Trans,cis-2,6-Nonadienal

trans,cis-2,6-Nonadienal
Names
Preferred IUPAC name
(2E,6Z)-Nona-2,6-dienal
Other names
(E,Z)-2,6-Nonadienal
Violet leaf aldehyde
Cucumber aldehyde
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.008.345 Edit this at Wikidata
UNII
  • InChI=1S/C9H14O/c1-2-3-4-5-6-7-8-9-10/h3-4,7-9H,2,5-6H2,1H3/b4-3-,8-7+
    Key: HZYHMHHBBBSGHB-ODYTWBPASA-N
  • CC/C=C\CC/C=C/C=O
Properties
C9H14O
Molar mass 138.210 g·mol−1
Appearance Colorless oil
Hazards
GHS labelling:
GHS07: Exclamation mark
Warning
H315, H317
P261, P264, P272, P280, P302+P352, P321, P332+P313, P333+P313, P362, P363, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

trans,cis-2,6-Nonadienal (also known as (E,Z)-2,6-nonadienal or "cucumber aldehyde") is an organic compound that is classified as a doubly unsaturated derivative of nonanal. The molecule consists of a α,β-unsaturated aldehyde with an isolated alkene group. The compound having an odour described as "green, fatty, dry, cucumber, violet leaf, melon", has attracted attention as the essence of cucumbers, but it is also found in bread crust and freshly cut watermelon.

Biosynthesis

Isotopic labeling has indicated that nonadienal is formed from α-linolenic acid. Such reactions are typically catalyzed by hydroperoxide lyases.

See also

References

  1. ↑ "(E,Z)-2,6-nonadienal". scentsandflavors.com. Retrieved 2 August 2026.
  2. ↑ Kula, Jozef; Sadowska, Halina (1993). "Unsaturated aliphatic C9-aldehydes as natural flavorants: (E,Z)-2,6-nonadienal". Perfumer & Flavorist. 18: 23–25.
  3. ↑ Schieberle, P.; Ofner, S.; Grosch, W. (January 1990). "Evaluation of Potent Odorants in Cucumbers (Cucumis sativus) and Muskmelons (Cucumis melo) by Aroma Extract Dilution Analysis". Journal of Food Science. 55 (1): 193–195. doi:10.1111/j.1365-2621.1990.tb06050.x.
  4. ↑ Cho, In Hee; Peterson, Devin G. (2010). "Chemistry of Bread Aroma: A Review". Food Science and Biotechnology. 19: 575–582. doi:10.1007/s10068-013-0240-4.
  5. ↑ Grosch, Werner; Schwarz, Jorg M. (May 1971). "Linoleic and linolenic acid as precursors of the cucumber flavor". Lipids. 6 (5): 351–352. doi:10.1007/BF02531828. S2CID 38868077.