Chemistry:Β-Pinene

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β-Pinene is a monoterpene, an organic compound found in plants. It is the less abundant of the two isomers of pinene, the other being α-pinene.[1] It is a colorless liquid soluble in alcohol, but not water. It has a woody-green pine-like smell.

β-Pinene is one of the most abundant compounds released by forest trees.[2] If oxidized in air, the allylic products of the pinocarveol and myrtenol family prevail.[3]

Sources

Many plants from many botanical families contain the compound, including:

The clear compound is produced by distillation of turpentine oils.[9]

Uses

β-Pinene is usedin the production of other aroma compounds. It converts to myrcene upon heating at 500 °C. Nerol is obtained by careful fractional distillation of crude nerol from myrcene[10]).[11]

Reaction with formaldehyde (Prins reaction) converts β-pinene to nopol. When nopol is acetylated, the result is nopyl acetate, which is used as fragrance material.[9][12]

References

  1. ↑ Charles S. Sell (2013), "Terpenoids", in Arza Seidel, Kirk-Othmer Chemical Technology of Cosmetics, John Wiley & Sons, pp. 247–374, ISBN 978-1-118-40692-2 
  2. ↑ Geron, C., et al. (2000). A review and synthesis of monoterpene speciation from forests in the United States. Atmospheric Environment 34(11), 1761-81.
  3. ↑ 3.0 3.1 Neuenschwander, U.; Meier, E.; Hermans, I. (2011). "Peculiarities of β-pinene autoxidation". ChemSusChem 4 (11): 1613–21. doi:10.1002/cssc.201100266. PMID 21901836. 
  4. ↑ Li, Rong; Jiang, Zi-Tao (2004). "Chemical composition of the essential oil of Cuminum cyminum L. From China". Flavour and Fragrance Journal 19 (4): 311–313. doi:10.1002/ffj.1302. 
  5. ↑ Wang, L.; Wang, Z.; Zhang, H.; Li, X.; Zhang, H. (2009). "Ultrasonic nebulization extraction coupled with headspace single drop microextraction and gas chromatography-mass spectrometry for analysis of the essential oil in Cuminum cyminum L". Analytica Chimica Acta 647 (1): 72–7. doi:10.1016/j.aca.2009.05.030. PMID 19576388. 
  6. ↑ Tinseth, G. The Essential Oil of Hops: Hop Aroma and Flavor in Hops and Beer. Brewing Techniques January/February 1994. Accessed July 21, 2010.
  7. ↑ Hillig, Karl W (October 2004). "A chemotaxonomic analysis of terpenoid variation in Cannabis". Biochemical Systematics and Ecology 32 (10): 875–891. doi:10.1016/j.bse.2004.04.004. ISSN 0305-1978. 
  8. ↑ 8.0 8.1 8.2 8.3 Santana de Oliveira, Mozaniel (2022). Essential oils: applications and trends in food science and technology. Cham, Switzerland: Springer. ISBN 978-3-030-99476-1. 
  9. ↑ 9.0 9.1 Surburg, Horst; Panten, Johannes (2016). Common fragrance and flavor materials: preparation, properties and uses (6. completely revised and updated ed.). Weinheim: Wiley-VCH Verlag GmbH & Co. KGaA. ISBN 978-3-527-33160-4. 
  10. ↑ Opdyke, D. L. J. (2013-10-22) (in en). Monographs on Fragrance Raw Materials: A Collection of Monographs Originally Appearing in Food and Cosmetics Toxicology. Elsevier. ISBN 978-1-4831-4797-0. https://books.google.com/books?id=IDkvBQAAQBAJ. 
  11. ↑ Mattiello, Joseph J. (1945) (in en). Protective and Decorative Coatings. U.S. Government Printing Office. https://books.google.com/books?id=2GouxJ7nsuYC. 
  12. ↑ Opdyke, D. L. J. (2013-10-22) (in en). Monographs on Fragrance Raw Materials: A Collection of Monographs Originally Appearing in Food and Cosmetics Toxicology. Elsevier. ISBN 978-1-4831-4797-0. https://books.google.com/books?id=IDkvBQAAQBAJ. 



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