Linoleate/linoleic acid

Linoleic acid (= Linolic acid Widespread Helianthus annuum Bitter - burning bitter ... 

AI3-11132 CCRIS 650 EINECS 200-470-9 Emersol 310 Emersol 315 Extra Linoleic 90 FEMA No. 3380 Grape seed oil HSDB 5200 Linoleic acid a-Linoleic acid 9Z,12Z-Linoleic acid cis.cis-Linoleic acid 9-cis,12-cis-Linoleic acid Linolic acid NSC 281243 9,12-Octadecadienoic acid 9,12-Octadecadienolc acid (9Z,12Z)- 9,12-Octadecadienoic acid, (Z,Z)- (Z,Z)-9,12-Octadecadienoic acid Oils, grape Oils, grape seed Polylin 515 Polylin No. 515 Telfairic acid Unifac 6550. Unsaturated fatty acid used in manufacture of paints, coatings, emulsifiers, vitamins. Oil bpi = 230-232" d2 = 0.914 insoluble in H2O, soluble in organic solvents. Arizona CasChem Henkel/Emery Hercules Inc. Langley Smith Ltd. 

The right balance of n-6 and n-3 polyunsaturated fatty acids (PUFA) is important for good health. The n-3 PUFA such as eicosapentaenoic acid PA) and docosahexaenoic acid (DHA) are mainly found in fish oils. Marine plants can convert a-linolenic acid (ALA) into EPA and DHA, which find their way through the food chain to fish tissues. Another source of n-3 PUFA is the ALA that is found mainly in flaxseed, canola, and soybean oils. Unlike plants, mammals cannot convert oleic acid into linoleic acid, linoleic acid into ALA, or convert n-6 PUFA to n-3 PUFA. Linoleic acid and n-3 PUFA are therefore known as essential fatty acids (1). 

CAS 60-33-3 EINECS/ELINCS 200-470-9 Synonyms Leinoleic acid 9,12-Linoleic acid Linolic acid 9,12-Octadeca-dienoic acid cis,cis-9,12-Octadecadienoic acid (Z,Z)-9,12-Octadeca-dienoic acid... 

Linoleic acid. See Linoleic acid Linoleic acid amide. See Linoleamide Linoleic acid, copper salt. See Copper linoleate Linoleic acid diethanolamide. See Linoleamide DEA... 

SDS emulsion of linoleic acid Linoleic acid micelle oxidation induced by AAPH monitored hy conjugated diene (234 nm) Not specific, influenced by physical micelle properties of emulsion, not real oil-in-water emulsion, artificial inducer, inappropriate substrate Pryor cf a/. (1988, 1993)... 

The use of the isotonic soy bean oil emulsion Intraiipid "Vit-rum" to cover about 407o of the caloric requirement T> rmits peripheral vein infusions to be used exclusively for up several weeks. Furthermore, this regimen ensures a sufficient supply of the essential linoleic acid. Linoleic acid deficiency which is inevitable unless at least 107o of the caloric needs is covered with Intralipid, leads to skin changes, alterations of cellular and other membranes, and increases the caloric requirement by about 207o (16). 

Synonyms 9,12-Octadecadienoic acidi 9,12-linoleic acid linolic acid... 

Muller, B., Gautier, A, Dean, C, and Kuhn, J.-C. (1995) Process for the enzymatic preparation of aliphatic alcohols and aldehydes from linoleic acid, linoleic acid, or a natural precursor. Patent US 5,464,761 A,... 

The linoleic acid series, C H2 -402, with two double bonds. 

Linoleic acid [463-40-1] Linoleic acid [60-33-2] Linoleic acid [60-33-3]... 

In the area of moleculady designed hot-melt adhesives, the most widely used resins are the polyamides (qv), formed upon reaction of a diamine and a dimer acid. Dimer acids (qv) are obtained from the Diels-Alder reaction of unsaturated fatty acids. Linoleic acid is an example. Judicious selection of diamine and diacid leads to a wide range of adhesive properties. Typical shear characteristics are in the range of thousands of kilopascals and are dependent upon temperature. Although hot-melt adhesives normally become quite brittle below the glass-transition temperature, these materials can often attain physical properties that approach those of a stmctural adhesive. These properties severely degrade as the material becomes Hquid above the melt temperature. 

Separation of Fatty Acids. Tall oil is a by-product of the pulp and paper manufacturiag process and contains a spectmm of fatty acids, such as palmitic, stearic, oleic, and linoleic acids, and rosia acids, such as abietic acid. The conventional refining process to recover these fatty acids iavolves iatensive distillation under vacuum. This process does not yield high purity fatty acids, and moreover, a significant degradation of fatty acids occurs because of the high process temperatures. These fatty and rosia acids can be separated usiag a UOP Sorbex process (93—99) (Tables 8 and 9). 

A USDA report indicates that between 1967 and 1988, butter consumption remained stable at 2 kg per capita, margarine dropped from 5.1 to 4.7 kg, and measured total fat intake per day dropped from 84.6 to 73.3 g (14). This study also projects that the reduced consumption of tropical oils is only temporary and will return to former use levels, possibly even higher. One reason for this projected rise in tropical oil consumption is the knowledge of the beneficial effects of medium-chain length acids high in lauric oils. There is a keen interest in omega-3 fatty acids, as well as linoleic acid, contained in fish oils. 

The unsaturated fatty acids, linoleic [60-33-3] and linolenic [463-40-17, contain two and three double bonds and are considered beneficial components of the diet. The double bond is an essential ingredient for human nutrition when it is in the correct position on the fat molecule. Humans are unable to insert the double bond at the omega-3 and -6 position. Therefore, fatty acids containing double bonds at these positions are essential in the diet, including linoleic and linolenic acids. They are accordingly described as essential fatty acids (EFA) (23). 

