Emcic acid

Soybean meal is the most frequently used source of supplemental protein in the United States (5). Cottonseed meal is another important protein supplement. Both meals are by-products from oil extraction of the seeds. Canola meal is derived from rapeseed low in emcic acid [112-86-7] and glucosinolates. Linseed (derived from flax seed), peanut, sunflower, safflower, sesame, coconut, and palm kernel meals are other sources of supplemental protein that are by-products of oil extraction (4). 

Nylon-13,13 and Nylon-13. The ingredients for nylon-13,13 [26796-68-9] [26796-70-3] and nylon-13 [14465-66-8], [26916-48-3] and their copolymers have become available in developmental quantities from a natural source, crambe and rapeseed oil (176). Emcic acid [112-86-7] is obtained in high yield approaching 50 wt % from the oil and oxidatively cleaved to produce the dicarboxyhc acid, brassyUc acid [505-55-2] and pelargonic acid ... 

Brackets signify a trivial name no longer ia use. At 101.3 kPa = 1 atm unless otherwise noted ia kPa as a subscript. At 20°C unless otherwise noted by a superscript number (°C). At 20°C unless otherwise noted. To convert to cal, divide by 4.184. 70°C. Heat of combustion (Uquid). At50°C. To convert kPa to mm Hg, multiply by 7.5. In the alkenoic series of molecular formula 2 2 metbacrylic, undecjlenic, oleic, and emcic acids have important appHcations (Table 2). Acryhc and metbacrylic acids have a petrochemical origin, and undecylenic, oleic, and emcic acids have natural origins (see Acrylic ACID AND DERIVATIVES Methacrylic acid and derivatives). Table 2. Physical Properties of the Straight-Chain Alkenoic Acids, (2n-2) 2 ... 

Crambe was introduced to the United States in the 1970s. It is an oilseed, the oil of which is very high in emcic acid [112-86-7] (13-docosanoic acid), C22H42O2. This oil can be used to provide industrial lubricants, especially those needed for the basic oxygen furnace process for making steel (qv). Crambe is grown in relatively small volume in the midwestem United States. 

Brassylic Acid. This acid is commercially available from Nippon Mining Company (Tokyo, Japan). It is made by a fermentation process (76). Several years ago, Emery Group, Henkel Corp. (Cincinnati, Ohio) produced brassyUc acid via ozonization of emcic acid primarily for captive use in making dimethyl brassylate and ethylene brassylate. A pilot-scale preparation based on ozonization of emcic acid has been described in which brassyUc acid yields of 72—82% were obtained in purities of 92—95%. Recrystallization from toluene gave purities of 99% (77). 

Most of the products Hsted in Tables 1—3 are based on manufacture from tall oil fatty acids. Dimer acids based on other feedstocks (eg, oleic acid) may have different properties. A European manufacturer recently announced availabiUty of a 44-carbon dimer acid, presumably made from an emcic acid feedstock (7). 

Palmitic acid 5-9% Stearic acid 2%+ Bchcnic acid 2.5% Stearic acid 2.5-5.5% have a lower emcic acid... 

Elongation by two carbon atoms occurs commonly in fatty acid biosynthesis. It is a variant of de novo chain-lengthening and occurs with acetyl or malonyl CoA or ACP derivatives. The substrate is any preformed saturated or unsaturated acid. For example, erucic (22 1) in high-emcic acid rapeseed oil and nervonic acid (24 1) in seed oil are formed from oleic acid by two and three elongations, respectively ... 

Mustard Brassica alba, B. hirta, B. nigra, B. juncea, B. carinata). The seeds contain 24 0% of oil characterized by the presence of erucic acid. Typical values are oleic 23%, linoleic 9%, linolenic 10%, eicosenoic 8%, and emcic acid 43% (141, 142). The plant is grown extensively in India (59, 79). 

The name canola was registered by the Western Canadian Oilseed Cmshers in 1978 and subsequently transferred to the Canola Council of Canada in 1980. It included those cultivars containing less than 5% emcic acid in the oil and 3 mg/g aliphatic glucosinolates in the meal. In 1986, the definition of canola was amended to B. napus and B. rapa lines with less than 2% emcic acid in the oil and less than 30 pmol/g glucosinolates in the air-dried, oil-free meal. The oil was added to the Generally Recognized as Safe (GRAS) list of food products in the United States. 

The stigma of the emcic acid (C22 ln - 9) in rapeseed oil has lingered despite firm evidence that this fatty acid was more of a threat to rats than to humans. It is sufficient to say that the discovery of chain shortening of emcic acid to oleic acid by peroxisomes was one of the most fundamental breakthroughs in understanding fatty acid metabolism in the last few decades. Once in the oleic acid form, the emcic acid residue is as readily catabolized by mitochondria, as are palmitic and other fatty acids (4). The reduction of emcic acid in rapeseed oil resulted in a marked increase in octadecanoic acids, and their contribution in canola oil is around 95% of all fatty acids present (Table 2). 

The proposed Codex standard for edible low emcic acid rapeseed gives the maximum levels permitted for iron, copper, lead, and arsenic. Although these metals are found in other edible oils and are present naturally in the seed, nevertheless, they can also be introduced during handling and processing. Diosady et al. (48) and Elson et al. (49) examined the effect of processing on trace elements in canola... 

Rapeseed has long been a source of cooking oil and has important industrial uses such as lubricants for high-temperature applications, especially those leading to environmental release of the lubricant antislip agents in plastics manufacturing fabric softeners and additional oleochemical applications. However, the emcic acid... 

The Austrian Biofuels Institute currently maintains an ongoing database on the global biodiesel industry (49). Their current statistics reveal that most biodiesel is obtained from canola (low emcic acid rapeseed 84%) and sunflower (13%). European biodiesel production dominated world production in 2000 and Europeans have chosen canola oil as the mainstay for manufacturing biodiesel. However, recent facility constmction (50) and legislative action (51) in North America may lead to rapid increases in biodiesel production (Table 2). The State of Minnesota has passed legislation that mandates the inclusion of 2% biodiesel in all diesel fuel sold in the state (51). European and American biodiesel production is rapidly increasing. In 2000, U.S. production was just 22 ML (Table 3). 

Carlson, K.D., and D. L. Van Dyne, Industrial Uses for High Emcic Acid Oils from Crambe and Rapeseed, MP-Univ.-Mo-Ext.-Div., MP678 32 (Oct. 1992). 

At first, low emcic acid (less than 5%, meanwhile less than 2.5%) cultivars were developed. Later, one was also successful in breeding low glucosinolate varieties, finally yielding so-called double-zero cultivars now almost exclusively sown. In Canada, this rapeseed especially suited for edible purposes is referred to as canola [3]. As erucic acid has been primarily replaced by oleic acid, the fatty acid fraction of low-erucic acid rapeseed oil is composed of 52-66% oleic acid, 17-25% linoleic acid, and 8-11% Hnolenic acid. 

Impallomeni, G., Ballistreri, A., Camemolla, G.M. et al. (2011) Synthesis and characterization of poly(3-hydroxyaUtanoates) from Brassica carinata oil with high content of emcic acid and from very long chain fatty acids. International Journal of Biological Macromolecules, 48(1), 137-145. 

Warner, K., Frankel, E.N. and Mounts, T.L. Flavor and oxidative stability of soybean, sunflower and low-emcic acid rapeseed oils. J. Am. Oil Chem. Soc. 66,558-564 (1989). 

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