Farnesol

Farnesol
IUPAC name	(2E,6E)-3,7,11-trimethyldodeca-2,6,10-trien-1-ol
Identifiers
CAS number	4602-84-0 Y
SMILES	CC(=CCC\C(=C\CC\C(=C\CO)\C)\C)C
Properties
Molecular formula	C15H26O
Molar mass	222.37 g mol−1
Density	0.887 g/cm3
Boiling point	111 °C at 0.35 mmHg
Y (what is this?)  (verify) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
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. Farnesol is the alcohol derivative of Farnesol Pyrophosphate. It is the building block of most (possibly all) acyclic sesquiterpenoids and is an important starting compound for organic synthesis.

It 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.

Farnesol has been suggested to function as a chemopreventative and anti-tumor agent ^[2].

History of the name

The compound is from a flower extract with a long history of use in perfumery. The pure substance farnesol was named (ca. 1900-1905) from the type species Acacia farnesiana, the Farnese acacia, the flowers of which provided it commercially, as a floral essence. This particular acacia species in turn is named after Odoardo Cardinal 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.^[3] The plant itself was brought to the Farnese gardens from the Caribbean and Central America, where it originates.^[4]

Health & Safety information

Farnesol should be avoided by people with perfume allergy^[5].

References

1. ^ [1]http://quitsmoking.about.com/cs/nicotineinhaler/a/cigingredients.htm
2. ^ Joo JH, Jetten AM (June 2009). "Molecular mechanisms involved in farnesol-induced apoptosis". Cancer Lett.. doi:10.1016/j.canlet.2009.05.015. PMID 19520495. 
3. ^ http://dictionary.reference.com/browse/farnesol Etymology of farnesol, accessed August 27, 2009.
4. ^ HENRY TRIMBLE AND F. D. MACFARLAND., AMERICAN JOURNAL OF PHARMACY, Volume 57, #3, March, 1885
5. ^ Survey and health assessment of chemical substances in massage oils

See also

• Farnesylation
• Farnesene
• Nerolidol