Erucic acid seed oils

The above list does not include cocoa butter nor minor oils such as rice bran oil or safflower oil. Nor does it distinguish between oils from a common botanical source with a modified fatty acid composition, such as canola oil and high-erucic rape seed oil, linseed oil and linola, or the various types of sunflower oil. 

In the Orient, both rapeseed and mustard oils are used extensively for food and large quantities of mustard are produced for oil in India, Pakistan and Bangladesh. In Canada and Europe there is no production of mustard oil for edible oil purposes. All edible Canadian rapeseed oil is now from canola varieties, i.e., derived from seed low in erucic acid and low in glucosino-lates. High erucic acid rapeseed oil is used exclusively for industrial purposes, such as lubricants, slip agents for molds, and polymers. In Canada these high erucic acid oils are produced and marketed separately from canola oil. Rapeseed oils in the Western World are either very low in erucic acid for edible use or very high (over 40%) in erucic acid for industrial use. 

From 1965-1969 the Saskatchewan Wheat Pool contracted production of low erucic acid seed obtained from Agriculture Canada, Saskatoon, and crushed commercial quantities for evaluation of the oil by Canada Packers and other edible oil processors. Higher costs were involved in handling the low erucic seed and processors were unwilling to pay a premium therefore, production remained at a low level. With an abundance of European sunflower oil available for salad oil production, interest in low erucic and stabilized salad oil was also dampened. 

If rapeseed (oil) did not exist, it would have to be invented. This paraphrase of a statement originally applied to rubber has literally become true for the oil currently produced in Canada and elsewhere which is widely known as LEAR (low erucic acid rapeseed) oil. If produced from seed of Brassica napus or Brassica campestris low in both erucic acid (<5% of total fatty acids) and glucosinolates (<3 mg/g glucosinolates measured as 3-bute-nyl isothiocyanate) the oil can be called canola oil, since "canola" is a... 

DESCRIPTION Low erucic acid rapeseed oil (synonyms low erucic acid turnip rape oil low erucic acid colza oil) is produced from the low erucic acid oil-bearing seeds of varieties derived from the Brassica napus L., Brassica campestris L. species. 

Until recently the fatty acid composition of rapeseed oil was quite different from that of other edible vegetable oils from 40 to 60% of the fatty acid components of rapeseed oil consisted of the long chain fatty acids, erucic and eicosenoic. This unusual fatty acid composition has been the subject of numerous nutritional studies. Detrimental effects attributed to the long chain fatty acid components of rapeseed oil stimulated plant breeders to search for genetically controlled variation in these components. Rape plants which produce seed oil essentially without erucic acid were isolated (Ste-fansson et al., 1961) and this characteristic was incorporated into cultivars suitable for commercial production. The new "low erucic acid" rapeseed oils contain only the fatty acid components found in other edible vegetable oils traditionally used as food in the Western World. 

The magnitude of the variation in the composition of rapeseed oil and meal now commercially available has created a need for new terms to describe the products derived from rapeseed. The fatty acid composition of most edible vegetable oils such as soybean, sunflower, or cottonseed oils, varies within narrow limits. Thus, the species or commodity name (e.g., soybean oil) provides a reasonable description of the fatty add composition of soybean oil. In contrast, the erucic acid content of commercially available rapeseed oil may vary from near zero to 55%, and the oleic acid from 10 to more than 60%. A number of terms have been proposed or utilized to describe the new rapeseed oil whose fatty acid composition has been altered by the elimination of erucic acid these include low erucic acid rape-seed oil (LEAR), canbra, and canola. Similar terms such as high erucic acid rapeseed oil (HEAR) and common or traditional rapeseed oil have been used to describe rapeseed oil whose fatty acid composition includes substantial amounts of erucic acid. 

The production of HEAR has been controlled by the Canadian Crushing Industry through contracts to meet expected demands for oil. Up to the present time only one company has been involved in this market and there has been no evidence of high erucic acid seed appearing in the edible oil export market. The Canadian Crushing Industry will continue to control this market as it is in their own best interests for the erucic acid content of Canadian rapeseed to remain low. 

Fig. 2. Gross and histological appearance (oil red O staining) of hearts from rats fed diets containing 20% by weight of the following oils 1. soybean oil, 2. low erucic acid rapeseed oil (0.5% 22 1), 3. high erucic acid rapeseed oil (28.8%, 22 1), and 4. mustard seed oil (54.1%, 22 1).

Distillation of fatty acids is important in industry where it is used primarily to separate saturated acids such as (i) 16 0 and 18 0 from hydrogenated tallow and seed oils, (ii) 18 0, 20 0, 22 0 and 24 0 from hydrogenated fish oils and high-erucic acid rapeseed oil and (hi) 8 0, 10 0, 12 0 and 14 0 from hydrogenated lauric oils (coconut, palmkernel, babassu). The temperatures range from 160 to 230 C at pressures below 20 mm in specially constructed stills (up to 7 ft in diameter) which run continuously. It has been claimed that it should be possible to separate stearic and oleic acid by distillation (Stage, 1984). 

