Ambrettolide

Natural musk was used extensively in perfumery until the late 19th century, when economic and ethical motives led to the adoption of synthetic musk, which is now used almost exclusively. Polycyclic musks are not biodegradable, and macrocyclic musks have supplanted them.

Origin and Production

Ambrettolide is not reported as being found in nature, unlike (Z)-7-hexadecen-16-olide, which occurs in ambrette seed oil and is also referred to as ambrettolide. Some plants, such as Angelica archangelica or Abelmoschus moschatus, produce musky-smelling macrocyclic lactone compounds. Such compounds are used in perfumery as substitutes for animal musk or to alter the smell of a mixture of other musks. The seeds of Abelmoschus moschatus have a sweet, flowery, heavy fragrance similar to that of musk. Musk mallow seed oil was once frequently used in perfumes as a substitute for animal musk, but synthetic musks have now mostly replaced it because of its high cost.

Chemistry

In general, musks from animals are ketones, and plant musks are lactones, which are cyclic esters. Ring size matters in determining the smell of these ring compounds: molecules with about 14-19 atoms in the ring tend to have a musky smell. Macrocyclic musks are often lactones, containing ester linkages, and these are more susceptible to biodegradation than the carbonyl groups usually found in polycyclic musks. ChEBI classes isoambrettolide as a macrolide.

Chemical Properties

Ambrettolide is sparingly soluble in chloroform and methanol. Its water solubility is 15 μg/L at 25 °C. The acute oral LD50 in rats and the acute dermal LD50 in rabbits both exceeded 5 g/kg.