Jasminaldehyde
α-pentylcinnamaldehyde, commonly referred to as jasmine aldehyde or jasminaldehyde, is a fine chemical used as an aroma compound in perfumes. It is responsible for jasmine's characteristic scent.
Synthesis
Jasminaldehyde used in industry is commonly derived not from jasmine essential oil, but ultimately from the castor bean plant. The process starts with ricinoleic acid, the principal constituent of castor oil. This compound undergoes cracking to undecylenic acid (used mainly to produce Nylon 11) and heptanal. The heptanal, once distilled, is then reacted with benzaldehyde in the presence of a basic catalyst (trans-aldol condensation) to give jasminaldehyde and water. The foul-smelling 2-pentylnon-2-enal is an unwanted byproduct (self-condensation of the benzaldehyde). [1] [2]
This parallels the preparation hexyl cinnamaldehyde from octanal and benzaldehyde.
References
- ^ Heynderickx, Philippe M. (2019-08-05). "Activity Coefficients for Liquid Organic Reactions: Towards a Better Understanding of True Kinetics with the Synthesis of Jasmin Aldehyde as Showcase". International Journal of Molecular Sciences. 20 (15): 3819. doi:10.3390/ijms20153819. ISSN 1422-0067. PMC 6695740. PMID 31387255.
{{cite journal}}: CS1 maint: PMC format (link) CS1 maint: unflagged free DOI (link) - ^ G. A. Burdock, Fenaroli’s Handbook of Flavor Ingredients, Fifth Edition, 2005, CRC Press, Boca Raton, Fl., ISBN 0-8493-3034-3.