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Fenchol

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Fenchol
(1R)-endo-(+)-Fenchol
Names
IUPAC name (1R,2R,4S)-1,3,3-Trimethyl-2-norbornanol
Other names Fenchyl alcohol
Identifiers
CAS Number
3D model (JSmol)
ChEMBL
ChemSpider
ECHA InfoCard 100.015.127 Edit this at Wikidata
EC Number
  • 216-639-5
PubChem CID
UNII
CompTox Dashboard (EPA)
InChI
  • InChI=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/s1Key: IAIHUHQCLTYTSF-OYNCUSHFSA-N
SMILES
  • CC1(C2CCC(C2)(C1O)C)C
Properties
Chemical formula C10H18O
Molar mass 154.253 g·mol
Density 0.942 g/cm
Melting point 39 to 45 °C (102 to 113 °F; 312 to 318 K)
Boiling point 201 °C (394 °F; 474 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). ☒N verify (what is  ?) Infobox references
Chemical compound

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

  1. Datasheet at chemexper.com
  2. "FES - (-)-endo-fenchol synthase, chloroplastic precursor - Ocimum basilicum (Sweet basil) - FES gene & protein". www.uniprot.org.
  3. Kotan, Recep; Kordali, Saban; Cakir, Ahmet (August 2007). "Screening of antibacterial activities of twenty-one oxygenated monoterpenes". Zeitschrift für Naturforschung C. 62 (7–8): 507–513. doi:10.1515/znc-2007-7-808. PMID 17913064.
  4. Matasyoh, Josphat C.; Kiplimo, Joyce J.; Karubiu, Nicholas M.; Hailstorks, Tiffany P. (2006). "Chemical composition and antimicrobial activity of essential oil of Tarchonanthus camphoratus". Food Chemistry. 101 (3): 1183–1187. doi:10.1016/j.foodchem.2006.03.021.
  5. Satterwhite, D. M.; Wheeler, C. J.; Croteau, R. (15 November 1985). "Biosynthesis of monoterpenes. Enantioselectivity in the Enzymatic Cyclization of Linalyl Pyrophosphate to (-)-endo-Fenchol". The Journal of Biological Chemistry. 260 (26): 13901–8. doi:10.1016/S0021-9258(17)38661-1. PMID 4055764.

External links

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