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Farnesol

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Farnesol
Skeletal formula of farnesol
Skeletal formula of farnesol
Ball-and-stick model
Ball-and-stick model
Names
IUPAC name (2E,6E)-3,7,11-trimethyldodeca-2,6,10-trien-1-ol
Identifiers
CAS Number
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
DrugBank
ECHA InfoCard 100.022.731 Edit this at Wikidata
KEGG
PubChem CID
UNII
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C15H26O/c1-13(2)7-5-8-14(3)9-6-10-15(4)11-12-16/h7,9,11,16H,5-6,8,10,12H2,1-4H3Key: CRDAMVZIKSXKFV-UHFFFAOYSA-N
  • InChI=1/C15H26O/c1-13(2)7-5-8-14(3)9-6-10-15(4)11-12-16/h7,9,11,16H,5-6,8,10,12H2,1-4H3Key: CRDAMVZIKSXKFV-UHFFFAOYAI
SMILES
  • OCC=C(CCC=C(CC\C=C(/C)C)C)C
Properties
Chemical formula C15H26O
Molar mass 222.37 g/mol
Density 0.887 g/cm
Boiling point 111 °C at 0.35 mmHg
283-284.00 °C at 760 mmHg
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). ☒verify (what is  ?) Infobox references
Chemical compound

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.

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. It is a flavoring ingredient.

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. The plant itself was brought to the Farnese gardens from the Caribbean and Central America, where it originates.

Health effects

Farnesol has been suggested to function as a chemopreventative and anti-tumor agent. Farnesol is used as a deodorant in cosmetic products because of its anti-bacterial activity. Farnesol should be avoided by people with perfume allergy.

References

  1. List of Additives in Cigarettes
  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 (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. {{cite journal}}: Unknown parameter |month= ignored (help)
  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. Survey and health assessment of chemical substances in massage oils

See also

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