General Description
Colorless to pale yellow liquid with a mild odor. Floats on water.
Reactivity Profile
OLEIC ACID is a carboxylic acid. Carboxylic acids donate hydrogen ions if a base is present to accept them. They react in this way with all bases, both organic (for example, the amines) and inorganic. Their reactions with bases, called "neutralizations", are accompanied by the evolution of substantial amounts of heat. Neutralization between an acid and a base produces water plus a salt. Carboxylic acids with six or fewer carbon atoms are freely or moderately soluble in water; those with more than six carbons are slightly soluble in water. Soluble carboxylic acid dissociate to an extent in water to yield hydrogen ions. The pH of solutions of carboxylic acids is therefore less than 7.0. Many insoluble carboxylic acids react rapidly with aqueous solutions containing a chemical base and dissolve as the neutralization generates a soluble salt. Carboxylic acids in aqueous solution and liquid or molten carboxylic acids can react with active metals to form gaseous hydrogen and a metal salt. Such reactions occur in principle for solid carboxylic acids as well, but are slow if the solid acid remains dry. Even "insoluble" carboxylic acids may absorb enough water from the air and dissolve sufficiently in OLEIC ACID to corrode or dissolve iron, steel, and aluminum parts and containers. Carboxylic acids, like other acids, react with cyanide salts to generate gaseous hydrogen cyanide. The reaction is slower for dry, solid carboxylic acids. Insoluble carboxylic acids react with solutions of cyanides to cause the release of gaseous hydrogen cyanide. Flammable and/or toxic gases and heat are generated by the reaction of carboxylic acids with diazo compounds, dithiocarbamates, isocyanates, mercaptans, nitrides, and sulfides. Carboxylic acids, especially in aqueous solution, also react with sulfites, nitrites, thiosulfates (to give H2S and SO3), dithionites (SO2), to generate flammable and/or toxic gases and heat. Their reaction with carbonates and bicarbonates generates a harmless gas (carbon dioxide) but still heat. Like other organic compounds, carboxylic acids can be oxidized by strong oxidizing agents and reduced by strong reducing agents. These reactions generate heat. A wide variety of products is possible. Like other acids, carboxylic acids may initiate polymerization reactions; like other acids, they often catalyze (increase the rate of) chemical reactions.
Air & Water Reactions
Keep this compound well closed; protect OLEIC ACID(112-80-1) from air and light. . May form peroxides upon exposure to air. This is taken to account for an explosion that occurred, by the mixing of the acid with aluminum, [J. Chem. Educ., 1956, 36, 308]. Water Insoluble.
Health Hazard
Industrial use of compound involves no known hazards. Ingestion causes mild irritation of mouth and stomach. Contact with eyes or skin causes mild irritation.
Fire Hazard
This chemical is combustible.
Description
Oleic acid has a faint fatty odor.
Chemical Properties
Oleic acid, C17H33COOH, also known as red oil, elaine oil, and octadecenoic acid, is a yellowish unsaturated fatty acid with an aroma similar to lard. Oleic acid consists chiefly of (Ζ)-9-octadecenoic acid together with varying amounts of saturated and other unsaturated acids. It is insoluble in water, but soluble in most organic solvents. Oleic acid is the main component in cooking and olive oils.It is used for making aluminum oleate, which thickens lubricating oil, and in the preparation of soaps and cosmetics.
Occurrence
Reported found in apple, banana, cranberry, guava, grapes, melon, papaya, ginger, hop oil, ginger, beef fat,
beer, rum, whiskies, cider, sherry, tea, goat milk, butterfat, celery, cheese, blue cheese, munster cheese, other cheeses, cognac, country
cured ham, pork fat, potato, raspberry oil, tomato, peanut oil, coconut meat, avocado, mushroom, fenugreek, tamarind, kelp,
cardamom, rice, dill seed, sake, buckwheat, malt, wort, roasted chicory root and cape gooseberry.
Definition
ChEBI: An octadec-9-enoic acid in which the double bond at C-9 has Z (cis) stereochemistry.
Definition
cis-9-octadecenoic acid (or oleic acid) is a
naturally occurring carboxylic acid present
(as glycerides) in fats and oils:
CH3(CH2)7CH:CH(CH2)7COOH.
Definition
octadecenoic acid: A straightchainunsaturated fatty acid with theformula C17H33COOH. Cis-octadec-9-enoic acid has the formulaCH3(CH2)7CH:CH(CH2)7COOH.The glycerides of this acid are foundin many natural fats and oils.
