Omega-9 fatty acids (ω−9 fatty acids or ''n''−9 fatty acids) are a family of unsaturated

fatty acid In chemistry, particularly in biochemistry, a fatty acid is a carboxylic acid with an aliphatic chain, which is either saturated or unsaturated. Most naturally occurring fatty acids have an unbranched chain of an even number of carbon atoms, f ...

s which have in common a final carbon–carbon

double bond In chemistry, a double bond is a covalent bond between two atoms involving four bonding electrons as opposed to two in a single bond. Double bonds occur most commonly between two carbon atoms, for example in alkenes. Many double bonds exist betwee ...

in the omega−9 position; that is, the ninth bond from the

methyl In organic chemistry, a methyl group is an alkyl derived from methane, containing one carbon atom bonded to three hydrogen atoms, having chemical formula . In formulas, the group is often abbreviated as Me. This hydrocarbon group occurs in ...

end of the fatty acid. Unlike

omega-3 fatty acid Omega−3 fatty acids, also called Omega-3 oils, ω−3 fatty acids or ''n''−3 fatty acids, are polyunsaturated fatty acids (PUFAs) characterized by the presence of a double bond, three atoms away from the terminal methyl group in their chem ...

s and omega-6 fatty acid, omega−9 fatty acids are not classed as essential fatty acids (EFA). This is both because they can be created by the human body from

unsaturated fat An unsaturated fat is a fat or fatty acid in which there is at least one double bond within the fatty acid chain. A fatty acid chain is monounsaturated if it contains one double bond, and polyunsaturated if it contains more than one double bond ...

, and are therefore not essential in the diet, and because the lack of an omega−6 double bond keeps them from participating in the reactions that form the eicosanoids.

Background

Some omega−9 fatty acids are common components of

animal fat Animal fats and oils are lipids derived from animals: oils are liquid at room temperature, and fats are solid. Chemically, both fats and oils are composed of triglycerides. Although many animal parts and secretions may yield oil, in commerci ...

and

vegetable oil Vegetable oils, or vegetable fats, are oils extracted from seeds or from other parts of fruits. Like animal fats, vegetable fats are ''mixtures'' of triglycerides. Soybean oil, grape seed oil, and cocoa butter are examples of seed oils, or f ...

. Two omega−9 fatty acids important in industry are: *

Oleic acid Oleic acid is a fatty acid that occurs naturally in various animal and vegetable fats and oils. It is an odorless, colorless oil, although commercial samples may be yellowish. In chemical terms, oleic acid is classified as a monounsaturated o ...

(18:1, ''n''−9), which is a main component of

olive oil Olive oil is a liquid fat obtained from olives (the fruit of ''Olea europaea''; family Oleaceae), a traditional tree crop of the Mediterranean Basin, produced by pressing whole olives and extracting the oil. It is commonly used in cooking: ...

, macadamia oil and other monounsaturated fats *

Erucic acid Erucic acid is a monounsaturated omega-9 fatty acid, denoted 22:1ω9. It has the chemical formula CH3(CH2)7CH=CH(CH2)11COOH. It is prevalent in wallflower seed and other plants in the family Brassicaceae, with a reported content of 20 to 54% i ...

(22:1, ''n''−9), which is found in

rapeseed Rapeseed (''Brassica napus ''subsp.'' napus''), also known as rape, or oilseed rape, is a bright-yellow flowering member of the family Brassicaceae (mustard or cabbage family), cultivated mainly for its oil-rich seed, which naturally contains a ...

wallflower ''Erysimum'', or wallflower, is a genus of flowering plants in the cabbage family, Brassicaceae. It includes more than 150 species, both popular garden plants and many wild forms. The genus ''Cheiranthus'' is sometimes included here in whole o ...

seed, and

mustard seed Mustard seeds are the small round seeds of various mustard plants. The seeds are usually about in diameter and may be colored from yellowish white to black. They are an important spice in many regional foods and may come from one of three diff ...

. Rapeseed with high erucic acid content is grown for commercial use in paintings and coatings as a

drying oil A drying oil is an oil that hardens to a tough, solid film after a period of exposure to air, at room temperature. The oil hardens through a chemical reaction in which the components crosslink (and hence, polymerize) by the action of oxygen (no ...

. Canola oil comes from a

cultivar A cultivar is a type of cultivated plant that people have selected for desired traits and when propagated retain those traits. Methods used to propagate cultivars include: division, root and stem cuttings, offsets, grafting, tissue culture ...

of the rapeseed plant that has been bred, or in some cases genetically modified, to contain very little erucic acid. Under severe conditions of EFA deprivation, mammals will elongate and desaturate oleic acid to make Mead acid, (20:3, ''n''−9). This has been documented to a lesser extent in one study following vegetarians and semi-vegetarians who followed diets without substantial sources of EFA.

References

External links

* {{DEFAULTSORT:Omega-9 Fatty Acid Fatty acids Alkenoic acids de:Omega-n-Fettsäuren#Omega-9-Fettsäuren

Background

See also

References

External links