Cyclopentadecanolide

Cyclopentadecanolide
Names
	IUPAC name 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	106‐02‐5;
3D model (JSmol)	Interactive image;
ChemSpider	205386;
ECHA InfoCard	100.003.050
EC Number	203‐354‐6;
PubChem CID	235414;
CompTox Dashboard (EPA)	DTXSID6044359 ;
	InChI InChI=1S/C15H28O2/c16-15-13-11-9-7-5-3-1-2-4-6-8-10-12-14-17-15/h1-14H2 Key: FKUPPRZPSYCDRS-UHFFFAOYSA-N; InChI=1/C15H28O2/c16-15-13-11-9-7-5-3-1-2-4-6-8-10-12-14-17-15/h1-14H2 Key: FKUPPRZPSYCDRS-UHFFFAOYAJ;
	SMILES O=C1CCCCCCCCCCCCCCO1;
Properties
Chemical formula	C15H28O2
Molar mass	240.387 g·mol−1
Appearance	colorless crystals
Odor	musklike
Density	0.940
Melting point	37 to 38 °C (99 to 100 °F; 310 to 311 K)
Boiling point	169 °C (336 °F; 442 K)
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Cyclopentadecanolide is a natural macrolide lactone and a synthetic musk.

Natural occurrence

Cyclopentadecanolide occurs in small quantities in angelica root essential oil and is responsible for its musklike odor.^[1]

Cyclopentadecanolide is produced synthetically by ring expansion of cyclododecanone. Another synthesis route is the depolymerization of polyesters of 15-hydroxypentadecanoic acid.^[1]

Cyclopentadecanolide is used as a musklike perfume fixative in fine fragrances and as a flavoring agent.^[2] It is a substitute for the extremely expensive animal musk.^[1]

^ ^a ^b ^c Karl-Georg Fahlbusch; et al. (2007), "Flavors and Fragrances", Ullmann's Encyclopedia of Industrial Chemistry (7th ed.), Wiley, p. 75
^ George A. Burdock (2010), "ω-PENTADECALACTONE", Fenaroli's Handbook of Flavor Ingredients (6th ed.), Taylor & Francis, p. 1597