Erucic acid

Chembox new
ImageFile=Erucic acid.pngImageSize=300px
IUPACName=("Z")-Docos-13-enoic acid
OtherNames=
Section1= Chembox Identifiers
CASNo=112-86-7
PubChem=5281116
SMILES=CCCCCCCCC=CCCCCCCCCCCCC(=O)O
Section2= Chembox Properties
Formula=C₂₂H₄₂O₂
MolarMass=338.57 g/mol
Appearance=
Density=0.860 g/cm³
MeltingPtC=33.8
BoilingPt=381.5 °C (decomposes)
Solubility=
Section3= Chembox Hazards
MainHazards=
FlashPt=
Autoignition=

Erucic acid is a monounsaturated omega-9 fatty acid, denoted 22:1 ω-9. It is prevalent in rapeseed, wallflower seed, and mustard seed, making up 40-50% of their oils. Erucic acid is also known as "cis"-13-docosenoic acid and the trans isomer is known as brassidic acid.

Uses

It has many of the same uses as mineral oils but with the advantage that it is more readily bio-degradable. 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 paints. Erucic acid will readily form many organic compounds. Adding this ability to its polymerizing characteristics makes it very suitable for use as organic matrices that need to be polymeric. This makes it especially useful in the manufacture of emulsions to coat photographic films and papers. A complex cocktail of many different erucic acid compounds is commonly used in just one roll of color film. It is widely used to produce emollients, especially for skin and healthcare products. Like other fatty acids, it gets converted into surfactants.Erucic acid is especially valued in tribology 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 cetane rating, and good lubrication qualities, erucic acid can be a valuable component of bio-diesel.When converted into behenyl alcohol (CH₃(CH₂)₂₁OH), erucic acid has many further uses such as a pour point depressant, enabling liquids to flow at a lower temperature and silver behenate for use in photography. [Economic Research Service, USDA (September 1996) [http://www.ers.usda.gov/publications/IUS6/ius6c.pdf Crambe, Industrial Rapeseed, and Tung Provide Valuable Oils] . "Fats and Oils", Industrial Uses; Page 18. Retrieved 2007-01-29 ]

Sources of erucic acid

The name "erucic" means: of or pertaining to eruca; which is a genus of flowering plants in the family Brassicaceae. It is also the Latin for coleworth; which today, is better known as kale.Erucic acid is produced naturally (together with other fatty acids) across a great range of green plants, but especially so in members of the brassica family. It is highest in some of the rapeseed varieties of brassicas, kale and mustard being some of the highest, followed by Brussels spouts and broccoli. For industrial purposes, a "High-Erucic Acid Rapeseed" (HEAR) has been developed. These cultivars can yield 40% to 60% of the total oil recovered as erucic acid.

