Camphene

Camphene is a bicyclic organic compound. It is one of the most pervasive monoterpenes. As with other terpenes, it is insoluble in water, flammable, colorless, and has a pungent smell.^[1] It is a minor constituent of many essential oils such as turpentine, cypress oil, camphor oil, citronella oil, neroli, ginger oil, valerian, and mango.^[2] It is produced industrially by isomerization of the more common alpha-pinene using a solid acid catalyst such as titanium dioxide.^[3]

Camphene is used in the preparation of fragrances and as a food additive for flavoring. These include isobornyl acetate. The aroma of the racemate is described as woody, herbal, fir needle, camphoreous, terpenic, cooling, pine, citrus, green, minty, and spicy.^[4] The aroma of dextro enantiomer is described as fresh, herbal, woody, fir needle, and camphoreous,^[5] whereas that of the laevo enantiomer is fresh, woody, fir needle, and terpenic.^[6]

Biosynthesis

Camphene is biosynthesized from linalyl pyrophosphate via a sequence of carbocationic intermediates.^[7]

References

↑ Eggersdorfer, Manfred (2000). "Ullmann's Encyclopedia of Industrial Chemistry". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a26_205.
↑ Pino, Jorge A.; Mesa, Judith; Muñoz, Yamilie; Martí, M. Pilar; Marbot, Rolando (2005). "Volatile Components from Mango (Mangifera indicaL.) Cultivars". Journal of Agricultural and Food Chemistry 53 (6): 2213–2223. doi:10.1021/jf0402633. PMID 15769159.
↑ Sell, Charles S. (2006). "Terpenoids". Kirk-Othmer Encyclopedia of Chemical Technology. doi:10.1002/0471238961.2005181602120504.a01.pub2. ISBN 0471238961.
↑ "camphene". Scents and Flavors. https://scentsandflavors.com/database/9dbb4f98-c0ef-4a06-ac0b-640297625b70.
↑ "(+)-camphene". Scents and Flavors. https://scentsandflavors.com/database/9dbb5289-9f97-4495-bd5e-e814566cf23f.
↑ "(-)-camphene". Scents and Flavors. https://scentsandflavors.com/database/9dbb51f0-d34e-4511-a0c7-4a04a4718227.
↑ ^7.0 ^7.1 Croteau, R.; Satterwhite, D. M.; Cane, D. E.; Chang, C. C. (1988). "Biosynthesis of Monoterpenes. Enantioselectivity in the Enzymatic Cyclization of (+)- and (-)-Linalyl Pyrophosphate to (+)- and (-)-Pinene and (+)- and (-)-Camphene". The Journal of Biological Chemistry 263 (21): 10063–71. doi:10.1016/S0021-9258(19)81477-1. PMID 3392006.

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[1] Eggersdorfer, Manfred (2000). "Ullmann's Encyclopedia of Industrial Chemistry". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a26_205.

[2] Pino, Jorge A.; Mesa, Judith; Muñoz, Yamilie; Martí, M. Pilar; Marbot, Rolando (2005). "Volatile Components from Mango (Mangifera indicaL.) Cultivars". Journal of Agricultural and Food Chemistry 53 (6): 2213–2223. doi:10.1021/jf0402633. PMID 15769159.

[3] Sell, Charles S. (2006). "Terpenoids". Kirk-Othmer Encyclopedia of Chemical Technology. doi:10.1002/0471238961.2005181602120504.a01.pub2. ISBN 0471238961.

[4] "camphene". Scents and Flavors. https://scentsandflavors.com/database/9dbb4f98-c0ef-4a06-ac0b-640297625b70.

[5] "(+)-camphene". Scents and Flavors. https://scentsandflavors.com/database/9dbb5289-9f97-4495-bd5e-e814566cf23f.

[6] "(-)-camphene". Scents and Flavors. https://scentsandflavors.com/database/9dbb51f0-d34e-4511-a0c7-4a04a4718227.

[Crot-7] 7.0 ^7.1 Croteau, R.; Satterwhite, D. M.; Cane, D. E.; Chang, C. C. (1988). "Biosynthesis of Monoterpenes. Enantioselectivity in the Enzymatic Cyclization of (+)- and (-)-Linalyl Pyrophosphate to (+)- and (-)-Pinene and (+)- and (-)-Camphene". The Journal of Biological Chemistry 263 (21): 10063–71. doi:10.1016/S0021-9258(19)81477-1. PMID 3392006.

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Camphene

Topic: Chemistry

Biosynthesis

References