Saturated acids with an even number of carbon atoms per molecule are usually isolated by distillation of esters from an appropriate source. These include esters from lauric-rich oils (Cio, C12, C14), palm oil and cottonseed oil (C16), hydrogenated animal fats and seed oils (Cig) and hydrogenated high-erucic acid rape oil (C22). These acids are commercially available in high purity at a reasonable cost. 

Canadian mnstard seed prodnction has been ranging from 105,0001 in 2001-2002 to 306,0001 in 2004-2005. In 2006, the total world mustard exports were 315,0001, 55% of which were Canadian mustard. In 2006-2007, Saskatchewan dominated Canadian mustard seed production, with 78% of total production. The area seeded for mustard in 2006 in Saskatchewan was 280,000 acres, which yielded 776 pounds per acre (Agriculture and Agri-Food Canada, 2007). These data show that mustard seeds are available in large quantity in Canada. Because it contains a high level of erucic acid, mustard oil does not meet Canadian spedlications for edible purpose, but it could be utilized for other purposes such as feedstock for biodiesel production. 

A more successful approach was described by Zou et al. (1997), with yeast mutant SLCl-1 gene encoding enzyme capable of utilizing a broad range of substrates. In contrast to Limnanthes LPAATs, expression of yeast SLCl-1 affected not only the stereochemical composition of seed oil, but also total erucic acid and oil content. The total content of erucic acid increased to as much as 56% compared with 45% in the control. Studies carried out with LPAAT genes showed that additional genes have to be introduced to optimize... 

By way of a specific example let us consider erucic acid. The main commercial source of erucic acid is a specially bred form of rape seed (HEAR) as pointed out above. With European consumption being around 60 000 tpa almost 40 000 ha of land are used to grow rapeseed for erucic acid production in Europe. The high level of erucic found in this type of rape seed oil make it unsuitable for human consumption, owing to the indigestibility of such large amounts of this acid. Erucic acid is also the major fatty acid to be found in nasturtium and crambe seeds (up to 75% and 56% respectively), and it is also found in the salad herb, rocket. 

Z 11 eicosenoic (gondoic) acid, Z 13 docosenoic (erucic) acid, 11,12 dihydroxyeicosanoic acid, 13,14 dihydroxydocosanoic acid Oils from Brassicaeae seeds [12,44,45]... 

Brassica alba (L.) Rabenh. B. juncea (L.) Czem. et Coss. Bai Jie Zi (Indian mustard) (seed, young shoot) Sinigrin, myrocin, sinapic acid, sinapine, potassium myronate, mustard oil, allyl isothiocyanate, behenic acid, erucic acid, benzyl isothiocyanate, eicosenic acid.48-50 Relieve bladder inflammation, hemorrhage, abscesses, lumbago, rheumatism, stomach disorders. 

Erucic acid is a constituent of various natural oils but is most conveniently obtained from rape seed oil. The process described above is essentially that of Reimer and Will.1 Methods have been developed for obtaining pure erucic acid free from saturated acids,2 but these involve time-consuming procedures of fractional precipitation and crystallization, and necessarily give poor yields. The product obtained above is satisfactory for most purposes. 

Table 4.1.4A. Canola seed cooked (IFN 5-04-597). The entire seed of the species Brassica napus or B. campestris, the oil component of which contains less than 2% erucic acid and the solid component of which contains less than 30pmol of any one or any mixture of 3-butenyl glucosinolate, 4-pentenyl glucosinolate, 2-hydroxy-3-butenyl glucosinolate and 2-hydroxy-4-pentenyl glucosinolate per g of air-dry, oil-free solid (GLC method of the Canadian Grain Commission). (From CFIA, 2007.)...

Canola Oil occurs as a light yellow oil. It is typically obtained by a combination of mechanical expression followed by n-hexane extraction, from the seed of the plant Brassica juncea, Brassica napus, or Brassica rapa (Fam. Cruciferae). The plant varieties are those producing oil-bearing seeds with a low erucic acid (C22 i) content. It is a mixture of triglycerides composed of both saturated and unsaturated fatty acids. It is refined, bleached, and deodorized to substantially remove free fatty acids phospholipids color odor and flavor components and miscellaneous, other non-oil materials. It can be hydrogenated to reduce the level of unsaturated fatty acids for functional purposes in foods. It is a liquid at 0° and above. 

Seedfats are characterized by low contents of saturated fatty acids. They contain palmitic, oleic, linoleic, and linolenic acids. Sometimes unusual fatty acids may be present, such as erucic acid in rapeseed oil. Recent developments in plant breeding have made it possible to change the fatty acid composition of seed oils dramatically. Rapeseed oil in which the erucic acid has been replaced by oleic acid is known as canola oil. Low linolenic acid soybean oil can be obtained, as... 

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