Erucic acid is a

monounsaturated In nutrition, biology, and chemistry, fat usually means any ester of fatty acids, or a mixture of such compounds, most commonly those that occur in living beings or in food. The term often refers specifically to triglycerides (triple est ...

omega-9 fatty acid Omega-9 fatty acids (ω−9 fatty acids or ''n''−9 fatty acids) are a family of unsaturated fatty acids which have in common a final carbon–carbon double bond in the omega−9 position; that is, the ninth bond from the methyl end of the fat ...

, denoted 22:1ω9. It has the chemical formula CH₃(CH₂)₇CH=CH(CH₂)₁₁COOH. It is prevalent in

wallflower ''Erysimum'', or wallflower, is a genus of flowering plants in the cabbage family, Brassicaceae. It includes more than 150 species, both popular garden plants and many wild forms. The genus ''Cheiranthus'' is sometimes included here in whole o ...

seed and other plants in the family

Brassicaceae Brassicaceae () or (the older) Cruciferae () is a medium-sized and economically important family of flowering plants commonly known as the mustards, the crucifers, or the cabbage family. Most are herbaceous plants, while some are shrubs. The le ...

, with a reported content of 20 to 54% in high erucic acid

rapeseed Rapeseed (''Brassica napus ''subsp.'' napus''), also known as rape, or oilseed rape, is a bright-yellow flowering member of the family Brassicaceae (mustard or cabbage family), cultivated mainly for its oil-rich seed, which naturally contains a ...

oil and 42% in

mustard oil Mustard oil can mean either the pressed oil used for cooking, or a pungent essential oil also known as volatile oil of mustard. The essential oil results from grinding mustard seed, mixing the grounds with water, and extracting the resulting vol ...

. Erucic acid is also known as ''cis''-13-docosenoic acid and the

trans isomer Trans- is a Latin prefix meaning "across", "beyond", or "on the other side of". Used alone, trans may refer to: Arts, entertainment, and media * Trans (festival), a former festival in Belfast, Northern Ireland, United Kingdom * ''Trans'' (film ...

is known as brassidic acid.

Uses

Erucic acid has many of the same uses as mineral oils, but it is more readily biodegradable than some. It has limited ability to polymerize and dry for use in oil

paint Paint is any pigmented liquid, liquefiable, or solid mastic composition that, after application to a substrate in a thin layer, converts to a solid film. It is most commonly used to protect, color, or provide texture. Paint can be made in many ...

s. Like other

fatty acid In chemistry, particularly in biochemistry, a fatty acid is a carboxylic acid with an aliphatic chain, which is either saturated or unsaturated. Most naturally occurring fatty acids have an unbranched chain of an even number of carbon atoms, fr ...

s, it can be converted into

surfactant Surfactants are chemical compounds that decrease the surface tension between two liquids, between a gas and a liquid, or interfacial tension between a liquid and a solid. Surfactants may act as detergents, wetting agents, emulsifiers, foaming ...

s or

lubricant A lubricant (sometimes shortened to lube) is a substance that helps to reduce friction between surfaces in mutual contact, which ultimately reduces the heat generated when the surfaces move. It may also have the function of transmitting forces, t ...

s, and can be used as a precursor to

biodiesel Biodiesel is a form of diesel fuel derived from plants or animals and consisting of long-chain fatty acid esters. It is typically made by chemically reacting lipids such as animal fat (tallow), soybean oil, or some other vegetable oil with ...

fuel. Derivatives of erucic acid have many further uses, such as

behenyl alcohol 1-Docosanol, also known as behenyl alcohol, is a saturated fatty alcohol containing 22 carbon atoms, used traditionally as an emollient, emulsifier, and thickener in cosmetics. In July 2000, docosanol was approved for medical use in the United ...

