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Erucic Acid and Erucamide

By Alan Bruzel

Rapeseed (Brassica napus) is an interesting plant that has been bred as two varieties, yielding either a High Erucic Acid Rape oil (HEAR) or a Low Erucic Acid Rape oil (LEAR). HEAR oil contains as much as fifty percent of the unpalatable monounsaturated fatty acid, erucic acid (cis-13-docosenoic acid), and is used as an industrial lubricant. LEAR oil has less than two percent erucic acid, and enjoys commercial success under the name of canola oil: a vegetable oil with less saturated fat than corn oil or soybean oil. (Rapeseed growers know to keep their high erucic acid producing plants far apart from the low erucic acid producers, as cross-pollination by insects leads to hybrids too low in erucic acid for industry and too high in erucic acid for cuisine.)

Erucic acid melting point 34oC

Erucic acid is present in rapeseed oil as glycerol trierucate, which is employed as a high temperature lubricant. Unlike synthetic or petroleum-based products, this lubricant is renewable – a fact to be borne in mind during times of recurrent oil crises. Also, glycerol trierucate serves as an interim treatment, but not a cure, for adrenoleukodystrophy (ALD), a progressively debilitating disease involving the nervous system, adrenal cortex, and testis. ALD patients accumulate saturated very long chain fatty acids (VLCFA) whose levels may be reduced by ingesting Lorenzo's Oil: a mixture of glycerol trioleate and glycerol trierucate. The strategy is to shift the ALD patient from producing saturated VLCFA by liberally administering the monounsaturated fatty acids present in Lorenzo's Oil. Apparently, the unsaturated VLCFA consequently produced by the patient are less harmful than the saturated VLCFA normally generated in ALD.

A further useful property of erucic acid is conferred by its amide, erucamide (cis-13-docosenoic acid amide). Polyethylene and polypropylene items such as bread wrappers, garbage bags, and plastic films all include a thin coating of erucamide that improves handling and prevents the plastic from sticking to itself.

Erucamide melting point 80oC

What the Web Has to Say about:
Erucic Acid and Erucamide

Bioactive Amides of Fatty Acids
Review article by V. V. Bezuglov, M. Yu. Bobrov, and A. V. Archakov, in Biochemistry (Moscow), 63, 27, 1998, describing angiogenic activity of erucamide.

Canola: A Promising Oilseed
Describes differences between industrial rapeseed and canola. From J. Alan Weber, Robert L. Myers, and Harry C. Minor, University of Missouri at Columbia.

Crambe: A New Industrial Crop in Limbo
Article by Koert J. Lessman concerning a potential oilseed plant, Crambe abyssinica.

Potential of High Erucic Acid Rapeseed Oil as a Hydraulic Fluid
Hydraulic fluid properties of raw rapeseed oil. From University of Idaho study, Development of Rapeseed Biodiesel for Use in High-Speed Diesel Engines.

Seed Oil Modification
Genetically altering the oil content of plants. From the National Research Council of Canada.

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