Title: d-Fenchone
CAS Registry Number: 4695-62-9
CAS Name: (1
S)-1,3,3-Trimethylbicyclo[2.2.1]heptan-2-one
Synonyms: 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.