Misplaced Pages

Erucic acid: Difference between revisions

Article snapshot taken from Wikipedia with creative commons attribution-sharealike license. Give it a read and then ask your questions in the chat. We can research this topic together.
Browse history interactively← Previous editContent deleted Content addedVisualWikitext
Revision as of 01:10, 24 January 2012 edit166.147.96.162 (talk) →Health concernsTag: section blanking← Previous edit Latest revision as of 01:11, 17 December 2024 edit undoArthurfragoso (talk | contribs)Extended confirmed users2,184 edits Fixes image on dark mode 
(144 intermediate revisions by 93 users not shown)
Line 1: Line 1:
{{Use dmy dates|date=March 2024}}
{{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 22:1 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 4.1% of their oils.<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= |year=1977 }}</ref> Erucic acid is also known as ''cis''-13-docosenoic acid and the ] is known as brassidic acid. '''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 == == 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:
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 ] for use in oil ]s. Like other ]s, it can be converted into ]s, lubricant and is a precursor to ].


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


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


] 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>
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.<ref name=Bao/> For industrial purposes, a ''Low-Erucic Acid Rapeseed'' (LEAR) has been developed, which contains fats derived from oleic acid instead of erucic acid.<ref name=Ullmann>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. {{DOI|10.1002/14356007.a10_245.pub2}}</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 == == Biochemistry ==
{{further|]}} {{further|Lipid metabolism}}
Erucic acid is produced by elongation of oleic acid via oleoyl-] and ].<ref name=Bao>Xiaoming Bao, Mike Pollard, and John Ohlrogge"The Biosynthesis of Erucic Acid in Developing Embryos of Brassica rapa" Plant Physiol. 1998, vol 118, pp.183–190. 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 ] ].
PMID 9733537</ref> Erucic acid is broken down into shorter-chain fatty acids in the human liver by the long-chain ] ].


== Health effects == == Health effects ==
Epidemiological studies suggest that, in regions where mustard oil is still used in a traditional manner, mustard oil may afford some protection against cardiovascular diseases. In this sense 'traditional' means that (a) the oil is used fresh and (b) vegetable fats count only as a small percentage of the total caloric intake. Whether this effect is due to the nature of erucic acid ''per se'' to make the blood platelets less sticky, or to the presence of a reasonably high percentage of α-linolenic acid, or to a combination of properties of fresh unrefined oil, is as yet uncertain. Care needs to be taken with such epidemiological studies to exclude the possibility of early deaths from other causes skewing the results. The fact that early asymptomatic coronary disease is readily detectable post mortem and is absent in the mustard oil cohorts tends to add weight to the hypothesis that mustard oil is protective.<ref>{{cite journal |author=Rastogi T, Reddy KS, Vaz M, ''et al.'' |title=Diet and risk of ischemic heart disease in India |journal=Am. J. Clin. Nutr. |volume=79 |issue=4 |pages=582–92 |year=2004 |month=April |pmid=15051601 |doi= |url=http://www.ajcn.org/cgi/content/full/79/4/582 }}</ref>


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>
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>
For the reasons given above, it is not advisable for nursing mothers or babies to eat food containing erucic acid.<ref name=fsa>Food Standards Australia New Zealand (June 2003) : ''A Toxicological Review and Risk Assessment .'' Technical report series No. 21; Page 4 paragraph 1; ISBN 0 642 34526 0, ISSN 1448-3017</ref>
<ref>{{cite web
|url=http://www.food.gov.uk/news/newsarchive/2004/sep/erucic
|title=Food Standards Agency - Agency issues warning on erucic acid
|accessdate=2007-11-02
|format=
|work=
|date=2 September 2004
}}</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 />
The high percentage of erucic acid in ] has led to the latter being banned for food use in the ] and other countries.


