Farnesol
{{chembox
| Verifiedfields = changed
| Watchedfields = changed
| verifiedrevid = 461098987
| Name = Farnesol
| ImageFile = Farnesol.svg
| ImageSize = 250px
| ImageName = Skeletal formula of farnesol
| ImageFile1 = Farnesol-3D-balls.png
| ImageSize1 = 250px
| ImageName1 = Ball-and-stick model
| PIN = (2E,6E)-3,7,11-Trimethyldodeca-2,6,10-trien-1-ol
|Section1={{Chembox Identifiers
| IUPHAR_ligand = 3215
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 3210
| PubChem = 3327
| ChEMBL_Ref = {{ebicite|changed|EBI}}
| ChEMBL = 25308
| UNII_Ref = {{fdacite|changed|FDA}}
| UNII = EB41QIU6JL
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 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
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = CRDAMVZIKSXKFV-UHFFFAOYSA-N
| PubChem1 = 445070
| PubChem1_Comment = (2E,6E)-
| ChemSpiderID1_Ref = {{chemspidercite|changed|chemspider}}
| ChemSpiderID1 = 392816
| ChemSpiderID1_Comment = (2E,6E)-
| SMILES1 = OC/C=C(/CC/C=C(/CC\C=C(/C)C)C)C
| SMILES1_Comment = (2E,6E)-
| InChI3 = 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+
| InChI3_Comment = (2E,6E)-
| InChIKey3 = CRDAMVZIKSXKFV-YFVJMOTDSA-N
| CASNo_Ref = {{cascite|correct|CAS}}
| CASNo = 4602-84-0
| KEGG_Ref = {{keggcite|correct|kegg}}
| KEGG = C01493
| DrugBank_Ref = {{drugbankcite|correct|drugbank}}
| DrugBank = DB02509
| ChEBI_Ref = {{ebicite|correct|EBI}}
| ChEBI = 28600
| SMILES = OCC=C(CCC=C(CC\C=C(/C)C)C)C
}}
|Section2={{Chembox Properties
| C=15 | H=26 | O=1
| MolarMass = 222.37 g/mol
| Appearance = Clear colorless liquid
| Odor = Floral
| Density = 0.887 g/cm3
| MeltingPt =
| BoilingPtC = 283 to 284.00
| BoilingPt_notes = at 760 mmHg
111 °C at 0.35 mmHg
}}
}}
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 and peony perfumes.{{Cite web |title=Духи с запахом пиона - Лучшие пионовые парфюмы с фото - Описания духов с ароматом пиона - Парфюмерия с пионом. |url=https://duhipion.ru/ |access-date=2025-03-13 |website=duhipion.ru}} Farnesol and its ester derivatives are important precursors for a variety of other compounds used as fragrances and vitamins.
=Cosmetics=
Farnesol is used as a deodorant in cosmetic products.{{cite journal | doi = 10.1111/j.1467-2494.2006.00283.x | pmid = 18492144 | last1 = Kromidas | first1 = L | last2 = Perrier | first2 = E | last3 = Flanagan | first3 = J | last4 = Rivero | first4 = R | last5 = Bonnet | first5 = I | title = Release of antimicrobial actives from microcapsules by the action of axillary bacteria | journal = International Journal of Cosmetic Science | year = 2006 | volume = 28 | issue = 2 | pages = 103–108| s2cid = 46366332 }} Farnesol is subject to restrictions on its use in perfumery, because some people may become sensitised to it.{{cite web|url=http://www.ifraorg.org/en-us/standards_restricted/s3/p4 |title=Standards Restricted - IFRA International Fragrance Association |access-date=2012-07-19 |url-status=dead |archive-url=https://web.archive.org/web/20111230042603/http://www.ifraorg.org/en-us/standards_restricted/s3/p4 |archive-date=2011-12-30 }}
Natural source and synthesis
=In nature=
The pyrophosphate ester of farnesol is 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.
:File:Farnesyl pyrophosphate skeletal.svg
Farnesol is used by the fungus Candida albicans as a quorum sensing molecule that inhibits filamentation.{{cite journal|title=Quorum Sensing in the Dimorphic Fungus Candida albicans Is Mediated by Farnesol|author=Jacob M. Hornby|journal=Applied and Environmental Microbiology|year=2001|volume=67|issue=7|pages=2982–2992|doi=10.1128/AEM.67.7.2982-2992.2001|pmid=11425711|pmc=92970|bibcode=2001ApEnM..67.2982H}}
=Commercial production=
Obtaining farnesol from natural sources is uneconomical. In industry, farnesol is produced from linalool.{{cite book |doi=10.1002/0471238961.2005181602120504.a01.pub2|chapter=Terpenoids |title=Kirk-Othmer Encyclopedia of Chemical Technology |year=2006 |last1=Sell |first1=Charles S. |isbn=0471238961 }}
:File:GeranylacetoneToFarnesolviaNerolidol.svg, which can be isomerized to farnesol.]]{{clear-left}}
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.{{cite encyclopedia|url=https://dictionary.reference.com/browse/farnesol|title=farnesol|access-date=August 27, 2009|encyclopedia=Dictionary.com}} The plant itself was brought to the Farnese gardens from the Caribbean and Central America, where it originates.{{cite journal |url=https://www.swsbm.com/AJP/AJP_1885_No_3.pdf |title=The Essential Oil Industry in Grasse |first=F. A. |last=Fluckiger |journal=American Journal of Pharmacy |volume=57 |issue=3 |date=March 1885}}