Record Information
Version1.0
Creation date2010-04-08 22:12:09 UTC
Update date2018-05-29 01:23:50 UTC
Primary IDFDB015966
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameTerpinolene
DescriptionConstituent of many essential oils e.g. Citrus, Mentha, Juniperus, Myristica subspecies Parsnip oil (Pastinaca sativa) is a major source (40-70%). Flavouring ingredient. Terpinolene is found in many foods, some of which are coriander, ceylon cinnamon, pine nut, and caraway.
CAS Number586-62-9
Structure
Thumb
Synonyms
SynonymSource
1,4(8)-p-MenthadieneChEBI
1-Methyl-4-(1-methylethylidene)-1-cyclohexeneChEBI
1-Methyl-4-(1-methylethylidene)cyclohexeneChEBI
4-Isopropylidene-1-methylcyclohexeneChEBI
alpha-TerpinoleneChEBI
IsoterpineneChEBI
TerpinolenChEBI
a-TerpinoleneGenerator
Α-terpinoleneGenerator
1,4(8)-TerpadieneHMDB
1-Methyl-4-(1-methylethylidene)-cyclohexeneHMDB
1-Methyl-4-(1-methylethylidene)cyclohexene, 9ciHMDB
1-Methyl-4-(propan-2-ylidene)cyclohexeneHMDB
1-Methyl-4-isopropylidene-1-cyclohexeneHMDB
4-Isopropylidene-1-methyl-cyclohexeneHMDB
alpha -TerpinoleneHMDB
Cyclohexene, 3-methyl-6-(1-methylethylidene)- (9ci)HMDB
FEMA 3046HMDB
α-Terpinolenebiospider
1-Methyl-4-(1-methylethylidene)cyclohexene, 9CIdb_source
Cyclohexene, 1-methyl-4-(1-methylethylidene)-biospider
Cyclohexene, 3-methyl-6-(1-methylethylidene)- (9CI)biospider
Terpinolenedb_source
α-terpinoleneGenerator
Predicted Properties
PropertyValueSource
Water Solubility1.38 g/LALOGPS
logP3.82ALOGPS
logP3.12ChemAxon
logS-2ALOGPS
Physiological Charge0ChemAxon
Hydrogen Acceptor Count0ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area0 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity47.29 m³·mol⁻¹ChemAxon
Polarizability17.76 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC10H16
IUPAC name1-methyl-4-(propan-2-ylidene)cyclohex-1-ene
InChI IdentifierInChI=1S/C10H16/c1-8(2)10-6-4-9(3)5-7-10/h4H,5-7H2,1-3H3
InChI KeyMOYAFQVGZZPNRA-UHFFFAOYSA-N
Isomeric SMILESCC(C)=C1CCC(C)=CC1
Average Molecular Weight136.238
Monoisotopic Molecular Weight136.125200515
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.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassMonoterpenoids
Direct ParentMenthane 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 FrameworkAliphatic homomonocyclic compounds
External Descriptors
Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionC 88.16%; H 11.84%DFC
Melting Point< 25 oC
Boiling PointBp 186°DFC
Experimental Water Solubility0.0095 mg/mL at 23 oCLI,J et al.(1998)
Experimental logP4.47LI,J ET AL (1998)
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
Densityd2020 0.86DFC
Refractive Indexn20D 1.4900DFC
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-009f-9400000000-68d00c428f3eca0ec8a8View in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-001l-9400000000-960c0e59a9b4fbc2f209View in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-009f-9400000000-68d00c428f3eca0ec8a8View in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-001l-9400000000-960c0e59a9b4fbc2f209View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-006x-9300000000-9316ff5aec80ce021334View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-3900000000-b14825d366b8c8e2ab12View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000j-9500000000-18b9e19b4b2f2fd07710View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-1000-9100000000-59a2560a612381b96a85View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0900000000-954e07bd601b6ad95425View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-1900000000-e9d35affdc69e9aca942View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-014u-6900000000-e560043bc5cf9af10365View in MoNA
MSMass Spectrum (Electron Ionization)splash10-0006-9400000000-2d00513ea08f32f70cc4View in MoNA
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
ChemSpider ID10979
ChEMBL IDCHEMBL454697
KEGG Compound IDC06075
Pubchem Compound ID11463
Pubchem Substance IDNot Available
ChEBI ID9457
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB36994
CRC / DFC (Dictionary of Food Compounds) IDKLQ41-R:KLQ41-R
EAFUS ID3610
Dr. Duke IDTERPINOLENE|ALPHA-TERPINOLENE
BIGG IDNot Available
KNApSAcK IDC00000861
HET IDNot Available
Flavornet ID586-62-9
GoodScent IDrw1007171
SuperScent ID11463
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / Bioactivities
DescriptorIDDefinitionReference
allelochemicDUKE
anti feedantDUKE
anti nitrosaminicDUKE
antioxidant22586 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
deodorantDUKE
flavor48318 A substance, extract, or preparation for diffusing or imparting an agreeable or attractive smell.DUKE
fungicide24127 A substance used to destroy fungal pests.DUKE
perfumery48318 A substance, extract, or preparation for diffusing or imparting an agreeable or attractive smell.DUKE
pesticide25944 Strictly, a substance intended to kill pests. In common usage, any substance used for controlling, preventing, or destroying animal, microbiological or plant pests.DUKE
sedative35717 A central nervous system depressant used to induce drowsiness or sleep or to reduce psychological excitement or anxiety.CHEBI
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
Flavours
FlavorCitations
pine
  1. 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
  2. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
plastic
  1. 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
  2. Dunkel, M. et al. SuperScent – a database of flavors and scents. Nucleic Acids Research 2008, doi:10.1093/nar/gkn695
fresh
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
woody
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
sweet
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
citrus
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).
— Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.