Cyclopentadecanolide

Cyclopentadecanolide is a natural macrolide lactone and a synthetic musk.

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	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	34 °C (93 °F; 307 K)[1]
Boiling point	98 °C (208 °F; 371 K)[2] 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

Natural occurrence

Cyclopentadecanolide occurs in small quantities in angelica root essential oil and is responsible for its musklike odor.^[3]

Production

Cyclopentadecanolide is produced synthetically by ring expansion of cyclotetradecanone. Another synthesis route is the depolymerization of polyesters of 15-hydroxypentadecanoic acid.^[3]

Uses

Cyclopentadecanolide is used as a musklike perfume fixative in fine fragrances and as a flavoring agent.^[4] It is a substitute for the extremely expensive animal musk.^[3]

References

1. Morales-Serna, José Antonio; Sánchez, Ericka; Velázquez, Ricardo; Bernal, Jorge; García-Ríos, Eréndira; Gaviño, Rubén; Negrón-Silva, Guillermo; Cárdenas, Jorge (2010). "Highly efficient macrolactonization of ω-hydroxy acids using benzotriazole esters: synthesis of Sansalvamide A". Organic & Biomolecular Chemistry. 8 (21): 4940–4948. doi:10.1039/c0ob00161a. ISSN 1477-0520. PMID 20820651.
2. Bestmann, Hans Jürgen; Schobert, Rainer (1989). "Kumulierte Ylide XX. Synthesen (E)-α,β-ungesättigter macrocyclischer Lactone durch intramolekulare Wittig-Olefinierung via Triphenylphosphoranylidenkete2". Synthesis (in German). 1989 (6): 419–423. doi:10.1055/s-1989-27271. ISSN 0039-7881. Archived from the original on 2018-06-05. Retrieved 2021-12-06.
3. Fahlbusch, Karl-Georg; et al. (2007). "Flavors and Fragrances". Ullmann's Encyclopedia of Industrial Chemistry (7th ed.). Wiley. p. 75.
4. Burdock, George A. (2010). "ω-PENTADECALACTONE". Fenaroli's Handbook of Flavor Ingredients (6th ed.). Taylor & Francis. p. 1597. ISBN 9781420090772.