American Musk. I. The Chemical Constitution of the Musk of the Louisiana Muskrat¹

Abstract

¿\s(i4)"cholestene (300 mg.) was oxidized with chromic acid by the same procedure as used in the oxidation of 8cholestene,8 and the reaction product was divided into a ketone and a hydrocarbon fraction. The ketone fraction was indicated to contain a mixture of ketones since a crystalline product was not obtained either directly or as a semicarbazone or an oxime. The hydrocarbon fraction on repeated recrystallization from acetone-methanol yielded 12 mg. of A8,I4-cholestadiene, m. p. 83-84°, which gave no depression in mixed melting point with a sample of 8'14cholestadiene obtained by the action of perbenzoic acid on As(n).cholestene. A8,14-Cholestadiene was recovered unchanged after being refluxed with maleic anhydride in benzene for nine hours. Catalytic hydrogenation of A8'14-cholestadiene in ethyl acetate with palladium catalyst yielded a compound in the form of needles, m. p. 52-54°, which gave no depression in mixed melting point with A8^14kcholestene.Bromine Titrations.-The cholestadienes were titrated with bromine in the same manner as that described for the titration of 8-, A8'14^-and A14-cholestenes.s It was found that 3 • 5-cholestadiene, A6,8(l4'-cholestadiene, A7,a^uj-Ch0lestadiene, A7,14-cholestadiene and A8,14-cholestadiene in chloroform solution consumed 1.01, 2.24, 3.04, 2.66 and 3.22 molar equivalents of bromine, respectively, dissolved in chloroform. Using a methanol solution of the compound and a methanol solution of bromine, the same compounds consumed 1.02, -, 1.65, 1.76 and 1.83 molar equivalents of bromine, respectively.The authors wish to express their appreciation to Mr. . M. Gladrow of the physical chemistry department for helpful assistance in obtaining the absorption spectrum data. Summary 6•8(14)-, (11)-, 7•14-and 8• "-cholestadienes were prepared. The methods of preparation and the specific rotations of these cholestadienes were compared with those of the known analogous unsaturated steroid derivatives.

Muskrat Populations

“…With the enlargement of these glands, a yellowish, musky-smelling substance is secreted and deposited at stations along the routes of travel of muskrats, and at defecating posts, bases of lodges, and mud bars. Stevens and Erickson (1942) concluded that the musk oil contained a mixture of cyclopentadecanol and cycloheptadecanol and corresponding odoriferous ketones. The scent retains its properties sufficiently long after exposure to air to serve effectively as an advertising medium -up to several days in intensities readily detected by the human nose and possibly for weeks under circumstances favoring retention.…”

The Chemistry and Fragrance of Natural Musk Compounds

“…A sexual function has not been established, but seems probable, since in both sexes the musk glands reach their maximum development in the rutting season (Stevens and Erickson, 1942). Both sexes have scent glands, just as in the case of the civet cat of Abyssinia, but in contrast to the musk deer of Asia, of which the male alone produces musk.…”

“…Muskrat Stevens and Erickson (1942) studied the scent glands of the Louisiana muskrat. Muskrat Stevens and Erickson (1942) studied the scent glands of the Louisiana muskrat.…”

“…According to Stevens and Erickson (1942), musk oil distilled from Louisiana muskrat consists of cyclohepta decanol (58 % ) and cyclopentadecanol (40 % ) together with 2 % of the ketones cycloheptadecanone and cyclopentadecanone. According to Stevens and Erickson (1942), musk oil distilled from Louisiana muskrat consists of cyclohepta decanol (58 % ) and cyclopentadecanol (40 % ) together with 2 % of the ketones cycloheptadecanone and cyclopentadecanone.…”

Synthesis of Macrocyclic Musk‐Like Compounds through Ring‐Expansion Metathesis and Tebbe Olefination as Key Steps

“…Ruzicka [2] in 1926, demonstrated that the civetone, a musk-like ketone had a macrocyclic structure that Sack [3] had isolated in a yield of 6-8 % from the glands of the civet cat. Following this discovery, numerous macrocyclic ketones were discovered, including muscone (Walbaum [4] and Ruzicka [5,6] ) from Siberian musk deer and exaltone (Stevens and Erickson) [7] from muskrat. These substances are now generated on an industrial scale and utilized by the flavour and fragrance (F&F) industry as perfume ingredients.…”