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Bovine Metabolome Database



Showing metabocard for (+)-a-Pinene (BMDB06525)

Legend: metabolite field enzyme field

Version 1.0
Creation Date 2007-05-23 15:25:36
Update Date 2009-06-05 16:05:15
Accession Number BMDB06525
Common Name (+)-a-Pinene
Description α-Pinene is an organic compound of the terpene class, one of two isomers of pinene. It is an alkene and it contains a reactive four-membered ring. 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 (−)-α-pinene is more common in European pines, whereas the 1R,5R- or (+)-α-isomer is more common in North America. The racemic mixture is present in some oils such as eucalyptus oil. The four-membered ring in α-pinene 1 makes it a reactive hydrocarbon, prone to skeletal rearrangements such as the Wagner-Meerwein rearrangement. For example, attempts to perform hydration or hydrogen halide addition with the alkene functionality typically lead to rearranged products. of under acidic conditions. With concentrated sulfuric acid and ethanol the major products are terpineol 2 and its ethyl ether 3, while glacial acetic acid gives the corresponding acetate ester 4. With dilute acids, terpin hydrate 5 becomes the major product. With one molar equivalent of anhydrous HCl, the simple addition product 6a can be formed at low temperature in the presence of ether, but it is very unstable. At normal temperatures, or if no ether is present, the major product is bornyl chloride 6b, along with a small amount of fenchyl chloride 6c. For many years 6b (also called "artificial camphor") was referred to as "pinene hydrochloride", until it was confirmed as identical with bornyl chloride made from camphene. If more HCl is used, achiral 7 (dipentene hydrochloride) is the major product along with some 6b. Nitrosyl chloride followed by base leads to the oxime 8 which can be reduced to "pinylamine" 9. Both 8 and 9 are stable compounds containing an intact four-membered ring, and these compounds helped greatly in identifying this important component of the pinene skeleton. (Wikipedia)
Synonyms
  1. (+)-Pin-2(3)-ene
  2. (1R)-2,6,6-Trimethylbicyclo[3.1.1]hept-2-ene
  3. (1R,5R)-2,6,6-Trimethylbicyclo[3.1.1]hept-2-ene
  4. 1R-a-Pinene
  5. 1R-(+)-a-pinene
  6. 2,6,6-Trimethylbicyclo[3.1.1]hept-2-ene
  7. Alpha-pinene(dextro)
  8. 2,6,6-trimethyl-Bicyclo(3.1.1)hept-2-ene
  9. 1R-alpha-Pinene
  10. 1R-(+)-alpha-pinene
  11. (+)-alpha-Pinene
Chemical IUPAC Name (1S,5S)-4,7,7-trimethylbicyclo[3.1.1]hept-3-ene
Chemical Formula C10H16
Chemical Structure Structure
Chemical Taxonomy
Kingdom
  • Organic
Super Class
  • Miscellanous
Class
  • Monoterpenes
Sub Class
  • Unclassified compounds
Family
  • Mammalian_Metabolite
Species
  • alkene
Biofunction
Application
Source
  • Endogenous
Average Molecular Weight 136.234
Monoisotopic Molecular Weight 136.125198
Isomeric SMILES CC1=CCC2CC1C2(C)C
Canonical SMILES CC1=CCC2CC1C2(C)C
KEGG Compound ID C06306 Link Image
BioCyc ID ALPHA-PINENE-OXIDE Link Image
BiGG ID 47909 Link Image
Wikipedia Link Not Available
METLIN ID Not Available
PubChem Compound 82227 Link Image
PubChem Substance 10219259 Link Image
ChEBI ID 28261 Link Image
CAS Registry Number 7785-70-8
InChI Identifier InChI=1/C10H16/c1-7-4-5-8-6-9(7)10(8,2)3/h4,8-9H,5-6H2,1-3H3
Synthesis Reference Not Available
Melting Point (Experimental) -62 oC
Experimental Water Solubility Not Available Source: PhysProp
Predicted Water Solubility 0.00497 mg/mL at 25 oC [MEYLAN,WM et al. (1996)]; 0.158 mg/mL [Predicted by ALOGPS] Calculated using ALOGPS
Physiological Charge 0
State Liquid
Experimental LogP/Hydrophobicity 4.44 [GRIFFIN,S ET AL. (1999)] Source: PhysProp
Predicted LogP/Hydrophobicity 3.66 [Predicted by ALOGPS]; 4.2 [Predicted by PubChem via XLOGP] Calculated using ALOGPS
Material Safety Data Sheet (MSDS)
MOL File Show
SDF File Show
PDB File Show
2D Structure
3D Structure
Experimental PDB ID Not Available
Experimental 1H NMR Spectrum Not Available
Experimental 13C NMR Spectrum Not Available
Experimental 13C HSQC Spectrum Not Available
Predicted 1H NMR Spectrum Show Image
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Predicted 13C NMR Spectrum Show Image
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Mass Spectrum Not Available
Simplified TOCSY Spectrum Not Available
BMRB Spectrum Not Available
Cellular Location
  • Cytoplasm
  • Extracellular
Biofluid Location Not Available
Tissue Location Not Available
Concentrations (Normal)
Biofluid Breast_Milk
Value 0.000983 +/- 0.000378 uM
Age NA
Sex NA
Condition Normal
Comments In raw milk samples for diets based on hay
References
Biofluid Breast_Milk
Value 0.000529 +/- 0.000454 uM
Age NA
Sex NA
Condition Normal
Comments In raw mild samples for diets based on maize silage
References
Biofluid Breast_Milk
Value 0.000378 +/- 0.000151 uM
Age NA
Sex NA
Condition Normal
Comments In raw mild samples for diets based on grass silage
References
Concentrations (Abnormal) Not Available
Pathway Names Not Available
HMDB Pathways Not Available
KEGG Pathways Not Available
SimCell Pathways Not Available
General References Not Available