Cis-3-Hexenal

Last updated
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 OOjs UI icon edit-ltr-progressive.svg
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).

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]

Contents

Occurrence

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. O2aseLyaseFatty.png
Biosynthesis of cis-3-hexenal from linolenic acid via the hydroperoxide by the action of a lipoxygenase followed by a hydroperoxide lyase.

See also

Related Research Articles

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<i>cis</i>-3-Hexen-1-ol Chemical compound

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Green leaf volatiles (GLV) are volatile organic compounds that are released when plants suffer tissue damage. Specifically, they include aldehydes, esters, and alcohols of 6-carbon compounds released after wounding. These compounds are very quickly produced and emitted, and are used by nearly every green plant. Plants constantly release GLVs, but un-stressed plants release them in much smaller amounts. Some of these chemicals act as signaling compounds between either plants of the same species, of other species, or even vastly different lifeforms like insects. Some, although not necessarily all, of these chemicals act essentially as plant pheromones.[12] GLVs also have antimicrobial properties to prevent infection at the site of injury.

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trans,cis-2,6-Nonadienal is an organic compound that is classified as a doubly unsaturated derivative of nonanal. The molecule consists of a α,β-unsaturated aldehyde with an isolated alkene group. The compound has attracted attention as the essence of cucumbers, but it is also found in bread crust and freshly cut watermelon.

<span class="mw-page-title-main">Smell of freshly cut grass</span>

The smell of freshly cut grass is an odour caused by green leaf volatiles (GLVs) released by damaged grass. Mechanical damage from activities such as lawnmowing results in the release of cis-3-hexenal and other compounds that contribute to a grassy or "green" smell. cis-3-Hexenal has a low odour detection threshold that humans can perceive at concentrations as low as 0.25 parts per billion.

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. doi:10.1016/j.pbi.2006.03.002. PMID   16595187.