Cis-3-Hexenal

cis-3-Hexenal, also known as (Z)-3-hexenal and leaf aldehyde, is an organic compound with the formula CH₃CH₂CH=CHCH₂CHO. It is classified as an unsaturated aldehyde. It is a colorless liquid and an aroma compound with an intense odor of freshly cut grass and leaves.^[1][2]

cis-3-Hexenal

Names
Preferred IUPAC name (3Z)-Hex-3-enal
Other names (Z)-Hex-3-enal cis-3-Hexenal Leaf aldehyde
Identifiers
CAS Number	6789-80-6
3D model (JSmol)	Interactive image
ChEBI	CHEBI:23292
ChemSpider	559032
ECHA InfoCard	100.027.141
EC Number	229-854-4
KEGG	C16310
PubChem CID	643941
UNII	6V54TKA96C
CompTox Dashboard (EPA)	DTXSID30884335
InChI InChI=1/C6H10O/c1-2-3-4-5-6-7/h3-4,6H,2,5H2,1H3/b4-3- Key: GXANMBISFKBPEX-ARJAWSKDBM
SMILES O=CC\C=C/CC
Properties
Chemical formula	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

Occurrence

It is one of the major volatile compounds in ripe tomatoes, although it tends to isomerize into the conjugated trans-2-hexenal.^[3] 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.^[4]

Biosynthesis of cis-3-hexenal from linolenic acid via the hydroperoxide by the action of a lipoxygenase followed by a hydroperoxide lyase.^[5]

See also

• cis-3-Hexen-1-ol has a similar but weaker odor and is used in flavors and perfumes.
• 1-Hexanol, another volatile organic compound, also considered responsible for the freshly mowed grass odor

External links

• Hexenal

References

1. Cotton, Simon (2017). "Molecule of the Month: Hexenal". Chm.bris.ac.uk. doi:10.6084/m9.figshare.5245834. Retrieved 2018-07-26. {{cite journal}}: Cite journal requires |journal= (help)
2. Hexenal / Chemistry World, Royal Society of Chemistry, 27 November 2013
3. Buttery, Ron G.; Teranishi, Roy; Ling, Louisa C. (1987). "Fresh tomato aroma volatiles: A quantitative study". Journal of Agricultural and Food Chemistry. 35 (4): 540–544. doi:10.1021/jf00076a025.
4. Ashraf El-Sayed. "Pheromone database". Pherobase.com. Retrieved 2018-07-26.
5. KenjiMatsui (2006). "Green leaf volatiles: hydroperoxide lyase pathway of oxylipin metabolism". Current Opinion in Plant Biology. 9 (3): 274–280. Bibcode:2006COPB....9..274M. doi:10.1016/j.pbi.2006.03.002. PMID 16595187.