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{{Use dmy dates|date=March 2024}} |
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{{chembox |
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{{chembox |
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| Verifiedfields = changed |
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| Watchedfields = changed |
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| verifiedrevid = 407471451 |
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| verifiedrevid = 476997120 |
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|ImageFile=Erucic acid.png |
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| ImageFile =Erucic acid v2.svg |
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|ImageSize=300px |
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| ImageSize =300px |
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| ImageClass = skin-invert |
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|IUPACName=(''Z'')-Docos-13-enoic acid |
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| PIN =(13''Z'')-Docos-13-enoic acid |
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|OtherNames= |
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| OtherNames =C22:1 (]) |
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|Section1= {{Chembox Identifiers |
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| Section1={{Chembox Identifiers |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| CASNo =112-86-7 |
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| Beilstein = 1728049 |
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| ChEBI_Ref = {{ebicite|correct|EBI}} |
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| ChEBI = 28792 |
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| ChEMBL_Ref = {{ebicite|correct|EBI}} |
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| ChEMBL = 1173380 |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID = 4444561 |
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| ChemSpiderID = 4444561 |
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| EINECS = 204-011-3 |
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| Gmelin = 177365 |
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| KEGG_Ref = {{keggcite|correct|kegg}} |
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| KEGG = C08316 |
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| PubChem =5281116 |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| UNII = 075441GMF2 |
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| UNII = 075441GMF2 |
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| KEGG_Ref = {{keggcite|changed|kegg}} |
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| KEGG = C08316 |
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| 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- |
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| 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- |
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| InChIKey = DPUOLQHDNGRHBS-KTKRTIGZBD |
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| InChIKey = DPUOLQHDNGRHBS-KTKRTIGZBD |
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| ChEMBL_Ref = {{ebicite|correct|EBI}} |
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| ChEMBL = 1173380 |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChI = 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- |
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| StdInChI = 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- |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChIKey = DPUOLQHDNGRHBS-KTKRTIGZSA-N |
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| StdInChIKey = DPUOLQHDNGRHBS-KTKRTIGZSA-N |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| CASNo=112-86-7 |
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| PubChem=5281116 |
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| ChEBI = 28792 |
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| SMILES = O=C(O)CCCCCCCCCCC\C=C/CCCCCCCC |
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| SMILES = O=C(O)CCCCCCCCCCC\C=C/CCCCCCCC |
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|Section2= {{Chembox Properties |
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|Section2={{Chembox Properties |
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| C=22 | H=42 | O=2 |
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| Formula=C<sub>22</sub>H<sub>42</sub>O<sub>2</sub> |
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| Appearance =White waxy solid |
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| MolarMass=338.57 g/mol |
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| Density =0.860 g/cm<sup>3</sup> |
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| Appearance=white waxy solid |
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| MeltingPtC =33.8 |
