2-Decenal

2-Decenal (dec-2-enal) is an organic compound with the chemical formula of C10H18O. It exists as a pair of cis and trans isomers, (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 part of the essential oil of coriander. 2-Decenal is also used as a flavoring agent.

2-Decenal
Names
Preferred IUPAC name
Dec-2-enal
Other names
Dec-2-en-1-al
2-Decenaldehyde
Dec-2-enaldehyde
3-Heptylacrolein
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.021.339
EC Number
  • 223-472-1
  • (E): 223-474-2
UNII
  • InChI=1S/C10H18O/c1-2-3-4-5-6-7-8-9-10-11/h8-10H,2-7H2,1H3/b9-8+
    Key: MMFCJPPRCYDLLZ-CMDGGOBGSA-N
  • CCCCCCC/C=C/C=O
Properties
C10H18O
Molar mass 154.253 g·mol−1
Appearance Clear to yellow, oily liquid
Density 0.841 g/mL
Melting point −16 °C (3 °F; 257 K)
Boiling point 79 °C (174 °F; 352 K)
Hazards
GHS labelling:
GHS07: Exclamation mark
Warning
H315, H319
P264, P280, P302+P352, P305+P351+P338, P321, P332+P313, P337+P313, P362
NFPA 704 (fire diamond)
NFPA 704 four-colored diamond
2
1
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 reported 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 distaste 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] and is a part of the disagreeable odor emitted by the brown marmorated stink bug (Halyomorpha halys).

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 synthesized by reacting octanal with ethyl vinyl ether, and subsequently hydrolyzing the mixture.

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. S2CID 87980895.
  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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