OLEIC ACID

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 name derives from the
Latin word oleum, which means oil. It is the most common fatty acid in nature. Salts of oleic
acid are called oleates.
Names
Preferred IUPAC name
(9Z)-Octadec-9-enoic acid
Other names
Oleic acid
(9Z)-Octadecenoic acid
(Z)-Octadec-9-enoic acid
cis-9-Octadecenoic acid
cis-Δ9-Octadecenoic acid
18:1 cis-9

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.

Properties
Chemical formula
C18H34O2
Molar mass
282.468 g·mol−1
Appearance Pale yellow or brownish yellow oily liquid with lard-like odor
Density
0.895 g/mL
Melting point
 13 to 14 °C (55 to 57 °F; 286 to 287Properties
Chemical formula
C18H34O2
Molar mass
282.468 g·mol−1
Appearance Pale yellow or brownish yellow oily liquid with lard-like odor
Density
0.895 g/mL
Melting point
13 to 14 °C (55 to 57 °F; 286 to 287 K)
Boiling point
360 °C (680 °F; 633 K)[1]

Solubility in water
Insoluble
Solubility in Ethanol
Soluble
Magnetic susceptibility(χ)
-208.5·10−6 cm3/molProperties K)
Boiling point
360 °C (680 °F; 633 K)[1]

Solubility in water
Insoluble
Solubility in Ethanol
Soluble
Triglycerides of oleic acid comprise the majority of olive oil. Free oleic acid renders 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, 20-80% of sunflower oil, 15-20% of grape seed oil, sea buckthorn oil, and
sesame oil, and 14% of poppyseed oil. High oleic variants of plant sources like sunflower
(~80%) and canola oil (70%) has also been developed. It also comprises 22.18% of the fats from
the fruit of the durian species Durio graveolens. Likewise Karuka contains 52.39% oleic
acid.[11] 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 only to palmitic acid.
As an insect pheromone
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.
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.
Uses:
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.
Oleic acid is used as a soldering flux in stained glass work for joining lead came.
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.

Health effects
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.
Related information
Evidence from epidemiological studies suggests that a higher proportion of monounsaturated
fatty acids (MUFA), notably oleic acid, in the diet is linked with a reduction in the risk of
coronary heart disease (CHD). To achieve this benefit, olive oil as a major source of oleic acid is
to replace a similar amount of saturated fat and not increase the total number of daily calories.
The biochemical bases of the ameliorative effect of oleic acid are thought to be modification of
plasma lipid and lipoprotein concentrations, inhibition of coagulation, improvement of glucose
homeostasis, and attenuation of inflammation and oxidative status in fasting conditions. More
recently, a body of evidence has grown that supports the hypotheses that postprandial
metabolism of dietary fats plays a causal role in the pathogenesis and progression of CHD.
However, the relevance of oleic acid regarding saturated fatty acids (SFA), notably palmitic acid,
in dietary fats to influence postprandial metabolic processes is only partially understood. The
proportion of oleic acid and palmitic acid in olive oil, compared to other dietary fats, could
provide benefits and be considered as a nutritional determinant, at least, for regulation of
coagulation and glucose homeostasis during the postprandial state.Although a low-fat diet is
associated with a reduction in concentrations of total and plasma LDL cholesterol, important
differences in the response to diet have been found between individuals, which may be one of the
explanations for the poor success of dietary recommendations in the prevention of certain
disorders. The concept of gene–diet interaction describes the modulation of the effect of a dietary
component on a specific phenotype by a genetic variant. Numerous studies have shown that
variation between individuals in their response to changes in diet is determined by genetic
factors. Indirect evidence comes from the general observation that the phenotypic response to
diet is partly determined by the basal value of the phenotype, which itself is affected by genetic
factors. The macronutrient that has received the most attention relates to the interaction between
genes and dietary fat. A clear example of this can be seen in the regulation of peroxisome
proliferator activated receptors (PPARs). PPARs are sensitive to lipids and play an important
role in lipid and glucose metabolism. Advances in molecular genetics have enabled the study of
genetic variation in one or more candidate genes to determine the role played by these genes in
genotype–phenotype interactions. Study of single nucleotide polymorphisms (SNPs) is necessary
for more precise determination of the genetic effects in gene–diet interactions. In this field of
gene–diet interactions, two different concepts have emerged: nutrigenetics and nutrigenomics.
References:
https://en.wikipedia.org/wiki/Oleic_acid
https://pubchem.ncbi.nlm.nih.gov/compound/Oleic-acid