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| Density=0.860 g/cm<sup>3</sup> |
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| BoilingPtC = 381.5 |
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| MeltingPtC=33.8 |
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| BoilingPt=381.5 °C (decomposes) |
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| BoilingPt_notes = (decomposes) |
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| Solubility =Insoluble |
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| Solubility=insoluble in water soluble in methanol and ethanol |
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| SolubleOther = Soluble |
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}} |
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| Solvent = ] and ] |
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|Section3= {{Chembox Hazards |
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| MainHazards= |
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| FlashPt=349.9°C |
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| Autoignition= |
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|Section3={{Chembox Hazards |
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| GHS_ref=<ref>{{cite web |title=Erucic acid |url=https://pubchem.ncbi.nlm.nih.gov/compound/5281116#section=Safety-and-Hazards |website=pubchem.ncbi.nlm.nih.gov |access-date=3 January 2022 |language=en}}</ref> |
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| GHSPictograms = {{GHS07}} |
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| GHSSignalWord = Warning |
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| HPhrases = {{H-phrases|315|319|335}} |
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| PPhrases = {{P-phrases|261|264|271|280|302+352|304+340|305+351+338|312|321|332+313|337+313|362|403+233|405|501}} |
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| MainHazards = |
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| FlashPtC = 349.9 |
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| AutoignitionPtC = |
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'''Erucic acid''' is a ] ] ], denoted 22:1 ω-9. It has the formula CH<sub>3</sub>(CH<sub>2</sub>)<sub>7</sub>CH=CH(CH<sub>2</sub>)<sub>11</sub>COOH. It is prevalent in ], ] seed, and ], making up 40-50% of their oils. Erucic acid is also known as ''cis''-13-docosenoic acid and the ] is known as brassidic acid. |
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'''Erucic acid''' is a ] ], denoted 22:1ω9. It has the chemical formula: {{chem2| CH<sub>3</sub>(CH2)7CH\dCH(CH2)11CO2H}}. It is prevalent in ] seed and other plants in the family ], with a reported content of 20 to 54% in high erucic acid ]<ref>{{cite journal |first=M. R. |last=Sahasrabudhe |title=Crismer values and erucic acid contents of rapeseed oils |journal=Journal of the American Oil Chemists' Society |volume=54 |issue=8 |pages=323–324 |doi=10.1007/BF02672436 |year=1977 |s2cid=84400266 }}</ref> and 42% in ]. Erucic acid is also known as ''cis''-13-docosenoic acid and the ] is known as brassidic acid. |
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== Uses == |
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== Uses == |
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Erucic acid is a precursor to ], a C13-] that is used to make specialty ]s and ]s. The conversion entails ], which selectively cleaves the C=C bond in erucic acid: |
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It has many of the same uses as mineral oils, but with the advantage that it is more readily biodegradable. Its high tolerance to temperature makes it suitable for transmission oil. Its ability to polymerize and dry means it can be - and is - used as a binder for oil ]s. Erucic acid will readily form many ]. Adding this ability to its polymerizing characteristics makes it very suitable for use as ] that need to be polymeric. This makes it especially useful in the manufacture of ] to coat photographic films and papers. A complex cocktail of many different erucic acid compounds is commonly used in color film. It is widely used to produce ]s, especially for skin and healthcare products. Like other ]s, it gets converted into ]s. |
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CH<sub>3</sub>(CH2)7CH\dCH(CH2)11CO2H + O3 + 0.5 O2 -> CH3(CH2)7CO2H + HO2C(CH2)11CO2H |
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Erucic acid is especially valued in ] as a superior lubricant. When used in the manufacture of plastic films in the form of erucamide, it migrates to the surfaces and so resists the sticking of each film to its neighbor. Being a hydrocarbon of high calorific value, with a very low flash point, high ], and good lubrication qualities, erucic acid can be a valuable component of ]. |
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]s of erucic acid are used as lubricants and surfactants.<ref name=Ullmann/> |
