

Showing Compound Card for Terpinolene (CDB000209)

Structure for CDB000209 (Terpinolene)