Erucic Acid

Erucic acid also is known as cis-13-Docosenoic acid, is a monounsaturated very-long-chain fatty acid with a 22-carbon backbone and a single double bond originating from the 9th position from the methyl end, with the double bond in the cis configuration. It is a monounsaturated omega-9 fatty acid, and it has the chemical formula CH3(CH2)7CH=CH(CH2)11COOH. It occurs mainly in the seeds of the Brassicaceae species (e.g. rapeseed or mustard seed, and seeds from vegetable crops such as kales, cabbages, and turnips) at high concentrations.

Erucic acid is prevalent in wallflower seed with a reported content of 20 to 54% in high erucic acid oil, and 42% in mustard oil. It’s also called cis-13-docosenoic acid and also the trans isomer is thought as brassidic acid. This has many of the same applications as mineral oils but with the difference that it is bio-degradable more readily.

Erucic acid has limited potential for polymerization and dry use in oil paints. This can be converted into surfactants or lubricants like other fatty acids and can be used as a precursor to biodiesel gasoline. A high-temperature tolerance makes it ideal for conveyance oil. The ability to polymerize and dry ensures it can be used and is used as an oil paint binder. Enhanced levels of eicosenoic acid and erucic acid were associated with developmental regression in the red blood cell membranes of autistic subjects.

High-erucic acid oils are either used as lubricants directly (e.g. when making rubber additives) or in formulations. They are also used in the clothing, steel, and shipping industries as spinning lubricants; as oils for cutting, metal shaping, rolling, processing, and drilling; and as marine lubes. Derivatives of erucic acid have many further uses, like behenyl alcohol (CH3(CH2)21OH), pour point depressant (enabling liquids to flow at a lower temperature), and silver behenate, to be used in photography.

Long-chain acyl-coenzyme A (CoA) dehydrogenase, produced in the liver, is actually broken down by erucic acid. And this enzyme splits this long chain of fatty acids into fatty acids of a shorter chain. Food-grade oil (also called vegetable oil, rapeseed 00 oil, low erucic acid rape oil, LEAR oil, and rapeseed canola-equivalent oil) is regulated to a maximum of twenty-two erucic acid by weight within the USA and 5% within the EU, with special regulations for infant food.

Erucic acid for use in polyester processing can also be oxidatively cleaved to brassylic acid. Rapeseed is used for industrial purposes and for the production of erucic acid; a ‘low-erucic acid rapeseed’ (LEAR) was developed for food purposes (canola), which contains fats derived from oleic acid instead of erucic acid. Human infants have relatively low amounts of this enzyme and for this reason; babies should not be given high in erucic acid foods. Erucic acid is associated with isovaleric acidemia which is an inborn metabolism defect.

 

Information Sources:

chemicalbook.com

pubchem.ncbi.nlm.nih.gov

wikipedia