Oleic acid 3-oxidation

Intermediates in Oleic Acid Oxidation What is the structure of the partially oxidized fatty acyl group that is formed when oleic acid, 18 1 (A9), has undergone three cycles of /3 oxidation What are the next two steps in the continued oxidation of this intermediate ... 

Another example, similar to that of the oleic acid oxidation, is provided by the study (Mittelmann and Palmer, 36) of the rate of oxidation of triolein films. Their results will be considered in more detail below, where their mathematical analysis will be discussed. 

Isooctyl alcohol Isophthalic acid, Isopropanolamine, Isostearic acid, Itaconic acid, Jayflex DHP Jayflex DINA Jayflex DIOP Jonrez IC-2805 Kenplast G Lanolin alcohol Maleic acid Maleic anhydride, Mekon White 2-Mercaptoethanol 3-Methoxybutanol Methoxyethanol Methoxyethyl acrylate. Methyl acetyl ricinoleate Methyl caprate. Methyl laurate. Methyl linoleate Methyl oleate Methylpropanediol Neopentyl glycol Nonanolc acid, Nopalcol 4-0 Nomlacresin, Octoxynol 2-Octyi-l-decanol Octyl palmitate. Oleic acid. Oxidized soybean oil Paroll 142 ... 

Cultures were treated with 30 pM trans-lO, cis-12 CLA, cis-9, trans- CLA, or vehicle for 72 h, then radiolabeled glucose and oleic acid uptake, conversion to lipid, and oxidation were measured (24). Radiolabeled glucose and oleic acid uptake were lower in insulin-stimulated cultures treated with trans- 0, cis- 2 CLA compared with all other treatments. De novo lipogenesis and oleic acid conversion to lipid were lower in trans- 0, cis-12 CLA-treated cultures compared to their respective controls. Radiolabeled glucose and oleic acid oxidation were lower in cultures treated with trans-10, cis-12 CLA compared with all other treatments. These data show that trans-10, cis-12 CLA decreases human adipocyte TG content by reducing glucose and fatty acid uptake and conversion to lipid. 

Fig. 19 Activation of oleic acid oxidation (EC50) and agonism of individual PPAR subtypes by acids 48 and 49 [97]...

The purity of trans-l0,cis-l2, cis-9,trans-ll, trans-l0,trans-l2 and trans-9,trans-ll CLA-Me isomers used was 99.0, 90.3, 95.0 and 96.0%, respectively, when analyzed by GC (20). The purity of trans- 0,cis-l2 and cis-9,trans-l CLA-Me fractions separated from the synthetic CLA in acetone at -68 C and dien -71 °C was 92.5 and 87.3%, respectively, but the purity was further increased to 99.0 and 90.3%, respectively, by urea treatment. Impurities, such as saturated fatty acids, oleic acid, oxidation by-products, trans,trans-CLA isomers and cis,cis-CLA isomers, were easily removed from the trans-l0,cis-l2 CLA-Me fraction by urea treatment, but not from the cis-9,trans-l 1 CLA-Me fraction. Interestingly, the trans-l0,trans-l2 or tram-9,tram- 1 CLA-Me fraction was not a single compound, but contained a mixture of positional isomers of tram,tram CLA-Me, when mialyzed by Ag -HPLC. The tram- Q,tram- 2 CLA-Me fraction contained 2.8% tram- 2,tram- A, 14.9% tram-, tram- i, 34.3% tram- Q,tram- 2, 33.8% tram-9,tram-l, 11.6% fra s-8,/ram-10, and 2.6% tram-1,tram-9 CLA-Me, whereas the tram-9,tram- CLA-Me contained 1.5% tram- 2,tram- A, 10.2% tram-, tram- i, 33.8% tram- tl, tram- 2, 38.5% tram-9,tram-W, 13.8% tram-Z,tram- ti, and 2.2% tram-1,tram-9 CLA-Me. 

HOOO(CH2)7COOH. Colourless plates, m.p. lOfi C. Made by the oxidation of oleic acid with ozones. 

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 ... 

