Fenchol

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title: "Fenchol" type: doc version: 1 created: 2026-02-28 author: "Wikipedia contributors" status: active scope: public tags: ["secondary-alcohols", "monoterpenes", "cyclohexanols"] topic_path: "general/secondary-alcohols" source: "https://en.wikipedia.org/wiki/Fenchol" license: "CC BY-SA 4.0" wikipedia_page_id: 0 wikipedia_revision_id: 0

| Verifiedfields = changed | Watchedfields = changed | verifiedrevid = 424674127 | Reference = | 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 = | 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, and comprises 15.9% of the volatile oils of some species of Aster.

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

Oxidation of fenchol gives fenchone.

References

References

  1. [http://www.chemexper.com/index.shtml?main=http://www.chemexper.com/search/cas/2217-02-9.html Datasheet] at chemexper.com
  2. "FES - (-)-endo-fenchol synthase, chloroplastic precursor - Ocimum basilicum (Sweet basil) - FES gene & protein".
  3. Kotan, Recep. (August 2007). "Screening of antibacterial activities of twenty-one oxygenated monoterpenes". Zeitschrift für Naturforschung C.
  4. Matasyoh, Josphat C.. (2006). "Chemical composition and antimicrobial activity of essential oil of ''Tarchonanthus camphoratus''". Food Chemistry.
  5. Satterwhite, D. M.. (15 November 1985). "Biosynthesis of monoterpenes. Enantioselectivity in the Enzymatic Cyclization of Linalyl Pyrophosphate to (-)-endo-Fenchol". The Journal of Biological Chemistry.

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secondary-alcoholsmonoterpenescyclohexanols