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trans,cis-2,6-Nonadienal

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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
CAS Number
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.008.345 Edit this at Wikidata
PubChem CID
UNII
CompTox Dashboard (EPA)
InChI
  • 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
SMILES
  • CC/C=C\CC/C=C/C=O
Properties
Chemical formula C9H14O
Molar mass 138.210 g·mol
Appearance Colorless oil
Hazards
GHS labelling:
Pictograms GHS07: Exclamation mark
Signal word Warning
Hazard statements H315, H317
Precautionary statements 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 , 100 kPa). Infobox references
Chemical compound

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, 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

  • 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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