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Fatty aldehyde

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Chemical structure of the fatty aldehyde dodecanal

Fatty aldehydes are aliphatic, long-chain aldehydes which may be mono- or polyunsaturated. The fatty aldehydes include compounds such as octanal, nonanal, decanal or dodecanal. The nomenclature is derived from the nomenclature of the alkanes, the ending -al is added to indicate the aldehyde group.

Occurrence

Fatty aldehydes are a natural component of many natural ingredients such as the essential oils of various citrus fruits. Decanal, for example, is a component of orange peel. The pheromone cocktails of various insect pheromones contain fatty aldehydes. Fat aldehydes were also detected in the heart muscle of mammals.

Preparation

Fatty aldehydes can be prepared by dehydrogenation of fatty alcohols on copper-zinc catalysts. By the hydroformylation of alkenes, fatty aldehydes are produced on a large industrial scale.

Use

A large proportion of the fatty aldehydes prepared by hydroformylation is directly processed further to fatty alcohols. Many fatty aldehydes find use as a fragrance in perfume production. An example is 2-methylundecanal which is the typical odor component of Chanel No. 5. Decanal, whose sweet, flowery odor reminiscents of orange peels, is used, among other things, as a flavoring agent in the food industry and as a perfume in the perfume industry.

See also

References

  1. Kehai Liu, Qiulin Chen, Yanjun Liu, Xiaoyan Zhou, Xichang Wang: "Isolation and Biological Activities of Decanal, Linalool, Valencene, and Octanal from Sweet Orange Oil". In: Journal of Food Science 77, 2012, S. C1156–C1161, doi:10.1111/j.1750-3841.2012.02924.x.
  2. Gerhard Kasang, Karl Ernst Kaißling, Otto Vostrowsky, Hans Jürgen Bestmann: "Bombykal, eine zweite Pheromonkomponente des Seidenspinners Bombyx mori L." In: Angewandte Chemie. 90, 1978, S. 74–75, doi:10.1002/ange.19780900132.
  3. John R. Gilbertson et al.: "Natural occurrence of free fatty aldehydes in bovine cardiac muscle". In: Journal of Lipid Research 13.4 (1972): S. 491–499.
  4. DE 10044809, Albrecht Schwerin, Lothar Friesenhagen, Gerrit Pelzer, Bernhard Gutsche, "Verfahren zur Herstellung von Aldehyden", published 2002-01-10 
  5. Ernst Wiebus, Boy Cornils: "Die großtechnische Oxosynthese mit immobilisiertem Katalysator" In: Chemie Ingenieur Technik 66, 1994, S. 916–923, doi:10.1002/cite.330660704.
  6. "Chemistry in its element - 2-Methylundecanal" (in German). Archived from the original on 2014-05-28. Retrieved 2014-06-20.
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