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Derivatives of erucic acid have many further uses, such as ] (CH<sub>3</sub>(CH<sub>2</sub>)<sub>21</sub>OH), a ] depressant (enabling liquids to flow at a lower temperature), and ], for use in photography.<ref>{{ cite journal | author = Economic Research Service, USDA | year = 1996 | url = http://www.ers.usda.gov/publications/IUS6/ius6c.pdf | format = pdf | title = Crambe, Industrial Rapeseed, and Tung Provide Valuable Oils | journal = Fats and Oils, Industrial Uses | pages = 18 }}</ref> It is also used as an ingredient in appetite suppressants. |
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] of erucic acid gives ], {{chem2|CH3(CH2)21OH}}, a ] depressant (enabling liquids to flow at a lower temperature), and ], for use in photography.<ref>{{cite journal | author = Economic Research Service, USDA | year = 1996 | url = https://www.ers.usda.gov/webdocs/outlooks/37342/32910_ius6c_002.pdf | title = Crambe, Industrial Rapeseed, and Tung Provide Valuable Oils | journal = Fats and Oils, Industrial Uses | pages = 17–23 | url-status = live | archive-url = https://web.archive.org/web/20061010225533/http://ers.usda.gov/publications/IUS6/ius6c.pdf | archive-date = 10 October 2006 }}</ref> |
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== Sources of erucic acid == |
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] |
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The name ''erucic'' means: of or pertaining to ]; which is a genus of ]s in the family ]. It is also the Latin for coleworth, which today is better known as ]. |
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== Sources of erucic acid == |
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Erucic acid is produced naturally (together with other fatty acids) across a great range of green plants, but especially so in members of the ] family. It is highest in some of the ] varieties of brassicas, kale and mustard being some of the highest, followed by Brussels spouts and broccoli.{{Citation needed|date=November 2010}} For industrial purposes, a ''High-Erucic Acid Rapeseed'' (HEAR) has been developed.{{Citation needed|date=November 2010}} These cultivars can yield 40% to 60% of the total oil recovered as erucic acid.{{Citation needed|date=November 2010}} |
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The name ''erucic'' means "of or pertaining to '']''", which is a genus of ]s in the family ]. The genus includes colewort ('']''), which today is better known as ] (US) or rocket (UK). |
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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 '']''. For industrial purposes and production of erucic acid, ] is used; for food purposes a 'low-erucic acid rapeseed' (LEAR) has been developed (]), which contains fats derived from ] instead of erucic acid.<ref name=Ullmann>{{cite book|doi=10.1002/14356007.a10_245.pub2 |chapter=Fatty Acids |title=Ullmann's Encyclopedia of Industrial Chemistry |year=2006 |last1=Anneken |first1=David J. |last2=Both |first2=Sabine |last3=Christoph |first3=Ralf |last4=Fieg |first4=Georg |last5=Steinberner |first5=Udo |last6=Westfechtel |first6=Alfred |isbn=3527306730 }}</ref> |
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== Biochemical effects == |
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{{further|]}} |
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Erucic acid is broken down into shorter-chain fatty acids in the human liver by the long-chain ] ]. A four-to-one mixture of erucic acid and ] constitutes ]; an experimental treatment for a rare neurobiology disorder ]. ] has been seen in patients treated with Lorenzo's oil, probably related to its erucic acid content.<ref name="pmid7847331">{{cite journal | author = Crowther MA, Barr RD, Kelton J, Whelan D, Greenwald M | title = Profound thrombocytopenia complicating dietary erucic acid therapy for adrenoleukodystrophy | journal = ] | volume = 48 | issue = 2 | pages = 132–3 | year = 1995 | month = February | pmid = 7847331 | doi = | url = | issn = }}</ref> The high percentage of erucic acid in ] has led to the latter being banned for food use in the ] and other countries.{{Citation needed|date=November 2010}} |
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== Health concerns == |
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== Biochemistry == |
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{{further|Lipid metabolism}} |
