Cis-3-Hexenal

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
EC Number
  • 229-854-4
KEGG
PubChem CID
UNII
  • InChI=1/C6H10O/c1-2-3-4-5-6-7/h3-4,6H,2,5H2,1H3/b4-3-
    Key: GXANMBISFKBPEX-ARJAWSKDBM
  • O=CC\C=C/CC
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, 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.

Occurrence

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

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

See also