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>
== Health concerns ==
Before ], plant breeders were aiming to produce a less-bitter-tasting multi-purpose oil from rapeseed that would appeal to a larger market by making it more palatable for cattle and other livestock. While it was possible to breed out much of the pungent-tasting glucosinolates, one of the dominant erucic acid genes would get stripped out of the genome as well, greatly reducing its valuable erucic acid content.{{Reference necessary|date=January 2012}} Studies on rats show lipodosis problems when fed high quantities of erucic acid, however, so this did not hinder saleability.<ref name=Charlton/> Later trials showed that rats had the same problems with other vegetable fatty acids,<ref>{{cite journal |author=Neat CE, Thomassen MS, Osmundsen H |title=Effects of high-fat diets on hepatic fatty acid oxidation in the rat. Isolation of rat liver peroxisomes by vertical-rotor centrifugation by using a self-generated, iso-osmotic, Percoll gradient |journal=Biochem. J. |volume=196 |issue=1 |pages=149–59 |year=1981 |month=April |pmid=6272750 |pmc=1162977 |doi= |url=}}</ref> because rats are poor at metabolising some fats.<ref name=Kramer>{{cite journal |author=Kramer JK, Hulan HW, Trenholm HL, Corner AH |title=Growth, lipid metabolism and pathology of two strains of rats fed high fat diets |journal=J. Nutr. |volume=109 |issue=2 |pages=202–13 |year=1979 |month=February |pmid=430222 |doi= |url=http://jn.nutrition.org/cgi/pmidlookup?view=long&pmid=430222}}</ref> The plant breeding industry later changed "low erucic acid" to be its ] over that of its competitors.{{citation needed|date=October 2010}}


== References ==
There are not many studies done on humans with erucic acid; the majority are carried out by the food science industry on animals. Animal studies failed to show negative events occurring from feeding of erucic acid, and the studies were repeated under increasingly unnatural scenarios. In one case, neonate piglets that have a limited ability to absorb these fats had their normal sow's milk replaced solely with rapeseed oil for one hundred percent of their calorific needs.<ref name=Kramer/> The studies showed that lipidoses suffered by the piglets proved to be only a transient effect; the liver automatically responded by increasing enzyme levels to cope with the unusual diet, and the lipidoses subsided.
{{Reflist}}


==External links==
A recent study recorded the higher rates of lung cancer in countries with populations that cook over solid fuel ] and ] fires and stoves. The possibility of production of smoke from heated oil was also considered, and it was established that rapeseed oil, which contains erucic acid, can cause increased ]s through emissions under high heat. However, the report also showed a variety of cooking oils also did this at similar heats.<ref>S Kurt, Baan R, Grosse Y, Secretan B, (2006) . WHO International Agency for Research on Cancer Monograph Working Group. PDF 52kb. Retrieved 2007-01-29</ref>
*


