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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
CAS Number
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.027.141 Edit this at Wikidata
EC Number
  • 229-854-4
KEGG
PubChem CID
UNII
CompTox Dashboard (EPA)
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
Density 0.851 g/cm
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 , 100 kPa). Infobox references
Chemical compound

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

External links

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.
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