3968. d-Fenchone

Nomenclature

CAS number: 4695-62-9
(1S)-1,3,3-Trimethylbicyclo[2.2.1]heptan-2-one; d-1,3,3-trimethyl-2-norbornanone; d-1,3,3-trimethyl-2-norcamphanone.
C10H16O; mol wt 152.23.
C 78.90%, H 10.59%, O 10.51%.

Description and references

Occurs in fennel oil and in the essential oil of Lavandula stoechas L., Labiatae. Isoln: Wallach, Ann. 263, 129 (1891); 353, 209 (1907); 369, 63 (1909); Shavrygin, J. Appl. Chem. USSR 12, 1201 (1939). Total synthesis: Boyle et al., Chem. Commun. 1971, 395; G. Buchbauer, H. C. Rohner, Ann. 1981, 2093. Toxicity study: P. M. Jenner et al., Food Cosmet. Toxicol. 2, 327 (1964). Review: Simonsen, The Terpenes vol. II (Cambridge, 2nd ed., 1949) pp 560-580; D. L. J. Opdyke, Food Cosmet. Toxicol. 14, Suppl., 769-771 (1976).

Chemical structure

Properties

Oily liq. Camphor-like odor. d418 0.948. mp 6.1°. bp760 193.5°; bp100 122°; bp20 82°; bp15 66°. [α]D20 +66.9°. nD18 1.4636. Practically insol in water (pH of satd soln 6.82). Very sol in abs alcohol, ether. LD50 orally in rats: 6.16 g/kg (Jenner).

Use

As flavor in foods; in perfumes.

Therapeutic Category

Counterirritant.