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Concept
Oleic acid
Summary
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 omega-9 fatty acid, abbreviated with a lipid number of 18:1 cis-9, and a main product of Δ9-desaturase. It has the formula . The name derives from the Latin word oleum, which means oil. It is the most common fatty acid in nature. The salts and esters of oleic acid are called oleates. It is part of many oils and thus used in a lot of artificial food, as well as for soap.
Fatty acids (or their salts) often do not occur as such in biological systems. Instead fatty acids such as oleic acid occur as their esters, commonly triglycerides, which are the greasy materials in many natural oils. Oleic acid is the most common monounsaturated fatty acid in nature. It is found in fats (triglycerides), the phospholipids that make membranes, cholesterol esters, and wax esters.
Triglycerides of oleic acid comprise the majority of olive oil (about 70%). Olive oil exceeding 2% free oleic acid is graded unfit for human consumption. It also makes up 59–75% of pecan oil, 61% of canola oil, 36–67% of peanut oil, 60% of macadamia oil, 20–80% of sunflower oil, 15–20% of grape seed oil, sea buckthorn oil, 40% of sesame oil, and 14% of poppyseed oil. High oleic variants of plant sources such as sunflower (~80%) and canola oil (70%) also have been developed. Karuka contains 52.39% oleic acid. It is abundantly present in many animal fats, constituting 37 to 56% of chicken and turkey fat, and 44 to 47% of lard.
Oleic acid is the most abundant fatty acid in human adipose tissue, and second in abundance in human tissues overall, following palmitic acid.
The biosynthesis of oleic acid involves the action of the enzyme stearoyl-CoA 9-desaturase acting on stearoyl-CoA. In effect, stearic acid is dehydrogenated to give the monounsaturated derivative, oleic acid.
Oleic acid undergoes the reactions of carboxylic acids and alkenes.
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