Fenchol or 1,3,3-trimethyl-2-norbornanol is a monoterpenoid and an isomer of borneol. It is a colorless or white solid. It occurs widely in nature.
The naturally occurring enantiomere (1R)-endo-(+)-fenchol is used extensively in perfumery. Fenchol gives basil its characteristic scent, and comprises 15.9% of the volatile oils of some species of Aster.
It is biosynthesized from geranyl pyrophosphate via isomerization to linalyl pyrophosphate.
Oxidation of fenchol gives fenchone.
External links
References
"FES - (-)-endo-fenchol synthase, chloroplastic precursor - Ocimum basilicum (Sweet basil) - FES gene & protein". www.uniprot.org. https://www.uniprot.org/uniprot/Q5SBP2 ↩
Kotan, Recep; Kordali, Saban; Cakir, Ahmet (August 2007). "Screening of antibacterial activities of twenty-one oxygenated monoterpenes". Zeitschrift für Naturforschung C. 62 (7–8): 507–513. doi:10.1515/znc-2007-7-808. PMID 17913064. https://doi.org/10.1515%2Fznc-2007-7-808 ↩
Matasyoh, Josphat C.; Kiplimo, Joyce J.; Karubiu, Nicholas M.; Hailstorks, Tiffany P. (2006). "Chemical composition and antimicrobial activity of essential oil of Tarchonanthus camphoratus". Food Chemistry. 101 (3): 1183–1187. doi:10.1016/j.foodchem.2006.03.021. /wiki/Doi_(identifier) ↩
Satterwhite, D. M.; Wheeler, C. J.; Croteau, R. (15 November 1985). "Biosynthesis of monoterpenes. Enantioselectivity in the Enzymatic Cyclization of Linalyl Pyrophosphate to (-)-endo-Fenchol". The Journal of Biological Chemistry. 260 (26): 13901–8. doi:10.1016/S0021-9258(17)38661-1. PMID 4055764. https://doi.org/10.1016%2FS0021-9258%2817%2938661-1 ↩