ALPHA-TERPINENE (CHEM007618)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-19 02:28:10 UTC
Update Date2016-11-09 01:13:38 UTC
Accession NumberCHEM007618
Identification
Common NameALPHA-TERPINENE
ClassSmall Molecule
DescriptionOne of three isomeric monoterpenes differing in the positions of their two double bonds (beta- and gamma-terpinene being the others). In alpha-terpinene the double bonds are at the 1- and 3-positions of the p-menthane skeleton.
Contaminant Sources
  • EAFUS Chemicals
  • FooDB Chemicals
  • HPV EPA Chemicals
  • ToxCast & Tox21 Chemicals
Contaminant TypeNot Available
Chemical 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 Mass136.238 g/mol
Monoisotopic Mass136.125 g/mol
CAS Registry Number99-86-5
IUPAC Name1-methyl-4-(propan-2-yl)cyclohexa-1,3-diene
Traditional Nameterpinene
SMILESCC(C)C1=CC=C(C)CC1
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
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
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
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 FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-006x-9500000000-e60fb974334faa2cf625Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-00du-6900000000-41fde84dbd73528ad68fSpectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-006x-9500000000-e60fb974334faa2cf625Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-00du-6900000000-41fde84dbd73528ad68fSpectrum
GC-MSGC-MS Spectrum - GC-EI-Q (Non-derivatized)splash10-006x-9500000000-e78a04a46a017816d9f9Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-006x-9300000000-9e298f76f2606ff289faSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-2900000000-52130a4409b06401c277Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-9700000000-349bdb9de1ad5c9d7917Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-1000-9100000000-4f3636bfa36656ebc350Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0900000000-954e07bd601b6ad95425Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-0900000000-e41a6714348b3249ddacSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-014u-5900000000-9a9e0414dcb34d920983Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000j-9600000000-17d717eb220781ad4cc1Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0536-9100000000-3f771329175d59bc664cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00mo-9000000000-68b4409b06699bad322fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0900000000-a013b4ae27f975ab5621Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-0900000000-a013b4ae27f975ab5621Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00kf-9400000000-20ffbcb6b8f03ba79f67Spectrum
MSMass Spectrum (Electron Ionization)splash10-0096-9400000000-322df4fdc907d6ef5f6fSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB0036995
FooDB IDFDB007475
Phenol Explorer IDNot Available
KNApSAcK IDC00003060
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkTerpinene
Chemspider ID7182
ChEBI ID10334
PubChem Compound ID7462
Kegg Compound IDC09898
YMDB IDYMDB16096
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=15621337
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=16780354
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=20387784
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=22164802
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=23833899
6. https://www.ncbi.nlm.nih.gov/pubmed/?term=24020201
7. https://www.ncbi.nlm.nih.gov/pubmed/?term=8655097
8. 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.
9. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9.
10. 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.
11. 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.
12. Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621.
13. Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.
14. The lipid handbook with CD-ROM