Civetone

Civetone
Names
	IUPAC name (9Z)-Cycloheptadec-9-en-1-one
	Other names cis-Civetone; 9-Cycloheptadecen-1-one; Cycloheptadeca-9-en-1-one; (Z)-9-Cyclohepta-decen-1-one
Identifiers
CAS Number	542-46-1 ;
3D model (JSmol)	Interactive image;
ChemSpider	4475121 ;
ECHA InfoCard	100.008.013
EC Number	208‐813‐4;
PubChem CID	5315941;
UNII	P0K30CV1UE ;
CompTox Dashboard (EPA)	DTXSID80883434 ;
	InChI InChI=1S/C17H30O/c18-17-15-13-11-9-7-5-3-1-2-4-6-8-10-12-14-16-17/h1-2H,3-16H2/b2-1- Key: ZKVZSBSZTMPBQR-UPHRSURJSA-N ; InChI=1/C17H30O/c18-17-15-13-11-9-7-5-3-1-2-4-6-8-10-12-14-16-17/h1-2H,3-16H2/b2-1- Key: ZKVZSBSZTMPBQR-UPHRSURJBS;
	SMILES O=C1CCCCCCC/C=C\CCCCCCC1;
Properties
Chemical formula	C17H30O
Molar mass	250.4195
Appearance	Crystalline solid
Density	0.917 at 33 °C
Melting point	31 to 32 °C (88 to 90 °F; 304 to 305 K)
Boiling point	342 °C (648 °F; 615 K)
Solubility in oils	soluble
Solubility in ethanol	soluble
Solubility in water	slightly soluble
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Civetone is a macrocyclic ketone and the main odorous constituent of civet oil.^[1] It is a pheromone sourced from the African civet. It has a strong musky odor that becomes pleasant at extreme dilutions.^[2] Civetone is closely related to muscone, the principal odoriferous compound found in musk; the structure of both compounds was elucidated by Leopold Ružička.^[3] Today, civetone can be synthesized from precursor chemicals found in palm oil.^[4]

Uses

Civetone is used as a perfume fixative and flavor.

In order to attract jaguars to camera traps, field biologists have used the cologne Calvin Klein's Obsession For Men. It is believed that the civetone in the cologne resembles a territorial marking.^[5]

References

^ The Merck Index, 15th Ed. (2013), p. 418, Monograph 2334, O'Neil: The Royal Society of Chemistry. Available online at: http://www.rsc.org/Merck-Index/monograph/mono1500002334
^ Bedoukian, Paul Z. "Perfumery and Flavoring Synthetics", 2nd ed., p. 248, Elsevier, New York, 1967.
^ Sell, Charles S. (1999). "Ingredients for the Modern Perfumery Industry". In Pybus, David H.; Sell, Charles S. (eds.). The Chemistry of Fragrances (1st ed.). Royal Society of Chemistry Publishing. pp. 51–124. ISBN 9780854045280.
^ Yuen-May Choo, Kay-Eng Ooi and Ing-Hong Ooi (August 1994). "Synthesis of civetone from palm oil products". Journal of the American Oil Chemists' Society. Springer Berlin / Heidelberg. 71 (8): 911–913. doi:10.1007/bf02540473. ISSN 0003-021X. S2CID 85189919.
^ "You'll Never Guess How Biologists Lure Jaguars To Camera Traps". Scientific American Blog Network.

[1] The Merck Index, 15th Ed. (2013), p. 418, Monograph 2334, O'Neil: The Royal Society of Chemistry. Available online at: http://www.rsc.org/Merck-Index/monograph/mono1500002334

[2] Bedoukian, Paul Z. "Perfumery and Flavoring Synthetics", 2nd ed., p. 248, Elsevier, New York, 1967.

[3] Sell, Charles S. (1999). "Ingredients for the Modern Perfumery Industry". In Pybus, David H.; Sell, Charles S. (eds.). The Chemistry of Fragrances (1st ed.). Royal Society of Chemistry Publishing. pp. 51–124. ISBN 9780854045280.

[4] Yuen-May Choo, Kay-Eng Ooi and Ing-Hong Ooi (August 1994). "Synthesis of civetone from palm oil products". Journal of the American Oil Chemists' Society. Springer Berlin / Heidelberg. 71 (8): 911–913. doi:10.1007/bf02540473. ISSN 0003-021X. S2CID 85189919.

[5] "You'll Never Guess How Biologists Lure Jaguars To Camera Traps". Scientific American Blog Network.

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