{{chembox | Verifiedfields = changed | Watchedfields = changed | verifiedrevid = 424674127 | Reference =<ref>[http://www.chemexper.com/index.shtml?main=http://www.chemexper.com/search/cas/2217-02-9.html Datasheet] at chemexper.com</ref> | ImageFile =(1R)-endo-(+)-Fenchol.svg | ImageSize =150px | ImageCaption = (1''R'')-''endo''-(+)-Fenchol | IUPACName =(1''R'',2''R'',4''S'')-1,3,3-Trimethyl-2-norbornanol | OtherNames = Fenchyl alcohol |Section1={{Chembox Identifiers | CASNo_Ref = {{cascite|correct|CAS}} | CASNo =1632-73-1 | CASNo_Comment = (unspecified isomer) | CASNo1 =2217-02-9 | CASNo1_Comment = ((1''R'')-endo-(+)) | ChemSpiderID = 14665 | EC_number = 216-639-5 | PubChem = 15406 | PubChem_Comment = (unspecified isomer) | PubChem1 = 6997371 | PubChem1_Comment = ((1''R'')-endo-(+)) | UNII = 410Q2GK1HF | ChEMBL = 3188732 | StdInChI=1S/C10H18O/c1-9(2)7-4-5-10(3,6-7)8(9)11/h7-8,11H,4-6H2,1-3H3/t7-,8-,10+/m0/s1 | StdInChIKey = IAIHUHQCLTYTSF-OYNCUSHFSA-N | SMILES =CC1(C2CCC(C2)(C1O)C)C }} |Section2={{Chembox Properties | C=10 | H=18 | O=1 | Appearance = | Density = 0.942 g/cm<sup>3</sup> | MeltingPtC = 39 to 45 | MeltingPt_notes = | BoilingPtC = 201 | Solubility = }} |Section3={{Chembox Hazards | MainHazards = | FlashPt = | AutoignitionPt = }} }}
'''Fenchol''' or 1,3,3-trimethyl-2-norbornanol is a monoterpenoid and an isomer of borneol. It is a colorless or white solid. It occurs widely in nature.
The naturally occurring enantiomere (1''R'')-endo-(+)-fenchol is used extensively in perfumery. Fenchol gives basil its characteristic scent,<ref>{{cite web|url=https://www.uniprot.org/uniprot/Q5SBP2|title=FES - (-)-endo-fenchol synthase, chloroplastic precursor - Ocimum basilicum (Sweet basil) - FES gene & protein|website=www.uniprot.org}}</ref><ref>{{cite journal |title=Screening of antibacterial activities of twenty-one oxygenated monoterpenes |author=Kotan, Recep |author2=Kordali, Saban |author3=Cakir, Ahmet |journal=Zeitschrift für Naturforschung C |date=August 2007 |volume=62 |issue=7–8 |pages=507–513 |doi=10.1515/znc-2007-7-808 |pmid=17913064 |doi-access=free}}</ref> and comprises 15.9% of the volatile oils of some species of ''Aster''.<ref>{{cite journal |title=Chemical composition and antimicrobial activity of essential oil of ''Tarchonanthus camphoratus'' |author=Matasyoh, Josphat C. |author2=Kiplimo, Joyce J. |author3=Karubiu, Nicholas M. |author4=Hailstorks, Tiffany P. |journal=Food Chemistry |year=2006 |volume=101 |issue=3 |pages=1183–1187 |doi=10.1016/j.foodchem.2006.03.021}}</ref>
It is biosynthesized from geranyl pyrophosphate via isomerization to linalyl pyrophosphate.<ref>{{cite journal |title=Biosynthesis of monoterpenes. Enantioselectivity in the Enzymatic Cyclization of Linalyl Pyrophosphate to (-)-endo-Fenchol |author=Satterwhite, D. M. |author2=Wheeler, C. J. |author3=Croteau, R. |journal=The Journal of Biological Chemistry |date=15 November 1985 |volume=260 |issue=26 |pages=13901–8 |doi=10.1016/S0021-9258(17)38661-1 |pmid=4055764|doi-access=free }}</ref>
Oxidation of fenchol gives fenchone.
== See also == * Juniperol * Myrtenol
==References== {{reflist}}
== External links== * [http://www.thegoodscentscompany.com/data/rw1054341.html 3D-image]
Category:Secondary alcohols Category:Monoterpenes Category:Cyclohexanols