Record Information
Version1.0
Creation date2010-04-08 22:07:38 UTC
Update date2018-05-29 00:41:35 UTC
Primary IDFDB007475
Secondary Accession Numbers
  • FDB015967
  • FDB003993
Chemical Information
FooDB NameTerpenene
DescriptionAlpha-terpinene, also known as 1-isopropyl-4-methyl-1,3-cyclohexadiene or 1-methyl-4-(1-methylethyl)-1,3-cyclohexadiene, is a member of the class of compounds known as menthane monoterpenoids. Menthane monoterpenoids 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, alpha-terpinene is considered to be an isoprenoid lipid molecule. Alpha-terpinene is a camphoraceous, citrus, and herbal tasting compound and can be found in a number of food items such as summer savory, cabbage, pot marjoram, and wild celery, which makes alpha-terpinene a potential biomarker for the consumption of these food products. Alpha-terpinene can be found primarily in saliva. Alpha-terpinene exists in all eukaryotes, ranging from yeast to humans.
CAS NumberNot Available
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
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
Ontology
OntologyShould have ontology for this compound
Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionNot Available
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
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 IDNot Available
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound IDNot Available
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDNot Available
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDTERPENENE
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
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 / BioactivitiesNot Available
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
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).