α -Pinene
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Names | |||
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IUPAC name
(1S,5S)-2,6,6-Trimethylbicyclo[3.1.1]hept-2-ene ((−)-
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Identifiers | |||
3D model (JSmol)
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ChEBI |
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ChemSpider | |||
ECHA InfoCard | 100.029.161 | ||
EC Number |
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KEGG | |||
PubChem CID
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RTECS number |
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UNII |
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UN number | 2368 | ||
CompTox Dashboard (EPA)
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Properties | |||
C10H16 | |||
Molar mass | 136.238 g·mol−1 | ||
Appearance | Clear colorless liquid | ||
Density | 0.858 g/mL (liquid at 20 °C) | ||
Melting point | −62.80 °C; −81.04 °F; 210.35 K[1] | ||
Boiling point | 155 °C (311 °F; 428 K)[1] | ||
Very low | |||
Solubility | Insoluble in chloroform, diethyl ether | ||
Solubility in acetic acid | Miscible | ||
Solubility in ethanol | Miscible | ||
Solubility in acetone | Miscible | ||
Vapor pressure | 0.5 kPa | ||
Chiral rotation ([
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−50.7° (1S,5S-Pinene) | ||
Hazards | |||
Occupational safety and health (OHS/OSH): | |||
Main hazards
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Flammable | ||
GHS labelling: | |||
Danger | |||
H226, H302, H304, H315, H317, H410 | |||
P210, P233, P240, P241, P242, P243, P261, P264, P270, P272, P273, P280, P301+P310, P301+P312, P302+P352, P303+P361+P353, P321, P330, P331, P332+P313, P333+P313, P362, P363, P370+P378, P391, P403+P235, P405, P501 | |||
NFPA 704 (fire diamond) | |||
Flash point | 33 °C (91 °F; 306 K) | ||
255 °C (491 °F; 528 K) | |||
Explosive limits | 0.8% v/v (lower) 6% v/v (upper) | ||
Lethal dose or concentration (LD, LC): | |||
LD50 (median dose)
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300-2000 mg/kg (rat, oral) > 5 g/kg (rabbit, dermal) | ||
LC50 (median concentration)
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625 ppm/min (rat) | ||
Safety data sheet (SDS) | Fisher Scientific | ||
Related compounds | |||
Related alkene
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Related compounds
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borneol, camphor, terpineol | ||
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Reactivity
[edit]Commercially important derivatives of
With one molar equivalent of anhydrous HCl, the simple addition product 6a can be formed at low temperature in the presence of diethyl 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.[6] 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.[7]
Under aerobic oxidation conditions, the main oxidation products are pinene oxide, verbenyl hydroperoxide, verbenol and verbenone.[8]
Atmospheric role
[edit]Monoterpenes, of which
Properties and usage
[edit]References
[edit]- ^ a b "
α -Pinene". Archived from the original on 2018-01-30. Retrieved 2018-01-29. - ^ Simonsen, J. L. (1957). The Terpenes. Vol. 2 (2nd ed.). Cambridge: Cambridge University Press. pp. 105–191.
- ^ PDR for Herbal Medicine. Montvale, NJ: Medical Economics Company. p. 1100.
- ^ Zebib, Bachar; Beyrouthy, Marc El; Sarfi, Carl; Merah, Othmane (2015-04-16). "Chemical Composition of the Essential Oil of Satureja myrtifolia (Boiss. & Hohen.) from Lebanon". Journal of Essential Oil-bearing Plants. 18 (1): 248–254. doi:10.1080/0972060X.2014.890075. ISSN 0972-060X. S2CID 95564601. Archived from the original on 2016-08-04.
- ^ Sell, Charles S. (2006). "Terpenoids". Kirk-Othmer Encyclopedia of Chemical Technology. doi:10.1002/0471238961.2005181602120504.a01.pub2. ISBN 0471238961.
- ^ Richter, G.H. (1952). Textbook of Organic Chemistry (3rd ed.). New York, NY: John Wiley & Sons. pp. 663–668.
- ^ Ružička, L.; Trebler, H. (1921). "Zur Kenntnis des Pinens. III. Konstitution des Nitrosopinens und seiner Umwandlungsprodukte" [On the science of pinene. III. Constitution of nitrosopinene and its transformation products]. Helvetica Chimica Acta. 4: 566–574. doi:10.1002/hlca.19210040161.
