Showing Compound gamma-Terpinene (FDB015968)

Record Information

Version

1.0

Creation date

2010-04-08 22:12:09 UTC

Update date

2020-09-17 15:31:31 UTC

Primary ID

FDB015968

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

gamma-Terpinene

Description

gamma-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. gamma-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.

CAS Number

99-85-4

Structure

MOL SDF PDB SMILES InChI

Synonyms

Synonym	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
1-Isopropyl-4-methyl-cyclohexa-1,4-diene	biospider
1-Methyl-4-(1-methylethyl)-1,4-cyclohexadiene, 9CI	db_source
1-Methyl-4-isopropylcyclohexadiene-1,4	biospider
1,4-Cyclohexadiene, 1-methyl-4-(1-methylethyl)-	biospider
1,4-Cyclohexadiene, 1-methyl-4-isopropyl-	biospider
FEMA 3559	db_source
gamma-terpinene	biospider
P-Mentha-1,4-diene	ChEBI
γ-terpinene	Generator

Predicted Properties

Property	Value	Source
Water Solubility	0.54 g/L	ALOGPS
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

Chemical Formula

C10H16

IUPAC name

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

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

Isomeric SMILES

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

Average Molecular Weight

136.238

Monoisotopic Molecular Weight

136.125200515

Classification

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:

Process

Naturally occurring process:

Biological process:

Cellular process:

Cell signaling

Role

Industrial application:

Biological role:

Physico-Chemical Properties

Physico-Chemical Properties - Experimental

Property	Value	Reference
Physical state	Liquid
Physical Description	Not Available
Mass Composition	C 88.16%; H 11.84%	DFC
Melting Point	-10 oC
Boiling Point	Bp 183°	DFC
Experimental Water Solubility	0.00868 mg/mL at 22 oC	LI,J & PERDUE,EM (1995)
Experimental logP	4.50	LI,J & PERDUE,EM (1995)
Experimental pKa	Not Available
Isoelectric point	Not Available
Charge	Not Available
Optical Rotation	Not Available
Spectroscopic UV Data	Not Available
Density	Not Available
Refractive Index	Not Available

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

External Links

ChemSpider ID

ChEMBL ID

KEGG Compound ID

Pubchem Compound ID

Pubchem Substance ID

Not Available

ChEBI ID

Not Available

Phenol-Explorer ID

Not Available

DrugBank ID

Not Available

HMDB ID

HMDB05806

CRC / DFC (Dictionary of Food Compounds) ID

KLQ43-T:KLQ43-T

EAFUS ID

3606

Dr. Duke ID

GAMMA-TERPINENE

BIGG ID

Not Available

KNApSAcK ID

C00003061

HET ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

Flavornet ID

99-85-4

GoodScent ID

rw1017031

SuperScent ID

Not Available

Wikipedia ID

Terpinene

Phenol-Explorer Metabolite ID

Not Available

Duplicate IDS

Not Available

Old DFC IDS

Not Available

Associated Foods

Food	Content Range	Average	Reference
Food			Reference

Biological Effects and Interactions

Health Effects / Bioactivities

Descriptor	ID	Definition	Reference
Acaricide	22153	An agent that kills mites and ticks, used to control infestations and prevent diseases like scabies and tick-borne illnesses. Therapeutically, acaricides are applied topically or systemically to treat parasitic infections, reducing discomfort and preventing disease transmission. Key medical uses include treating acariasis, demodectic mange, and tick paralysis.	DUKE
Angiotensin converting enzyme inhibitor	35457	An agent that blocks the conversion of angiotensin I to angiotensin II, reducing blood pressure and fluid retention. Therapeutically, it's used to treat hypertension, heart failure, and protect kidney function in diabetes, thereby reducing the risk of cardiovascular disease and stroke.	DUKE
Aldose reductase inhibitor	48550	An agent that blocks the activity of aldose reductase, an enzyme involved in glucose metabolism. It reduces oxidative stress and inflammation, commonly used in managing diabetic complications, such as neuropathy, nephropathy, and retinopathy.	DUKE
Anti acetylcholinesterase	38462	An agent that inhibits acetylcholinesterase, increasing acetylcholine levels. It enhances cholinergic transmission, used therapeutically to treat Alzheimer's disease, myasthenia gravis, and glaucoma, improving cognitive function, muscle strength, and reducing intraocular pressure.	DUKE
Anti feedant		A substance that inhibits normal feeding behavior, found in certain plants, deterring insects and animals from consuming them. Its therapeutic applications include pest control, while key medical uses involve managing insect-borne diseases and reducing crop damage.	DUKE
Anti-oxidant	22586	An agent that neutralizes free radicals, reducing oxidative stress and cell damage. Its biological role involves protecting cells from harm, and it has therapeutic applications in managing chronic diseases, such as cancer, diabetes, and neurodegenerative disorders, with key medical uses including anti-aging, anti-inflammatory, and cardio protective effects.	DUKE
Name	48318	flavor	DUKE
Insectifuge	24852	A substance that repels insects, playing a biological role in plant defense. Therapeutically, it has applications in preventing insect-borne diseases. Key medical uses include topical repellents for malaria, dengue fever, and other vector-borne illnesses, reducing the risk of transmission.	DUKE
Irritant		An agent that causes slight inflammation or discomfort, stimulating a biological response. Therapeutically, it can be used to increase blood flow or stimulate healing. Key medical uses include treating wounds, skin conditions, and respiratory issues, such as congestion, by inducing a mild inflammatory response to promote recovery.	DUKE
Perfumery	48318	The art of creating fragrances, playing a biological role in emotional and sensory stimulation. Therapeutically, perfumery has applications in aromatherapy, reducing stress and anxiety. Key medical uses include mood enhancement, pain management, and promoting relaxation, with certain scents exhibiting anti-anxiety and anti-depressant properties.	DUKE
Pesticide	25944	An agent that kills or repels pests, playing a biological role in controlling insect, weed, and fungal populations. Therapeutically, pesticides have limited applications, but some are used to treat ectoparasitic infestations, such as lice and scabies. Key medical uses include topical treatments for head lice and scabies, highlighting their role in managing parasitic infections.	DUKE

Enzymes

Not Available

Pathways

Not Available

Metabolism

Not Available

Biosynthesis

Not Available

Organoleptic Properties

Flavours

Flavor	Citations
gasoline	Arn, H, Acree TE. “Flavornet: A database of aroma compounds based on odor potency in natural products”. Developments in Food Science 40 (1998): 27. doi:10.1016/S0167-4501(98)80029-0
turpentine	Arn, H, Acree TE. “Flavornet: A database of aroma compounds based on odor potency in natural products”. Developments in Food Science 40 (1998): 27. doi:10.1016/S0167-4501(98)80029-0
lime	The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
oily	The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
woody	The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
terpene	The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
lemon	The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
tropical	The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
herbal	The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
bitter	Ayana Wiener, Marina Shudler, Anat Levit, Masha Y. Niv. BitterDB: a database of bitter compounds. Nucleic Acids Res 2012, 40(Database issue):D413-419. DOI:10.1093/nar/gkr755