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
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.008.013
EC Number
  • 208‐813‐4
UNII
  • 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- checkY
    Key: ZKVZSBSZTMPBQR-UPHRSURJSA-N checkY
  • 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
  • O=C1CCCCCCC/C=C\CCCCCCC1
Properties
C17H30O
Molar mass 250.426 g·mol−1
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).
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Infobox references

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 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.[5]

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. 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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