Showing Compound Terpinolene (FDB015966)

Record Information

Version

1.0

Creation date

2010-04-08 22:12:09 UTC

Update date

2019-11-26 03:12:30 UTC

Primary ID

FDB015966

Secondary Accession Numbers

FDB007967

Chemical Information

FooDB Name

Terpinolene

Description

Terpinolene, 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 molecule, practically insoluble (in water), and relatively neutral. Terpinolene is a potentially toxic compound.

CAS Number

586-62-9

Structure

MOL SDF PDB SMILES InChI

Synonyms

Synonym	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
α-Terpinolene	biospider
1-Methyl-4-(1-methylethylidene)cyclohexene, 9CI	db_source
Cyclohexene, 1-methyl-4-(1-methylethylidene)-	biospider
Cyclohexene, 3-methyl-6-(1-methylethylidene)- (9CI)	biospider
α-terpinolene	Generator

Predicted Properties

Property	Value	Source
Water Solubility	1.38 g/L	ALOGPS
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	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Chemical Formula

C10H16

IUPAC name

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

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

Isomeric SMILES

CC(C)=C1CCC(C)=CC1

Average Molecular Weight

136.238

Monoisotopic Molecular Weight

136.125200515

Classification

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

Process

Naturally occurring process:

Biological process:

Biochemical process:

Chemical reaction:

Lipid peroxidation

Biochemical pathway:

Cellular process:

Cell signaling

Role

Industrial application:

Food and nutrition:

Flavoring agent

Biological role:

Physico-Chemical Properties - Experimental

Property	Value	Reference
Physical state	Not Available
Physical Description	Not Available
Mass Composition	C 88.16%; H 11.84%	DFC
Melting Point	< 25 oC
Boiling Point	Bp 186°	DFC
Experimental Water Solubility	0.0095 mg/mL at 23 oC	LI,J et al.(1998)
Experimental logP	4.47	LI,J ET AL (1998)
Experimental pKa	Not Available
Isoelectric point	Not Available
Charge	Not Available
Optical Rotation	Not Available
Spectroscopic UV Data	Not Available
Density	d2020 0.86	DFC
Refractive Index	n20D 1.4900	DFC

Spectra

Spectrum Type	Description	Splash Key	View
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-009f-9400000000-68d00c428f3eca0ec8a8	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-001l-9400000000-960c0e59a9b4fbc2f209	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-009f-9400000000-68d00c428f3eca0ec8a8	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-001l-9400000000-960c0e59a9b4fbc2f209	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - GC-EI-Q (Non-derivatized)	splash10-0006-9500000000-3a9b5aafe573ed72e592	JSpectraViewer \| MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-006x-9300000000-9316ff5aec80ce021334	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-000i-3900000000-b14825d366b8c8e2ab12	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-000j-9500000000-18b9e19b4b2f2fd07710	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-1000-9100000000-59a2560a612381b96a85	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-000i-0900000000-954e07bd601b6ad95425	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-000i-1900000000-e9d35affdc69e9aca942	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-014u-6900000000-e560043bc5cf9af10365	JSpectraViewer
MS	Mass Spectrum (Electron Ionization)	splash10-0006-9400000000-2d00513ea08f32f70cc4	JSpectraViewer \| MoNA
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer

External Links

ChemSpider ID

ChEMBL ID

KEGG Compound ID

Pubchem Compound ID

Pubchem Substance ID

Not Available

ChEBI ID

9457

Phenol-Explorer ID

Not Available

DrugBank ID

Not Available

HMDB ID

HMDB36994

CRC / DFC (Dictionary of Food Compounds) ID

KLQ41-R:KLQ41-R

EAFUS ID

3610

Dr. Duke ID

TERPINOLENE|ALPHA-TERPINOLENE

BIGG ID

Not Available

KNApSAcK ID

C00000861

HET ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

Flavornet ID

586-62-9

GoodScent ID

rw1007171

SuperScent ID

11463

Wikipedia ID

Not Available

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
allelochemic			DUKE
anti feedant			DUKE
anti nitrosaminic			DUKE
antioxidant	22586	A substance that opposes oxidation or inhibits reactions brought about by dioxygen or peroxides. In European countries, E-numbers for permitted antioxidant food additives are from E 300 to E 324.	DUKE
deodorant			DUKE
flavor	48318	A substance, extract, or preparation for diffusing or imparting an agreeable or attractive smell.	DUKE
fungicide	24127	A substance used to destroy fungal pests.	DUKE
perfumery	48318	A substance, extract, or preparation for diffusing or imparting an agreeable or attractive smell.	DUKE
pesticide	25944	Strictly, a substance intended to kill pests. In common usage, any substance used for controlling, preventing, or destroying animal, microbiological or plant pests.	DUKE
sedative	35717	A central nervous system depressant used to induce drowsiness or sleep or to reduce psychological excitement or anxiety.	CHEBI

Enzymes

Not Available

Pathways

Not Available

Metabolism

Not Available

Biosynthesis

Not Available

Organoleptic Properties

Flavours

Flavor	Citations
pine	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 The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
plastic	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 Dunkel, M. et al. SuperScent – a database of flavors and scents. Nucleic Acids Research 2008, doi:10.1093/nar/gkn695
fresh	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.
sweet	The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
citrus	The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.