Erucic acid

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Erucic acid
Erucic acid.png
Names
Preferred IUPAC name
(13Z)-Docos-13-enoic acid
Other names
Identifiers
3D model (JSmol)
1728049
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.003.647 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 204-011-3
177365
KEGG
PubChem CID
UNII
  • InChI=1S/C22H42O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21-22(23)24/h9-10H,2-8,11-21H2,1H3,(H,23,24)/b10-9- Yes check.svgY
    Key: DPUOLQHDNGRHBS-KTKRTIGZSA-N Yes check.svgY
  • InChI=1/C22H42O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21-22(23)24/h9-10H,2-8,11-21H2,1H3,(H,23,24)/b10-9-
    Key: DPUOLQHDNGRHBS-KTKRTIGZBD
  • O=C(O)CCCCCCCCCCC\C=C/CCCCCCCC
Properties
C22H42O2
Molar mass 338.576 g·mol−1
AppearanceWhite waxy solid
Density 0.860 g/cm3
Melting point 33.8 °C (92.8 °F; 306.9 K)
Boiling point 381.5 °C (718.7 °F; 654.6 K) (decomposes)
Insoluble
Solubility in methanol and ethanol Soluble
Hazards
GHS labelling: [1]
GHS-pictogram-exclam.svg
Warning
H315, H319, H335
P261, P264, P271, P280, P302+P352, P304+P340, P305+P351+P338, P312, P321, P332+P313, P337+P313, P362, P403+P233, P405, P501
Flash point 349.9 °C (661.8 °F; 623.0 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Yes check.svgY  verify  (what is  Yes check.svgYX mark.svgN ?)

Erucic acid is a monounsaturated omega-9 fatty acid, denoted 22:1ω9. It has the chemical formula: CH3(CH2)7CH=CH(CH2)11CO2H. It is prevalent in wallflower seed and other plants in the family Brassicaceae, with a reported content of 20 to 54% in high erucic acid rapeseed oil [2] and 42% in mustard oil. Erucic acid is also known as cis-13-docosenoic acid and the trans isomer is known as brassidic acid.

Uses

Erucic acid is a precursor to brassylic acid, a C13-dicarboxylic acid that is used to make specialty polyamides and polyesters. The conversion entails ozonolysis, which selectively cleaves the C=C bond in erucic acid:

CH3(CH2)7CH=CH(CH2)11CO2H + O3 + 0.5 O2 → CH3(CH2)7CO2H + HO2C(CH2)11CO2H

Amides of erucic acid are used as lubricants and surfactants. [3]

Hydrogenation of erucic acid gives behenyl alcohol, CH3(CH2)21OH, a pour point depressant (enabling liquids to flow at a lower temperature), and silver behenate, for use in photography. [4]

Sources of erucic acid

The seed oil of the rape plant is rich in erucic acid. RanscombeFarmRape9919.JPG
The seed oil of the rape plant is rich in erucic acid.

The name erucic means "of or pertaining to Eruca ", which is a genus of flowering plants in the family Brassicaceae. The genus includes colewort ( E. sativa ), which today is better known as arugula (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 . For industrial purposes and production of erucic acid, rapeseed is used; for food purposes a 'low-erucic acid rapeseed' (LEAR) has been developed (canola), which contains fats derived from oleic acid instead of erucic acid. [3]

Biochemistry

Erucic acid is produced by elongation of oleic acid via oleoyl-coenzyme A and malonyl-CoA. [5] Erucic acid is broken down into shorter-chain fatty acids in the human liver by the long-chain acyl CoA dehydrogenase enzyme.

Health effects

As early as 1977, the use of rapeseed oil was deemed safe as a food additive. [6]

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." [7] "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. 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." [7]

Food-grade rapeseed oil (also known as canola oil, 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 Europe. [6] [8]

Related Research Articles

<span class="mw-page-title-main">Fat</span> Esters of fatty acid or triglycerides

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.

Essential fatty acids, or EFAs, are fatty acids that are required by humans and other animals for normal physiological function that cannot be synthesized in the body.⁠ As they are not synthesized in the body, the essential fatty acids – alpha-linolenic acid (ALA) and linoleic acid – must be obtained from food or from a dietary supplement. Essential fatty acids are needed for various cellular metabolic processes and for the maintenance and function of tissues and organs. These fatty acids also are precursors to vitamins, cofactors, and derivatives, including prostaglandins, leukotrienes, thromboxanes, lipoxins, and others.

