Cannabis Compound Database: Showing Compound Card for alpha-Terpinene (CDB000207)

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

Record Information

Version

1.0

Created at

2020-03-18 23:28:44 UTC

Updated at

2020-12-07 19:07:15 UTC

CannabisDB ID

CDB000207

Secondary Accession Numbers

Not Available

Cannabis Compound Identification

Common Name

alpha-Terpinene

Description

Alpha-Terpinene is one of four isomers of terpinene (the other three being beta terpinene, gamma terpenine, and delta terpinine or terpimolene) that differ in the position of carbon-carbon double bonds. Alpha-Terpinene belongs to the class of organic compounds known as menthane monoterpenes. These are monoterpenes 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. alpha-Terpinene is a naturally occurring monoterpene found in allspice, cardamom, and marjoram. alpha-Terpinene is a constituent of many essential oils with oil from Litsea ceylanica being is a major source (20%) of it. alpha-Terpinene has been found in Citrus, Eucalyptus and Juniperus species, and cannabis plants (PMID:6991645 ). Œ±-Terpinene is a flavouring agent and is produced industrially by acid-catalyzed rearrangement of Œ±-pinene. It has perfume and flavoring properties but is mainly used to confer a pleasant odor to industrial fluids.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
1-Isopropyl-4-methyl-1,3-cyclohexadiene	ChEBI
1-Methyl-4-(1-methylethyl)-1,3-cyclohexadiene	ChEBI
p-Mentha-1,3-diene	ChEBI
Terpilene	ChEBI
a-Terpinene	Generator
Α-terpinene	Generator
1-Isopropyl-4-methyl-cyclohexa-1,3-diene	HMDB
1-Isopropyl-4-methylcyclohexa-1,3-diene	HMDB
1-Methyl-4-(propan-2-yl)cyclohexa-1,3-diene	HMDB
1-Methyl-4-isopropyl-1,3-cyclohexadiene	HMDB
1-Methyl-4-isopropylcyclohexadiene-1,3	HMDB
alpha -Terpinene	HMDB
FEMA 3558	HMDB
1,4-p-Menthadiene	HMDB
beta-Terpinene	HMDB
gamma-Terpinene	HMDB
4-Isopropyl-1-methyl-1,3-cyclohexadiene	PhytoBank
alpha-Terpinen	PhytoBank
α-Terpinen	PhytoBank
alpha-Terpinene	PhytoBank

Chemical Formula

C₁₀H₁₆

Average Molecular Weight

136.24

Monoisotopic Molecular Weight

136.1252

IUPAC Name

1-methyl-4-(propan-2-yl)cyclohexa-1,3-diene

Traditional Name

terpinene

CAS Registry Number

99-86-5

SMILES

CC(C)C1=CC=C(C)CC1

InChI Identifier

InChI=1S/C10H16/c1-8(2)10-6-4-9(3)5-7-10/h4,6,8H,5,7H2,1-3H3

InChI Key

YHQGMYUVUMAZJR-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
Cyclic olefin
Unsaturated aliphatic hydrocarbon
Unsaturated hydrocarbon
Olefin
Hydrocarbon
Aliphatic homomonocyclic compound

Molecular Framework

Aliphatic homomonocyclic compounds

External Descriptors

monoterpene (CHEBI:10334 )
Menthane monoterpenoids (C09898 )
Cyclic monoterpenes (C09898 )
Menthane monoterpenoids (LMPR0102090026 )
a monoterpenoid (CPD-8735 )

Ontology

Disposition

Route of exposure:

Enteral:

Ingestion

Extracellular

Subcellular:

Biofluid and excreta:

Saliva

Role

Industrial application:

Personal care products:

Perfuming agent

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	Not Available	Not Available
logP	4.25	Not Available