(CH₃(CH₂)₂₁OH), a

pour point The pour point of a liquid is the temperature below which the liquid loses its flow characteristics. It is defined as the minimum temperature in which the oil has the ability to pour down from a beaker. In crude oil a high pour point is generally ...

depressant (enabling liquids to flow at a lower temperature), and

silver behenate Silver behenate is a silver salt of the long-chain fatty acid behenic acid. It is a possible low-angle diffraction standard that was characterized using the powder diffraction technique. Description With the National Institute of Standards and T ...

, for use in photography.

Sources of erucic acid

The name ''erucic'' means "of or pertaining to ''

Eruca ''Eruca'' is a genus of flowering plants in the family Brassicaceae, native to the Mediterranean region, which includes the leaf vegetable known as arugula or rocket. The number of species is disputed, with some authorities only accepting a sin ...

''", which is a genus of

flowering plant Flowering plants are plants that bear flowers and fruits, and form the clade Angiospermae (), commonly called angiosperms. The term "angiosperm" is derived from the Greek words ('container, vessel') and ('seed'), and refers to those plants th ...

s in the family

. The genus includes colewort ('' E. sativa''), which today is better known as

arugula Arugula (American English) or rocket (Commonwealth English) (''Eruca vesicaria''; syns. ''Eruca sativa'' Mill., ''E. vesicaria'' subsp. ''sativa'' (Miller) Thell., ''Brassica eruca'' L.) is an edible annual plant in the family Brassicaceae used a ...

(US) or rocket (UK). Erucic acid is produced naturally (together with other fatty acids) across a great range of green plants, but especially so in members of the genus ''

Brassica ''Brassica'' () is a genus of plants in the cabbage and mustard family (Brassicaceae). The members of the genus are informally known as cruciferous vegetables, cabbages, or mustard plants. Crops from this genus are sometimes called ''cole cr ...

''. For industrial purposes and production of erucic acid,

is used; for food purposes a 'low-erucic acid rapeseed' (LEAR) has been developed (

canola Close-up of canola blooms Canola flower Rapeseed oil is one of the oldest known vegetable oils. There are both edible and industrial forms produced from rapeseed, the seed of several cultivars of the plant family Brassicaceae. Historically, i ...

), which contains fats derived from

oleic acid Oleic acid is a fatty acid that occurs naturally in various animal and vegetable fats and oils. It is an odorless, colorless oil, although commercial samples may be yellowish. In chemical terms, oleic acid is classified as a monounsaturated omega ...

instead of erucic acid.David J. Anneken, Sabine Both, Ralf Christoph, Georg Fieg, Udo Steinberner, Alfred Westfechtel "Fatty Acids" in Ullmann's Encyclopedia of Industrial Chemistry 2006, Wiley-VCH, Weinheim.

Biochemistry

Erucic acid is produced by elongation of oleic acid via oleoyl-

coenzyme A Coenzyme A (CoA, SHCoA, CoASH) is a coenzyme, notable for its role in the synthesis and oxidation of fatty acids, and the oxidation of pyruvate in the citric acid cycle. All genomes sequenced to date encode enzymes that use coenzyme A as a subs ...

and

malonyl-CoA Malonyl-CoA is a coenzyme A derivative of malonic acid. Functions It plays a key role in chain elongation in fatty acid biosynthesis and polyketide biosynthesis. Fatty acid biosynthesis Malonyl-CoA provides 2-carbon units to fatty acids and commi ...

. Erucic acid is broken down into shorter-chain fatty acids in the human liver by the long-chain

acyl CoA dehydrogenase Acyl-CoA dehydrogenases (ACADs) are a class of enzymes that function to catalyze the initial step in each cycle of fatty acid β-oxidation in the mitochondria of cells. Their action results in the introduction of a trans double-bond between C2 ( ...

enzyme Enzymes () are proteins that act as biological catalysts by accelerating chemical reactions. The molecules upon which enzymes may act are called substrates, and the enzyme converts the substrates into different molecules known as products. A ...

