cis-3-Hexenal

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cis-3-Hexenal
File:Cis-3-hexenal.svg
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
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EC Number
  • 229-854-4
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KEGG
UNII
  • {{#property:P3117}}Lua error in Module:EditAtWikidata at line 29: attempt to index field 'wikibase' (a nil value).
  • 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

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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]

File:O2aseLyaseFatty.png
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

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References

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  1. ^ Lua error in Module:Citation/CS1/Configuration at line 2172: attempt to index field '?' (a nil value).
  2. ^ Hexenal / Chemistry World, Royal Society of Chemistry, 27 November 2013
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