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

| MeltingPt_ref = {{cite journal |last1=Morales-Serna |first1=José Antonio |last2=Sánchez |first2=Ericka |last3=Velázquez |first3=Ricardo |last4=Bernal |first4=Jorge |last5=García-Ríos |first5=Eréndira |last6=Gaviño |first6=Rubén |last7=Negrón-Silva |first7=Guillermo |last8=Cárdenas |first8=Jorge |date=2010 |title=Highly efficient macrolactonization of ω-hydroxy acids using benzotriazole esters: synthesis of Sansalvamide A |url=http://xlink.rsc.org/?DOI=c0ob00161a |journal=Organic & Biomolecular Chemistry |language=en |volume=8 |issue=21 |pages=4940–4948 |doi=10.1039/c0ob00161a |pmid=20820651 |issn=1477-0520|url-access=subscription }}

| BoilingPtC = 98

| BoilingPt_notes = at 0.02 Torr

| BoilingPt_ref = {{cite journal |last1=Bestmann |first1=Hans Jürgen |last2=Schobert |first2=Rainer |date=1989 |title=Kumulierte Ylide XX. Synthesen (E)-α,β-ungesättigter macrocyclischer Lactone durch intramolekulare Wittig-Olefinierung via Triphenylphosphoranylidenkete2 |url=https://www.thieme-connect.de/products/ejournals/abstract/10.1055/s-1989-27271 |journal=Synthesis |language=de |volume=1989 |issue=6 |pages=419–423 |doi=10.1055/s-1989-27271 |issn=0039-7881 |access-date=2021-12-06 |archive-url=https://web.archive.org/web/20180605135810/https://www.thieme-connect.de/DOI/DOI?10.1055%2Fs-1989-27271 |archive-date=2018-06-05|url-access=subscription }}

| Solubility =

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|Section3={{Chembox Hazards

| MainHazards =

| FlashPt =

| AutoignitionPt =

}}

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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.

References