Not to be confused with linolenic acid or alpha-linolenic acid or lipoic acid or linolelaidic acid.
Linoleic acid
Watchedfieldschanged
Verifiedrevid476999843
Pin(9Z,12Z)-Octadeca-9,12-dienoic acid
Othernamescis,cis-9,12-Octadecadienoic acid
C18:2 (Lipid numbers)

Linoleic acid (LA) is an organic compound with the formula CH3(CH2)4CH\dCHCH2CH\dCH(CH2)7COOH. Both alkene groups (\sCH\dCH\s) are cis. It is a fatty acid sometimes denoted 18:2 (n−6) or 18:2 cis-9,12. A linoleate is a salt or ester of this acid.[1]

Linoleic acid is a polyunsaturated, omega−6 fatty acid. It is a colorless liquid that is virtually insoluble in water but soluble in many organic solvents.[2] It typically occurs in nature as a triglyceride (ester of glycerin) rather than as a free fatty acid.[3] It is one of two essential fatty acids for humans, who must obtain it through their diet,[4] and the most essential, because the body uses it as a base to make the others.

The word "linoleic" derives , reflecting the fact that it was first isolated from linseed oil.

History

In 1844, F. Sacc, working at the laboratory of Justus von Liebig, isolated linoleic acid from linseed oil.[5][6] In 1886, K. Peters determined the existence of two double bonds.[7] Its essential role in human diet was discovered by G. O. Burr and others in 1930.[8] Its chemical structure was determined by T. P. Hilditch and others in 1939, and it was synthesized by R. A. Raphael and F. Sondheimer in 1950.[9]

In physiology

Main articles: Fatty acid desaturase and Fatty acid synthesis

The consumption of linoleic acid is vital to proper health, as it is an essential fatty acid.[10]

Metabolism and eicosanoids

Linoleic acid (LA: C18H32O2; 18:2,n−6) is a precursor to arachidonic acid (AA: C20H32O2; 20:4,n−6) with elongation and unsaturation.[10] AA is the precursor to some prostaglandins,[11] leukotrienes (LTA, LTB, LTC), thromboxane (TXA)[12] and the N-acylethanolamine (NAE) arachidonoylethanolamine (AEA: C22H37NO2; 20:4,n−6),[13] and other endocannabinoids and eicosanoids.[14]

The metabolism of LA to AA begins with the conversion of LA into gamma-linolenic acid (GLA), effected by Δ6 desaturase.[15] GLA is converted to dihomo-γ-linolenic acid (DGLA), the immediate precursor to AA.

LA is also converted by various lipoxygenases, cyclooxygenases, cytochrome P450 enzymes (the CYP monooxygenases), and non-enzymatic autoxidation mechanisms to mono-hydroxyl products viz., 13-Hydroxyoctadecadienoic acid, and 9-Hydroxyoctadecadienoic acid; these two hydroxy metabolites are enzymatically oxidized to their keto metabolites, 13-oxo-octadecadienoic acid and 9-oxo-octadecdienoic acid. Certain cytochrome P450 enzymes, the CYP epoxygenases, catalyze oxidation of LA to epoxide products viz., its 12,13-epoxide, vernolic acid, and its 9,10-epoxide, coronaric acid. These linoleic acid products are implicated in human physiology and pathology.[16]

Hydroperoxides derived from the metabolism of anandamide (AEA: C22H37NO2; 20:4,n−6), or its linoleoyl analogues, are by a lipoxygenase action found to be competitive inhibitors of brain and immune cell FAAH, the enzyme that breaks down AEA and other endocannabinoids, and the compound linoleoyl-ethanol-amide (C20H37NO2; 18:2,n−6), an N-acylethanolamine,[clarification needed] - the ethanolamide of linoleic acid (LA: C18H32O2; 18:2,n−6) and its metabolized incorporated ethanolamine (MEA: C2H7NO),[17] is the first natural inhibitor of FAAH, discovered.[18][19]

Uses and reactions

Linoleic acid is a component of quick-drying oils, which are useful in oil paints and varnishes. These applications exploit the lability of the doubly allylic C\sH groups (\sCH\dCH\sCH2\sCH\dCH\s) toward oxygen in air (autoxidation). Addition of oxygen leads to crosslinking and formation of a stable film.[20]

Reduction of the carboxylic acid group of linoleic acid yields linoleyl alcohol.[21]

Linoleic acid is a surfactant with a critical micelle concentration of 1.5e-4 M at pH 7.5.[citation needed]

Linoleic acid has become increasingly popular in the beauty products industry because of its beneficial properties on the skin. Research points to linoleic acid's anti-inflammatory, acne reductive, skin-lightening and moisture retentive properties when applied topically on the skin.[22][23][24][25]

Linoleic acid is also used in some bar of soap products.

Dietary sources

See also: Vegetable oil#Composition of fats

It is abundant in safflower, and corn oil, and comprises over half their composition by weight. It is present in medium quantities in soybean oils, sesame, and almonds.[26][27]

Name% LA†ref.
Salicornia oil75%[28]
Poppyseed oil74%[29]
Safflower oil72–78%[30]
Grape seed oil70%[31]
Evening Primrose oil65–80%[32]
Cardoon oil60%[33][34]
Wheat germ oil56%[35][36]
Hemp oil54.3%[37]
Cottonseed oil54%[38][39]
Corn oil51.9%[40]
Prickly Pear seed oil50–78%[41]
Walnut oil50–72%[42][43]
Melon seed oil50–70%[44]
Soybean oil50.9%[45]
Sesame oil45%[46][47]
Pumpkin seed oil42–59%[48]
Rice bran oil39%
Argan oil37%
Pistachio oil32.7%
Peach oil29%[49]
Almonds24%
Sunflower oil20.5%[50]
Peanut oil19.6%[51]
Chicken fat18–23%[52]
Canola oil17.8%[53]
Egg yolk16%
Linseed oil (flax), cold pressed14.2%[54]
Lard10%
Palm oil10%
Olive oil8.4%[55]
Tallow3%
Cocoa butter3%
Macadamia oil2%
Butter2%
Coconut oil2%
 †average value, except the items where a range is given

Other occurrences

Cockroaches release oleic and linoleic acid upon death, which discourages other roaches from entering the area. This is similar to the mechanism found in ants and bees, which release oleic acid upon death.[56]

While polyunsaturated fatty acids are unusual in plant cuticles, a diunsaturated dicarboxylic acid has been reported as a component of the surface waxes or polyesters of some plant species. Thus, octadeca-c6,c9-diene-1,18-dioate, a derivative of linoleic acid, is present in Arabidopsis and Brassica napus cuticle.[57] Taxoleic acid is isomeric to linoleic acid.

Health effects

Consumption of linoleic acid has been associated with lowering the risk of cardiovascular disease, diabetes and premature death.[58][59][60] There is high-quality evidence that increased intake of linoleic acid decreases total blood cholesterol and low-density lipoprotein.[61] Higher in vivo circulating and tissue levels of linoleic acid are associated with a lower risk of major cardiovascular events.[62] Clinical trials have shown that increased linoleic acid intake does not increase markers of inflammation or oxidative stress.[63][64]

The American Heart Association advises people to replace saturated fat with linoleic acid to reduce CVD risk.[65]

See also

References

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Further reading