2-Decenal

2-decenal, or dec-2-enal is an organic compound with the chemical formula of C10H18O. It exists as a pair of diastereomers, (2E)-2-decenal and (2Z)-2-decenal. It is an oily, clear liquid under normal conditions, that may be yellow due to impurities. 2-decenal is described as having a strong, waxy odor. It is found in animal food (in trace quantities), and is an essential oil of coriander. 2-decenal is also used as a flavoring agent.

2-Decenal
Names
IUPAC name
Dec-2-enal
Systematic IUPAC name
(2E)-2-Decenal
Other names
Dec-2-enal
Dec-2-en-1-al
2-Decenaldehyde
Dec-2-enaldehyde
3-heptylacrolein
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
EC Number
  • 223-472-1
  • (2E)-: 223-474-2
Properties
C10H18O
Molar mass 154.25 g/mol
Appearance Clear to yellow, oily liquid
Density 0.841 g/mL
Melting point -16°C
Boiling point 79 °C
Hazards
GHS pictograms
GHS Signal word Warning
GHS hazard statements
 H315, H319
P264, P280, P302+352, P305+351+338, P321, P332+313, P337+313, P362
NFPA 704 (fire diamond)
Flammability code 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g. canola oilHealth code 2: Intense or continued but not chronic exposure could cause temporary incapacitation or possible residual injury. E.g. chloroformReactivity code 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no code
1
2
0
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Occurrence

2-decenal is found in a wide variety of foods. It has been reportedly found in bitter orange peel, blackberry, ginger, butter, mushroom, kiwi, bacon fat, roast beef, beef fat, heated beef fat, bilberries, carrot root, boiled chicken, chicken broth, cranberry press residue, ham, lingonberry, orange, heated pork fat, potato chip, soy bean, boiled mutton, tea, roasted hazelnuts, french fries, tomato, wheat bread, roasted pecans, rice, roasted peanuts and coriander leaf[1]. Alongside (E)-2-dodecenal, the presence of this aldehyde in coriander leaf has been linked to a commonly reported distate for the herb among people with a certain variant of the OR6A2 gene.[2]

2-decenal is also found as an additive in cigarettes[3].

Applications

2-decenal can be used as a nematicide (a pesticide used to kill plant-parasitic nematodes). It is a mutagen, but it also has a biological role as a pheromone, which is released by an organism when damaged by a predator which warns other individuals that there is a danger[4].

Synthesis

2-decenal can be synthesised by reacting octanal with ethyl vinyl ether, and subsequently hydrolysing the mixture.

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References
  1. "TRANS-2-DECENAL | 3913-71-1". www.chemicalbook.com. Retrieved 2020-02-18.
  2. Callaway E (September 2012). "Soapy taste of coriander linked to genetic variants". Nature. doi:10.1038/nature.2012.11398.
  3. "Cigarette Ingredients - Chemicals in Cigarettes". 2016-01-21. Archived from the original on 2016-01-21. Retrieved 2020-02-18.
  4. "(2E)-dec-2-enal (CHEBI:133455)". www.ebi.ac.uk. Retrieved 2020-02-18.
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