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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2012-09-11 22:14:18 UTC
Update Date2022-03-07 02:55:08 UTC
HMDB IDHMDB0036995
Secondary Accession Numbers
  • HMDB36995
Metabolite 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 ). ±-Terpinene is a flavouring agent and is produced industrially by acid-catalyzed rearrangement of ±-pinene. It has perfume and flavoring properties but is mainly used to confer a pleasant odor to industrial fluids.
Structure
Data?1563862962
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 Weight136.238
Monoisotopic Molecular Weight136.125200515
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

Biological location

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point< 25 °CNot Available
Boiling Point173.00 to 175.00 °C. @ 760.00 mm HgThe Good Scents Company Information System
Water Solubility5.92 mg/L @ 25 °C (est)The Good Scents Company Information System
LogP4.25Not Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular 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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+131.57731661259
DarkChem[M-H]-128.2131661259
DeepCCS[M+H]+139.3830932474
DeepCCS[M-H]-136.05830932474
DeepCCS[M-2H]-172.95830932474
DeepCCS[M+Na]+148.49630932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
alpha-TerpineneCC(C)C1=CC=C(C)CC11160.6Standard polar33892256
alpha-TerpineneCC(C)C1=CC=C(C)CC1980.8Standard non polar33892256
alpha-TerpineneCC(C)C1=CC=C(C)CC11021.7Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - alpha-Terpinene EI-B (Non-derivatized)splash10-006x-9500000000-e60fb974334faa2cf6252017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - alpha-Terpinene EI-B (Non-derivatized)splash10-00du-6900000000-41fde84dbd73528ad68f2017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - alpha-Terpinene EI-B (Non-derivatized)splash10-006x-9500000000-e60fb974334faa2cf6252018-05-18HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - alpha-Terpinene EI-B (Non-derivatized)splash10-00du-6900000000-41fde84dbd73528ad68f2018-05-18HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - alpha-Terpinene GC-EI-Q (Non-derivatized)splash10-006x-9500000000-e78a04a46a017816d9f92020-07-08HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - alpha-Terpinene GC-MS (Non-derivatized) - 70eV, Positivesplash10-006x-9300000000-9e298f76f2606ff289fa2016-09-22Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - alpha-Terpinene GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
MSMass Spectrum (Electron Ionization)splash10-0096-9400000000-322df4fdc907d6ef5f6f2015-03-01Not AvailableView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - alpha-Terpinene 10V, Positive-QTOFsplash10-000i-2900000000-52130a4409b06401c2772015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - alpha-Terpinene 20V, Positive-QTOFsplash10-000i-9700000000-349bdb9de1ad5c9d79172015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - alpha-Terpinene 40V, Positive-QTOFsplash10-1000-9100000000-4f3636bfa36656ebc3502015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - alpha-Terpinene 10V, Negative-QTOFsplash10-000i-0900000000-954e07bd601b6ad954252015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - alpha-Terpinene 20V, Negative-QTOFsplash10-000i-0900000000-e41a6714348b3249ddac2015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - alpha-Terpinene 40V, Negative-QTOFsplash10-014u-5900000000-9a9e0414dcb34d9209832015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - alpha-Terpinene 10V, Positive-QTOFsplash10-000j-9600000000-17d717eb220781ad4cc12021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - alpha-Terpinene 20V, Positive-QTOFsplash10-0536-9100000000-3f771329175d59bc664c2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - alpha-Terpinene 40V, Positive-QTOFsplash10-00mo-9000000000-68b4409b06699bad322f2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - alpha-Terpinene 10V, Negative-QTOFsplash10-000i-0900000000-a013b4ae27f975ab56212021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - alpha-Terpinene 20V, Negative-QTOFsplash10-000i-0900000000-a013b4ae27f975ab56212021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - alpha-Terpinene 40V, Negative-QTOFsplash10-00kf-9400000000-20ffbcb6b8f03ba79f672021-09-24Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biospecimen Locations
  • Saliva
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Not SpecifiedNormal details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB 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
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1016031
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Parveen M, Hasan MK, Takahashi J, Murata Y, Kitagawa E, Kodama O, Iwahashi H: Response of Saccharomyces cerevisiae to a monoterpene: evaluation of antifungal potential by DNA microarray analysis. J Antimicrob Chemother. 2004 Jul;54(1):46-55. Epub 2004 Jun 16. [PubMed:15201226 ]
  2. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
  3. Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
  4. Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
  5. Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
  6. 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 ]
  7. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .
  8. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.