d-Fenchone

Title: d-Fenchone
CAS Registry Number: 4695-62-9
CAS Name: (1S)-1,3,3-Trimethylbicyclo[2.2.1]heptan-2-one
Additional Names: d-1,3,3-trimethyl-2-norbornanone; d-1,3,3-trimethyl-2-norcamphanone
Molecular Formula: C10H16O
Molecular Weight: 152.23
Percent Composition: C 78.90%, H 10.59%, O 10.51%
Literature 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).
Properties: Oily liq. Camphor-like odor. d418 0.948. mp 6.1°. bp760 193.5°; bp100 122°; bp20 82°; bp15 66°. [a]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).
Melting point: mp 6.1°
Boiling point: bp760 193.5°; bp100 122°; bp20 82°; bp15 66°
Optical Rotation: [a]D20 +66.9°
Index of refraction: nD18 1.4636
Density: d418 0.948
Toxicity data: LD50 orally in rats: 6.16 g/kg (Jenner)
Use: As flavor in foods; in perfumes.
Therap-Cat: Counterirritant.
D-Fucose D-Galactosamine D-Galactose D-Galacturonic Acid D-Glucaric Acid