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Civetone

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Civetone
Names
Preferred 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
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.008.013 Edit this at Wikidata
EC Number
  • 208‐813‐4
PubChem CID
UNII
CompTox Dashboard (EPA)
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 250.426 g·mol
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 , 100 kPa). ☒N verify (what is  ?) Infobox references
Chemical compound

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

Uses

Civetone is a synthetic musk used as a perfume fixative and flavor.

In order to attract jaguars to camera traps, field biologists have used the Calvin Klein-brand male cologne Obsession. It is believed that the civetone in the cologne resembles a territorial marking.

See also

References

  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. 71 (8). Springer Berlin / Heidelberg: 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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