Definition
oleic acid: An unsaturated fattyacid with one double bond,CH3(CH2)7CH:CH(CH2)7COOH; r.d. 0.9;m.p. 13°C. Oleic acid is one of themost abundant constituent fattyacids of animal and plant fats, occurringin butterfat, lard, tallow,groundnut oil, soya-bean oil, etc.Its systematic chemical name is cisoctadec-9-enoic acid.
Production Methods
Oleic acid is obtained by the hydrolysis of various animal and
vegetable fats or oils, such as olive oil, followed by separation of the
liquid acids. It consists chiefly of (Ζ)-9-octadecenoic acid. Oleic acid
that is to be used systemically should be prepared from edible
sources.
Pharmaceutical Applications
Oleic acid is used as an emulsifying agent in foods and topical
pharmaceutical formulations. It has also been used as a penetration enhancer in transdermal formulations,to improve the bioavailability
of poorly water-soluble drugs in tablet formulations,
and as part of a vehicle in soft gelatin capsules, in topical
microemulsion formulations,in oral self-emulsifying drug
delivery systems,in oral mucoadhesive patches,and in a
metered dose inhaler.Oleic acid was shown to be an important
factor in the hypoglycemic effect produced by multiple emulsions
containing insulin intended for intestinal delivery of insulin.
The phase behavior of sonicated dispersions of oleic acid has
been described,and mechanisms for the topical penetrationenhancing
actions of oleic acid have been presented.
Oleic acid has been reported to act as an ileal ‘brake’ that slows
down the transit of luminal contents through the distal portion of
the small bowel.
Oleic acid labeled with 131I and 3H is used in medical imaging.
Biochem/physiol Actions
Oleic acid is a colourless, odourless fatty acid that blocks the glucose production and food intake when administered intracerebroventricularly.
Safety
Oleic acid is used in oral and topical pharmaceutical formulations.
In vitro tests have shown that oleic acid causes rupture of red
blood cells (hemolysis), and intravenous injection or ingestion of a
large quantity of oleic acid can therefore be harmful. The effects of
oleic acid on alveolar and buccal epithelial cells in vitro have
also been studied; the in vitro and in vivo effects of oleic acid on rat
skin have been reported. Oleic acid is a moderate skin irritant; it
should not be used in eye preparations.
An acceptable daily intake for the calcium, sodium, and
potassium salts of oleic acid was not specified by the WHO since
the total daily intake of these materials in foods was such that they
did not pose a hazard to health.
LD50 (mouse, IV): 0.23 g/kg
LD50 (rat, IV): 2.4 mg/kg
LD50 (rat, oral): 74 g/kg
Carcinogenicity
Some recent studies suggested that oleic acid may
decrease the incidence of mammary gland tumors of some
rodent species. In a reviewof several fatty acids, Ip concludes
that there is little evidence for the protective effect of oleic
acid on the development of cancer.
storage
On exposure to air, oleic acid gradually absorbs oxygen, darkens in
color, and develops a more pronounced odor. At atmospheric
pressure, it decomposes when heated at 80–100°C.
Oleic acid should be stored in a well-filled, well-closed container,
protected from light, in a cool, dry place.
Purification Methods
Purify the acid by fractional crystallisation from its melt, followed by molecular distillation at 10 -3mm, or by conversion to its methyl ester, the free acid can be crystallised from acetone at -40o to -45o (12mL/g). For purification by the use of lead and lithium salts, see Keffler and McLean [J Soc Chem Ind (London) 54 176T 1935]. Purification based on direct crystallisation from acetone is described by Brown and Shinowara [J Am Chem Soc 59 6 1937, pK White J Am Chem Soc 72 1857 1950]. [Beilstein 2 H 463, 2 I 198, 2 II 429, 2 III 1387, 2 IV 1641.]
Incompatibilities
Incompatible with aluminum, calcium, heavy metals, iodine
solutions, perchloric acid, and oxidizing agents. Oleic acid reacts
with alkalis to form soaps.
Regulatory Status
GRAS listed. Included in the FDA Inactive Ingredients Database
(inhalation and nasal aerosols, tablets, topical and transdermal
preparations). Included in nonparenteral medicines (metered dose
inhalers; oral capsules; oral prolonged release granules; topical
creams and gels) licensed in the UK. Included in the Canadian List of
Acceptable Non-medicinal Ingredients.
