Record Information
Version1.0
Creation date2010-04-08 22:12:09 UTC
Update date2018-05-29 01:23:52 UTC
Primary IDFDB015967
Secondary Accession NumbersNot Available
Chemical Information
FooDB Namealpha-Terpinene
DescriptionConstituent of many essential oils e.g. Citrus, Eucalyptus and Juniperus subspecies Oil of Litsea ceylanica is a major source (20%). Flavouring agent The terpinenes are three isomeric hydrocarbons that are classified as terpenes. They each have the same molecular formula and carbon framework, but they differ in the position of carbon-carbon double bonds. alpha-Terpinene has been isolated from cardamom and marjoram oils, and from other natural sources. beta-Terpinene has no known natural source, but has been prepared synthetically from sabinene. gamma-Terpinene is natural and has been isolated from a variety of plant sources. alpha-Terpinene is found in many foods, some of which are common oregano, allspice, cardamom, and sweet bay.
CAS Number99-86-5
Structure
Thumb
Synonyms
SynonymSource
1-Isopropyl-4-methyl-1,3-cyclohexadieneChEBI
1-Methyl-4-(1-methylethyl)-1,3-cyclohexadieneChEBI
p-Mentha-1,3-dieneChEBI
TerpileneChEBI
a-TerpineneGenerator
Α-terpineneGenerator
1-Isopropyl-4-methyl-cyclohexa-1,3-dieneHMDB
1-Isopropyl-4-methylcyclohexa-1,3-dieneHMDB
1-Methyl-4-(propan-2-yl)cyclohexa-1,3-dieneHMDB
1-Methyl-4-isopropyl-1,3-cyclohexadieneHMDB
1-Methyl-4-isopropylcyclohexadiene-1,3HMDB
alpha -TerpineneHMDB
FEMA 3558HMDB
1,4-p-MenthadieneMeSH
beta-TerpineneMeSH
gamma-TerpineneMeSH
α-Terpinenebiospider
1,3-Cyclohexadiene, 1-methyl-4-(1-methylethyl)-biospider
1,3-Cyclohexadiene, 1-methyl-4-isopropyl-biospider
alpha-Terpinenebiospider
P-Mentha-1,3-dieneChEBI
α-terpineneGenerator
Predicted Properties
PropertyValueSource
Water Solubility0.5 g/LALOGPS
logP4.51ALOGPS
logP3.16ChemAxon
logS-2.4ALOGPS
Physiological Charge0ChemAxon
Hydrogen Acceptor Count0ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area0 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity47.55 m³·mol⁻¹ChemAxon
Polarizability17.59 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC10H16
IUPAC name1-methyl-4-(propan-2-yl)cyclohexa-1,3-diene
InChI IdentifierInChI=1S/C10H16/c1-8(2)10-6-4-9(3)5-7-10/h4,6,8H,5,7H2,1-3H3
InChI KeyYHQGMYUVUMAZJR-UHFFFAOYSA-N
Isomeric SMILESCC(C)C1=CC=C(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
  • 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 PointBp755 173.5-174.8°DFC
Experimental Water SolubilityNot Available
Experimental logP4.25GRIFFIN,S ET AL. (1999)
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive Indexn20D 1.4780DFC
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-006x-9500000000-e60fb974334faa2cf625View in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-00du-6900000000-41fde84dbd73528ad68fView in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-006x-9500000000-e60fb974334faa2cf625View in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-00du-6900000000-41fde84dbd73528ad68fView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-006x-9300000000-9e298f76f2606ff289faView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-2900000000-52130a4409b06401c277View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-9700000000-349bdb9de1ad5c9d7917View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-1000-9100000000-4f3636bfa36656ebc350View 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-0900000000-e41a6714348b3249ddacView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-014u-5900000000-9a9e0414dcb34d920983View in MoNA
MSMass Spectrum (Electron Ionization)splash10-0096-9400000000-322df4fdc907d6ef5f6fView in MoNA
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
ChemSpider ID7182
ChEMBL IDCHEMBL2251642
KEGG Compound IDC09898
Pubchem Compound ID7462
Pubchem Substance IDNot Available
ChEBI ID10334
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB36995
CRC / DFC (Dictionary of Food Compounds) IDKLQ42-S:KLQ42-S
EAFUS ID3607
Dr. Duke IDALPHA-TERPINENE|MENTHA-1,3-DIENE
BIGG IDNot Available
KNApSAcK IDC00003060
HET IDNot Available
Flavornet ID99-86-5
GoodScent IDrw1016031
SuperScent ID7462
Wikipedia IDTerpinene
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
acaricide22153 A substance used to destroy pests of the subclass Acari (mites and ticks).DUKE
angiotensin converting enzyme inhibitor35457 An EC 3.4.15.* (peptidyl-dipeptidase) inhibitor that interferes with the action of peptidyl-dipeptidase A (EC 3.4.15.1).DUKE
aldose reductase inhibitor48550 An EC 1.1.1.* (oxidoreductase acting on donor CH-OH group, NAD(+) or NADP(+) acceptor) inhibitor that interferes with the action of aldehyde reductase (EC 1.1.1.21).DUKE
anti acetylcholinesterase38462 An EC 3.1.1.* (carboxylic ester hydrolase) inhibitor that interferes with the action of enzyme acetylcholinesterase (EC 3.1.1.7), which helps breaking down of acetylcholine into choline and acetic acid.DUKE
anti nitrosaminicDUKE
anti spasmodic52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
flavor48318 A substance, extract, or preparation for diffusing or imparting an agreeable or attractive smell.DUKE
insecticide24852 Strictly, a substance intended to kill members of the class Insecta. In common usage, any substance used for preventing, destroying, repelling or controlling insects.DUKE
insectifuge24852 Strictly, a substance intended to kill members of the class Insecta. In common usage, any substance used for preventing, destroying, repelling or controlling insects.DUKE
cytochrome-P450-2B1 inhibitor50183 An enzyme inhibitor that interferes with the activity of cytochrome P450 involved in catalysis of organic substances.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
spasmogenicDUKE
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
Flavours
FlavorCitations
lemon
  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.
camphoraceous
  1. Dunkel, M. et al. SuperScent – a database of flavors and scents. Nucleic Acids Research 2008, doi:10.1093/nar/gkn695
woody
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
terpene
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
herbal
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
medicinal
  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.