Cyclopentadecanolide

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

Cyclopentadecanolide is an organic compound with the formula (CH₂)₁₁CO₂. 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. ^[3]

Cyclopentadecanolide is produced 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.