AMBRETTOLIDE

Chemical properties

AMBRETTOLIDE is not reported as being found in nature, in contrast to (Z)-7-hexadecen-16-olide, which occurs in ambrette seed oil and which is also referred to as ambrettolide. It is a colorless to slightly yellow liquid, d²⁰₄ 0.949–0.957, n²⁰_D 1.477–1.482, with an intense and powerful musk odor. It is prepared by treating aleuritic acid (9,10,16-trihydroxyhexadecanoic acid) with trimethyl orthoformate to give a dioxolane derivative. Reaction with acetic anhydride yields ??-acetoxy (E)-9-hexadecenoic acid methyl ester. This is lactonized with potassium hydroxide to give the title compound .

Occurrence

Found in oil of ambrette seed[Givaudan Index, 1961).

The Uses of AMBRETTOLIDE

Ambrettolide is a macrocyclic lactone that naturally occurs in ambrette seed oil. Ambrettolide is nontoxic, has a musky odour, and is commonly used as a fixative in perfume formulations.

Preparation

From bromohexadecenoic acid(Bedoukian, 1967).

Definition

ChEBI: Isoambrettolide is a macrolide.

Production Methods

Many patented methods are known, few are commercially feasible. From Bromo hexadecenoic acid, or from Dihydroxy palmitic acid, or from Aleuritic acid, or from Juniperic acid, etc.

Flammability and Explosibility

Not classified