cis-3-Hexenal

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cis-3-Hexenal
Cis-3-hexenal chemical structure.png
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 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]

Occurrence[edit]

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[edit]

External links[edit]

References[edit]

  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. ^ 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: 274–280. doi:10.1016/j.pbi.2006.03.002. PMID 16595187.