cis-3-Hexenal
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]
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| Names | |
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| Preferred IUPAC name
(3Z)-Hex-3-enal | |
| Other names
(Z)-Hex-3-enal cis-3-Hexenal Leaf aldehyde | |
| Identifiers | |
3D model (JSmol) |
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| ChEBI | |
| ChemSpider | |
| ECHA InfoCard | 100.027.141 |
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| KEGG | |
PubChem CID |
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| UNII | |
CompTox Dashboard (EPA) |
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| 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 |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references | |
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.[5]
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
References
- 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) - Hexenal / Chemistry World, Royal Society of Chemistry, 27 November 2013
- 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.
- Ashraf El-Sayed. "Pheromone database". Pherobase.com. Retrieved 2018-07-26.
- 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.
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