Multiply unsaturated linolenic and linoleic acid residues make triglycerides more vulnerable to oxidative degradation than oleic acid which is relatively stable. It is therefore desirable to hydrogenate the most unsaturated residues selectively without production of large quantities of stearic (fully saturated) acid. The stepwise reduction of an unsaturated oil may be visualized as ... 

If first-order kinetics are assumed, k /is the linoleic selectivity ratio and k l is the selectivity ratio for reduction of linoleic acid to stearic acid. Figure 2 shows a typical course of hydrogenation for soybean oil the rate constants are = 0.367, = 0.159, and k = 0.013. With a selective nickel catalyst,... 

The antagonisms that exist between unsaturated fatty acids, and carotene and vitamin E are compHcated and largely undefined. Linoleic acid acts as an antivitamin to i7/-a-tocopherol [59-02-9, 1406-18-9, 10191-41-0] (vitamin E) by reducing availabiHty through direct intestinal destmction. Various Hpoxidases destroy carotenes and vitamin A (73). Dicoumarol [66-76-2] (3,3 -methylenebis(4-hydroxycoumarin)) is a tme antimetaboHte of vitamin K [12001 -79-5] but seems to occur only in clover and related materials that are used primarily as animal feeds (74). 

Driers. These are generally soaps of cobalt, manganese, and other metals formed with organic acids such as linoleic, naphthenic, and other organic acids. They catalyze oxidation of drying oils (qv), and thus are used in inks that dry by oxidation (see Driers and metallic soaps). 

Amide yields of up to 90—95% are reported from lauric acid and urea (1 1 mole ratio) by ramping the reaction temperature from 140 to 190°C over 4 hours. Oleic, stearic, linoleic, and ricinoleic acids gave similar results (19,20). The reaction does not form significant quantities of bisamides, but rehes on the decomposition of a substituted urea amide, releasing CO2 and NH. ... 

Refluxing linoleic acid and a primary or secondary alkyl amine with -toluenesulfonic acid in toluene for 8—18 h also yields the substituted amides (32—34). The reaction of methyl esters with primary or secondary amines to make substituted amides is catalyzed with sodium methoxide. Reactions are rapid at 30°C under anhydrous conditions (35). Acid chlorides can also be used. Ai,A/-dibutyloleamide [5831-80-17 has been prepared from oleoyl chloride and dibutyl amine (36). 

Lipids. Representative fatty acid compositions of the unprocessed triglyceride oils found in the four oilseeds are given in Table 4 (see Fats and FATTY oils). Cottonseed, peanut, and sundower oils are classified as oleic—linoleic acid oils because of the high (>50%) content of these fatty acids. Although the oleic and linoleic acid content of soybean oils is high, it is distinguished from the others by a content of 4—10% of linolenic acid, and hence is called a linolenic acid oil. 

Considering their heat sensitivity, the separation of fatty acids and rosin with minimal degradation by fractional distillation under vacuum and/or in the presence of steam is surprisingly good (3). Tad od rosin (TOR) contains about 2% fatty acid and smad amounts of neutrals. Tad od fatty acid (TOFA) contains as Htde as 1.2% rosin and 1.7% neutrals. In typical U.S. TOFA, 49% of the fatty acids is oleic, 45% linoleic, and 3% palmitic, stearic, and eicosatrienoic acid. TOR and TOFA are upgraded to resins and chemicals for the manufacture of inks (qv), adhesives (qv), coatings (qv), and lubricants (see Lubrication AND lubricants). 

Liquid Ghromatography/Mass Spectrometry. Increased use of Hquid chromatography/mass spectrometry (Ic/ms) for stmctural identification and trace analysis has become apparent. Thermospray Ic/ms has been used to identify by-products in phenyl isocyanate precolumn derivatization reactions (74). Five compounds resulting from the reaction of phenyUsocyanate and the reaction medium were identified two from a reaction between phenyl isocyanate and methanol, two from the reaction between phenyl isocyanate and water, and one from the polymerisation of phenyl isocyanate. There were also two reports of derivatisation to enhance either the response or stmctural information from thermospray Ic/ms for linoleic acid hpoxygenase metabohtes (75) and for cortisol (76). 

The polyunsaturated aliphatic monocarboxyhc acids having industrial significance include sorbic, linoleic, linolenic, eleostearic, and various polyunsaturated fish acids (Table 3). Of these, only sorbic acid (qv) is made synthetically. The other acids, except those from tall oil, occur naturally as glycerides and are used mosdy in this form. 

Conjugation as well as geometric and positional isomerization occur when an alkadienoic acid such as linoleic acid is treated with a strong base at an elevated temperature. CycHc fatty acids result from isomerization of linolenic acid ia strong base at about 250°C (58). Conjugated fatty acids undergo the Diels-Alder reaction with many dienophiles including ethylene, propylene, acryUc acid, and maleic anhydride. 

When tallow fatty acids are the feed, stearic acid (actually 60/40 C16/C18) and oleic acids are the products. Solvent separation is also used to separate stearic acid from isostearic acid when hydrogenated monomer is the feed, and oleic acid from linoleic acid when using tall oil fatty acids as feed. 

Liquid—hquid extraction can be used to obtain high purity linoleic acid from safflower fatty acids or linoleic acid from linseed fatty acids using furfural and hexane as solvents (18). High purity linoleic acid has been obtained from sunflower fatty acids using a dimethylformamide and hexane solvent system (19). 

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