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Linoleic acid is an organic compound with the formula COOH(CH2)7CH=CHCH2CH=CH(CH2)4CH3. Both alkene groups 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.
The word "linoleic" derives from the Latinlinum "flax" + oleum "oil", reflecting the fact that it was first isolated from linseed oil.
The consumption of linoleic acid is vital to proper health, as it is an essential fatty acid. In rats, a diet deficient in linoleate (the salt form of the acid) has been shown to cause mild skin scaling, hair loss,
and poor wound healing.
The metabolism of LA to AA begins with the conversion of LA into gamma-Linolenic acid (GLA), effected by ?6desaturase. GLA is converted to dihomo-?-linolenic acid (DGLA), the immediate precursor to AA. One of the possible fates of AA is to be transformed into a group of metabolites called eicosanoids during the inflammatory response and during physical activity; eicosanoids are a class of paracrine hormones. The three types of eicosanoids are prostaglandins, thromboxanes, and leukotrienes. Eicosanoids produced from AA tend to promote (not cause) inflammation and promote growth during and after physical activity in healthy humans. For example, both AA-derived thrombaxane and leukotrieneB4 are proaggregatory and vasoconstrictive eicosanoids during inflammation. The oxidized metabolic products of linoleic acid, such as 9-hydroxyoctadecanoic acid and 13-hydroxyoctadecanoic acid, have also been shown to activate TRPV1, the capsaicin receptor, and through this might play a major role in hyperalgesia and allodynia.
Linoleic acid is used in making quick-drying oils, which are useful in oil paints and varnishes. These applications exploit the easy reaction of the linoleic acid with oxygen in air (autoxidation), which leads to crosslinking and formation of a stable film called linoxyn.
Reduction of linoleic acid yields linoleyl alcohol. Linoleic acid is a surfactant with a critical micelle concentration of 1.5 x 10-4 M @ pH 7.5.
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.
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.
^Evidence suggests that infants must acquire ?6desaturase breast milk. Breast-milk fed babies have higher concentrations of GLA than formula-fed babies, while formula-fed babies have elevated concentrations of LADavid F. Horrobin (1993). "Fatty acid metabolism in health and disease: the role of ?-6-desaturase". American Journal of Clinical Nutrition. 57 (5 Suppl): 732S-7S. doi:10.1093/ajcn/57.5.732S. PMID8386433.
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^R. A. Raphael and Franz Sondheimer (1950): "The synthesis of long-chain aliphatic acids from acetylenic compounds. Part III. The synthesis of linoleic acid". Journal of the Chemical Society (Resumed), article 432, doi:10.1039/jr9500002100