Showing Compound Card for alpha-Terpinene (CDB000207)

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Record Information
Version1.0
Created at2020-03-18 23:28:44 UTC
Updated at2020-12-07 19:07:15 UTC
CannabisDB IDCDB000207
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common Namealpha-Terpinene
DescriptionAlpha-Terpinene is one of four isomers of terpinene (the other three being beta terpinene, gamma terpenine, and delta terpinine or terpimolene) that differ in the position of carbon-carbon double bonds. Alpha-Terpinene belongs to the class of organic compounds known as menthane monoterpenes. These are monoterpenes 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. alpha-Terpinene is a naturally occurring monoterpene found in allspice, cardamom, and marjoram. alpha-Terpinene is a constituent of many essential oils with oil from Litsea ceylanica being is a major source (20%) of it. alpha-Terpinene has been found in Citrus, Eucalyptus and Juniperus species, and cannabis plants (PMID:6991645 ). α-Terpinene is a flavouring agent and is produced industrially by acid-catalyzed rearrangement of α-pinene. It has perfume and flavoring properties but is mainly used to confer a pleasant odor to industrial fluids.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
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-MenthadieneHMDB
beta-TerpineneHMDB
gamma-TerpineneHMDB
4-Isopropyl-1-methyl-1,3-cyclohexadienePhytoBank
alpha-TerpinenPhytoBank
α-TerpinenPhytoBank
alpha-TerpinenePhytoBank
Chemical FormulaC10H16
Average Molecular Weight136.24
Monoisotopic Molecular Weight136.1252
IUPAC Name1-methyl-4-(propan-2-yl)cyclohexa-1,3-diene
Traditional Nameterpinene
CAS Registry Number99-86-5
SMILES
CC(C)C1=CC=C(C)CC1
InChI Identifier
InChI=1S/C10H16/c1-8(2)10-6-4-9(3)5-7-10/h4,6,8H,5,7H2,1-3H3
InChI KeyYHQGMYUVUMAZJR-UHFFFAOYSA-N
Chemical Taxonomy
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
Disposition

Route of exposure:

Source:

Biological location:

Role

Industrial application:

Biological role:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point< 25 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
logP4.25Not Available
Predicted Properties
PropertyValueSource
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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
EI-MSMass Spectrum (Electron Ionization)splash10-0096-9400000000-322df4fdc907d6ef5f6f2015-03-01View Spectrum
GC-MSalpha-Terpinene, non-derivatized, GC-MS Spectrumsplash10-006x-9500000000-e60fb974334faa2cf625Spectrum
GC-MSalpha-Terpinene, non-derivatized, GC-MS Spectrumsplash10-00du-6900000000-41fde84dbd73528ad68fSpectrum
GC-MSalpha-Terpinene, non-derivatized, GC-MS Spectrumsplash10-006x-9500000000-e60fb974334faa2cf625Spectrum
GC-MSalpha-Terpinene, non-derivatized, GC-MS Spectrumsplash10-00du-6900000000-41fde84dbd73528ad68fSpectrum
GC-MSalpha-Terpinene, non-derivatized, GC-MS Spectrumsplash10-006x-9500000000-e78a04a46a017816d9f9Spectrum
Predicted GC-MSalpha-Terpinene, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-006x-9300000000-9e298f76f2606ff289faSpectrum
Predicted GC-MSalpha-Terpinene, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-2900000000-52130a4409b06401c2772015-04-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-9700000000-349bdb9de1ad5c9d79172015-04-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-1000-9100000000-4f3636bfa36656ebc3502015-04-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0900000000-954e07bd601b6ad954252015-04-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-0900000000-e41a6714348b3249ddac2015-04-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-014u-5900000000-9a9e0414dcb34d9209832015-04-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000j-9600000000-17d717eb220781ad4cc12021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0536-9100000000-3f771329175d59bc664c2021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00mo-9000000000-68b4409b06699bad322f2021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0900000000-a013b4ae27f975ab56212021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-0900000000-a013b4ae27f975ab56212021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00kf-9400000000-20ffbcb6b8f03ba79f672021-09-24View Spectrum
NMR
TypeDescriptionView
1D NMR1H NMR Spectrum (1D, 400 MHz, CDCl3, experimental)Spectrum
1D NMR13C NMR Spectrum (1D, 15.09 MHz, CDCl3, experimental)Spectrum
Pathways
Pathways
Protein Targets
EnzymesNot Available
TransportersNot Available
Metal BindingsNot Available
ReceptorsNot Available
Transcriptional FactorsNot Available
Concentrations Data
Cannabis CultivarStatusValueReferenceDetails
Blue DreamDetected and Quantified0.137 mg/g dry wt details
Blue DreamDetected and Quantified0.178 mg/g dry wt details
Blue DreamDetected and Quantified0.283 mg/g dry wt details
Blue DreamDetected and Quantified0.291 mg/g dry wt details
Dairy QueenDetected and Quantified0.115 mg/g dry wt details
Dark Shadow HazeDetected and Quantified0.114 mg/g dry wt details
Golden SageDetected and Quantified0.251 mg/g dry wt details
Grizzly KushDetected and Quantified0.142 mg/g dry wt details
HemlockDetected and Quantified0.156 mg/g dry wt details
Lemon SherbetDetected and Quantified0.134 mg/g dry wt details
Lemon SkunkDetected and Quantified0.166 mg/g dry wt details
LohanDetected and Quantified0.084 mg/g dry wt details
Sensi StarDetected and Quantified0.12 mg/g dry wt
    • David S. Wishart,...
 details
Sensi Star (Pure Indica)Detected and Quantified0.13 +/- 0.01 mg/g dry wt
    • David S. Wishart,...
 details
White WidowDetected and Quantified0.151 mg/g dry wt details
HMDB IDHMDB0036995
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB007475
KNApSAcK IDC00003060
Chemspider ID7182
KEGG Compound IDC09898
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkTerpinene
METLIN IDNot Available
PubChem Compound7462
PDB IDNot Available
ChEBI ID10334
References
General References
  1. Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. [PubMed:6991645 ]