Oleic Acid
Title: Oleic Acid
CAS Registry Number: 112-80-1
CAS Name: (Z)-9-Octadecenoic acid
Molecular Formula: C18H34O2
Molecular Weight: 282.46
Percent Composition: C 76.54%, H 12.13%, O 11.33%
Literature References: Obtained by the hydrolysis of various animal and vegetable fats and oils. Prepn from olive oil: Biochem. Prep. 2, 100 (1952). Separation from olive oil by double fractionation via urea adducts: Rubin, Paisley, Biochem. Prep. 9, 113 (1962). Stereochemistry: Thieme, Ann. 343, 354 (1905). Synthesis: Robinson, Robinson, J. Chem. Soc. 127, 175 (1925). 13C-NMR studies: W. Stoffel et al., Z. Physiol. Chem. 353, 1962 (1972); J. G. Batchelor et al., J. Org. Chem. 39, 1698 (1974). Toxicity data: L. Orö, A. Wretlind, Acta Pharmacol. Toxicol. 18, 141 (1961). Exptl use of 131I-labelled oleic acid in myocardial imaging: F. J. Bonte et al., Radiology 108, 195 (1973). Review of diagnostic use of 3H-oleic acid in pancreatic function: N. T. Pedersen, Digestion 37, Suppl. 1, 25-34 (1987).
Properties: Pure oleic acid is a colorless or nearly colorless liq (above 5-7°). d2525 ~0.895. Solidifies to cryst mass, mp 4°. bp100 286°. At atm pressure it dec when heated at 80-100°. nD18 1.463; nD26 1.4585. Iodine no. 89.9; acid value 198.6. On exposure to air, especially when impure, it oxidizes and acquires a yellow to brown color and rancid odor. Practically insol in water. Sol in alcohol, benzene, chloroform, ether, fixed and volatile oils. Keep well closed, protected from light. LD50 i.v. in mice: 230±18 mg/kg (Orö, Wretlind). Several grades of the acid are available in commerce, varying in color from pale yellow to red-brown and, depending on the amount of saturated acid present, becoming turbid at 8-16°. The acid of commerce usually contains 7-12% saturated acids, e.g., stearic, palmitic; also some linoleic, etc., unsaturated acids.
Melting point: mp 4°
Boiling point: bp100 286°
Index of refraction: nD18 1.463; nD26 1.4585
Density: d2525 ~0.895
Toxicity data: LD50 i.v. in mice: 230±18 mg/kg (Orö, Wretlind)
Derivative Type: Methyl ester
Additional Names: Methyl oleate
Molecular Formula: C19H36O2
Molecular Weight: 296.49
Percent Composition: C 76.97%, H 12.24%, O 10.79%
Literature References: Prepd by refluxing oleic acid with p-toluene sulfonic acid in methanol: Rubin, Paisley, loc. cit. Iodine no. 85.6.
Properties: d418 0.879. nD26 1.4510. bp2 168-170°. Miscible with anhydr ethanol, ether.
Boiling point: bp2 168-170°
Index of refraction: nD26 1.4510
Density: d418 0.879
Derivative Type: Ethyl ester
Additional Names: Ethyl oleate; (Z)-9-octadecenoic acid ethyl ester
Molecular Formula: C20H38O2
Molecular Weight: 310.51
Percent Composition: C 77.36%, H 12.34%, O 10.31%
Properties: Yellowish, oily liquid. d 0.87. bp 205-208° (some dec). Insol in water. Misc with alcohol, ether.
Boiling point: bp 205-208° (some dec)
Density: d 0.87
Derivative Type: Barium salt
Additional Names: Barium oleate
Molecular Formula: C36H66BaO4
Molecular Weight: 700.23
Percent Composition: C 61.75%, H 9.50%, Ba 19.61%, O 9.14%
Properties: Yellowish-white, granular masses. Poisonous! Practically insol in water. Slightly sol in boiling alcohol.
Derivative Type: Sodium salt
CAS Registry Number: 143-19-1
Trademarks: Eunatrol
Molecular Formula: C18H33NaO2
Molecular Weight: 304.44
Percent Composition: C 71.01%, H 10.93%, Na 7.55%, O 10.51%
Properties: White powder, slight tallow-like odor. Sol in ~10 parts water, ~20 parts alcohol. Generally contains small quantities of the sodium salts of stearic, etc. acids. Alkaline in aq solns due to hydrolysis but not in alcohol solns.
CAUTION: Mildly irritating to skin, mucous membranes.
Use: Prepn of Turkey red oil, soft soap and other oleates; in polishing compds; waterproofing textiles, oiling wool; manuf driers; thickening lubricating oils. Pharmaceutic aid (solvent). The barium salt in rodent extermination.
Therap-Cat: Diagnostic aid (pancreatic function).
Keywords: Diagnostic Aid.

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