Cyclopentadecanolide

Names

Preferred IUPAC name 1-Oxacyclohexadecan-2-one

Other names Angelica lactone; Muskalactone; Muskolactone; Exaltolide; Pentalide; Pentadecanolide; Pentadecalactone; 15-Hydroxypentadecanoic acid, lactone; 15-Hydroxypentadecanoic acid-epsilon-lactone; Pentadecanoic acid, 15-hydroxy-, E-lactone; ω-Pentadecalactone; omega-Pentadecalactone; ω-Lactone; 2-Pentadecalone; Pentadecan-15-olide; 1,15-Pentadecanolide

Identifiers

CAS Number

3D model (JSmol)

ChemSpider

ECHA InfoCard

EC Number203‐354‐6

PubChem CID

CompTox Dashboard (EPA)

InChI InChI=1S/C15H28O2/c16-15-13-11-9-7-5-3-1-2-4-6-8-10-12-14-17-15/h1-14H2Key: FKUPPRZPSYCDRS-UHFFFAOYSA-NInChI=1/C15H28O2/c16-15-13-11-9-7-5-3-1-2-4-6-8-10-12-14-17-15/h1-14H2Key: FKUPPRZPSYCDRS-UHFFFAOYAJ

SMILES O=C1CCCCCCCCCCCCCCO1

Properties

Chemical formulaC15H28O2

Molar mass240.387 g·mol−1

AppearanceColorless crystals

OdorMusklike

Density0.940

Melting point34 °C (93 °F; 307 K)

Boiling point98 °C (208 °F; 371 K) at 0.02 Torr

Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Cyclopentadecanolide is an organic compound with the formula (CH2)14CO2. A colorless solid, it is classified as macrolide lactone. It has some use in perfumery.

Occurrence and production

Cyclopentadecanolide occurs in small quantities in angelica root essential oil and is responsible for its musklike odor.

Cyclopentadecanolide is produced by ring expansion of cyclotetradecanone. Another synthesis route is the depolymerization of polyesters of 15-hydroxypentadecanoic acid.

Uses

Cyclopentadecanolide is used as a musklike perfume fixative in fine fragrances and as a flavoring agent. Its aroma is described as "musk, animal, powdery, natural, fruity, tobacco, coumarinic, heliotrope, and licorice". It is a substitute for the extremely expensive animal musk.