Civetone

from Wikipedia, the free encyclopedia
Structural formula
Structure of civetone
General
Surname Civetone
other names
  • ( Z ) -9-Cycloheptadecen-1-one
  • cis -9-cycloheptadecen-1-one
  • ( Z ) -Cycloheptadec-9-en-1-one
  • cis -cycloheptadec-9-en-1-one
Molecular formula C 17 H 30 O
Brief description

colorless crystals

External identifiers / databases
CAS number 542-46-1
EC number 208-813-4
ECHA InfoCard 100.008.013
PubChem 5315941
Wikidata Q198354
properties
Molar mass 250.41 g · mol -1
Physical state

firmly

density

0.91 g cm −3

Melting point

32.5 ° C

boiling point

343 ° C

solubility
  • slightly soluble in water
  • soluble in ethanol and oils
Refractive index

1.4820 (at 37 ° C)

safety instructions
GHS labeling of hazardous substances
no GHS pictograms
H and P phrases H: no H-phrases
P: no P-phrases
Toxicological data

5010 mg kg −1 ( LD 50 ,  rat ,  oral )

As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions . Refractive index: Na-D line , 20 ° C

Civetone is a chemical compound from the group of cyclic ketones .

Occurrence

African civet

The natural substance civetone is a main component of the fragrance civet - the anal secretion of the African civet cat . It is one of the oldest known perfume ingredients. Civetone is closely related to muscone . Both compounds have the structure of a large cyclic molecule. The structure was clarified by Leopold Ružička in 1926.

Extraction and presentation

Zibetone can be obtained synthetically by Dieckmann cyclization ( Dieckmann condensation ) of 9-octadecene-1,18-dicarboxylic acid dialkyl esters or Ti-Claisen condensation .

use

Civetone is widely used as a fragrance in perfumes, soaps, and other household chemicals. To lure wild cats such as jaguars, cheetahs and tigers near an automatic camera trap , field biologists use Calvin Klein's eau de Cologne "Obsession for men" as a lure, which contains synthetic civetone, among other things.

Individual evidence

  1. ↑ Entry on CIVETONE in the CosIng database of the EU Commission, accessed on February 26, 2020.
  2. ↑ a b c Cycloheptadeca-9-en-1-one (JECFA evaluation)
  3. ↑ a b Walter Widmer: Contribution to the synthesis of cibetone , 1942, ETH Zurich, doi: 10.3929 / ethz-a-000092338 .
  4. ↑ a b Entry on cibetone in the ChemIDplus database of the United States National Library of Medicine (NLM), accessed on October 24, 2017.
  5. ↑ Template: CL Inventory / not harmonized There is not yet a harmonized classification for this substance . A labeling of (Z) -9-cycloheptadecen-1-one in the Classification and Labeling Inventory of the European Chemicals Agency (ECHA), accessed on October 24, 2017, is reproduced from a self-classification by the distributor .
  6. ↑ MSDS on chinaperfumer.com (PDF file; 33 kB).
  7. ↑ freshpatents.com ( Memento of the original from October 19, 2013 in the Internet Archive ) Info: The archive link was inserted automatically and has not yet been checked. Please check the original and archive link according to the instructions and then remove this notice. @1@ 2Template: Webachiv / IABot / www.freshpatents.com
  8. ↑ Development of Efficient and Practical Ti-Claisen Condensation and the Related Aldol Reaction (PDF file; 280 kB).
  9. ↑ https://medium.com/starts-with-a-bang/weekend-diversion-obsession-for-cats-7266391e2861