Metabolism of erucic acid

Erucic acid is broken down in the human body by enzymes (long-chain acyl-coenzyme A (CoA) dehydrogenase) produced in the liver, which chop it into shorter-chain fatty acids, which are, in turn, broken down. For more information on this see: Lipid metabolism. Based on animal studies in adult pigs and piglets, it can be reasonably presumed that, in human infants that have not yet been weaned, these particular enzymes are in short supply (as the mother's milk is the normal food source during this period), although not totally absent. [cite journal
author=Kramer JK, Farnworth ER, Johnston KM, Wolynetz MS, Modler HW, Sauer FD |title=Myocardial changes in newborn piglets fed sow milk or milk replacer diets containing different levels of erucic acid |journal=Lipids |volume=25 |issue=11 |pages=729–37 |year=1990 |month=Nov |pmid=2280677 |doi= |url=] [cite journal
author=Farnworth ER, Wolynetz MS, Modler HW, Kramer JK, Sauer FD, Johnston KM |title=Backfat and carcass composition of piglets fed milk replacers containing vegetable oil compared with sow-reared piglets |journal=Reprod. Nutr. Dev. |volume=34 |issue=1 |pages=25–35 |year=1994 |pmid=8129839 |doi= |url=] Because of this, babies should not be given foods high in erucic acid. Before low-erucic acid oil rapeseed (LEAR & Canola) cultivars were developed, this situation was unlikely to present a realistic danger since erucic acid occurs in nature only along with bitter-tasting compounds that infants instinctively reject. In these new varieties, the bitterness or pungency has been considerably reduced to make it more palatable to humans and cattle; however erucic acid content is also greatly reduced well below the 2% limit on erucic acid content set by the FDA.Studies on rats have shown that they are less able to digest vegetable fats (whether or not they contain erucic acid) than humans and pigs. [cite journal |author=Hulan HW, Kramer JK, Mahadevan S, Sauer FD |title=Relationship between erucic acid and myocardial changes in male rats |journal=Lipids |volume=11 |issue=1 |pages=9–15 |year=1976 |month=Jan |pmid=1250074 |doi= |url=] [cite journal |author=Kramer JK, Farnworth ER, Thompson BK, Corner AH, Trenholm HL |title=Reduction of myocardial necrosis in male albino rats by manipulation of dietary fatty acid levels |journal=Lipids |volume=17 |issue=5 |pages=372–82 |year=1982 |month=May |pmid=7098776 |doi= |url=] [cite journal |author=de Wildt DJ, Speijers GJ |title=Influence of dietary rapeseed oil and erucic acid upon myocardial performance and hemodynamics in rats |journal=Toxicol. Appl. Pharmacol. |volume=74 |issue=1 |pages=99–108 |year=1984 |month=Jun |pmid=6729825 |doi= |url=http://linkinghub.elsevier.com/retrieve/pii/0041-008X(84)90275-8] Chariton et al. suggests that in rats: “Inefficient activation of erucic acidto erucyl-CoA and a low level of activity of triglyceride lipase and enzymes of betaoxidation for erucic acid probably contributeto the accumulation and retention of cardiac lipid.”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=Jul |pmid=1170010 |pmc=1277456 |doi= |url=] Before this process was fully understood, however, there developed a misunderstanding, which continues to be repeated until this day. See below.

Health effects

No negative health effects have ever been documented in humans, although it is advisable not to give un-weaned babies foods containing erucic acid for the reasons given above.Food Standards Australia New Zealand (June 2003) [http://www.foodstandards.gov.au/_srcfiles/Erucic%20acid%20monograph.pdf Erucic acid in food] : "A Toxicological Review and Risk Assessment ." Technical report series No. 21; Page 4 paragraph 1; ISBN 0 642 34526 0, ISSN 1448-3017] [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]

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 the (a) 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 in order 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. [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=Apr |pmid=15051601 |doi= |url=http://www.ajcn.org/cgi/content/full/79/4/582 ]

A four-to-one mixture of erucic acid and oleic acid constitutes Lorenzo's oil; an experimental treatment for a rare neurobiology disorder adrenoleukodystrophy.

The high percentage of erucic acid in mustard oil has led to its being banned for food use in the European Union and other countries.

Health concerns

Before genetic engineering, 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. Studies on rats show lipodosis problems when fed high quantities of erucic acid, however, so this did not hinder saleability. Later trials showed that rats had the same problems with other vegetable fatty acids, [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=Apr |pmid=6272750 |pmc=1162977 |doi= |url=] because rats are poor at metabolising some fats.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=Feb |pmid=430222 |doi= |url=http://jn.nutrition.org/cgi/pmidlookup?view=long&pmid=430222] The plant breeding industry later changed "low erucic acid" to be its unique selling proposition over that of its competitors.

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. 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.

A recent study recorded the higher rates of lung cancer in countries with populations that cook over solid fuel wood and biomass 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 lung carcinomas through emissions under high heat. However, the report also showed a variety of cooking oils also did this at similar heats. [S Kurt, Baan R, Grosse Y, Secretan B, (2006) [http://ehs.sph.berkeley.edu/krsmith/publications/2006%20pubs/Lancet-Oncology3.pdf Carcinogenicity of household solid fuel combustion and of high-temperature frying] . WHO International Agency for Research on Cancer Monograph Working Group. PDF 52kb. Retrieved 2007-01-29]

Cardiac concerns

The levels of erucic acid in human foods are restricted, in part, over concerns that it may adversely affect heart tissue.It promotes myocardial lesions in male adult rat animal models, however the same effects were not observed in female adult rats.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] 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]
Choline and inositol offered some protection against this damage, while alpha-linolenic acid may have aggravated it.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] Erucic acid is preferentially absorbed in myocardium tissuecite 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= |accessdate=2007-11-03] but is not metabolized there.

However, rats may present a poor animal model to study the effects of erucic acid on heart tissue due to poor ability to metabolize the substance.

References

See also

* Lorenzo's oil