cis-3-Hexenal

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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 Edit this at Wikidata
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).

cis-3-Hexenal, also known as (Z)-3-hexenal and leaf aldehyde, is colorless liquid and an aroma compound with an intense grassy-green odor of freshly cut green 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]

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 smell and is widely used in flavors and perfumes.

See also

References

  1. ^ Molecule of the Month: Hexenal
  2. ^ Hexenal / Chemistry World, Royal Society of Chemistry, 27 November 2013
  3. ^ Pheromone database