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. It has the formula CH3(CH2)7CH=CH(CH2)7COOH. The term "oleic" means related to, or derived from, olive oil, which is mostly composed of oleic acid-rich triglycerides.
|Preferred IUPAC name
3D model (JSmol)
|Molar mass||282.47 g·mol−1|
|Appearance||Pale yellow or brownish yellow oily liquid with lard-like odor|
|Melting point||13 to 14 °C (55 to 57 °F; 286 to 287 K)|
|Boiling point||360 °C (680 °F; 633 K)|
|Solubility in Ethanol||Soluble|
|Safety data sheet||JT Baker|
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
|what is ?)(|
Fatty acids (or their salts) do not often occur as such in biological systems. Instead fatty acids like oleic acid occur as their esters, commonly triglycerides, which are the greasy materials in many natural oils. Fatty acids can be obtained by the saponification of triglycerides.
Triglycerides of oleic acid comprise the majority of olive oil. Free oleic acid render olive oil inedible. It also makes up 59-75% of pecan oil, 61% of canola oil, 36-67% of peanut oil, 60% of macadamia oil, 20-85% of sunflower oil (the latter in the high oleic variant), 15-20% of grape seed oil, sea buckthorn oil, and sesame oil, and 14% of poppyseed oil. It also comprises 22.18% of the fats from the fruit of the durian species Durio graveolens. It is abundantly present in many animal fats, constituting 37 to 56% of chicken and turkey fat and 44 to 47% of lard.
As an insect pheromoneEdit
Oleic acid is emitted by the decaying corpses of a number of insects, including bees and Pogonomyrmex ants, and triggers the instincts of living workers to remove the dead bodies from the hive. If a live bee or ant is dabbed with oleic acid, it is dragged off for disposal as if it were dead. The oleic acid smell also may indicate danger to living insects, prompting them to avoid others who have succumbed to disease or places where predators lurk.
Production and chemical behaviorEdit
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. It is soluble in aqueous base to give soaps called oleates. Iodine adds across the double bond. Hydrogenation of the double bond yields the saturated derivative stearic acid. Oxidation at the double bond occurs slowly in air, and is known as rancidification in foodstuffs or drying in coatings. Reduction of the carboxylic acid group yields oleyl alcohol. Ozonolysis of oleic acid is an important route to azelaic acid. The coproduct is nonanoic acid:
- H17C8CH=CHC7H14CO2H + 4"O" → H17C8CO2H + HO2CC7H14CO2H
Esters of azelaic acid find applications in lubrication and plasticizers.
The stereoisomer of oleic acid is called elaidic acid or trans-9-octadecenoic acid. These isomers have distinct physical properties and biochemical properties. Elaidic acid, the most abundant trans fatty acid in diet, appears to have an adverse effect on health. A reaction that converts oleic acid to elaidic acid is called elaidinization.
Another naturally occurring isomer of oleic acid is petroselinic acid.
In chemical analysis, fatty acids are separated by gas chromatography of their methyl ester derivatives. Alternatively, separation of unsaturated isomers is possible by argentation thin-layer chromatography.
The principal use of oleic acid is as a component in many foods, in the form of its triglycerides. It is a component of the normal human diet as a part of animal fats and vegetable oils.
Oleic acid as its sodium salt is a major component of soap as an emulsifying agent. It is also used as an emollient. Small amounts of oleic acid are used as an excipient in pharmaceuticals, and it is used as an emulsifying or solubilizing agent in aerosol products.
Oleic acid is also used to induce lung damage in certain types of animals, for the purpose of testing new drugs and other means to treat lung diseases. Specifically in sheep, intravenous administration of oleic acid causes acute lung injury with corresponding pulmonary edema. This sort of research has been of particular benefit to premature newborns, for whom treatment for underdeveloped lungs (and associated complications) is often a matter of life and death.
Oleic acid is also widely used in the solution phase synthesis of nanoparticles, functioning as a kinetic knob to control the size and morphology of nanoparticles.
Oleic acid is a common monounsaturated fat in human diet. Monounsaturated fat consumption has been associated with decreased low-density lipoprotein (LDL) cholesterol, and possibly increased high-density lipoprotein (HDL) cholesterol. However, its ability to raise HDL is still debated.
Oleic acid may be responsible for the hypotensive (blood pressure reducing) effects of olive oil. Adverse effects also have been documented, however, since both oleic and monounsaturated fatty acid levels in the membranes of red blood cells have been associated with increased risk of breast cancer, although the consumption of oleate in olive oil has been associated with a decreased risk of breast cancer.
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