Farnesol
| Farnesol | |
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(2E,6E)-3,7,11-trimethyldodeca-2,6,10-trien-1-ol |
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| Identifiers | |
| CAS number | 4602-84-0  |
| PubChem | 3327 |
| ChemSpider | 3210 |
| UNII | X23PI60R17 |
| DrugBank | DB02509 |
| KEGG | C01493 |
| ChEBI | CHEBI:28600 |
| ChEMBL | CHEMBL25308  |
| Jmol-3D images | Image 1 |
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| Properties | |
| Molecular formula | C15H26O |
| Molar mass | 222.37 g mol−1 |
| Density | 0.887 g/cm3 |
| Boiling point |
111 °C at 0.35 mmHg |
 (verify) (what is:  / ?)Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) |
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| Infobox references | |
Farnesol is a natural organic compound which is an acyclic sesquiterpene alcohol found as a colorless liquid. It is insoluble in water, but miscible with oils. It is the building block of most, and possibly all, acyclic sesquiterpenoids and is an important starting compound for organic synthesis.
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[edit] 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.
[edit] 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 (ca. 1900-1905) after Farnese acacia tree (Vachellia farnesiana). The flowers from the tree were the commercial source of the floral essence. 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]
[edit] 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 should be avoided by people with perfume allergy.[6]
[edit] References
- ^ List of Additives in Cigarettes
- ^ http://dictionary.reference.com/browse/farnesol Etymology of farnesol, accessed August 27, 2009.
- ^ HENRY TRIMBLE AND F. D. MACFARLAND., AMERICAN JOURNAL OF PHARMACY, Volume 57, #3, March, 1885
- ^ 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. http://www.pubmedcentral.nih.gov/articlerender.fcgi?tool=pmcentrez&artid=2815016.
- ^ 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.
- ^ Survey and health assessment of chemical substances in massage oils
