Fatty aldehyde

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.

Chemical structure of the fatty aldehyde dodecanal

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.[1] The pheromone cocktails of various insect pheromones contain fatty aldehydes.[2] Fat aldehydes were also detected in the heart muscle of mammals.[3]

Preparation

Fatty aldehydes can be prepared by dehydrogenation of fatty alcohols on copper-zinc catalysts.[4] By the hydroformylation of alkenes, fatty aldehydes are produced on a large industrial scale.[5]

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.[6] 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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