Health effects

Studies done on laboratory animals in the early 1970sAmy McInnis, 21 May 200
The Transformation of Rapeseed Into Canola: A Cinderella Story
show that erucic acid appears to have toxic effects on the heart at high enough doses. However, more recent research has cast doubt on the relevance of rat studies to the human health of erucic acid. Rats are unusual in their inability to process erucic acid, and the symptoms in rats caused by a diet with high levels of erucic acid have not been observed in pigs, primates, or any other animals.Grice, H. & Heggtveit, H. (1983). The Relevance to Humans of Myocardial Lesions Induced in Rats by Marine and Rapeseed Oils. In High and Low Erucic Acid Rapeseed Oils. Elsevier. p. 560. An association between the consumption of rapeseed oil and increased myocardial lipidosis, or heart disease, has not been established for humans.Food Standards Australia New Zealand (June 2003
Erucic acid in food: A Toxicological Review and Risk Assessment
Technical report series No. 21; Page 4 paragraph 1; , ISSN 1448-3017 While there are reports of toxicity from long-term use of

Lorenzo's oil ''Lorenzo's Oil'' is a 1992 American drama film directed and co-written by George Miller. It is based on the true story of Augusto and Michaela Odone, parents who search for a cure for their son Lorenzo's adrenoleukodystrophy (ALD), leading to ...

(which contains erucic acid and other ingredients), there are no reports of harm to people from dietary consumption of erucic acid. Publication of animal studies with erucic acid through the 1970s led to governments worldwide moving away from oils with high levels of erucic acid, and tolerance levels for human exposure to erucic acid have been established based on the animal studies.U.S. Dept. of Health and Human Services
CFR - Code of Federal Regulations Title 21
1 April 2010. In 2003, Food Standards Australia set a provisional tolerable daily intake (PTDI) for an average adult of about 500 mg/day of erucic acid, extrapolated based on "the level that is associated with increased myocardial lipidosis in nursing pigs." "There is a 120-fold safety margin between this level and the level that is associated with increased myocardial lipidosis in nursing pigs. The dietary exposure assessment has concluded that the majority of exposure to erucic acid by the general population would come from the consumption of

colza oil Close-up of canola blooms Canola flower Rapeseed oil is one of the oldest known vegetable oils. There are both edible and industrial forms produced from rapeseed, the seed of several cultivars of the plant family Brassicaceae. Historically, i ...

. The dietary intake of erucic acid by an individual consuming at the average level is well below the PTDI; therefore, there is no cause for concern in terms of public health and safety. However, the individual consuming at a high level has the potential to approach the PTDI. This would be particularly so if the level of erucic acid in colza oil were to exceed 2% of the total fatty acids." Food-grade rapeseed oil (also known as

canola oil Close-up of canola blooms Canola flower Rapeseed oil is one of the oldest known vegetable oils. There are both edible and industrial forms produced from rapeseed, the seed of several cultivars of the plant family Brassicaceae. Historically, i ...

, rapeseed 00 oil, low erucic acid rapeseed oil, LEAR oil, and rapeseed canola-equivalent oil) is regulated to a maximum of 2% erucic acid by weight in the US and 2% in the EU (was 5% before 2019-11-19), with special regulations for infant food. Canola was bred from rapeseed cultivars of ''B. napus'' and ''B. rapa'' by Dr. Baldur Stefansson at the

University of Manitoba The University of Manitoba (U of M, UManitoba, or UM) is a Canadian public research university in the province of Manitoba.Canada Canada is a country in North America. Its ten provinces and three territories extend from the Atlantic Ocean to the Pacific Ocean and northward into the Arctic Ocean, covering over , making it the world's second-largest country by tot ...

in addition to being cultivated by ancient Chinese, Indian, and Japanese cultures. Canola oil is derived from a variety of

that is low in erucic acid, as opposed to colza oil.

References

External links

Erucic acid MS Spectrum
{{DEFAULTSORT:Erucic Acid Fatty acids Alkenoic acids