Cyclopentadecanolide is a natural

macrolide Macrolides are a class of mostly natural products with a large macrocyclic lactone ring to which one or more deoxy sugars, usually cladinose and desosamine, may be attached. Macrolides belong to the polyketide class of natural products. ...

lactone Lactones are cyclic carboxylic esters. They are derived from the corresponding hydroxycarboxylic acids by esterification. They can be saturated or unsaturated. Lactones are formed by lactonization, the intramolecular esterification of the corresp ...

and a synthetic musk.

Natural occurrence

Cyclopentadecanolide occurs in small quantities in angelica root

essential oil An essential oil is a concentrated hydrophobic liquid containing volatile (easily evaporated at normal temperatures) chemical compounds from plants. Essential oils are also known as volatile oils, ethereal oils, aetheroleum, or simply as the ...

and is responsible for its musklike odor.

Production

Cyclopentadecanolide is produced synthetically by ring expansion of cyclotetradecanone. Another synthesis route is the

depolymerization Depolymerization (or depolymerisation) is the process of converting a polymer into a monomer or a mixture of monomers. This process is driven by an increase in entropy. Ceiling temperature The tendency of polymers to depolymerize is indicated by ...

polyester Polyester is a category of polymers that contain one or two ester linkages in every repeat unit of their main chain. As a specific material, it most commonly refers to a type called polyethylene terephthalate (PET). Polyesters include some natura ...

s of 15-hydroxypentadecanoic acid.

Uses

Cyclopentadecanolide is used as a

musk Musk is a class of aromatic substances commonly used as base notes in perfumery. They include glandular secretions from animals such as the musk deer, numerous plants emitting similar fragrances, and artificial substances with similar odors. ' ...

like perfume fixative in fine fragrances and as a

flavoring agent A flavoring (or flavouring), also known as flavor (or flavour) or flavorant, is a food additive that is used to improve the taste or Sense of smell, smell of food. It changes the perceptual impression of food as determined primarily by the chem ...

. It is a substitute for the extremely expensive animal musk.

References

{{reflist Flavors Lactones Perfume ingredients Oxygen heterocycles Heterocyclic compounds with 1 ring