Fenchol

{{chembox

| Verifiedfields = changed

| Watchedfields = changed

| verifiedrevid = 424674127

| Reference =[http://www.chemexper.com/index.shtml?main=http://www.chemexper.com/search/cas/2217-02-9.html Datasheet] at chemexper.com

| ImageFile =(1R)-endo-(+)-Fenchol.svg

| ImageSize =150px

| ImageCaption = (1R)-endo-(+)-Fenchol

| IUPACName =(1R,2R,4S)-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 = ((1R)-endo-(+))

| ChemSpiderID = 14665

| EC_number = 216-639-5

| PubChem = 15406

| PubChem_Comment = (unspecified isomer)

| PubChem1 = 6997371

| PubChem1_Comment = ((1R)-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/cm³

| 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 (1R)-endo-(+)-fenchol is used extensively in perfumery. Fenchol gives basil its characteristic scent,{{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}}{{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}} and comprises 15.9% of the volatile oils of some species of Aster.{{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}}

It is biosynthesized from geranyl pyrophosphate via isomerization to linalyl pyrophosphate.{{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 }}

Oxidation of fenchol gives fenchone.