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 chloride6b, along with a small amount of fenchyl chloride6c. 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, achiral7 (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.
Monoterpenes, of which α-pinene is one of the principal species, are emitted in substantial amounts by vegetation, and these emissions are affected by temperature and light intensity. In the atmosphere alpha-pinene undergoes reactions with ozone, the OH radical or the NO3 radical, leading to low-volatility species which partly condense on existing aerosols, thereby generating secondary organic aerosols. This has been shown in numerous laboratory experiments for the mono- and sesquiterpenes. Products of α-pinene which have been identified explicitly are pinonaldehyde, norpinonaldehyde, pinic acid, pinonic acid and pinalic acid.
Simonsen, J. L. (1957) The Terpenes (2nd edition) Vol. 2 Cambridge:Cambridge University Press, pp 105-191.
PDR for Herbal Medicine. Montvale, NJ: Medical Economics Company. p. 1100
Richter, G. H. (1945) Textbook of Organic Chemistry, 2nd ed., John Wiley & Sons., New York, PP 663-666.
Ruzicka, L.; Trebler, H. (1921). "Zur Kenntnis des Pinens III Konstitution des Nitrosopinens und seiner Umwandlungsprodukte". Helvetica Chimica Acta4: 566. doi:10.1002/hlca.19210040161.
U. Neuenschwander (2010), "Mechanism of the Aerobic Oxidation of α-Pinene" (in German), ChemSusChem3 (1): pp. 75–84, doi:10.1002/cssc.200900228
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 Technology30 (8): 2580–2585. doi:10.1021/es950943+.
N. M. Donahue, K. M. Henry, T. F. Mentel, A. Kiendler-Scharr, C. Spindler, B. Bohn, T. Brauers, H. P. Dorn, H. Fuchs, R. Tillmann, A. Wahner, H. Saathoff, K.-H. Naumann, O. Mohler, T. Leisner, L. Muller, M.-C. Reinnig, T. Hoffmann, K. Salo, M. Hallquist, M. Frosch, M. Bilde, T. Tritscher, P. Barmet, A. P. Praplan, P. F. DeCarlo, J. Dommen, A. S. H. Prevot, U. Baltensperger (2012). "Aging of biogenic secondary organic aerosol via gas-phase OH radical reactions". Proceedings of the National Academy of Sciences. doi:10.1073/pnas.1115186109.
^ Russo, E. B (2011). "Taming THC: potential cannabis synergy and phytocannabinoid-terpenoid entourage effects". British Journal of Pharmacology163 (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.). Fitoterapia81: 413–419.