Chemistry:Cyclopentadecanolide
From HandWiki
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| Names | |
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| 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
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| Identifiers | |
3D model (JSmol)
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| 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). | |
| Infobox references | |
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.[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
- ↑ 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" (in en). Organic & Biomolecular Chemistry 8 (21): 4940–4948. doi:10.1039/c0ob00161a. ISSN 1477-0520. PMID 20820651. http://xlink.rsc.org/?DOI=c0ob00161a.
- ↑ Bestmann, Hans Jürgen; Schobert, Rainer (1989). "Kumulierte Ylide XX. Synthesen (E)-α,β-ungesättigter macrocyclischer Lactone durch intramolekulare Wittig-Olefinierung via Triphenylphosphoranylidenkete2" (in de). Synthesis 1989 (6): 419–423. doi:10.1055/s-1989-27271. ISSN 0039-7881. https://www.thieme-connect.de/products/ejournals/abstract/10.1055/s-1989-27271. Retrieved 2021-12-06.
- ↑ 3.0 3.1 3.2 Fahlbusch, Karl-Georg (2007). "Flavors and Fragrances". Ullmann's Encyclopedia of Industrial Chemistry (7th ed.). Wiley. p. 75.
- ↑ Burdock, George A. (2010). Fenaroli's Handbook of Flavor Ingredients (6th ed.). Taylor & Francis. p. 1597. ISBN 9781420090772.
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