Cannabis Compound Database: Showing Compound Card for gamma-Terpinene (CDB000208)

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Record Information

Version

1.0

Created at

2020-03-18 23:28:47 UTC

Updated at

2020-12-07 19:07:16 UTC

CannabisDB ID

CDB000208

Secondary Accession Numbers

Not Available

Cannabis Compound Identification

Common Name

gamma-Terpinene

Description

Œ≥-Terpinene belongs to the class of organic compounds known as menthane monoterpenoids. Monoterpenoids are terpenes that contain 10 carbon atoms and are comprised of two isoprene units. The biosynthesis of monoterpenes is known to occur mainly through the methyl-eritritol-phosphate (MEP) pathway in the plastids. 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. Menthanes 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 an isopropyl 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. Œ≥-Terpinene is one of 4 isomeric monoterpenes differing in the positions of their two double bonds (alpha- and beta-terpinene being the others). In gamma-terpinene the double bonds are at the 1- and 4-positions of the p-menthane skeleton. Œ≥-Terpinene has been detected as a volatile component in cannabis plant samples (PMID: 26657499 ).

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
1,4-p-Menthadiene	ChEBI
1-Isopropyl-4-methyl-1,4-cyclohexadiene	ChEBI
1-Isopropyl-4-methylcyclohexa-1,4-diene	ChEBI
1-Methyl-4-(1-methylethyl)-1,4-cyclohexadiene	ChEBI
1-Methyl-4-propan-2-ylcyclohexa-1,4-diene	ChEBI
4-Isopropyl-1-methyl-1,4-cyclohexadiene	ChEBI
Crithmene	ChEBI
Moslene	ChEBI
p-Mentha-1,4-diene	ChEBI
g-Terpinene	Generator
Γ-terpinene	Generator
1-Methyl-4-(propan-2-yl)cyclohexa-1,4-diene	HMDB
alpha Terpinene	HMDB
gamma Terpinene	HMDB
gamma-Terpinen	HMDB
Terpinene	HMDB
1-Methyl-4-isopropyl-1,4-cyclohexadiene	PhytoBank
gamma-Terpinene	PhytoBank
γ-Terpinen	PhytoBank

Chemical Formula

C₁₀H₁₆

Average Molecular Weight

136.24

Monoisotopic Molecular Weight

136.1252

IUPAC Name

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

Traditional Name

α terpinene

CAS Registry Number

99-85-4

SMILES

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

InChI Identifier

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

InChI Key

YKFLAYDHMOASIY-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as branched unsaturated hydrocarbons. These are hydrocarbons that contains one or more unsaturated carbon atoms, and an aliphatic branch.

Kingdom

Organic compounds

Super Class

Hydrocarbons

Class

Unsaturated hydrocarbons

Sub Class

Branched unsaturated hydrocarbons

Direct Parent

Branched unsaturated hydrocarbons

Alternative Parents

Substituents

Branched unsaturated hydrocarbon
Cyclic olefin
Unsaturated aliphatic hydrocarbon
Olefin
Aliphatic homomonocyclic compound

Molecular Framework

Aliphatic homomonocyclic compounds

External Descriptors

monoterpene (CHEBI:10577 )
Menthane monoterpenoids (C09900 )
Cyclic monoterpenes (C09900 )
Menthane monoterpenoids (LMPR0102090027 )
a monoterpenoid (CPD-8736 )

Ontology

Disposition

Route of exposure:

Enteral:

Ingestion

Source:

Food

Biological:

Plant

Biological location:

Biofluid and excreta:

Cell and elements:

Extracellular

Subcellular:

Role

Industrial application:

Biological role:

Physical Properties

State

Solid

Experimental Properties

Property	Value	Reference
Melting Point	-10 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.0087 mg/mL at 22 °C	Not Available
logP	4.50	LI,J & PERDUE,EM (1995)

