Farnesol

Farnesol is a natural 15-carbon organic compound which is an acyclic sesquiterpene alcohol. Under standard conditions, it is a colorless liquid. It is hydrophobic, and thus insoluble in water, but miscible with oils.

Farnesol
Names
IUPAC name
(2E,6E)-3,7,11-trimethyldodeca-2,6,10-trien-1-ol
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
DrugBank
ECHA InfoCard 100.022.731
KEGG
UNII
Properties
C15H26O
Molar mass 222.37 g/mol
Appearance Clear colorless liquid
Odor Floral
Density 0.887 g/cm3
Boiling point 283 to 284.00 °C (541.40 to 543.20 °F; 556.15 to 557.15 K) at 760 mmHg
111 °C at 0.35 mmHg
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Farnesol is produced from 5-carbon isoprene compounds in both plants and animals. Phosphate activated derivatives of farnesol are the building blocks of most, and possibly all, acyclic sesquiterpenoids. These compounds are doubled to form 30-carbon squalene, which in turn is the precursors for steroids in plants, animals, and fungi. As such, farnesol and its derivatives are important starting compounds for both natural and artificial organic synthesis.

Uses

Farnesol is present in many essential oils such as citronella, neroli, cyclamen, lemon grass, tuberose, rose, musk, balsam and tolu. It is used in perfumery to emphasize the odors of sweet floral perfumes. Its method of action for enhancing perfume scent is as a co-solvent that regulates the volatility of the odorants. It is especially used in lilac perfumes.

Farnesol is a natural pesticide for mites and is a pheromone for several other insects.

In a 1994 report released by five top cigarette companies, farnesol was listed as one of 599 additives to cigarettes.[1] It is a flavoring ingredient.

Natural source and synthesis

Farnesol is produced from isoprene compounds in both plants and animals. When geranyl pyrophosphate reacts with isopentenyl pyrophosphate, the result is the 15-carbon farnesyl pyrophosphate, which is an intermediate in the biosynthesis of sesquiterpenes such as farnesene. Oxidation can then provide sesquiterpenoids such as farnesol.

Farnesyl pyrophosphate

History of the name

Farnesol is found in a flower extract with a long history of use in perfumery. The pure substance farnesol was named (c. 1900–1905) after the Farnese acacia tree (Vachellia farnesiana), since the flowers from the tree were the commercial source of the floral essence in which the chemical was identified. This particular acacia species, in turn, is named after Cardinal Odoardo Farnese (1573–1626) of the notable Italian Farnese family which (from 1550 though the 17th century) maintained some of the first private European botanical gardens in the Farnese Gardens in Rome. The addition of the -ol ending results from it being chemically an alcohol.[2] The plant itself was brought to the Farnese gardens from the Caribbean and Central America, where it originates.[3]

Health effects

Farnesol has been suggested to function as a chemopreventative and anti-tumor agent.[4] Farnesol is used as a deodorant in cosmetic products because of its anti-bacterial activity.[5] Farnesol is subject to restrictions on its use in perfumery[6] as some people may become sensitised to it, however the evidence that farnesol can cause an allergic reaction in humans is disputed.[7] In a study, researchers found in a tissue culture that Balsam of Peru and farnesol were able to bind to CD1a molecules on the surface of Langerhans cells and active T cells. However, researcher de Jong notes that, "Our work shows how these chemicals can activate T cells in tissue culture, but we have to be cautious about claiming that this is definitively how it works in allergic patients. The study does pave the way for follow up studies to confirm the mechanism in allergic patients and design inhibitors of the response."[8] Despite this warning, some pop-science has taken the preliminary findings of this study to be conclusive evidence that farnesol causes an immunological response through this mechanism.[9] Even though the study did not test this on functional human skin.

Biological function

Farnesol is used by the fungus Candida albicans as a quorum sensing molecule that inhibits filamentation.[10]

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See also

References
  1. Terry Martin. "Big Tobacco's List of 599 Additives in Cigarettes". About.com Health. Retrieved 29 July 2015.
  2. http://dictionary.reference.com/browse/farnesol Etymology of farnesol, accessed August 27, 2009.
  3. HENRY TRIMBLE AND F. D. MACFARLAND., AMERICAN JOURNAL OF PHARMACY, Volume 57, #3, March, 1885
  4. Joo JH, Jetten AM (June 2009). "Molecular mechanisms involved in farnesol-induced apoptosis". Cancer Lett. 287 (2): 123–35. doi:10.1016/j.canlet.2009.05.015. PMC 2815016. PMID 19520495.
  5. Kromidas, L; Perrier, E; Flanagan, J; Rivero, R; Bonnet, I (2006). "Release of antimicrobial actives from microcapsules by the action of axillary bacteria". Int J Cosmet Sci. 28 (2): 103–108. doi:10.1111/j.1467-2494.2006.00283.x. PMID 18492144.
  6. "Archived copy". Archived from the original on 2011-12-30. Retrieved 2012-07-19.CS1 maint: archived copy as title (link)
  7. "Archived copy" (PDF). Archived from the original (PDF) on 2014-02-10. Retrieved 2012-07-19.CS1 maint: archived copy as title (link)
  8. "Study explains why some creams and cosmetics may cause a skin rash". EurekAlert!. Retrieved 2020-01-22.
  9. SciShow episode "Why Skin Creams Give You Rashes," Jan 10, 2010
  10. Jacob M. Hornby (2001). "Quorum Sensing in the Dimorphic Fungus Candida albicans Is Mediated by Farnesol". asm.org. 67 (7): 2982–2992. doi:10.1128/AEM.67.7.2982-2992.2001. PMC 92970. PMID 11425711. Retrieved 29 July 2015.
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