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Cyclopentadecanolide
Cyclopentadecanolide
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Cyclopentadecanolide
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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

[edit]

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

[edit]

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

[edit]
  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.
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