{{Fatty acids}}
=== Cardiac concerns ===
The levels of erucic acid in human foods are restricted, in part, over concerns that it may adversely affect heart tissue.<ref name=fsa /> However, these concerns seem to have been premature:
an early study had shown rapeseed oil, which contains erucic acid, promoted myocardial lesions in male adult rat animal models; but later studies revealed similar effects from other oils, containing no erucic acid ; also, the same effects were not observed in female adult rats.<ref name="Kramer">{{cite journal
|url=http://jn.nutrition.org/cgi/content/abstract/103/12/1696
|title=Growth Rate, Lipid Composition, Metabolism and Myocardial Lesions of Rats Fed Rapeseed Oils
|author=Kramer et al.|volume= 103 |issue=12|pages=1696 |journal= Journal of Nutrition
|accessdate=2007-12-10 |format=pdf |work=
|pmid=4752972
|year=1973
|month=Dec
|day=01
|last2=Mahadevan
|first2=S
|last3=Hunt
|first3=JR
|last4=Sauer
|first4=FD
|last5=Corner
|first5=AH
|last6=Charlton
|first6=KM}}</ref>
<ref name="Clandinin">{{cite journal
|author=Clandinin MT, Yamashiro S
|title=Dietary factors affecting the incidence of dietary fat-induced myocardial lesions
|journal=J. Nutr. |volume=112 |issue=4 |pages=825–8 |year=1982 |pmid=7200131
|doi= |accessdate=2007-12-10}}</ref>
] and ] offered some protection against this damage,<ref name="Clandinin" /> while ] may have aggravated it.<ref name="McCutcheon">{{cite journal
|author=McCutcheon JS, Umermura T, Bhatnager MK, Walker BL
|title=Cardiopathogenicity of rapeseed oils and oil blends differing in erucic, linoleic, and linolenic acid content
|journal=Lipids |volume=11 |issue=7 |pages=545–52 |year=1976
|pmid=948250
|doi=10.1007/BF02532900|accessdate=2007-12-10
}}</ref>
Erucic acid is preferentially absorbed in myocardium tissue<ref name=becker>{{cite journal |author=Becker W, Bruce A |title=Autoradiographic studies with fatty acids and some other lipids: a review |journal=Prog. Lipid Res. |volume=24 |issue=4 |pages=325–46 |year=1985 |pmid=3916594 |doi= 10.1016/0163-7827(85)90010-4|accessdate=2007-11-03}}</ref>
but is not metabolized there.<ref name=Kramer />


{{Authority control}}
As the above, these studies demonstrate, rats present a poor animal model to study the effects of erucic acid on human heart tissue due to their own poor ability to metabolize this fat.

==Low erucic acid rapeseed==
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 were 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>

Food grade rapeseed oil (also known as ] 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 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.

== References ==
{{Reflist|2}}

{{Fatty acids}}
{{Use dmy dates|date=October 2010}}


{{DEFAULTSORT:Erucic Acid}} {{DEFAULTSORT:Erucic Acid}}
] ]
]

]
]
]
]
]
]
]
]
]
]
]
]

Latest revision as of 01:11, 17 December 2024

Erucic acid
Names
Preferred IUPAC name (13Z)-Docos-13-enoic acid
Other names C22:1 (Lipid numbers)
Identifiers
CAS Number
3D model (JSmol)
Beilstein Reference 1728049
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.003.647 Edit this at Wikidata
EC Number
  • 204-011-3
Gmelin Reference 177365
KEGG
PubChem CID
UNII
CompTox Dashboard (EPA)
InChI
  • 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-Key: DPUOLQHDNGRHBS-KTKRTIGZSA-N
  • 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
SMILES
  • O=C(O)CCCCCCCCCCC\C=C/CCCCCCCC
Properties
Chemical formula C22H42O2
Molar mass 338.576 g·mol
Appearance White waxy solid
Density 0.860 g/cm
Melting point 33.8 °C (92.8 °F; 306.9 K)
Boiling point 381.5 °C (718.7 °F; 654.6 K) (decomposes)
Solubility in water Insoluble
Solubility in methanol and ethanol Soluble
Hazards
GHS labelling:
Pictograms GHS07: Exclamation mark
Signal word Warning
Hazard statements H315, H319, H335
Precautionary statements 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 , 100 kPa). checkY verify (what is  ?) Infobox references
Chemical compound

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 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\dCH(CH2)11CO2H + O3 + 0.5 O2 -> CH3(CH2)7CO2H + HO2C(CH2)11CO2H

Amides of erucic acid are used as lubricants and surfactants.

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.

Sources of erucic acid

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.

Biochemistry

Further information: Lipid metabolism

Erucic acid is produced by elongation of oleic acid via oleoyl-coenzyme A and malonyl-CoA. 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 in the United States.

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. 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, 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.

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

External links

Lipids: fatty acids
Saturated
ω−3 Unsaturated
ω−5 Unsaturated
ω−6 Unsaturated
ω−7 Unsaturated
ω−9 Unsaturated
ω−10 Unsaturated
ω−11 Unsaturated
ω−12 Unsaturated
Categories: