6313. Muscone

Nomenclature

CAS number: 541-91-3
3-Methylcyclopentadecanone; muskone; methylexaltone.
C16H30O; mol wt 238.41.
C 80.61%, H 12.68%, O 6.71%.

Description and references

The odorous principle of musk. Characterization of naturally occurring (-)-form: Ruzicka, Helv. Chim. Acta 9, 715 (1926). Structure: ibid. 1008. Synthesis of (±)-form: Ziegler, Weber, Ann. 512, 164 (1934); Ruzicka, Stoll, Helv. Chim. Acta 17, 1308 (1934); Hunsdiecker, Ber. 75B, 1197 (1942). Review of syntheses: S. Abe et al., Cosmet. Perfum. 88, 67 (1973). Recent syntheses: Stork, Macdonald, J. Am. Chem. Soc. 97, 1264 (1975); H. G. Fliri et al., Monatsh. Chem. 110, 245 (1979); C. Fehr et al., Helv. Chim. Acta 62, 2655 (1979); K. H. Schulte-Elte et al., ibid. 2673; G. Cantoni et al., J. Org. Chem. 45, 1906 (1980). Chiral synthesis of (R)-(-)- and (S)-(+)-forms: Q. Branca, A. Fischli, Helv. Chim. Acta 60, 925 (1977).

Chemical structure

Derivative

(-)-Form.

Properties

Oily liquid. Musk odor. bp 328°; bp0.5 130°. d417 0.9221. nD17 1.4802. [α]D17 -13°. Very slightly sol in water; miscible with alc.

Derivative

(±)-Form.

Properties

Oily liquid. bp0.01 90°. nD26 1.4767. uv max (ethanol): 285 nm (log ε 1.54).