Muscone (Molecule of the Month for May 1997)
Two of the oldest-known ingredients of perfumes, musk and civet, are odoriferous animal products that function as attractant pheromones in nature.
Musk originally came from the male musk deer Moschus moschiferus, a native of China and Tibet, while the sources of civet were the African and Asian civet cats Viverra civetta and Viverra zibetha. Both musk and civet were ancient articles of commerce.
Musk and civet have a heavy, musky odor that is still considered essential in perfumery. Through the years cheaper and more convenient natural sources of musky scents were found. Not only more accessible mammals, such as the muskrat, provided appropriate substitutes, but there were also an octopus, an alligator, and a snail that furnished musky essences; there is even a musk beetle.
Twentieth century chemical investigations of the active principles of musk and civet and the subsequent laboratory preparation of these compounds permitted synthetic chemicals to replace the animal products.
The major active compounds in natural musk and civet are two large-ring compounds known as muscone and civetone. Most of the rings in natural products contain five or six carbon atoms, and these compounds with fifteen- and seventeen membered rings are distinctly odd.
Musk deer are caught mainly for musk ("musk deer perfume"), present only in the males. Musk is secreted by a saccate gland located between the sex organs and the naval. In the past, musk was used in medicine in Europe and the East. The use of musk as a natural perfume base (used in preparing high quality scents) was discovered later. When this happened, the use of musk in perfume boomed. In Nepal in 1972, for example, an ounce of musk was worth more than an ounce of gold.
The musk deer has long been hunted for its prized "musk pouch." In 1855, around 81,200 sacs were exported from Russia to China through Kyakhta, and a few years later, Japan imported over 100,000 sacs in a single year. The musk deer population diminished greatly, and in 1927, only 5,089 sacs were collected. This lead to the classification of the animal as endangered.
Formal Chemical Name (IUPAC)
Update by Karl Harrison
(Molecule of the Month for May 1997 )