Predicted Properties

Property	Value	Source
logP	4.36	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	17.61 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)	splash10-0006-9300000000-97923633c0b05f03274f	2014-09-20	View Spectrum
GC-MS	gamma-Terpinene, non-derivatized, GC-MS Spectrum	splash10-0006-9200000000-b05d52aa0731550051f6	Spectrum
GC-MS	gamma-Terpinene, non-derivatized, GC-MS Spectrum	splash10-0006-9400000000-a5cb265912cd3b36ec3f	Spectrum
GC-MS	gamma-Terpinene, non-derivatized, GC-MS Spectrum	splash10-0006-9500000000-2b0e829aa7638afa325e	Spectrum
GC-MS	gamma-Terpinene, non-derivatized, GC-MS Spectrum	splash10-0006-9200000000-b05d52aa0731550051f6	Spectrum
GC-MS	gamma-Terpinene, non-derivatized, GC-MS Spectrum	splash10-0006-9400000000-a5cb265912cd3b36ec3f	Spectrum
GC-MS	gamma-Terpinene, non-derivatized, GC-MS Spectrum	splash10-0006-9500000000-2b0e829aa7638afa325e	Spectrum
GC-MS	gamma-Terpinene, non-derivatized, GC-MS Spectrum	splash10-0006-9200000000-85beacebb887bcf22446	Spectrum
Predicted GC-MS	gamma-Terpinene, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0006-9300000000-78ed493eae24d7cd7247	Spectrum
Predicted GC-MS	gamma-Terpinene, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-0019-8900000000-4f8f18604be188d356c8	2012-07-25	View Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-015c-9000000000-7cd3ebd6c5315af11ec5	2012-07-25	View Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-002f-9000000000-796d72dfa199c02320d2	2012-07-25	View Spectrum
MS/MS	LC-MS/MS Spectrum - EI-B (HITACHI M-80B) , Positive	splash10-0006-9200000000-ddf6ab2c599f6a3a0e04	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - EI-B (HITACHI M-80) , Positive	splash10-0006-9400000000-701e197e734bd825ea09	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - EI-B (HITACHI M-80) , Positive	splash10-0006-9500000000-156890c59245ff11b54d	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-Q-TOF/MS 25V, negative	splash10-000i-0900000000-98cfc7dd6d4b6ccbba0b	2020-07-21	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-Q-TOF/MS 30V, negative	splash10-0019-2900000000-898e1880d94396f2ba76	2020-07-21	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-000i-2900000000-7132f17a85333e784956	2015-04-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-000i-9700000000-f4bee8ac3721685bb606	2015-04-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-1000-9100000000-dbeffc46ec6acbacb6ef	2015-04-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-000i-0900000000-545d284bbb3189d5973d	2015-04-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-000i-0900000000-838b737755ef4340d8a2	2015-04-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-00ku-6900000000-6351b5255caae6105b15	2015-04-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-000m-9500000000-380389192d752a66b55d	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0036-9000000000-6d366a78065dacee15ff	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-00mo-9000000000-ce8dcdbeb3aaa0e18205	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	splash10-00kf-9600000000-571ac1102d9ec6dc4852	2021-09-23	View Spectrum

NMR

Type	Description	View
1D NMR	¹H NMR Spectrum (1D, 90 MHz, CDCl₃, experimental)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50.32 MHz, CDCl₃, experimental)	Spectrum
1D NMR	¹H NMR Spectrum (1D, CDCl₃, experimental)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, CDCl₃, experimental)	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 2 member 10	TAS2R10	12p13	Q9NYW0	details
Taste receptor type 2 member 16	TAS2R16	7q31.1-q31.3\|7q31	Q9NYV7	details
Taste receptor type 2 member 40	TAS2R40	7q34	P59535	details
Taste receptor type 2 member 3	TAS2R3	7q31.3-q32	Q9NYW6	details
Taste receptor type 2 member 4	TAS2R4	7q31.3-q32	Q9NYW5	details
Taste receptor type 2 member 7	TAS2R7	12p13	Q9NYW3	details
Taste receptor type 2 member 9	TAS2R9	12p13	Q9NYW1	details
Taste receptor type 2 member 50	TAS2R50	12p13.2	P59544	details
Taste receptor type 2 member 38	TAS2R38	7q34	P59533	details
Taste receptor type 2 member 31	TAS2R31	12p13.2	P59538	details
Taste receptor type 2 member 1	TAS2R1	5p15.31	Q9NYW7	details
Taste receptor type 2 member 20	TAS2R20	12p13.2	P59543	details
Taste receptor type 2 member 39	TAS2R39	7q34	P59534	details
Taste receptor type 2 member 19	TAS2R19	12p13.2	P59542	details
Taste receptor type 2 member 45	TAS2R45		P59539	details
Taste receptor type 2 member 30	TAS2R30	12p13.2	P59541	details
Taste receptor type 2 member 42	TAS2R42		Q7RTR8	details
Taste receptor type 2 member 41	TAS2R41	7q35	P59536	details
Taste receptor type 2 member 43	TAS2R43	12p13.2	P59537	details
Taste receptor type 2 member 5	TAS2R5	7q34	Q9NYW4	details
Taste receptor type 2 member 46	TAS2R46	12p13.2	P59540	details
Taste receptor type 2 member 13	TAS2R13	12p13.2	Q9NYV9	details
Taste receptor type 2 member 60	TAS2R60	7q35	P59551	details
Taste receptor type 2 member 8	TAS2R8	12p13.2	Q9NYW2	details
Taste receptor type 2 member 14	TAS2R14	12p13.2	Q9NYV8	details