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Erucic acid is a predominant component of the oil from rape ('']'' and ''B. camestris'') and mustard (''B. hirta'' and ''B. juncea'') seeds.<ref name=Hayes>{{cite book |first=Andrew Wallace |last=Hayes |title=Principles and methods of toxicology |edition=Fifth |publisher=Taylor and Francis |location=Boston, MA |year=2007 |isbn=1560328142 }}</ref> ] oil contains up to 45% erucic acid.<ref>{{cite journal |first=M. R. |last=Sahasrabudhe |title=Crismer values and erucic acid contents of rapeseed oils |journal=Journal of the American Oil Chemists' Society |volume=54 |issue=8 |pages=323–324 |doi=10.1007/BF02672436 |pmid= }}</ref> Food grade rapeseed oil (also known as ] oil, rapeseed 00 oil, low erucic acid rapeseed oil, LEAR oil, and rapeseed canola-equivalent oil) is limited by government regulation to a maximum of 2% erucic acid by weight in the USA<ref name=CFR21>{{cite web |author=U.S. Dept. of Health and Human Services |url=http://www.accessdata.fda.gov/scripts/cdrh/cfdocs/cfcfr/CFRSearch.cfm?fr=184.1555 |title=CFR - Code of Federal Regulations Title 21 |date=April 1, 2010 }}</ref> and 5% in the EU,<ref>{{cite paper |author=The Commission of the European Communities |url=http://eur-lex.europa.eu/LexUriServ/LexUriServ.do?uri=CELEX:31980L0891:EN:HTML |title=Commission Directive 80/891/EEC of 25 July 1980 relating to the Community method of analysis for determining the erucic acid content in oils and fats intended to be used as such for human consumption and foodstuffs containing added oils or fats |journal=EurLex Official Journal |volume=254 |date=1980-09-27 |pages=35–41 }}</ref> with special regulations for infant food. |
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Erucic acid is produced by elongation of oleic acid via oleoyl-] and ].<ref name=Bao>{{cite journal |author1=Bao Xiaoming |author2=Pollard Mike |author3=Ohlrogge John | year = 1998 | title = The Biosynthesis of Erucic Acid in Developing Embryos of Brassica rapa | journal = Plant Physiol | volume = 118 | issue = 1| pages = 183–190 | pmid = 9733537 | pmc=34854 | doi=10.1104/pp.118.1.183}}</ref> Erucic acid is broken down into shorter-chain fatty acids in the human liver by the long-chain ] ]. |
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== Health effects == |
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Before the advent of ], plant breeders were aiming to produce a less-bitter-tasting multi-purpose crop from oil-rapeseed that would appeal to a larger market by making it more palatable and safer for cattle and other livestock. While it was possible to breed out much of the pungent-tasting glucosinolates that was the cause of the problem, the traditional methods of ] resulted in one of the dominant erucic acid genes also getting stripped out of the genome in the process, thus greatly reducing its erucic acid content.{{reference necessary|date=November 2010}} Although this latter effect was an unintended consequence of the breeding program, it was noticed from studies on rats that they show signs of ] when fed high quantities of erucic acid.<ref name=Charlton>{{cite journal |author=Charlton KM, Corner AH, Davey K, Kramer JK, Mahadevan S, Sauer FD |title=Cardiac lesions in rats fed rapeseed oils |journal=Can. J. Comp. Med. |volume=39 |issue=3 |pages=261–9 |year=1975 |month=July |pmid=1170010 |pmc=1277456 |doi= |url=}}</ref> |
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As early as 1977, the use of rapeseed oil was deemed safe as a ] in the United States.<ref name=CFR21>U.S. Dept. of Health and Human Services, 1 April 2010.</ref> |
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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 ] in nursing pigs."<ref name=fsa>Food Standards Australia New Zealand (June 2003) {{Webarchive|url=https://web.archive.org/web/20181123112106/http://www.foodstandards.gov.au/publications/documents/Erucic%20acid%20monograph.pdf |date=23 November 2018 }} Technical report series No. 21; Page 4 paragraph 1; {{ISBN|0-642-34526-0}}, ISSN 1448-3017</ref> "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 ]. 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."<ref name=fsa /> |
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Food-grade rapeseed oil (also known as ], 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.<ref name=CFR21 /><ref>{{Cite web|url=https://eur-lex.europa.eu/eli/reg/2019/1870/corrigendum/2019-11-19/oj|title=EUR-Lex – 32019R1870R(01) – EN – EUR-Lex}}</ref> |
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== References == |
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== References == |
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{{Reflist|2}} |
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{{Reflist}} |
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== See also == |
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==External links== |
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* ] |
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{{Fatty acids}} |
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{{Fatty acids}} |
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{{Use dmy dates|date=October 2010}} |
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{{Authority control}} |
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{{DEFAULTSORT:Erucic Acid}} |
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{{DEFAULTSORT:Erucic Acid}} |
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