:Cis-3-Hexenal
{{DISPLAYTITLE:cis-3-Hexenal}}
{{chembox
|Name=cis-3-Hexenal
|ImageFile=Cis-3-hexenal.svg
|ImageSize=150px
|PIN = (3Z)-Hex-3-enal
|OtherNames = (Z)-Hex-3-enal
cis-3-Hexenal
Leaf aldehyde
|Section1= {{Chembox Identifiers
|CASNo = 6789-80-6
|ChEBI = 23292
|ChemSpiderID = 559032
|EC_number = 229-854-4
|KEGG = C16310
|PubChem = 643941
|UNII = 6V54TKA96C
|InChI = 1/C6H10O/c1-2-3-4-5-6-7/h3-4,6H,2,5H2,1H3/b4-3-
|InChIKey = GXANMBISFKBPEX-ARJAWSKDBM
|SMILES = O=CC\C=C/CC
}}
|Section2= {{Chembox Properties
|C=6 | H=10 | O=1
|Density=0.851 g/cm3
|BoilingPtC = 126
}}
|Section3= {{Chembox Related
|OtherFunction_label = alkenals
|OtherFunction = Acrolein
}}
}}
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.{{cite journal|url=http://www.chm.bris.ac.uk/motm/hexenal/hexenalh.htm |title=Hexenal | journal = Molecule of the Month |year=2017 |doi=10.6084/m9.figshare.5245834 |publisher=Chm.bris.ac.uk |accessdate=2018-07-26|last1=Cotton |first1=Simon }}[http://www.rsc.org/chemistryworld/2013/11/hexenal-grass-smell Hexenal] / Chemistry World, Royal Society of Chemistry, 27 November 2013
Occurrence
It is one of the major volatile compounds in ripe tomatoes, although it tends to isomerize into the conjugated trans-2-hexenal.{{cite journal |doi=10.1021/jf00076a025|title=Fresh tomato aroma volatiles: A quantitative study|year=1987|last1=Buttery|first1=Ron G.|last2=Teranishi|first2=Roy|last3=Ling|first3=Louisa C.|journal=Journal of Agricultural and Food Chemistry|volume=35|issue=4|pages=540–544}} 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.{{cite web|author=Ashraf El-Sayed |url=http://www.pherobase.com/database/compound/compounds-detail-Z3-6Ald.php |title=Pheromone database |publisher=Pherobase.com |date= |accessdate=2018-07-26}}
File:O2aseLyaseFatty.png via the hydroperoxide by the action of a lipoxygenase followed by a hydroperoxide lyase.{{cite journal|volume=9|year=2006|pages=274–280|journal=Current Opinion in Plant Biology|title=Green leaf volatiles: hydroperoxide lyase pathway of oxylipin metabolism|author=KenjiMatsui|issue=3 |doi=10.1016/j.pbi.2006.03.002|pmid=16595187|bibcode=2006COPB....9..274M }}]]
See also
- cis-3-Hexen-1-ol has a similar but weaker odor and is used in flavors and perfumes.
- 1-Hexanol, another volatile organic compound, also considered responsible for the freshly mowed grass odor
External links
- [https://www.chemistryworld.com/podcasts/hexenal/6836.article Hexenal]
References
{{reflist}}
{{DEFAULTSORT:Hexenal, cis-3-}}