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Linoleic acid ( LA) is an organic compound with the formula . 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.
Linoleic acid is a polyunsaturated, omega−6 fatty acid. It is a colorless liquid that is virtually insoluble in water but soluble in many . It typically occurs in nature as a triglyceride (ester of glycerol) rather than as a free fatty acid. It is one of two essential fatty acids for humans, who must obtain it through their diet, 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.
The metabolism of LA to AA begins with the conversion of LA into gamma-linolenic acid (GLA), effected by Δ6 desaturase.Evidence suggests that infants must acquire Δ6-desaturase breast milk. Breast-milk fed babies have higher concentrations of GLA than formula-fed babies, while formula-fed babies have elevated concentrations of LA. GLA is converted to dihomo-γ-linolenic acid (DGLA), the immediate precursor to AA.
LA is also converted by various , , cytochrome P450 enzymes (the CYP ), and non-enzymatic autoxidation mechanisms to mono-Hydroxy group 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 , 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.
derived from the metabolism of anandamide (AEA: ; 20:4,n−6), or its Linoleyl alcohol 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 (; 18:2,n−6), an N-acylethanolamine, - the ethanolamide of linoleic acid (LA: ; 18:Double bond,n−6) and its metabolized incorporated ethanolamine (MEA: ), is the first natural inhibitor of FAAH, discovered.
Reduction of the carboxylic acid group 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 Human skin.
Linoleic acid is also used in some Soap products.
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| †average value, except the items where a range is given | ||
The American Heart Association advises people to replace saturated fat with linoleic acid to reduce CVD risk.
F. Sacc (1844). "Ueber das Leinöl, seine physicalischen und chemischen Eigenschaften und seine Oxydationsproducte". Liebigs Annalen, volume 51, issue 2, pages 213–230. .
F. Sacc (1845). "Expériences sur les propriétés physiques et chimiques de l'huile de Lin". Neue Denkschriften der Allg. Schweizerischen Gesellschaft für die Gesammten Naturwissenschaften, volume 7, pages 191–208 in pdf.
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