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Fatty aldehyde

From Wikipedia, the free encyclopedia
Chemical structure of the fatty aldehydedodecanal

Fatty aldehydes arealiphatic, long-chainaldehydes which may be mono- orpolyunsaturated. The fatty aldehydes include compounds such asoctanal,nonanal,decanal ordodecanal. The nomenclature is derived from the nomenclature of thealkanes, the ending-al is added to indicate the aldehyde group.

Occurrence

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Fatty aldehydes are a natural component of manynatural ingredients such as theessential oils of various citrus fruits.Decanal, for example, is a component of orange peel.[1] Thepheromone cocktails of various insect pheromones contain fatty aldehydes.[2] Fat aldehydes were also detected in theheart muscle of mammals.[3]

Preparation

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Fatty aldehydes can be prepared bydehydrogenation offatty alcohols on copper-zinccatalysts.[4] By thehydroformylation ofalkenes, fatty aldehydes are produced on a large industrial scale.[5]

Use

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A large proportion of the fatty aldehydes prepared byhydroformylation is directly processed further tofatty alcohols. Many fatty aldehydes find use as afragrance in perfume production. An example is2-methylundecanal which is the typical odor component ofChanel No. 5.[6]Decanal, whose sweet, flowery odor reminiscents of orange peels, is used, among other things, as aflavoring agent in thefood industry and as a perfume in theperfume industry.

See also

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References

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  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 SeidenspinnersBombyx 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 fromthe original on 2014-05-28. Retrieved2014-06-20.
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