2252. Chrysanthenone

Nomenclature

CAS number: 473-06-3
2,7,7-Trimethylbicyclo[3.1.1]heptan-6-one; 2-pinen-7-one.
C10H14O; mol wt 150.22.
C 79.95%, H 9.39%, O 10.65%.

Description and references

A constituent of the essential oil of Chrysanthemum indicium L., also extracted from C. sinense Sabin, Compositae. Prepared by photochemical rearrangement of l- or d-verbenone, q.v.: Hurst, Whitham, J. Chem. Soc. 1960, 2864; Erman, J. Am. Chem. Soc. 89, 3828 (1967); Schuster, Widman, Tetrahedron Lett. 1971, 3571. Structure: Kotake, Nonaka, Ann. 607, 153 (1957); Blanchard, Chem. Ind. (London) 1958, 293. Chemistry: Erman, J. Am. Chem. Soc. 91, 779 (1969).

Chemical structure

Derivative

d-Form.

Properties

Herbaceous odor. bp12 88-89°. nD22 1.4720. [α]D +37° (c = 2.1 in chloroform). uv max: 290 nm (ε 120). Insoluble in water; sol in alcohol.