Cyclopentadecanolide

Chemical properties

Cyclopentadecanolide is a white crystalline low melting solid. melting at 36-37℃. to a colorless, viscous oil. B.P. 280℃. Delicately animal, musky and sweet, extremely tenacious odor of outstanding uniformity. Common use level in the perfume oil is about 0.1 to 0.4%.

Chemical properties

Cyclopentadecanolide occurs in small quantities in, for example, angelica root oil. It forms colorless crystals (mp 37–38°C) with a delicate, musk-like odor.

Chemical properties

ω-Pentadecalactone has an extraordinarily persistent, musk-like odor.

Occurrence

Originally reported found in the essential oil from angelica roots.

The Uses of Cyclopentadecanolide

As a fixative in perfumery.

The Uses of Cyclopentadecanolide

Pentadecanolide is a monomer used to make PGA-co-pentadecalactone polymers to be used in the development of directly compressed prolonged release tablets of slightly soluble drugs such as ketoprofen.

The Uses of Cyclopentadecanolide

Pentadecanolide may be used for the synthesis of poly(pentadecanolide) (PPDL) by Novozyme 435 catalyzed ring-opening polymerization. It may be employed as starting reagent for the synthesis of terminally-branched iso-fatty acids (iso-C₁₅-C₁₇).

What are the applications of Application

Pentadecanolide is a monomer used to make PGA-co-pentadecalactone polymers

Preparation

The main industrial syntheses start from compounds produced from cyclododecatriene: either by ring expansion of cyclododecanone or by depolymerization of polyesters of 15-hydroxypentadecanoic acid (from 1,12-dodecanediol).

Definition

ChEBI: Cyclopentadecanolide is a macrolide.

What are the applications of Application

Cyclopentadecanolide gives highly interesting effects when applied to certain flavors, e. g. alcoholic beverages, dentifrice flavors etc. There is very often a unanimous preference for the flavor that is properly treated with the hctone. Concentration in such flavors may be about 0.02 to 1.50 ppm calculated upon the finished consumer product. However, it should be kept in mind, that dentifrices are flavored at extremely high concentration (about 100) and it may therefore ghe an underestimated evaluation of the power of this Lactone, The most frequent abuse of Cyclopentadecanolide is that of over-dosage. It is also used extensively in Berry flavors, Liquor, Wine, Brandy, Fruit, Nut, Vanilla copositions, etc.

Aroma threshold values

Detection: 1 to 4 ppb

Taste threshold values

Taste characteristics at 75 ppm: vanilla bean, powdery helioropine, creamy and licorice.

Synthesis Reference(s)

Tetrahedron Letters, 34, p. 6107, 1993 DOI: 10.1016/S0040-4039(00)61741-0
The Journal of Organic Chemistry, 50, p. 2394, 1985 DOI: 10.1021/jo00213a044

General Description

Pentadecanolide is one of the major components, isolated from the root of Angelica archangelica L., species. It is a synthetic musk, which exists as a widespread contaminant in the environment.

Flammability and Explosibility

Non flammable

Trade name

Macrolide® (Symrise), Exaltolide®, Exaltolide®Total (Firmenich), Pentalide (Soda Aromatic).

Purification Methods

It has been recrystallised from MeOH (4 parts) at -15o. [Hundieck