Oleic acid
Oleic acid is a fatty acid that occurs naturally in various animal and vegetable fats and oils.
It is an odorless, colourless oil, although commercial samples may be yellowish.
In chemical terms, oleic acid is classified as a monounsaturated omega-9 fatty acid.
It has the formula CH3(CH2)7CH=CH(CH2)7COOH.
The term "oleic" means related to, or derived from, oil or olive, the oil of which is predominantly derived from oleic acid.
CCCCCCCC\C=C/CCCCCCCC(O)=O
(9Z)-Octadec-9-enoic acid
Other names
(9Z)-Octadecenoic acid
(Z)-Octadec-9-enoic acid
cis-9-Octadecenoic acid
cis-Δ9-Octadecenoic acid
Oleic acid
18:1 cis-9
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)

Solubility in water Insoluble
Solubility in methanol Soluble
Fatty acids (or as their salts) do not often occur as such in biological systems.
Instead fatty acids like oleic acid occur as their esters, commonly the triglycerides, which are the greasy materials in many natural oils.
Via the process of saponification, the fatty acids can be obtained.
Triglyceride esters of oleic acid compose the majority of olive oil, although there may be less than 2.0% as free acid in the virgin olive oil, with higher concentrations making the olive oil inedible.
It also makes up 59-75% of pecan oil,
36-67% of peanut oil,15-20% of grape seed oil, sea buckthorn oil, and sesame oil,and 14% of poppyseed oil.
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.
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 daubed 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.