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Cyclopentadecanolide

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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
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.003.050 Edit this at Wikidata
EC Number
  • 203‐354‐6
PubChem CID
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C15H28O2/c16-15-13-11-9-7-5-3-1-2-4-6-8-10-12-14-17-15/h1-14H2Key: FKUPPRZPSYCDRS-UHFFFAOYSA-N
  • InChI=1/C15H28O2/c16-15-13-11-9-7-5-3-1-2-4-6-8-10-12-14-17-15/h1-14H2Key: FKUPPRZPSYCDRS-UHFFFAOYAJ
SMILES
  • O=C1CCCCCCCCCCCCCCO1
Properties
Chemical formula C15H28O2
Molar mass 240.387 g·mol
Appearance Colorless crystals
Odor Musklike
Density 0.940
Melting point 34 °C (93 °F; 307 K)
Boiling point 98 °C (208 °F; 371 K) at 0.02 Torr
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). Infobox references
Chemical compound

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.

Production

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

Uses

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

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.
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