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New macrocyclic compounds from the secretions of the civet cat and the musk rat

1973; Royal Netherlands Chemical Society; Volume: 92; Issue: 8 Linguagem: Inglês

10.1002/recl.19730920813

1878-7096

D. A. van Dorp, R. Klok, D.H. Nugteren,

Analytical Chemistry and Chromatography

Abstract The odoriferous glands of the civet cat and the musk rat contain not only the limited number of macrocyclic components described in the classical literature, such as civetone (9 cis ‐cycloheptadecenone), but a whole spectrum of saturated and unsaturated cyclic ketones and alcohols. In the musk rat, peculiar compounds containing conjugated and/or triple bonds were found; the unsaturation was located here exclusively at the 5 and/or 7 position. The macrocyclic alcohols were always esterified with long chain fatty acids. The absolute configuration of the dextrorotatory unsaturated alcohols was established as S. Some of the new compounds have been made in quantity by total organic synthesis, viz. 5‐cyclopentadecynone, 5 cis ‐cyclopentadecenone, 5‐cycloheptadecynone, 5 cis ‐cycloheptadecenone and 9 cis ‐cyclononadecenone.