Transcriptional Factors

Not Available

Concentrations Data

Cannabis Cultivar	Status	Value	Reference	Details
8-Ball Kush	Detected and Quantified	0.079 mg/g dry wt	PMID: 30036388	details
9 Lb Hammer	Detected and Quantified	0.069 mg/g dry wt	PMID: 30036388	details
Blue Dream	Detected and Quantified	0.078 mg/g dry wt	PMID: 30036388	details
Blue Dream	Detected and Quantified	0.117 mg/g dry wt	PMID: 30036388	details
Blue Dream	Detected and Quantified	0.199 mg/g dry wt	PMID: 30036388	details
Blue Dream	Detected and Quantified	0.21 mg/g dry wt	PMID: 30036388	details
Bob Marley	Detected and Quantified	0.076 mg/g dry wt	PMID: 30036388	details
Chemdawg #4	Detected and Quantified	0.089 mg/g dry wt	PMID: 30036388	details
Dairy Queen	Detected and Quantified	0.08 mg/g dry wt	PMID: 30036388	details
Dark Shadow Haze	Detected and Quantified	0.121 mg/g dry wt	PMID: 30036388	details
FLO	Detected and Quantified	0.077 mg/g dry wt	PMID: 30036388	details
Golden Cobra	Detected and Quantified	0.171 mg/g dry wt	PMID: 30036388	details
Golden Sage	Detected and Quantified	0.154 mg/g dry wt	PMID: 30036388	details
Grape Stomper	Detected and Quantified	0.097 mg/g dry wt	PMID: 30036388	details
Grape Stomper	Detected and Quantified	0.166 mg/g dry wt	PMID: 30036388	details
Grizzly Kush	Detected and Quantified	0.165 mg/g dry wt	PMID: 30036388	details
Hash Plant	Detected and Quantified	0.056 mg/g dry wt	PMID: 30036388	details
Hemlock	Detected and Quantified	0.163 mg/g dry wt	PMID: 30036388	details
Jack Herer	Detected and Quantified	0.14 mg/g dry wt	PMID: 30036388	details
Lemon Goji	Detected and Quantified	0.131 mg/g dry wt	PMID: 30036388	details
Lemon Sherbet	Detected and Quantified	0.12 mg/g dry wt	PMID: 30036388	details
Lemon Skunk	Detected and Quantified	0.095 mg/g dry wt	PMID: 30036388	details
Lemon Skunk	Detected and Quantified	0.138 mg/g dry wt	PMID: 30036388	details
Liberty Haze	Detected and Quantified	0.139 mg/g dry wt	PMID: 30036388	details
Lohan	Detected and Quantified	0.069 mg/g dry wt	PMID: 30036388	details
Lucky Charms	Detected and Quantified	0.095 mg/g dry wt	PMID: 30036388	details
Moonshine Ghost Trane Haze	Detected and Quantified	0.077 mg/g dry wt	PMID: 30036388	details
Nightmare Cookie	Detected and Quantified	0.09 mg/g dry wt	PMID: 30036388	details
Orange Skunk	Detected and Quantified	0.08 mg/g dry wt	PMID: 30036388	details
Pipe Dream	Detected and Quantified	0.095 mg/g dry wt	PMID: 30036388	details
Platinum Delight	Detected and Quantified	0.104 mg/g dry wt	PMID: 30036388	details
Rocket Fuel	Detected and Quantified	0.117 mg/g dry wt	PMID: 30036388	details
Rollex OG	Detected and Quantified	0.073 mg/g dry wt	PMID: 30036388	details
Rosetta Stone	Detected and Quantified	0.064 mg/g dry wt	PMID: 30036388	details
Satori	Detected and Quantified	0.096 mg/g dry wt	PMID: 30036388	details
Sensi Star	Detected and Quantified	0.1 mg/g dry wt	David S. Wishart,...	details
Sensi Star (Pure Indica)	Detected and Quantified	0.10 +/- 0.00 mg/g dry wt	David S. Wishart,...	details
Skunk Haze	Detected and Quantified	0.079 mg/g dry wt	PMID: 30036388	details
Star Bud	Detected and Quantified	0.073 mg/g dry wt	PMID: 30036388	details
Star Killer	Detected and Quantified	0.066 mg/g dry wt	PMID: 30036388	details
Tangerine Dream	Detected and Quantified	0.097 mg/g dry wt	PMID: 30036388	details
White Widow	Detected and Quantified	0.112 mg/g dry wt	PMID: 30036388	details

External Links

HMDB ID

HMDB0005806

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

7461

PDB ID

Not Available

ChEBI ID

10577

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 ]
Rice S, Koziel JA: Characterizing the Smell of Marijuana by Odor Impact of Volatile Compounds: An Application of Simultaneous Chemical and Sensory Analysis. PLoS One. 2015 Dec 10;10(12):e0144160. doi: 10.1371/journal.pone.0144160. eCollection 2015. [PubMed:26657499 ]

Only showing the first 10 proteins. There are 25 proteins in total.

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Only showing the first 10 proteins. There are 25 proteins in total.

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Showing Compound Card for gamma-Terpinene (CDB000208)

Structure for CDB000208 (gamma-Terpinene)