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
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.003.050 Edit this at Wikidata
EC Number
  • 203‐354‐6
  • 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
  • O=C1CCCCCCCCCCCCCCO1
Properties
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).

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.[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] Its aroma is described as "musk, animal, powdery, natural, fruity, tobacco, coumarinic, heliotrope, and licorice".[5] 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. ^ a b c 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.
  5. ^ "omega-pentadecalactone". Scents and Flavors. Scents and Flavors. Retrieved 29 March 2026.

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