5505. Linoleic Acid

Nomenclature

CAS number: 60-33-3
(Z,Z)-9,12-Octadecadienoic acid; 9,12-linoleic acid; linolic acid.
C18H32O2; mol wt 280.45.
C 77.09%, H 11.50%, O 11.41%.

Description and references

An essential fatty acid. Major constituent of many vegetable oils, e.g., cottonseed, soybean, peanut, corn, sunflower seed, safflower, poppy seed, linseed, and perilla oils, where it occurs as a glyceride. Characteristic ingredient of semi-drying oils. Isoln: Swern, Parker, J. Am. Oil Chem. Soc. 30, 5 (1953); Parker et al., Biochem. Prep. 4, 86 (1955); McCutcheon, Org. Synth. coll. vol. III, 526 (1955). Summary of work on structure: T. P. Hilditch, The Chemical Constitution of Natural Fats (Chapman & Hall, London, 2nd ed. 1956). Synthesis: Raphael, Sondheimer, J. Chem. Soc. 1950, 2102; Gensler, Thomas, J. Am. Chem. Soc. 73, 4601 (1951); Walborsky et al., ibid. 2590; Nigam, Weedon, J. Chem. Soc. 1956, 4052; Osbond, Wickens, Chem. Ind. (London) 1959, 1288. Review of physiological role in mammals: H. S. Hansen, Trends Biochem. Sci. 11, 263 (1986).

Chemical structure

Properties

Colorless oil. Easily oxidized by air, cannot be distilled without decompn. Storage in ester form is recommended. d418 0.9038; d422 0.9007. mp 12°. bp1.4 202°; bp16 230°. nD11.5 1.4715; nD20 1.4699; nD21.5 1.4683; nD50 1.4588. Iodine value: 181.1. Thiocyanogen value 96.7. Freely sol in ether. Sol in abs alc. One ml dissolves in 10 ml petr ether. Miscible with dimethylformamide, fat solvents, oils.

Derivative

Aluminum salt.

Nomenclature

CAS number: 645-17-0
Al(C18H31O2)3; mol wt 865.29.
Al 3.12%, C 74.95%, H 10.83%, O 11.09%.

Properties

Yellow lumps or powder; linseed oil odor. Practically insol in water. Sol in oils, fixed alkali hydroxides.

Derivative

Methyl ester see Methyl Linoleate.

Derivative

Ethyl ester see Ethyl Linoleate.

Derivative

Cyclohexylamide.

Nomenclature

CAS number: 3207-50-9
Linolexamide; N-cyclohexyllinoleamide; Clinolamide.
C24H43NO; mol wt 361.60.
C 79.72%, H 11.99%, N 3.87%, O 4.42%.

Use

Manuf paints, coatings, emulsifiers, vitamins. Aluminum salt used to manuf lacquers.

Therapeutic Category

Nutrient (essential fatty acid).

Therapeutic Category (Veterinary)

Dietary supplement.