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Revision as of 12:53, 15 February 2012 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Saving copy of the {{chembox}} taken from revid 472900843 of page Erucic_acid for the Chem/Drugbox validation project (updated: '').  Latest revision as of 01:11, 17 December 2024 edit Arthurfragoso (talk | contribs)Extended confirmed users2,092 edits Fixes image on dark mode 
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{{Use dmy dates|date=March 2024}}
{{ambox | text = This page contains a copy of the infobox ({{tl|chembox}}) taken from revid of page ] with values updated to verified values.}}
{{chembox {{chembox
| Watchedfields = changed | Watchedfields = changed
| verifiedrevid = 443733783 | verifiedrevid = 476997120
|ImageFile=Erucic acid.png | ImageFile =Erucic acid v2.svg
|ImageSize=300px | ImageSize =300px
| ImageClass = skin-invert
|IUPACName=(''Z'')-Docos-13-enoic acid | PIN =(13''Z'')-Docos-13-enoic acid
|OtherNames=
| OtherNames =C22:1 (])
|Section1= {{Chembox Identifiers | Section1={{Chembox Identifiers
⚫ | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
⚫ | CASNo_Ref = {{cascite|correct|CAS}}
⚫ | CASNo =112-86-7
| Beilstein = 1728049
⚫ | ChEBI_Ref = {{ebicite|correct|EBI}}
⚫ | ChEBI = 28792
⚫ | ChEMBL_Ref = {{ebicite|correct|EBI}}
⚫ | ChEMBL = 1173380
⚫ | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 4444561 | ChemSpiderID = 4444561
| EINECS = 204-011-3
| Gmelin = 177365
⚫ | KEGG_Ref = {{keggcite|correct|kegg}}
⚫ | KEGG = C08316
⚫ | PubChem =5281116
| UNII_Ref = {{fdacite|correct|FDA}} | UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 075441GMF2 | UNII = 075441GMF2
⚫ | KEGG_Ref = {{keggcite|correct|kegg}}
⚫ | KEGG = C08316
| 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- | 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-
| InChIKey = DPUOLQHDNGRHBS-KTKRTIGZBD | InChIKey = DPUOLQHDNGRHBS-KTKRTIGZBD
⚫ | ChEMBL_Ref = {{ebicite|correct|EBI}}
⚫ | ChEMBL = 1173380
| StdInChI_Ref = {{stdinchicite|correct|chemspider}} | StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| 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- | 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-
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} | StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = DPUOLQHDNGRHBS-KTKRTIGZSA-N | StdInChIKey = DPUOLQHDNGRHBS-KTKRTIGZSA-N
⚫ | CASNo_Ref = {{cascite|correct|CAS}}
⚫ | CASNo=112-86-7
⚫ | PubChem=5281116
⚫ | ChEBI_Ref = {{ebicite|correct|EBI}}
⚫ | ChEBI = 28792
| SMILES = O=C(O)CCCCCCCCCCC\C=C/CCCCCCCC | SMILES = O=C(O)CCCCCCCCCCC\C=C/CCCCCCCC
}} }}
|Section2= {{Chembox Properties |Section2={{Chembox Properties
| C=22|H=42|O=2 | C=22 | H=42 | O=2
| Appearance=White waxy solid | Appearance =White waxy solid
| Density=0.860 g/cm<sup>3</sup> | Density =0.860 g/cm<sup>3</sup>
| MeltingPtC=33.8 | MeltingPtC =33.8
| BoilingPtC = 381.5
| BoilingPt=381.5 °C (decomposes)
| BoilingPt_notes = (decomposes)
| Solubility=Insoluble
| Solubility =Insoluble
| SolubleOther = Soluble
| Solvent = ] and ] | SolubleOther = Soluble
| Solvent = ] and ]
⚫ }}
⚫ |Section3= {{Chembox Hazards
| MainHazards=
| FlashPt= {{convert|349.9|C|F}}
| Autoignition=
}} }}
⚫ |Section3={{Chembox Hazards
| 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>
| GHSPictograms = {{GHS07}}
| GHSSignalWord = Warning
| HPhrases = {{H-phrases|315|319|335}}
| 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}}
| MainHazards =
| FlashPtC = 349.9
| AutoignitionPtC =
⚫ }}
}} }}

'''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.

== Uses ==
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:

CH<sub>3</sub>(CH2)7CH\dCH(CH2)11CO2H + O3 + 0.5 O2 -> CH3(CH2)7CO2H + HO2C(CH2)11CO2H

]s of erucic acid are used as lubricants and surfactants.<ref name=Ullmann/>

] 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&ndash;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>

== Sources of erucic acid ==
]
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).

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>

== Biochemistry ==
{{further|Lipid metabolism}}
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 ] ].

== Health effects ==

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>

In 2003, Food Standards Australia set a provisional tolerable daily intake (PTDI) for an average adult of about 500&nbsp;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 />

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>

== References ==
{{Reflist}}

==External links==
*

{{Fatty acids}}

{{Authority control}}

{{DEFAULTSORT:Erucic Acid}}
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