3674. Erucic Acid
Nomenclature
Description and references
A monoethenoid acid found in the seed fats of Cruciferae and Tropaeolaceae. It constitutes 40 to 50% of the total fatty acids of rapeseed, mustard and wallflower seed, and it represents up to 80% of fatty acids of nasturtium seeds, cf. K. S. Markley, Fatty Acids Part I (Interscience, New York, 2nd ed., 1960) p 138-139. Prepn of a crude product by alkaline hydrolysis of rapeseed oil: Noller, Talbot, Org. Synth. coll. vol. II, 258 (1943). A purer product is obtained by the method of Dorée and Pepper, J. Chem. Soc. 1942, 477, which involves a fractional precipitation and crystallization. Prepn of a pure product by acid soap crystallization: Chobanov et al., Chem. Ind. (London) 1965, 606. Synthesis: Bowman, J. Chem. Soc. 1950, 177, 325; Bounds et al., ibid. 1953, 2393. Treatment with nitric acid yields the trans isomer, brassidic acid, q.v.: Dorée, Pepper, loc. cit. Brief review: E. Lower, Manuf. Chem. 56(6), 61-63 (1985).
