( E , Z ) -Nona-2,6-dienal

Structural formula
General
Surname	(E, Z) -Nona-2,6-dienal
other names	trans -2, cis -6 nonadienal; ( E , Z ) -2,6-nonadiene-1-al; Violet leaf aldehyde; NONADIENAL ( INCI ) ;
Molecular formula	C 9 H 14 O
Brief description	colorless liquid
External identifiers / databases
EC number	209-178-6
ECHA InfoCard	100.008.345
PubChem	643731
Wikidata	Q158544
properties
Molar mass	138.21 g mol −1
Physical state	liquid
density	0.86 g cm −3 (25 ° C)
boiling point	94–95 ° C (at 24 hPa)
solubility	almost insoluble in water; soluble in ethanol;
Refractive index	1.474 (20 ° C)
safety instructions
GHS labeling of hazardous substances	no GHS pictograms
	no GHS pictograms
H and P phrases	H: no H-phrases
	P: no P-phrases
Toxicological data	> 5,000 mg kg −1 ( LD 50 , rat , oral )
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions . Refractive index: Na-D line , 20 ° C

( E , Z ) -Nona-2,6-dienal (also called violet leaf aldehyde ) is a chemical compound from the group of aldehydes .

Occurrence

( E , Z ) -Nona-2,6-dienal is one of the main components for the aroma of sour cherries . It is also the main component of the extract obtained from the leaves of the scented violet (hence the common name violet leaf aldehyde ) and is also found in cooked trout , cucumber and some other plants. In cucumbers, it is the main component of the odor. The German scorpion fly releases the compound as a sex attractant.

Extraction and presentation

( E , Z ) -Nona-2,6-dienal can be obtained from α-linolenic acid .

properties

( E , Z ) -Nona-2,6-dienal is a colorless liquid that smells like cucumber.

use

( E , Z ) -Nona-2,6-dienal is used in the form of violet leaf extract in very low concentration (due to the strong smell) as a component of some perfumes.

Web links

Zobrist, Fritz: On the constitution of violet leaf aldehyde. Dissertation, ETH Zurich, 1948 doi : 10.3929 / ethz-a-000090799 .

Individual evidence

↑ Entry on NONADIENAL in the CosIng database of the EU Commission, accessed on February 25, 2020.
↑ ^a ^b ^c ^d ^e ^f ^g ^h data sheet trans-2, cis-6-nonadienal, 95% from Sigma-Aldrich , accessed on May 6, 2012 ( PDF ).
↑ ^a ^b Entry on trans, cis-2,6-Nonadienal at TCI Europe, accessed on June 22, 2012.
↑ Entry on Nonadien-1-ale. In: Römpp Online . Georg Thieme Verlag, accessed on September 23, 2014.
↑ ^a ^b Horst Surburg, Johannes Panten: Common Fragrance and Flavor Materials: Preparation, Properties and Uses . John Wiley & Sons, 2006, ISBN 978-3-527-60789-1 , pp. 237 ( limited preview in Google Book search).
↑ Wolfgang Legrum: Fragrances, between stench and fragrance . Vieweg + Teubner, 2011, ISBN 978-3-8348-1245-2 , pp. 93, 102 ( limited preview in Google Book search).
^ Ralf G. Berger: Flavors and Fragrances: Chemistry, Bioprocessing and Sustainability . Springer, 2006, ISBN 978-3-540-49338-9 , pp. 172 ( limited preview in Google Book search).
↑ Journal of Chemical Ecology, Volume 33, Number 6 (2007), 1249–1256, doi : 10.1007 / s10886-007-9304-3 A Male Sex Pheromone in a Scorpionfly, Dagmar Kock, Joachim Ruther and Klaus Peter Sauer
↑ RH Buescher, Production and Stability of (E, Z) -2,6-Nonadienal, the Major Flavor Volatile of Cucumbers, 2006, doi : 10.1111 / j.1365-2621.2001.tb11346.x , Journal of Food Science, Volume 66 , Issue 2, pp. 357-361, March 2001.

[CosIng-1] Entry on NONADIENAL in the CosIng database of the EU Commission, accessed on February 25, 2020.

[Sigma-2] ↑ ^a ^b ^c ^d ^e ^f ^g ^h data sheet trans-2, cis-6-nonadienal, 95% from Sigma-Aldrich , accessed on May 6, 2012 ( PDF ).

[tci-3] Entry on trans, cis-2,6-Nonadienal at TCI Europe, accessed on June 22, 2012.

[4] Entry on Nonadien-1-ale. In: Römpp Online . Georg Thieme Verlag, accessed on September 23, 2014.

[Surburg-5] Horst Surburg, Johannes Panten: Common Fragrance and Flavor Materials: Preparation, Properties and Uses . John Wiley & Sons, 2006, ISBN 978-3-527-60789-1 , pp. 237 ( limited preview in Google Book search).

[Legrum-6] Wolfgang Legrum: Fragrances, between stench and fragrance . Vieweg + Teubner, 2011, ISBN 978-3-8348-1245-2 , pp. 93, 102 ( limited preview in Google Book search).

[Berger-7] Ralf G. Berger: Flavors and Fragrances: Chemistry, Bioprocessing and Sustainability . Springer, 2006, ISBN 978-3-540-49338-9 , pp. 172 ( limited preview in Google Book search).

[8] Journal of Chemical Ecology, Volume 33, Number 6 (2007), 1249–1256, doi : 10.1007 / s10886-007-9304-3 A Male Sex Pheromone in a Scorpionfly, Dagmar Kock, Joachim Ruther and Klaus Peter Sauer

[9] RH Buescher, Production and Stability of (E, Z) -2,6-Nonadienal, the Major Flavor Volatile of Cucumbers, 2006, doi : 10.1111 / j.1365-2621.2001.tb11346.x , Journal of Food Science, Volume 66 , Issue 2, pp. 357-361, March 2001.