Predicted Properties

Property	Value	Source
logP	4.51	ALOGPS
logP	3.16	ChemAxon
logS	-2.4	ALOGPS
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	0	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	0 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	47.55 m³·mol⁻¹	ChemAxon
Polarizability	17.59 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)	splash10-0096-9400000000-322df4fdc907d6ef5f6f	2015-03-01	View Spectrum
GC-MS	alpha-Terpinene, non-derivatized, GC-MS Spectrum	splash10-006x-9500000000-e60fb974334faa2cf625	Spectrum
GC-MS	alpha-Terpinene, non-derivatized, GC-MS Spectrum	splash10-00du-6900000000-41fde84dbd73528ad68f	Spectrum
GC-MS	alpha-Terpinene, non-derivatized, GC-MS Spectrum	splash10-006x-9500000000-e60fb974334faa2cf625	Spectrum
GC-MS	alpha-Terpinene, non-derivatized, GC-MS Spectrum	splash10-00du-6900000000-41fde84dbd73528ad68f	Spectrum
GC-MS	alpha-Terpinene, non-derivatized, GC-MS Spectrum	splash10-006x-9500000000-e78a04a46a017816d9f9	Spectrum
Predicted GC-MS	alpha-Terpinene, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-006x-9300000000-9e298f76f2606ff289fa	Spectrum
Predicted GC-MS	alpha-Terpinene, 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-2900000000-52130a4409b06401c277	2015-04-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-000i-9700000000-349bdb9de1ad5c9d7917	2015-04-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-1000-9100000000-4f3636bfa36656ebc350	2015-04-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-000i-0900000000-954e07bd601b6ad95425	2015-04-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-000i-0900000000-e41a6714348b3249ddac	2015-04-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-014u-5900000000-9a9e0414dcb34d920983	2015-04-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-000j-9600000000-17d717eb220781ad4cc1	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0536-9100000000-3f771329175d59bc664c	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-00mo-9000000000-68b4409b06699bad322f	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-000i-0900000000-a013b4ae27f975ab5621	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-000i-0900000000-a013b4ae27f975ab5621	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-00kf-9400000000-20ffbcb6b8f03ba79f67	2021-09-24	View Spectrum

NMR

Type	Description		View
1D NMR	¹H NMR Spectrum (1D, 400 MHz, CDCl₃, experimental)		Spectrum
1D NMR	¹³C NMR Spectrum (1D, 15.09 MHz, CDCl₃, experimental)		Spectrum

Pathways

Not Available

Protein Targets

Enzymes

Not Available

Transporters

Not Available

Metal Bindings

Not Available

Receptors

Not Available

Transcriptional Factors

Not Available

Concentrations Data

Cannabis Cultivar	Status	Value	Reference	Details
Blue Dream	Detected and Quantified	0.137 mg/g dry wt	PMID: 30036388	details
Blue Dream	Detected and Quantified	0.178 mg/g dry wt	PMID: 30036388	details
Blue Dream	Detected and Quantified	0.283 mg/g dry wt	PMID: 30036388	details
Blue Dream	Detected and Quantified	0.291 mg/g dry wt	PMID: 30036388	details
Dairy Queen	Detected and Quantified	0.115 mg/g dry wt	PMID: 30036388	details
Dark Shadow Haze	Detected and Quantified	0.114 mg/g dry wt	PMID: 30036388	details
Golden Sage	Detected and Quantified	0.251 mg/g dry wt	PMID: 30036388	details
Grizzly Kush	Detected and Quantified	0.142 mg/g dry wt	PMID: 30036388	details
Hemlock	Detected and Quantified	0.156 mg/g dry wt	PMID: 30036388	details
Lemon Sherbet	Detected and Quantified	0.134 mg/g dry wt	PMID: 30036388	details
Lemon Skunk	Detected and Quantified	0.166 mg/g dry wt	PMID: 30036388	details
Lohan	Detected and Quantified	0.084 mg/g dry wt	PMID: 30036388	details
Sensi Star	Detected and Quantified	0.12 mg/g dry wt	David S. Wishart,...	details
Sensi Star (Pure Indica)	Detected and Quantified	0.13 +/- 0.01 mg/g dry wt	David S. Wishart,...	details
White Widow	Detected and Quantified	0.151 mg/g dry wt	PMID: 30036388	details

External Links

HMDB ID

HMDB0036995

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Terpinene

METLIN ID

Not Available

PubChem Compound

7462

PDB ID

Not Available

ChEBI ID

10334

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 ]

Showing Compound Card for alpha-Terpinene (CDB000207)

Structure for CDB000207 (alpha-Terpinene)