<span class="mw-page-title-main">Vegetable oil</span> Oil extracted from seeds or from other parts of plants

Vegetable oils, or vegetable fats, are oils extracted from seeds or from other parts of edible plants. Like animal fats, vegetable fats are mixtures of triglycerides. Soybean oil, grape seed oil, and cocoa butter are examples of seed oils, or fats from seeds. Olive oil, palm oil, and rice bran oil are examples of fats from other parts of plants. In common usage, vegetable oil may refer exclusively to vegetable fats which are liquid at room temperature. Vegetable oils are usually edible.

<span class="mw-page-title-main">Rapeseed</span> Plant species grown for its oil-rich seed

Rapeseed, also known as rape and oilseed rape, is a bright-yellow flowering member of the family Brassicaceae, cultivated mainly for its oil-rich seed, which naturally contains appreciable amounts of erucic acid. The term "canola" denotes a group of rapeseed cultivars that were bred to have very low levels of erucic acid and which are especially prized for use as human and animal food. Rapeseed is the third-largest source of vegetable oil and the second-largest source of protein meal in the world.

<span class="mw-page-title-main">Lorenzo's oil</span> Mixture of modified vegetable oils used in treating adrenoleukodystrophy

Lorenzo's oil is a liquid solution made of 4 parts glycerol trioleate and 1 part glycerol trierucate, which are the triacylglycerol forms of oleic acid and erucic acid. It is prepared from olive oil and rapeseed oil. It is used in the investigational treatment of asymptomatic patients with adrenoleukodystrophy (ALD), a nervous system disorder.

<span class="mw-page-title-main">Oleic acid</span> Monounsaturated omega-9 fatty 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 due to the presence of impurities. In chemical terms, oleic acid is classified as a monounsaturated omega-9 fatty acid, abbreviated with a lipid number of 18:1 cis-9, and a main product of Δ9-desaturase. It has the formula CH3−(CH2)7−CH=CH−(CH2)7−COOH. The name derives from the Latin word oleum, which means oil. It is the most common fatty acid in nature. The salts and esters of oleic acid are called oleates. It is a common component of oils, and thus occurs in many types of food, as well as in soap.

<span class="mw-page-title-main">Mustard oil</span> Oil derived from mustard plants

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 isolating the resulting volatile oil by distillation. It can also be produced by dry distillation of the seed. Pressed mustard oil is used as cooking oil in some cultures, but sale is restricted in some countries due to high levels of erucic acid. Varieties of mustard seed low in erucic acid have been cultivated.

In biochemistry and nutrition, a monounsaturated fat is a fat that contains a monounsaturated fatty acid (MUFA), a subclass of fatty acid characterized by having a double bond in the fatty acid chain with all of the remaining carbon atoms being single-bonded. By contrast, polyunsaturated fatty acids (PUFAs) have more than one double bond.

Richard Keith Downey, is a Canadian agricultural scientist known for plant breeding and, as one of the originators of canola. He conducted his research at Agriculture and Agri-Food Canada (AAFC) and is largely responsible for transforming rapeseed into canola. His pioneering research has made him known as the "Father of Canola".

<i>Brassica rapa</i> Species of flowering plant

Brassica rapa is a plant species growing in various widely cultivated forms including the turnip ; Komatsuna, napa cabbage, bomdong, bok choy, and rapini.

<span class="mw-page-title-main">Sunflower oil</span> Oil pressed from the seed of Helianthus annuus

Sunflower oil is the non-volatile oil pressed from the seeds of the sunflower. Sunflower oil is commonly used in food as a frying oil, and in cosmetic formulations as an emollient.

Omega-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 fatty acid.

<span class="mw-page-title-main">Behenic acid</span> Chemical compound

Behenic acid is a carboxylic acid, the saturated fatty acid with formula C21H43COOH. In appearance, it consists of white solid although impure samples appear yellowish.

Pelargonic acid, also called nonanoic acid, is an organic compound with structural formula CH3(CH2)7CO2H. It is a nine-carbon fatty acid. Nonanoic acid is a colorless oily liquid with an unpleasant, rancid odor. It is nearly insoluble in water, but very soluble in organic solvents. The esters and salts of pelargonic acid are called pelargonates or nonanoates.

