2-Decenal

2-Decenal
Names
	Preferred IUPAC name Dec-2-enal
	Other names Dec-2-en-1-al; 2-Decenaldehyde; Dec-2-enaldehyde; 3-Heptylacrolein
Identifiers
CAS Number	3913-71-1 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:134220; (E): CHEBI:133455;
ChEMBL	(E): ChEMBL507518;
ChemSpider	18652;
ECHA InfoCard	100.021.339
EC Number	223-472-1; (E): 223-474-2;
PubChem CID	5283345;
UNII	E93S23U2BU ;
CompTox Dashboard (EPA)	DTXSID8052065 ;
	InChI 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;
	SMILES CCCCCCC/C=C/C=O;
Properties
Chemical formula	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:
Pictograms
Signal word	Warning
Hazard statements	H315, H319
Precautionary statements	P264, P280, P302+P352, P305+P351+P338, P321, P332+P313, P337+P313, P362
NFPA 704 (fire 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

2-Decenal (dec-2-enal) is an organic compound with the chemical formula of C₁₀ H₁₈ O. 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.

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

^ "TRANS-2-DECENAL | 3913-71-1". www.chemicalbook.com. Retrieved 2020-02-18.
^ Callaway E (September 2012). "Soapy taste of coriander linked to genetic variants". Nature. doi:10.1038/nature.2012.11398. S2CID 87980895.
^ "Cigarette Ingredients - Chemicals in Cigarettes". 2016-01-21. Archived from the original on 2016-01-21. Retrieved 2020-02-18.
^ "(2E)-dec-2-enal (CHEBI:133455)". www.ebi.ac.uk. Retrieved 2020-02-18.

[1] "TRANS-2-DECENAL | 3913-71-1". www.chemicalbook.com. Retrieved 2020-02-18.

[Callaway_2012-2] 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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