2335. Civetone

Nomenclature

CAS number: 542-46-1
(Z)-9-Cycloheptadecen-1-one.
C17H30O; mol wt 250.42.
C 81.54%, H 12.07%, O 6.39%.

Description and references

17-Membered macrocyclic musk, constituent of civet: Ruzicka, Helv. Chim. Acta 9, 230 (1926); Ruzicka et al., ibid. 10, 695 (1927). Occurs in nature as cis-form. Synthesis of cis-civetone: Stoll et al., ibid. 31, 543 (1948); J. Tsuji, T. Mondai, Tetrahedron Lett. 1977, 3285; E. Seoane et al., Chem. Ind. (London) 1978, 165. Synthesis of trans-form: H. Hunsdiecker, Ber. 77, 185 (1944); H. H. Mathur, S. C. Bhattacharyya, J. Chem. Soc. 1968, 114. Crystal and molecular structure of cis-civetone: G. Bernardinelli, R. Gerdil, Helv. Chim. Acta 65, 558 (1982).

Chemical structure

Properties

Crystals, mp 31-32°. Musky odor becoming pleasant in extreme dilns. d433 0.917. bp742 342°; bp2 59°. nD33.4 1.4830.

Use

In perfumery.