Camelina oil or False flax oil is a pressed seed oil, derived from the Camelina sativa or false flax, also called gold of pleasure. False flax has long been grown in Europe, and its oil used as a lamp oil until the 18th century. In recent times, it has been explored for use in cosmetic and skin care products. It has a high content of omega-3 and is used as a food supplement by some cultures. It is registered under the name "Olej rydzowy tradycyjny" as a Traditional Speciality Guaranteed product in the European Union and the United Kingdom.

Decene is an organic compound with the chemical formula C10H20. Decene contains a chain of ten carbon atoms with one double bond, making it an alkene. There are many isomers of decene depending on the position and geometry of the double bond. Dec-1-ene is the only isomer of industrial importance. As an alpha olefin, it is used as a comonomer in copolymers and is an intermediate in the production of epoxides, amines, oxo alcohols, synthetic lubricants, synthetic fatty acids and alkylated aromatics.

<span class="mw-page-title-main">Nervonic acid</span> Chemical compound

Nervonic acid is a fatty acid. It is a monounsaturated analog of lignoceric acid (24:0). It is also known as selacholeic acid and cis-15-tetracosenoic acid. Its name derives from the Latin word nervus, meaning nerve or sinew.

<i>Brassica carinata</i> Species of plant in the family Brassicaceae

Brassica carinata is a species of flowering plant in the Brassicaceae family. It is referred to by the common names Ethiopian rape or Ethiopian mustard. It is believed to be a hybrid between Brassica nigra and Brassica oleracea.

<span class="mw-page-title-main">Cooking oil</span> Oil consumed by humans, of vegetable or animal origin

Cooking oil is a plant or animal liquid fat used in frying, baking, and other types of cooking. Oil allows higher cooking temperatures than water, making cooking faster and more flavorful, while likewise distributing heat, reducing burning and uneven cooking. It sometimes imparts its own flavor. Cooking oil is also used in food preparation and flavoring not involving heat, such as salad dressings and bread dips.

<span class="mw-page-title-main">Rapeseed oil</span> Vegetable oil

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, it was restricted as a food oil due to its content of erucic acid, which in laboratory studies was shown to be damaging to the cardiac muscle of laboratory animals in high quantities and which imparts a bitter taste, and glucosinolates, which made many parts of the plant less nutritious in animal feed. Rapeseed oil from standard cultivars can contain up to 54% erucic acid.

References

  1. "Erucic acid". pubchem.ncbi.nlm.nih.gov. Retrieved 3 January 2022.
  2. Sahasrabudhe, M. R. (1977). "Crismer values and erucic acid contents of rapeseed oils". Journal of the American Oil Chemists' Society. 54 (8): 323–324. doi:10.1007/BF02672436. S2CID   84400266.
  3. 1 2 Anneken, David J.; Both, Sabine; Christoph, Ralf; Fieg, Georg; Steinberner, Udo; Westfechtel, Alfred (2006). "Fatty Acids". Ullmann's Encyclopedia of Industrial Chemistry. doi:10.1002/14356007.a10_245.pub2. ISBN   3527306730.
  4. Economic Research Service, USDA (1996). "Crambe, Industrial Rapeseed, and Tung Provide Valuable Oils" (PDF). Fats and Oils, Industrial Uses: 17–23. Archived (PDF) from the original on 10 October 2006.
  5. Bao Xiaoming; Pollard Mike; Ohlrogge John (1998). "The Biosynthesis of Erucic Acid in Developing Embryos of Brassica rapa". Plant Physiol. 118 (1): 183–190. doi:10.1104/pp.118.1.183. PMC   34854 . PMID   9733537.
  6. 1 2 U.S. Dept. of Health and Human Services, CFR – Code of Federal Regulations Title 21 1 April 2010.
  7. 1 2 Food Standards Australia New Zealand (June 2003) Erucic acid in food: A Toxicological Review and Risk Assessment Archived 23 November 2018 at the Wayback Machine Technical report series No. 21; Page 4 paragraph 1; ISBN   0-642-34526-0, ISSN 1448-3017
  8. "EUR-Lex – 32019R1870R(01) – EN – EUR-Lex".