| Oleic acid | |
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(9Z)-Octadec-9-enoic acid
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other names
(9Z)-Octadecenoic acid
(Z)-Octadec-9-enoic acid cis-9-Octadecenoic acid cis-Δ9-Octadecenoic acid Oleic acid 18:1 cis-9 |
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| Identifiers | |
| CAS number | 112-80-1  |
| SMILES |
CCCCCCCC\C=C/CCCCCCCC(O)=O
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| Properties | |
| Molecular formula | C18H34O2 |
| Molar mass | 282.4614 g/mol |
| Appearance | Pale yellow or brownish yellow oily liquid with lard-like odor |
| Density | 0.895 g/mL |
| Melting point |
13-14 °C (286 K) |
| Boiling point |
360 °C (633 K) (760mm Hg)[1] |
| Solubility in water | Insoluble |
| Solubility in methanol | Soluble |
| Hazards | |
| MSDS | JT Baker |
 (what is this?) (verify)Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) |
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| Infobox references | |
Oleic acid is a mono-unsaturated omega-9 fatty acid found in various animal and vegetable sources. It has the formula CH3(CH2)7CH=CH(CH2)7COOH.[2] The trans-isomer of oleic acid is called elaidic acid.
The term Oleic means related to, or derived from, oil or olive.
Contents |
Triglyceride esters of oleic acid comprise the majority of olive oil, though there may be less than 2.0% as actual free acid in the virgin olive oil, while higher concentrations make the olive oil inedible. It also makes up 36-67% of peanut oil,[3] 15-20% of grape seed oil, sea buckthorn oil, and sesame oil, [4] and 14% of poppyseed oil.[5]
Oleic acid is the most abundant fatty acid in human adipose tissue.[6]
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[7] or ant[8][9] is daubed with oleic acid, it is dragged off as if it were dead. This is why oleic acid is also sometimes referred as "smell of death". The repellent smell indicates to living insects how to avoid others that have succumbed to disease or places where predators lurk. This "death recognition system" based on a simple fatty acid likely evolved over 400 million years ago.[10]
Oleic acid exhibits the reactions of carboxylic acids and alkenes. It is soluble in aqueous base to give Salts called oleates. Iodine adds across the double bond. Hydrogenation of the double bond give the saturated derivative called stearic acid. Oxidation at the double bond occurs slowly in air and is known as rancidification in foodstuffs and drying in coatings. Reduction of the carboxylic acid group yields oleyl alcohol.
As an excipient in pharmaceuticals, oleic acid is used as an emulsifying or solubilizing agent in aerosol products.[11]
Oleic acid may hinder the progression of ALD, or Adrenoleukodystrophy, a fatal disease that affects the brain and adrenal glands.[12]
Oleic acid may help boost memory.[13]
Oleic and monounsaturated fatty acid levels in the membranes of red blood cells have been associated with increased risk of breast cancer.[14] Oleic acid may be responsible for the hypotensive (blood pressure reducing) effects of olive oil.[15]
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  | Sea buckthorn: New crop opportunity - Sea Buckthorn: New Crop Opportunity |
| | 445639 - Oleic Acid - PubChem Public Chemical Database |
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