Record Information
Version1.0
Creation date2010-04-08 22:11:14 UTC
Update date2018-05-29 01:11:35 UTC
Primary IDFDB014374
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 Number7785-26-4
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
(-)-a-pinenebiospider
(-)-alpha-Pinenemanual
(-)-α-pineneGenerator
(1S,5S)-2,6,6-Trimethylbicyclo[3.1.1]hept-2-enemanual
(1S,5S)-a-PineneGenerator
(1S,5S)-alpha-PineneChEBI
(1S,5S)-α-pineneGenerator
(1S)-(-)-a-Pinenebiospider
(1S)-2,6,6-trimethylbicyclo[3.1.1]hept-2-enemanual
1S-(-)-a-pinenebiospider
1S-a-Pinenebiospider
1S,5S-(-)-alpha-Pinenebiospider
a-pinene, (-)-biospider
L-a-pinenebiospider
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
Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateLiquid
Physical DescriptionNot Available
Mass CompositionC 88.16%; H 11.84%DFC
Melting Point-62 oC
Boiling PointBp 155-156°DFC
Experimental Water SolubilityNot Available
Experimental logP4.48GRIFFIN,S ET AL. (1999)
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical Rotation[a]23D -51.5 (neat) (99.8% ee)DFC
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0006-9100000000-efa1a7d8bd0221192f0dView in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0006-9100000000-efa1a7d8bd0221192f0dView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0079-1900000000-7a79889acc60a4543bcfView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0900000000-89e84f859d8f1f97d5c2View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-0900000000-fb8d56b761aae12a505cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00dr-0900000000-bfe7e4ba927cd83956b4View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0900000000-5e150dd4370565464dadView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-0900000000-5e150dd4370565464dadView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00kr-0900000000-b5dcbaea24fd03f1cbf9View in MoNA
ChemSpider ID389795
ChEMBL IDCHEMBL3109297
KEGG Compound IDC06308
Pubchem Compound ID440968
Pubchem Substance IDNot Available
ChEBI ID28660
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB35658
CRC / DFC (Dictionary of Food Compounds) IDJPV84-W:JPW52-Q
EAFUS IDNot Available
Dr. Duke ID(-)-ALPHA-PINENE
BIGG IDNot Available
KNApSAcK IDC00035786
HET IDNot Available
Flavornet IDNot Available
GoodScent IDrw1108601
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
sharp
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
warm
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
resinous
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
fresh
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
pine
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
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).
— Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.