Farnesol

Farnesol
Names
	Preferred IUPAC name (2E,6E)-3,7,11-Trimethyldodeca-2,6,10-trien-1-ol
Identifiers
CAS Number	4602-84-0 ;
3D model (JSmol)	Interactive image; (2E,6E)-: Interactive image;
ChEBI	CHEBI:28600 ;
ChEMBL	ChEMBL25308 ;
ChemSpider	3210 ; 392816 (2E,6E)- ;
DrugBank	DB02509 ;
ECHA InfoCard	100.022.731
IUPHAR/BPS	3215;
KEGG	C01493 ;
PubChem CID	3327; 445070 (2E,6E)-;
UNII	EB41QIU6JL ;
CompTox Dashboard (EPA)	DTXSID3032389 ;
	InChI InChI=1S/C15H26O/c1-13(2)7-5-8-14(3)9-6-10-15(4)11-12-16/h7,9,11,16H,5-6,8,10,12H2,1-4H3 Key: CRDAMVZIKSXKFV-UHFFFAOYSA-N ; (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;
	SMILES 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
Chemical formula	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). verify (what is ?) Infobox references

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]

References

^ ^a ^b Sell, Charles S. (2006). "Terpenoids". Kirk-Othmer Encyclopedia of Chemical Technology. doi:10.1002/0471238961.2005181602120504.a01.pub2. ISBN 0471238961.
^ 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.
^ "Standards Restricted - IFRA International Fragrance Association". Archived from the original on 2011-12-30. Retrieved 2012-07-19.
^ 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.
^ "farnesol". Dictionary.com. Retrieved August 27, 2009.
^ Fluckiger, F. A. (March 1885). "The Essential Oil Industry in Grasse" (PDF). American Journal of Pharmacy. 57 (3).

[KO-1] Sell, Charles S. (2006). "Terpenoids". Kirk-Othmer Encyclopedia of Chemical Technology. doi:10.1002/0471238961.2005181602120504.a01.pub2. ISBN 0471238961.

[web_reference-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).

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