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 checkY
3D model (JSmol)
  • Interactive image
ChEBI
  • CHEBI:134220
  • (E): CHEBI:133455
ChEMBL
  • (E): ChEMBL507518
ChemSpider
  • 18652
ECHA InfoCard 100.021.339 Edit this at Wikidata
EC Number
  • 223-472-1
  • (E): 223-474-2
PubChem CID
  • 5283345
UNII
  • E93S23U2BU checkY
CompTox Dashboard (EPA)
  • DTXSID8052065 Edit this at Wikidata
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
  • 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
 GHS07: Exclamation mark
Warning
Hazard statements
 H315, H319
Precautionary statements
 P264, P280, P302+P352, P305+P351+P338, P321, P332+P313, P337+P313, P362
NFPA 704 (fire diamond)
NFPA 704 four-colored diamondHealth 2: Intense or continued but not chronic exposure could cause temporary incapacitation or possible residual injury. E.g. chloroformFlammability 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g. canola oilInstability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no code
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
Chemical compound

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.

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.