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, (2''E'')-2-decenal and (2''Z'')-2-decenal. It is an oily, clear

liquid A liquid is a nearly incompressible fluid that conforms to the shape of its container but retains a (nearly) constant volume independent of pressure. As such, it is one of the four fundamental states of matter (the others being solid, gas, a ...

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 An essential oil is a concentrated hydrophobic liquid containing volatile (easily evaporated at normal temperatures) chemical compounds from plants. Essential oils are also known as volatile oils, ethereal oils, aetheroleum, or simply as the o ...

coriander 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 Ginger (''Zingiber officinale'') is a flowering plant whose rhizome, ginger root or ginger, is widely used as a spice A spice is a seed, fruit, root, bark, or other plant substance primarily used for flavoring or coloring food. Spices ...

, butter, mushroom,

kiwi Kiwi most commonly refers to: * Kiwi (bird), a flightless bird native to New Zealand * Kiwi (nickname), a nickname for New Zealanders * Kiwifruit, an edible berry * Kiwi dollar or New Zealand dollar, a unit of currency Kiwi or KIWI may also refe ...

bacon Bacon is a type of salt-cured pork made from various cuts, typically the belly or less fatty parts of the back. It is eaten as a side dish (particularly in breakfasts), used as a central ingredient (e.g., the bacon, lettuce, and tomato sand ...

fat, roast beef, beef fat, heated beef fat, bilberries,

carrot The carrot ('' Daucus carota'' subsp. ''sativus'') is a root vegetable, typically orange in color, though purple, black, red, white, and yellow cultivars exist, all of which are domesticated forms of the wild carrot, ''Daucus carota'', nat ...

root, boiled chicken, chicken broth, cranberry press residue, ham, lingonberry, orange, heated pork fat, potato chip,

soy bean The soybean, soy bean, or soya bean (''Glycine max'') is a species of legume native to East Asia, widely grown for its edible bean, which has numerous uses. Traditional unfermented food uses of soybeans include soy milk, from which tofu a ...

, boiled mutton, tea, roasted

hazelnut The hazelnut is the fruit of the hazel tree and therefore includes any of the nuts deriving from species of the genus ''Corylus'', especially the nuts of the species ''Corylus avellana''. They are also known as cobnuts or filberts according t ...

french fries French fries (North American English), chips (British English), finger chips ( Indian English), french-fried potatoes, or simply fries, are '' batonnet'' or ''allumette''-cut deep-fried potatoes of disputed origin from Belgium and France. Th ...

, tomato,

wheat bread Brown bread is bread made with significant amounts of whole grain flour, usually wheat, and sometimes dark-coloured ingredients such as molasses or coffee. In Canada, Ireland and South Africa, it is whole wheat bread; in the Maritimes and New En ...

, roasted pecans, rice, roasted peanuts, and

coriander Coriander (;

leaf. 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-Decenal is also found as an additive in

cigarette A cigarette is a narrow cylinder containing a combustible material, typically tobacco, that is rolled into thin paper for smoking. The cigarette is ignited at one end, causing it to smolder; the resulting smoke is orally inhaled via the opp ...

Applications

2-Decenal can be used as a nematicide (a pesticide used to kill plant-parasitic nematodes). It is a

mutagen In genetics, a mutagen is a physical or chemical agent that permanently changes nucleic acid, genetic material, usually DNA, in an organism and thus increases the frequency of mutations above the natural background level. As many mutations can ca ...

, but it also has a

biological Biology is the scientific study of life. It is a natural science with a broad scope but has several unifying themes that tie it together as a single, coherent field. For instance, all organisms are made up of cells that process hereditary in ...

role as a pheromone, which is released by an organism when damaged by a predator which warns other individuals that there is a danger.

Synthesis

2-Decenal can be synthesized by reacting

octanal Octanal is the organic compound, an aldehyde, with the chemical formula CH3(CH2)6CHO. A colorless fragrant liquid with a fruit-like odor, it occurs naturally in citrus oils. It is used commercially as a component in perfumes and in flavor produ ...

with ethyl vinyl ether, and subsequently hydrolyzing the mixture.

References

{{DEFAULTSORT:Decenal, 2- Aldehydes Fatty aldehydes