March, 1945
THESCENT OF THE COMMON SKUNK [CONTRIBUTION FROM THE STERLING CHEMICAL
LABORATORY OF Y A L E
407
UNIVERSITY]
American Musk. 111. The Scent of the Common Skunk BY PHILIP G. STEVENS The scent of the corniiion skunk (Mephitis therefore an unsaturated sulfide. On treatment mephitis) is so extraordinarily powerful and per- with inethyl iodide a t room temperature, A sistent that from tiine t o time i t has attracted attention from chemists. That some sulfur compound was present was recognized early,' but i t remained for Aldrich2 t o show that the principal odoriferous material is n-butyl mercaptan, accompanied by alkyl sulfides. Almost simultaneously Beckmann3 noted the occurrence of n-butyl mercaptan in the scent of the teledu (Mydaus rnarclzei Huet, a member of the Mustelidae family and thus closely related to the skunks) of the Philippine Islands, and believed the higherboiling oil was a disulfide. Not until 1937 was further work done on this type of secretion when Fester and Bertuzzi4 undertook a study of the scent of the South American zorrino (Conepatus sufocuns), isolating by steam distillation a small amount of oil which, from analytical data, appeared to contain n-butyl mercaptan, and an unsaturated Ca mercaptan, and the corresponding disulfide. In connection with attempts to discover new natural n i ~ s k and s ~ ~in~view of reference in the literature to skunk scent and perfume^,^,' an investigation of skunk scent was undertaken to learn whether any large ring compounds were present. Fresh scent (from Jfephitis mepliitis nigra) was treated with alcoholic mercuric chloride to remove mercaptans, and supposedly sulfides also, and the unchanged material was separated into two volatile and a non-volatile fraction. The latter material containing any large ring compounds present, was saponified, and the neutral material was fractionated, yielding a small amount of oil which, though having a not unpleasarzt, somewhat floral odor, and boiling as would a large ring alcoliol or ketone, had a composition corresponding approximately to C111T20S2,and gave, on oxidation, products with no niusk odor. The scent therefore contains no large ring compounds of the niusk or civet type; any fixative value, if any, must depend on other compounds. The volatile oils were repulsive i l l odor. The main, more volatile fraction, A, had the coinposition CsHllS, was insoluble in dilute potassium hydroxide, added bromine avidly, gave a precipitate with aqueous mercuric c h l o r ~ d e ,and ~ was (1) S w n r t s , A!176.,1 2 3 , 206 (I8ti2). (2) Aldrich, J . 1C~bll..\led., 1, 323 (lX9ti). (3) Beckmann, J'hnrm. Cenlr.alholle. 37, 527 (18OC). ( 4 ) Fester and Bertuzzi, I b v i s l i i de la Facullad dr (luimica I n d u s l r i o l l y Apricola, 5 , S,j ( 1 0 3 7 ) , Uiiiversidad Nacional del Litoral, RosBrio, Argentina. - ) Stevens xn
