3895. Eucalyptol

Nomenclature

CAS number: 470-82-6
1,3,3-Trimethyl-2-oxabicyclo[2.2.2]octane; 1,8-epoxy-p-menthane; cineole; cajeputol.
C10H18O; mol wt 154.25.
C 77.87%, H 11.76%, O 10.37%.

Description and references

The chief constituent of oil of eucalyptus: Cloez, Ann. 154, 372 (1870); Berry, Australas. J. Pharm. 1929, 203; from wormwood oil: Wallach, Brass, Ann. 225, 291 (1884). Identity with cajeputol: Wallach, ibid. 314. Identity with cineole: Jahns, Ber. 17, 2941 (1884). Structure: Wallach, Ann. 291, 342 (1896). Biosynthesis: Birch et al., Tetrahedron Letters, no. 3, 1 (1959). Activity: Jori et al., Eur. J. Pharmacol. 9, 362 (1970). Cockroach repellent activity: T. H. Maugh, Science 218, 278 (1982).

Chemical structure

Properties

Colorless liquid; camphor-like odor; spicy, cooling taste. d2525 0.921-0.923. bp 176-177°. mp 1.5°. nD20 1.455-1.460. Flash pt, closed cup: 118°F (48°C). Practically insol in water; miscible with alcohol, chloroform, ether, glacial acetic acid, oils.

Use

Pharmaceutic aid (flavor).