Record Information
Version1.0
Creation date2010-04-08 22:11:14 UTC
Update date2018-05-29 01:11:32 UTC
Primary IDFDB014366
Secondary Accession NumbersNot Available
Chemical Information
FooDB Namealpha-Pinene
DescriptionV. widely distributed in plants; reported in over 400 essential oils. Flavouring ingredient alpha-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 Number80-56-8
Structure
Thumb
Synonyms
SynonymSource
(+-)-2-PineneChEBI
(+-)-alpha-PineneChEBI
2-PineneChEBI
Acintene aChEBI
Pin-2(3)-eneChEBI
(+-)-a-PineneGenerator
(+-)-Α-pineneGenerator
(-)-a-PineneGenerator
(-)-Α-pineneGenerator
(+)-alpha-PineneHMDB
(+)-Pin-2(3)-eneHMDB
(1R)-2,6,6-Trimethylbicyclo[3.1.1]hept-2-eneHMDB
(1R,5R)-2,6,6-Trimethylbicyclo[3.1.1]hept-2-eneHMDB
1R-(+)-a-PineneHMDB
1R-(+)-alpha-PineneHMDB
1R-a-PineneHMDB
1R-alpha-PineneHMDB
2,6,6-Trimethyl-bicyclo(3.1.1)hept-2-eneHMDB
2,6,6-Trimethylbicyclo[3.1.1]hept-2-eneHMDB
alpha-Pinene(dextro)HMDB
Wilt prufHMDB
alpha-Pinene, pineneHMDB
alpha-PineneMeSH
2-Pinene, 8CIdb_source
2,6,6-trimethyl-Bicyclo(3.1.1)hept-2-enebiospider
2,6,6-Trimethylbicyclo(3.1.1)-2-hept-2-enebiospider
2,6,6-Trimethylbicyclo(3.1.1)-2-heptenebiospider
2,6,6-Trimethylbicyclo[3.1.1]hept-2-ene, 9CIdb_source
Alpha pinenebiospider
Alpha-pinenebiospider
Australenedb_source
Bicyclo[3.1.1]hept-2-ene, 2,6,6-trimethyl-biospider
FEMA 2902db_source
Firpenedb_source
Pinene, alphabiospider
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 name2,6,6-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
InChI KeyGRWFGVWFFZKLTI-UHFFFAOYSA-N
Isomeric SMILESCC1=CCC2CC1C2(C)C
Average Molecular Weight136.238
Monoisotopic Molecular Weight136.125200515
Classification
Description 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 PointNot Available
Experimental Water Solubility0.00249 mg/mL at 25 oCLI,J & PERDUE,EM (1995)
Experimental logP4.83LI,J & PERDUE,EM (1995)
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-002f-9100000000-a60ab99ee5e5c7f8221eView in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0006-9100000000-1005b74eeee7aefc15d2View in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-002f-9100000000-a60ab99ee5e5c7f8221eView in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0006-9100000000-1005b74eeee7aefc15d2View in MoNA
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, Positivesplash10-0079-3900000000-f1a2e0db65f2722f2ef7View 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
MSMass Spectrum (Electron Ionization)splash10-0006-9000000000-9b0f9df98b1755fa0b1fView in MoNA
ChemSpider IDNot Available
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound IDNot Available
Pubchem Substance IDNot Available
ChEBI ID36740
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDNot Available
CRC / DFC (Dictionary of Food Compounds) IDJPV84-W:JPV84-W
EAFUS ID3044
Dr. Duke IDALPHA-PINENE
BIGG IDNot Available
KNApSAcK IDC00000805
HET IDNot Available
Flavornet ID80-56-8
GoodScent IDrw1006351
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 / Bioactivities
DescriptorIDDefinitionReference
allelochemicDUKE
allergenic50904 A chemical compound which causes the onset of an allergic reaction by interacting with any of the molecular pathways involved in an allergy.DUKE
anti acne50177 A drug used to treat or prevent skin disorders or for the routine care of skin.DUKE
anti bacterial33282 A substance that kills or slows the growth of bacteria.DUKE
anti feedantDUKE
anti flu22587 A substance that destroys or inhibits replication of viruses.DUKE
anti inflammatory35472 A substance that reduces or suppresses inflammation.DUKE
anti pneumonic52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
anti septic33281 A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans.DUKE
anti spasmodic52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
anti staphylococcic33282 A substance that kills or slows the growth of bacteria.DUKE
anti viral22587 A substance that destroys or inhibits replication of viruses.DUKE
cancer preventive35610 A substance that inhibits or prevents the proliferation of neoplasms.DUKE
coleoptophileDUKE
expectorant52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
flavor48318 A substance, extract, or preparation for diffusing or imparting an agreeable or attractive smell.DUKE
herbicide24527 A substance used to destroy plant pests.DUKE
insecticide24852 Strictly, a substance intended to kill members of the class Insecta. In common usage, any substance used for preventing, destroying, repelling or controlling insects.DUKE
insectifuge24852 Strictly, a substance intended to kill members of the class Insecta. In common usage, any substance used for preventing, destroying, repelling or controlling insects.DUKE
Insectiphile24852 Strictly, a substance intended to kill members of the class Insecta. In common usage, any substance used for preventing, destroying, repelling or controlling insects.DUKE
irritantDUKE
cytochrome-P450-2B1 inhibitor50183 An enzyme inhibitor that interferes with the activity of cytochrome P450 involved in catalysis of organic substances.DUKE
perfumery48318 A substance, extract, or preparation for diffusing or imparting an agreeable or attractive smell.DUKE
pesticide25944 Strictly, a substance intended to kill pests. In common usage, any substance used for controlling, preventing, or destroying animal, microbiological or plant pests.DUKE
sedative35717 A central nervous system depressant used to induce drowsiness or sleep or to reduce psychological excitement or anxiety.DUKE
spasmogenicDUKE
tranquilizerDUKE
transdermalDUKE
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
Flavours
FlavorCitations
pine
  1. Arn, H, Acree TE. “Flavornet: A database of aroma compounds based on odor potency in natural products”. Developments in Food Science 40 (1998): 27. doi:10.1016/S0167-4501(98)80029-0
  2. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
turpentine
  1. Arn, H, Acree TE. “Flavornet: A database of aroma compounds based on odor potency in natural products”. Developments in Food Science 40 (1998): 27. doi:10.1016/S0167-4501(98)80029-0
fresh
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
camphor
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
sweet
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
earthy
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
woody
  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.