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Erucic acid

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Erucic acid
Names
Preferred IUPAC name
(13Z)-Docos-13-enoic acid
Other names
Identifiers
3D model (JSmol)
1728049
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.003.647 Edit this at Wikidata
EC Number
  • 204-011-3
177365
KEGG
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- checkY
    Key: DPUOLQHDNGRHBS-KTKRTIGZSA-N checkY
  • 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
Appearance White 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]
GHS07: Exclamation mark
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).
checkY verify (what is checkY☒N ?)

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

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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

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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

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Further information: Lipid metabolism

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

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

References

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  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. ^ a b 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. ^ a b U.S. Dept. of Health and Human Services, CFR – Code of Federal Regulations Title 21 1 April 2010.
  7. ^ a b 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".
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