- ^
Neuenschwander, U. (2010). "Mechanism of the Aerobic Oxidation of
α -Pinene". ChemSusChem (in German). 3 (1): 75–84. doi:10.1002/cssc.200900228. PMID 20017184. - ^ IUPAC Subcommittee on Gas Kinetic Data Evaluation
- ^ Odum, J. R.; Hoffmann, T.; Bowman, F.; Collins, D.; Flagan, R. C.; Seinfeld, J. H. (1996). "Gas/particle partitioning and secondary organic aerosol yields". Environmental Science and Technology. 30 (8): 2580–2585. Bibcode:1996EnST...30.2580O. doi:10.1021/es950943+.
- ^ Donahue, N. M.; Henry, K. M.; Mentel, T. F.; Kiendler-Scharr, A.; Spindler, C.; Bohn, B.; Brauers, T.; Dorn, H. P.; Fuchs, H.; Tillmann, R.; Wahner, A.; Saathoff, H.; Naumann, K.-H.; Mohler, O.; Leisner, T.; Muller, L.; Reinnig, M.-C.; Hoffmann, T.; Salo, K.; Hallquist, M.; Frosch, M.; Bilde, M.; Tritscher, T.; Barmet, P.; Praplan, A. P.; DeCarlo, P. F.; Dommen, J.; Prevot, A. S. H.; Baltensperger, U. (2012). "Aging of biogenic secondary organic aerosol via gas-phase OH radical reactions". Proceedings of the National Academy of Sciences. 109 (34): 13503–13508. Bibcode:2012PNAS..10913503D. doi:10.1073/pnas.1115186109. PMC 3427056. PMID 22869714.
- ^ a b c d Russo, E. B. (2011). "Taming THC: potential cannabis synergy and phytocannabinoid-terpenoid entourage effects". British Journal of Pharmacology. 163 (7): 1344–1364. doi:10.1111/j.1476-5381.2011.01238.x. PMC 3165946. PMID 21749363.
- ^ Nissen, L.; Zatta, A.; Stefanini, I.; Grandi, S.; Sgorbati, B.; Biavati, B.; et al. (2010). "Characterization and antimicrobial activity of essential oils of industrial hemp varieties (Cannabis sativa L.)". Fitoterapia. 81 (5): 413–419. doi:10.1016/j.fitote.2009.11.010. PMID 19969046.
- ^ Yang, H.; Woo, J.; Pae, A.-N.; Um, M.-Y.; Cho, N.-C.; Park, K.-D.; Yoon, M.; Kim, J.; Lee, C.-J.; Cho, S. (2016). "
α -Pinene, a major constituent of pine tree oils, enhances non-rapid eye movement sleep in mice through GABAA-benzodiazepine receptors". Molecular Pharmacology. 90 (5): 530–539. doi:10.1124/mol.116.105080. PMID 27573669. - ^ Russo, E. B.; McPartland, J. M. (2003). "Cannabis is more than simply
Δ 9-tetrahydrocannabinol". Psychopharmacology. 165 (4): 431–432. doi:10.1007/s00213-002-1348-z. PMID 12491031. S2CID 19504014. - ^ Turner, C. E.; Elsohly, M. A.; Boeren, E. G. (1980). "Constituents of Cannabis sativa L. XVII. A review of the natural constituents". Journal of Natural Products. 43 (2): 169–234. doi:10.1021/np50008a001. PMID 6991645.
- ^ Piomelli, D.; Russo, E. B. (2016). "The Cannabis sativa versus Cannabis indica debate: an interview with Ethan Russo, MD". Cannabis and Cannabinoid Research. 1 (1): 44–46. doi:10.1089/can.2015.29003.ebr. PMC 5576603. PMID 28861479.
- ^ Mahmoudvand, H.; Sheibani, V.; Keshavarz, H.; Shojaee, S.; Esmaeelpour, K.; Ziaali, N. (2016). "Acetylcholinesterase Inhibitor Improves Learning and Memory Impairment Induced by Toxoplasma gondii Infection". Iranian Journal of Parasitology. 11 (2): 177–185. PMC 5236094. PMID 28096851.
- ^ Mediavilla, V.; Steinemann, S. (1997). "Essential oil of Cannabis sativa L. strains". Journal of the International Hemp Association. 4: 80–82.