Cyclopentadecanolide
Chemical compound
From Wikipedia, the free encyclopedia
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.
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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 | |
| Identifiers | |
3D model (JSmol) |
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| ChemSpider | |
| ECHA InfoCard | 100.003.050 |
| EC Number |
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PubChem CID |
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CompTox Dashboard (EPA) |
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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).
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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]