9960. d-Verbenone

Nomenclature

CAS number: 18309-32-5
(1R)-4,6,6-Trimethylbicyclo[3.1.1]hept-3-en-2-one; (1R,5R)-(+)-2-pinen-4-one.
C10H14O; mol wt 150.22.
C 79.95%, H 9.39%, O 10.65%.

Description and references

A constituent of Spanish verbena oil (from Verbena triphylla L., Verbenaceae): Kerschbaum, Ber. 33, 885 (1900). Prepn from α-pinene: Bain, Gary, US 2911442 (1959 to Glidden). Structure: Blumann, Zeitschel, Ber. 46, 1178 (1913); Weinhaus, Schumm, Ann. 439, 20 (1924). Absolute configuration: Hurst, Whitham, J. Chem. Soc. 1960, 2864. Review: J. L. Simonsen, The Terpenes vol. II (University Press, Cambridge, 2nd ed., 1949) p 232-239.

Chemical structure

Properties

Oil. Characteristic odor. mp 6.5°. bp12 102-105°; bp760 227-228°. d20 0.9780. nD18 1.4957. [α]D18 +249.62°. uv max (ethanol): 253 nm (ε 6730). Practically insol in water. Miscible in all proportions with the usual organic solvents.