Record Information
Version1.0
Creation date2010-04-08 22:10:54 UTC
Update date2018-05-29 01:07:34 UTC
Primary IDFDB013765
Secondary Accession NumbersNot Available
Chemical Information
FooDB Name(+)-alpha-Pinene
Descriptionalpha-Pinene is an organic compound of the terpene class, one of two isomers of pinene. It is found in the oils of many species of many coniferous trees, notably the pine. It is also found in the essential oil of rosemary (Rosmarinus officinalis). Both enantiomers are known in nature; 1S,5S- or (-)-alpha-pinene is more common in European pines, whereas the 1R,5R- or (+)-alpha-isomer is more common in North America. The racemic mixture is present in some oils such as eucalyptus oil.
CAS Number7785-70-8
Structure
Thumb
Synonyms
SynonymSource
(+)-3,6,6-trimethylbicyclo[3.1.1]HEPT-2-eneChEBI
(1R,5R)-2,6,6-trimethylbicyclo[3.1.1]Hept-2-eneChEBI
(1R,5R)-alpha-PineneChEBI
alpha-Pinene(dextro)ChEBI
(1R,5R)-a-PineneGenerator
(1R,5R)-α-pineneGenerator
a-Pinene(dextro)Generator
α-pinene(dextro)Generator
(+)-(1R)-alpha-PineneHMDB
(+)-(1R)-α-PineneHMDB
(+)-(1R,5R)-alpha-PineneHMDB
(+)-(1R,5R)-α-PineneHMDB
(+)-2-PineneHMDB
(+)-alpha-PineneHMDB
(+)-α-PineneHMDB
(1R)-(+)-alpha-PineneHMDB
(1R)-(+)-α-PineneHMDB
(1R)-2,6,6-Trimethylbicyclo[3.1.1]hept-2-eneHMDB
(1R)-alpha-PineneHMDB
(1R)-α-PineneHMDB
(1R,5R)-(+)-alpha-PineneHMDB
(1R,5R)-(+)-α-PineneHMDB
(R)-(+)-alpha-PineneHMDB
(R)-(+)-α-PineneHMDB
(±)-2-PineneHMDB
(±)-alpha-PineneHMDB
(±)-α-PineneHMDB
2,6,6-Trimethylbicyclo[3.1.1]hept-2-eneHMDB
2-PineneHMDB
alpha-PineneHMDB
α-PineneHMDB
(+-)-2-PineneChEBI
(+-)-a-PineneGenerator
(+-)-alpha-PineneChEBI
(+-)-α-pineneGenerator
(+)-alpha-pinenebiospider
(+)-Pin-2(3)-enebiospider
(1R,5R)-2-Pinenebiospider
(1R,5R)-2,6,6-Trimethylbicyclo[3.1.1]hept-2-enebiospider
(1R,5R)-pin-2-enebiospider
1R-(+)-a-pinenebiospider
1R-(+)-alpha-pinenebiospider
1R-a-Pinenebiospider
1R-alpha-Pinenebiospider
a-PineneGenerator
Alpha-pinene(dextro)biospider
Bicyclo(3.1.1)hept-2-ene, 2,6,6-trimethyl-, (1R,5R)-biospider
Bicyclo[3.1.1]hept-2-ene, 2,6,6-trimethyl-, (1R)-biospider
Dextro-alpha-pinenebiospider
Pin-2(3)-eneChEBI
α-pineneGenerator
Predicted Properties
PropertyValueSource
Water Solubility0.16 g/LALOGPS
logP3.66ALOGPS
logP2.8ChemAxon
logS-2.9ALOGPS
Physiological Charge0ChemAxon
Hydrogen Acceptor Count0ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area0 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity44.72 m³·mol⁻¹ChemAxon
Polarizability17.22 ųChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC10H16
IUPAC name(1R,5R)-2,6,6-trimethylbicyclo[3.1.1]hept-2-ene
InChI IdentifierInChI=1S/C10H16/c1-7-4-5-8-6-9(7)10(8,2)3/h4,8-9H,5-6H2,1-3H3/t8-,9-/m1/s1
InChI KeyGRWFGVWFFZKLTI-RKDXNWHRSA-N
Isomeric SMILESCC1=CC[C@@H]2C[C@H]1C2(C)C
Average Molecular Weight136.234
Monoisotopic Molecular Weight136.125200512
Classification
DescriptionThis compound belongs to the class of organic compounds known as bicyclic monoterpenoids. These are monoterpenoids containing exactly 2 rings, which are fused to each other.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassMonoterpenoids
Direct ParentBicyclic monoterpenoids
Alternative Parents
Substituents
  • Pinane monoterpenoid
  • Bicyclic monoterpenoid
  • Branched unsaturated hydrocarbon
  • Polycyclic hydrocarbon
  • Cyclic olefin
  • Unsaturated aliphatic hydrocarbon
  • Unsaturated hydrocarbon
  • Olefin
  • Hydrocarbon
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Process

Naturally occurring process:

Role

Industrial application:

Biological role:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateLiquid
Physical DescriptionNot Available
Mass CompositionC 88.16%; H 11.84%DFC
Melting PointMp ?50°DFC
Boiling PointBp 155-156°DFC
Experimental Water SolubilityNot Available
Experimental logP4.44GRIFFIN,S ET AL. (1999)
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical Rotation[a]D +51.4 (neat) (99.6% ee)DFC
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0006-9100000000-efa1a7d8bd0221192f0dJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0006-9100000000-efa1a7d8bd0221192f0dJSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0079-1900000000-7a79889acc60a4543bcfJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0900000000-89e84f859d8f1f97d5c2JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-0900000000-fb8d56b761aae12a505cJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00dr-0900000000-bfe7e4ba927cd83956b4JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0900000000-5e150dd4370565464dadJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-0900000000-5e150dd4370565464dadJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00kr-0900000000-b5dcbaea24fd03f1cbf9JSpectraViewer
ChemSpider ID6402
ChEMBL IDCHEMBL442565
KEGG Compound IDC09880
Pubchem Compound ID6654
Pubchem Substance IDNot Available
ChEBI ID28261
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB06525
CRC / DFC (Dictionary of Food Compounds) IDJPV84-W:JGX37-J
EAFUS IDNot Available
Dr. Duke ID(+)-ALPHA-PINENE
BIGG ID47909
KNApSAcK IDC00034999
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDrw1137311
SuperScent IDNot Available
Wikipedia IDAlpha-Pinene
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
Flavours
FlavorCitations
harsh
  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.
minty
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
Files
MSDSshow
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.