Fenchol

Fenchol[1]
	; (1R)-endo-(+)-Fenchol
Names
	IUPAC name (1R,2R,4S)-1,3,3-Trimethyl-2-norbornanol
	Other names Fenchyl alcohol
Identifiers
CAS Number	1632-73-1 (unspecified isomer) ; 2217-02-9 ((1R)-endo-(+));
3D model (JSmol)	Interactive image;
ChEMBL	ChEMBL3188732;
ECHA InfoCard	100.015.127
PubChem CID	15406 (unspecified isomer); 6997371 ((1R)-endo-(+));
UNII	410Q2GK1HF;
CompTox Dashboard (EPA)	DTXSID1041970 ;
	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/s1 Key: IAIHUHQCLTYTSF-OYNCUSHFSA-N;
	SMILES CC1(C2CCC(C2)(C1O)C)C;
Properties
Chemical formula	C10H18O
Molar mass	154.253 g·mol−1
Density	0.942 g/cm3
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 [77 °F], 100 kPa).
	verify (what is ?)
	Infobox references

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 enantiopure (1R)-endo-(+)-fenchol is used extensively in perfumery. Fenchol gives basil its characteristic scent,[2][3] and comprises 15.9% of the volatile oils of some species of Aster.[4]

It is biosynthesized from geranyl pyrophosphate via isomerization to linalyl pyrophosphate.[5]

Oxidation of fenchol gives fenchone.

References

Datasheet at chemexper.com
"FES - (-)-endo-fenchol synthase, chloroplastic precursor - Ocimum basilicum (Sweet basil) - FES gene & protein". www.uniprot.org.
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.
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.
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. PMID 4055764.

External links

3D-image

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[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. PMID 4055764.