Β-Pinene Explained

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. 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.^[1] If oxidized in air, the allylic products of the pinocarveol and myrtenol family prevail.^[2]

Sources

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

• Cuminum cyminum^{[3] [4]}
• Humulus lupulus^[5]
• Pinus pinaster^[2]
• Clausena anisata
• Cannabis sativa^[6]
• Piper nigrum^[7]
• Myristica fragans .
• Citrus aurantiifolia
• Pistacia lentiscus

The clear compound is produced by distillation of turpentine oils.^[8]

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^[9]).^[10]

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.^[11]

Notes and References

1. Geron, C., et al. (2000). A review and synthesis of monoterpene speciation from forests in the United States. Atmospheric Environment 34(11), 1761-81.
2. 21901836. 2011. Neuenschwander. U.. Meier. E.. Hermans. I.. Peculiarities of β-pinene autoxidation. ChemSusChem. 4. 11. 1613–21. 10.1002/cssc.201100266.
3. 10.1002/ffj.1302. Chemical composition of the essential oil of Cuminum cyminum L. From China. 2004. Li. Rong. Jiang. Zi-Tao. Flavour and Fragrance Journal. 19. 4. 311–313.
4. 19576388 . 2009 . Wang . L. . Wang . Z. . Zhang . H. . Li . X. . Zhang . H. . 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 . 10.1016/j.aca.2009.05.030 .
5. Tinseth, G. The Essential Oil of Hops: Hop Aroma and Flavor in Hops and Beer. Brewing Techniques January/February 1994. Accessed July 21, 2010.
6. Hillig. Karl W. October 2004. A chemotaxonomic analysis of terpenoid variation in Cannabis. Biochemical Systematics and Ecology. 32. 10. 875–891. 10.1016/j.bse.2004.04.004. 0305-1978.
7. Book: Santana de Oliveira, Mozaniel . Essential oils: applications and trends in food science and technology . 2022 . Springer . 978-3-030-99476-1 . Cham, Switzerland.
8. Book: Surburg . Horst . Common fragrance and flavor materials: preparation, properties and uses . Panten . Johannes . 2016 . Wiley-VCH Verlag GmbH & Co. KGaA . 978-3-527-33160-4 . 6. completely revised and updated . Weinheim.
9. Book: Opdyke, D. L. J. . Monographs on Fragrance Raw Materials: A Collection of Monographs Originally Appearing in Food and Cosmetics Toxicology . 2013-10-22 . Elsevier . 978-1-4831-4797-0 . en.
10. Book: Mattiello, Joseph J. . Protective and Decorative Coatings . 1945 . U.S. Government Printing Office . en.
11. Book: Opdyke, D. L. J. . Monographs on Fragrance Raw Materials: A Collection of Monographs Originally Appearing in Food and Cosmetics Toxicology . 2013-10-22 . Elsevier . 978-1-4831-4797-0 . en.