trans,cis-2,6-Nonadienal

trans,cis-2,6-Nonadienal 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 has attracted attention as the essence of cucumbers,[1][2] but it is also found in bread crust[3] and freshly cut watermelon.

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
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).
Infobox references

Biosynthesis

Isotopic labeling has indicated that nonadienal is formed from α-linolenic acid.[4] Such reactions are typically catalyzed by hydroperoxide lyases.

See also
  • 2-Nonenal - another potent odorant in cucumber

References
  1. Kula, Jozef; Sadowska, Halina (1993). "Unsaturated aliphatic C9-aldehydes as natural flavorants: (E,Z)-2,6-nonadienal". Perfumer & Flavorist. 18: 23–25.
  2. 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.
  3. 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.
  4. 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.
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