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
CAS Number	557-48-2;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:7610;
ChemSpider	558840;
ECHA InfoCard	100.008.345
PubChem CID	643731;
UNII	93E895X03C;
CompTox Dashboard (EPA)	DTXSID1047104 ;
	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−1
Appearance	Colorless oil
Hazards
	GHS labelling:
Pictograms
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 [77 °F], 100 kPa). Infobox references

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.

Biosynthesis

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

References

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

[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.

[1]

[2]

[3]

[4]

Biosynthesis

See also

References