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Farnesol

Farnesol
Skeletal formula of farnesol
Ball-and-stick model
Names
Preferred 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 Edit this at Wikidata
KEGG
UNII
  • InChI=1S/C15H26O/c1-13(2)7-5-8-14(3)9-6-10-15(4)11-12-16/h7,9,11,16H,5-6,8,10,12H2,1-4H3 checkY
    Key: CRDAMVZIKSXKFV-UHFFFAOYSA-N checkY
  • (2E,6E)-: InChI=1S/C15H26O/c1-13(2)7-5-8-14(3)9-6-10-15(4)11-12-16/h7,9,11,16H,5-6,8,10,12H2,1-4H3/b14-9+,15-11+
    Key: CRDAMVZIKSXKFV-YFVJMOTDSA-N
  • OCC=C(CCC=C(CC\C=C(/C)C)C)C
  • (2E,6E)-: OC/C=C(/CC/C=C(/CC\C=C(/C)C)C)C
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).
☒N verify (what is checkY☒N ?)

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. As the pyrophosphate ester, farnesol is a precursor to many terpenes and terpenoids.

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. It enhances perfume scent by acting as a co-solvent that regulates the volatility of the odorants. It is especially used in lilac perfumes. Farnesol and its ester derivatives are important precursors for a variety of other compounds used as fragrances and vitamins.[1]

Cosmetics

Farnesol is used as a deodorant in cosmetic products.[2] Farnesol is subject to restrictions on its use in perfumery, because some people may become sensitised to it.[3]

Natural source and synthesis

In nature

Pyrophosphate-activated derivatives of farnesol are the building blocks of possibly all acyclic sesquiterpenoids. These compounds are doubled to form 30-carbon squalene, which is the precursor for steroids in plants, animals, and fungi.

Farnesyl pyrophosphate is produced from the reaction of geranyl pyrophosphate and isopentenyl pyrophosphate. Farnesyl pyrophosphate is the precursor to farnesol and farnesene.

Farnesyl pyrophosphate

Farnesol is used by the fungus Candida albicans as a quorum sensing molecule that inhibits filamentation.[4]

Commercial production

Obtaining farnesol from natural sources is uneconomical. In industry, farnesol is produced from linalool.[1]

Conversion of geranylacetone to nerolidol, which can be isomerized to farnesol.

History of the name

Farnesol was named (ca. 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 Italian Farnese family who (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 suffix implies an alcohol.[5] The plant itself was brought to the Farnese gardens from the Caribbean and Central America, where it originates.[6]

See also

References

  1. ^ a b Sell, Charles S. (2006). "Terpenoids". Kirk-Othmer Encyclopedia of Chemical Technology. doi:10.1002/0471238961.2005181602120504.a01.pub2. ISBN 0471238961.
  2. ^ Kromidas, L; Perrier, E; Flanagan, J; Rivero, R; Bonnet, I (2006). "Release of antimicrobial actives from microcapsules by the action of axillary bacteria". International Journal of Cosmetic Science. 28 (2): 103–108. doi:10.1111/j.1467-2494.2006.00283.x. PMID 18492144. S2CID 46366332.
  3. ^ "Standards Restricted - IFRA International Fragrance Association". Archived from the original on 2011-12-30. Retrieved 2012-07-19.
  4. ^ Jacob M. Hornby (2001). "Quorum Sensing in the Dimorphic Fungus Candida albicans Is Mediated by Farnesol". Applied and Environmental Microbiology. 67 (7): 2982–2992. Bibcode:2001ApEnM..67.2982H. doi:10.1128/AEM.67.7.2982-2992.2001. PMC 92970. PMID 11425711.
  5. ^ "farnesol". Dictionary.com. Retrieved August 27, 2009.
  6. ^ Fluckiger, F. A. (March 1885). "The Essential Oil Industry in Grasse" (PDF). American Journal of Pharmacy. 57 (3).
Quelle: https://en.wikipedia.org/wiki/Farnesol