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

fatty acid In chemistry, in particular in biochemistry, a fatty acid is a carboxylic acid with an aliphatic chain, which is either saturated and unsaturated compounds#Organic chemistry, saturated or unsaturated. Most naturally occurring fatty acids have an ...

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 betw ...

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 (whereas normal methane has the formula ). In formulas, the group is often abbreviated as ...

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 c ...

s and omega−6 fatty acids, omega−9 fatty acids are not classed as

essential fatty acids Essential fatty acids, or EFAs, are fatty acids that are required by humans and other animals for normal physiological function that cannot be synthesized in the body.⁠ As they are not synthesized in the body, the essential fatty acids al ...

(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 fat, monounsaturated if it contains one double bond, and polyunsaturated fat, polyunsaturated i ...

, 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

eicosanoid Eicosanoids are lipid signaling, signaling molecules made by the enzymatic or non-enzymatic oxidation of arachidonic acid or other polyunsaturated fatty acids (PUFAs) that are, similar to arachidonic acid, around 20 carbon units in length. Eicosa ...

Overview

Some omega−9 fatty acids are common components of

animal fat Animal fats are lipids derived from animals which are used by the animal for a multitude of functions, or can be used by humans for dietary, sanitary, and cosmetic purposes. Depending on the temperature of the fat, it can change between a solid s ...

and

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

. 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 due to the presence of impurities. In chemical terms, oleic acid is cl ...

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

olive oil Olive oil is a vegetable oil obtained by pressing whole olives (the fruit of ''Olea europaea'', a traditional Tree fruit, tree crop of the Mediterranean Basin) and extracting the oil. It is commonly used in cooking for frying foods, as a cond ...

macadamia oil Macadamia oil, also known as macadamia nut oil, is a non-volatile oil extracted from the nuts of the macadamia tree (''Macadamia integrifolia''), indigenous to Australia. This oil is used in culinary applications as a frying or salad oil, and in c ...

and other

monounsaturated fat In biochemistry and nutrition, a monounsaturated fat is a fat that contains a monounsaturated fatty acid (MUFA), a subclass of fatty acid characterized by having a double bond in the fatty acid chain with all of the remaining carbon atoms being s ...

s *

Erucic acid Erucic acid is a monounsaturated omega-9 fatty acid, denoted 22:1ω9. It has the chemical formula: . It is prevalent in wallflower seed and other plants in the family Brassicaceae, with a reported content of 20 to 54% in high erucic acid rapese ...

(22:1, ''n''−9), which is found in

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

, wallflower 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 Drying is a mass transfer process consisting of the removal of water or another solvent by evaporation from a solid, semi-solid or liquid. This process is often used as a final production step before selling or packaging products. To be conside ...

Canola oil Close-up of canola blooms Canola flower Rapeseed oil is one of the oldest known vegetable oils. There are both edible and industrial forms produced from rapeseed, the seed of several cultivars of the plant family Brassicaceae. Historical ...

comes from a

cultivar A cultivar is a kind of Horticulture, cultivated plant that people have selected for desired phenotypic trait, traits and which retains those traits when Plant propagation, propagated. Methods used to propagate cultivars include division, root a ...

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 Mead acid is an omega-9 fatty acid, first characterized by James F. Mead. As with some other omega-9 polyunsaturated fatty acids, animals can make Mead acid ''de novo''. Its elevated presence in the blood is an indication of essential fatty ac ...

, (20:3, ''n''−9). This has been documented to a lesser extent in one study following

vegetarians Vegetarianism is the practice of abstaining from the consumption of meat (red meat, poultry, seafood, insects, and the flesh of any other animal). It may also include abstaining from eating all by-products of animal slaughter. A person who pra ...

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

Overview

See also

References

External links