cis-3-Hexenal

cis-3-Hexenal, also known as (Z)-3-hexenal and leaf aldehyde, is a colorless liquid and an aroma compound with an intense odor of freshly cut grass and leaves.[1][2] It is one of the major volatile compounds in ripe tomatoes. It is produced in small amounts by most plants and it acts as an attractant to many predatory insects. It is also a pheromone in many insect species.[3]

Biosynthesis of cis-3-hexenal from linolenic acid via the hydroperoxide by the action of a lipoxygenase followed by a hydroperoxide lyase.[4]
cis-3-Hexenal
Names
Preferred IUPAC name
(3Z)-Hex-3-enal
Other names
(Z)-Hex-3-enal
cis-3-Hexenal
Leaf aldehyde
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.027.141
UNII
Properties
C6H10O
Molar mass 98.145 g·mol−1
Density 0.851 g/cm3
Boiling point 126 °C (259 °F; 399 K)
Related compounds
Related alkenals
 Acrolein

Crotonaldehyde
(E,E)-2,4-Decadienal

Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

cis-3-Hexenal is an aldehyde. It is relatively unstable and isomerizes into the conjugated trans-2-hexenal. The related alcohol cis-3-hexen-1-ol is much more stable. It has a similar but weaker odor and is widely used in flavors and perfumes.

See also

References
  1. "Molecule of the Month: Hexenal". Chm.bris.ac.uk. doi:10.6084/m9.figshare.5245834. Retrieved 2018-07-26.
  2. Hexenal / Chemistry World, Royal Society of Chemistry, 27 November 2013
  3. Ashraf El-Sayed. "Pheromone database". Pherobase.com. Retrieved 2018-07-26.
  4. KenjiMatsui (2006). "Green leaf volatiles: hydroperoxide lyase pathway of oxylipin metabolism". Current Opinion in Plant Biology. 9: 274–280. doi:10.1016/j.pbi.2006.03.002. PMID 16595187.
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