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Record Information
Version3.6
Creation Date2012-09-11 20:40:03 UTC
Update Date2016-02-11 02:44:01 UTC
HMDB IDHMDB35658
Secondary Accession NumbersNone
Metabolite Identification
Common Name(-)-alpha-Pinene
Description(-)-alpha-Pinene is found in almond. 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. (Wikipedia) (-)-alpha-Pinene belongs to the family of Bicyclic Monoterpenes. These are monoterpenes containing exactly 2 rings, which are fused to each other.
Structure
Thumb
Synonyms
ValueSource
(+)-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
(-)-a-PineneHMDB
(1S)-(-)-a-PineneHMDB
(1S)-2,6,6-trimethylbicyclo[3.1.1]Hept-2-eneHMDB
(1S,5S)-2,6,6-trimethylbicyclo[3.1.1]Hept-2-eneHMDB
1S,5S-(-)-alpha-PineneHMDB
1S-(-)-a-PineneHMDB
1S-a-PineneHMDB
L-a-PineneHMDB
Chemical FormulaC10H16
Average Molecular Weight136.234
Monoisotopic Molecular Weight136.125200512
IUPAC Name(1R,5R)-2,6,6-trimethylbicyclo[3.1.1]hept-2-ene
Traditional Name(+)-α-pinene
CAS Registry Number7785-26-4
SMILES
CC1=CC[C@H]2C[C@@H]1C2(C)C
InChI Identifier
InChI=1S/C10H16/c1-7-4-5-8-6-9(7)10(8,2)3/h4,8-9H,5-6H2,1-3H3/t8-,9-/m0/s1
InChI KeyInChIKey=GRWFGVWFFZKLTI-IUCAKERBSA-N
Chemical Taxonomy
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
  • Polycyclic hydrocarbon
  • Cyclic olefin
  • Olefin
  • Hydrocarbon
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External Descriptors
Ontology
StatusDetected and Quantified
Origin
  • Endogenous
  • Food
Biofunction
  • Cell signaling
  • Fuel and energy storage
  • Fuel or energy source
  • Membrane integrity/stability
  • Nutrient
Application
  • Nutrient
  • Stabilizers
  • Surfactants and Emulsifiers
Cellular locations
  • Extracellular
  • Membrane
Physical Properties
StateLiquid
Experimental Properties
PropertyValueReference
Melting Point-62 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogP4.48Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.16 mg/mLALOGPS
logP3.66ALOGPS
logP2.8ChemAxon
logS-2.9ALOGPS
Physiological Charge0ChemAxon
Hydrogen Acceptor Count0ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area0 Å2ChemAxon
Rotatable Bond Count0ChemAxon
Refractivity44.72 m3·mol-1ChemAxon
Polarizability17.22 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
SpectraNot Available
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biofluid Locations
  • Feces
  • Saliva
Tissue LocationNot Available
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot ApplicableAdult (>18 years old)Both
Normal
details
FecesDetected but not QuantifiedNot ApplicableAdult (>18 years old)Both
Normal
details
FecesDetected but not QuantifiedNot ApplicableAdult (>18 years old)Both
Normal
details
FecesDetected but not QuantifiedNot ApplicableAdult (>18 years old)Both
Normal
details
FecesDetected but not QuantifiedNot ApplicableAdult (>18 years old)Both
Normal
details
FecesDetected but not QuantifiedNot ApplicableAdult (>18 years old)Both
Normal
details
FecesDetected but not QuantifiedNot ApplicableAdult (>18 years old)Both
Normal
details
FecesDetected and Quantified0 - 285.06 ppmChildren (1-13 years old)Not Specified
Normal
details
FecesDetected but not QuantifiedNot ApplicableAdult (>18 years old)Both
Normal
details
SalivaDetected but not QuantifiedNot ApplicableAdult (>18 years old)Not SpecifiedNormal details
Abnormal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot ApplicableAdult (>18 years old)Both
Nonalcoholic fatty liver disease (NAFLD)
details
FecesDetected but not QuantifiedNot ApplicableAdult (>18 years old)Both
Nonalcoholic fatty liver disease (NAFLD)
details
FecesDetected but not QuantifiedNot ApplicableAdult (>18 years old)Both
Diarrhea-predominant IBS
details
FecesDetected and Quantified0 - 172.64 ppmChildren (1-13 years old)Not Specified
Treated celiac disease
details
FecesDetected but not QuantifiedNot ApplicableAdult (>18 years old)Both
Nonalcoholic fatty liver disease (NAFLD)
details
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB014374
KNApSAcK IDC00035786
Chemspider ID389795
KEGG Compound IDC06308
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkAlpha-Pinene
NuGOwiki LinkHMDB35658
Metagene LinkHMDB35658
METLIN IDNot Available
PubChem Compound440968
PDB IDNot Available
ChEBI ID28660
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.