Cyclopentadecanolide
Clash Royale CLAN TAG#URR8PPP
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| Names | |
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IUPAC name 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 |
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3D model (JSmol) |
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ChemSpider |
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ECHA InfoCard | 100.003.050 |
EC Number | 203‐354‐6 |
PubChem CID |
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InChI
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| Properties | |
Chemical formula | C15H28O2 |
Molar mass | 7002240387000000000♠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.
Contents
1 Natural occurrence
2 Production
3 Uses
4 References
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". Organic & Biomolecular Chemistry. 8 (21): 4940. doi:10.1039/c0ob00161a. ISSN 1477-0520..mw-parser-output cite.citationfont-style:inherit.mw-parser-output .citation qquotes:"""""""'""'".mw-parser-output .citation .cs1-lock-free abackground:url("//upload.wikimedia.org/wikipedia/commons/thumb/6/65/Lock-green.svg/9px-Lock-green.svg.png")no-repeat;background-position:right .1em center.mw-parser-output .citation .cs1-lock-limited a,.mw-parser-output .citation .cs1-lock-registration abackground:url("//upload.wikimedia.org/wikipedia/commons/thumb/d/d6/Lock-gray-alt-2.svg/9px-Lock-gray-alt-2.svg.png")no-repeat;background-position:right .1em center.mw-parser-output .citation .cs1-lock-subscription abackground:url("//upload.wikimedia.org/wikipedia/commons/thumb/a/aa/Lock-red-alt-2.svg/9px-Lock-red-alt-2.svg.png")no-repeat;background-position:right .1em center.mw-parser-output .cs1-subscription,.mw-parser-output .cs1-registrationcolor:#555.mw-parser-output .cs1-subscription span,.mw-parser-output .cs1-registration spanborder-bottom:1px dotted;cursor:help.mw-parser-output .cs1-ws-icon abackground:url("//upload.wikimedia.org/wikipedia/commons/thumb/4/4c/Wikisource-logo.svg/12px-Wikisource-logo.svg.png")no-repeat;background-position:right .1em center.mw-parser-output code.cs1-codecolor:inherit;background:inherit;border:inherit;padding:inherit.mw-parser-output .cs1-hidden-errordisplay:none;font-size:100%.mw-parser-output .cs1-visible-errorfont-size:100%.mw-parser-output .cs1-maintdisplay:none;color:#33aa33;margin-left:0.3em.mw-parser-output .cs1-subscription,.mw-parser-output .cs1-registration,.mw-parser-output .cs1-formatfont-size:95%.mw-parser-output .cs1-kern-left,.mw-parser-output .cs1-kern-wl-leftpadding-left:0.2em.mw-parser-output .cs1-kern-right,.mw-parser-output .cs1-kern-wl-rightpadding-right:0.2em
^ Bestmann, Hans Jürgen; Schobert, Rainer (1989). "Kumulierte Ylide XX.1Synthesen (E)-α,β-ungesättigter macrocyclischer Lactone durch intramolekulare Wittig-Olefinierung via Triphenylphosphoranylidenketen2". Synthesis (in German). 1989 (06): 419–423. doi:10.1055/s-1989-27271. ISSN 0039-7881.
^ abc Karl-Georg Fahlbusch; et al. (2007), "Flavors and Fragrances", Ullmann's Encyclopedia of Industrial Chemistry (7th ed.), Wiley, p. 75
^ George A. Burdock (2010), "ω-PENTADECALACTONE", Fenaroli's Handbook of Flavor Ingredients (6th ed.), Taylor & Francis, p. 1597