Cyclopentadecanolide
{{Chembox
| ImageFile1 = Exaltolid Strukturformel V1.svg
| ImageFile2 = Cyclopentadecanolide-3d.png
| PIN = 1-Oxacyclohexadecan-2-one
| OtherNames = 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
|Section1={{Chembox Identifiers
| CASNo = 106‐02‐5
| EINECS = 203‐354‐6
| PubChem = 235414
| ChemSpiderID = 205386
| InChI = 1/C15H28O2/c16-15-13-11-9-7-5-3-1-2-4-6-8-10-12-14-17-15/h1-14H2
| InChIKey = FKUPPRZPSYCDRS-UHFFFAOYAJ
| StdInChI = 1S/C15H28O2/c16-15-13-11-9-7-5-3-1-2-4-6-8-10-12-14-17-15/h1-14H2
| StdInChIKey = FKUPPRZPSYCDRS-UHFFFAOYSA-N
| SMILES = O=C1CCCCCCCCCCCCCCO1
}}
|Section2={{Chembox Properties
| C = 15
| H = 28
| O = 2
| Appearance = Colorless crystals
| Odor = Musklike
| Density = 0.940
| MeltingPtC = 34
| BoilingPtC = 98
| BoilingPt_notes = at 0.02 Torr
| Solubility =
}}
|Section3={{Chembox Hazards
| MainHazards =
| FlashPt =
| AutoignitionPt =
}}
}}
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.{{cite book |first=Karl-Georg |last=Fahlbusch |contribution=Flavors and Fragrances |title=Ullmann's Encyclopedia of Industrial Chemistry |edition=7th |publisher=Wiley |year=2007 |page=75 |display-authors=etal}}
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.{{cite book |entry=ω-PENTADECALACTONE |first=George A. |last=Burdock |title=Fenaroli's Handbook of Flavor Ingredients |edition=6th |publisher=Taylor & Francis |year=2010 |page=1597 |isbn=9781420090772}} It is a substitute for the extremely expensive animal musk.