Cyanide Wastes. Ozone is employed as a selective oxidant in laboratory-scale synthesis (7) and in commercial-scale production of specialty organic chemicals and intermediates such as fragrances, perfumes (qv), flavors, antibiotics (qv), hormones (qv), and vitamins (qv). In Japan, several metric tons per day (t/d) of piperonal [120-57-0] (3,4-methylenedioxybenzaldehyde) is manufactured in 87% yield via ozonolysis and reduction of isosafrole [93-16-3], Piperonal (or heHotropine [120-57-0]) has a pleasant odor and is used in perfumery. Oleic acid [112-80-1/, CH3(CH2 )7CH—CH(CH2 ). C02H, from tall oil (qv) is ozonated on a t/d scale to produce pelargonic, GgH2yG02H, and azelaic, H02G(GH2)yG02H, acids. Oleic acid also is ozonated in Japan... 

The diacids for these polymers are prepared via different processes. A2elaic acid [123-99-9] for nylon-6,9 [28757-63-3] is generally produced from naturally occurring fatty acids via oxidative cleavage of a double bond in the 9-position, eg, from oleic acid [112-80-1] ... 

The physical properties of the fatty acid ethoxylates depend on the nature of the fatty acid and even more on ethylene oxide content. As the latter increases, consistencies of the products change from free-flowing Hquids to slurries to firm waxes (qv). At the same time, odor, which is characteristic of the fatty acid, decreases in intensity. Odor and color stabiUty are important commercial properties, particularly in textile appHcations. Oleic acid esters, though possessing good functional properties, cannot be used because they tend to yellow on exposure to heat and air. 

Copper—cadmium and zinc—chromium oxides seem to provide most selectivity (38—42). Copper chromite catalysts are not selective. Reduction of red oil-grade oleic acid has been accompHshed in 60—70% yield and with high selectivity with Cr—Zn—Cd, Cr—Zn—Cd—Al, or Zn—Cd—A1 oxides (43). The reduction may be a homogeneously catalyzed reaction as the result of the formation of copper or cadmium soaps (44). 

Alkali fusion of oleic acid at about 350°C ia the Varrentrapp reaction causes double-bond isomerization to a conjugated system with the carboxylate group followed by oxidative cleavage to form palmitic acid (75). In contrast, alkaU fusion of riciaoleic acid is the commercial route to sebacic acid [111 -20-6] ... 

Oleic acid is a good deflocculant for oxide ceramic powders in nonpolar Hquids, where a stable dispersion is created primarily by steric stabilization. Tartaric acid, benzoic acid, stearic acid, and trichloroacetic acid are also deflocculants for oxide powders in nonpolar Hquids. 

A U.S. patent describes the reaction of commercial oleic acid with hydrogen peroxide in acetic acid foUowed by air oxidation using a heavy metal compound and an inorganic bromine or chlorine compound to catalyze the oxidation. ExceUent yields of dibasic acids are obtained (up to 99%) containing up to 72% azelaic acid (55). 

The dimer acids [61788-89-4] 9- and 10-carboxystearic acids, and C-21 dicarboxylic acids are products resulting from three different reactions of C-18 unsaturated fatty acids. These reactions are, respectively, self-condensation, reaction with carbon monoxide followed by oxidation of the resulting 9- or 10-formylstearic acid (or, alternatively, by hydrocarboxylation of the unsaturated fatty acid), and Diels-Alder reaction with acryUc acid. The starting materials for these reactions have been almost exclusively tall oil fatty acids or, to a lesser degree, oleic acid, although other unsaturated fatty acid feedstocks can be used (see Carboxylic acids. Fatty acids from tall oil Tall oil). 

Examples are given of common operations such as absorption of ammonia to make fertihzers and of carbon dioxide to make soda ash. Also of recoveiy of phosphine from offgases of phosphorous plants recoveiy of HE oxidation, halogenation, and hydrogenation of various organics hydration of olefins to alcohols oxo reaction for higher aldehydes and alcohols ozonolysis of oleic acid absorption of carbon monoxide to make sodium formate alkylation of acetic acid with isobutylene to make teti-h ty acetate, absorption of olefins to make various products HCl and HBr plus higher alcohols to make alkyl hahdes and so on. 

There has been only one major use for ozone today in the field of chemical synthesis the ozonation of oleic acid to produce azelaic acid. Oleic acid is obtained from either tallow, a by-product of meat-packing plants, or from tall oil, a byproduct of making paper from wood. Oleic acid is dissolved in about half its weight of pelargonic acid and is ozonized continuously in a reactor with approximately 2 percent ozone in oxygen it is oxidized for several hours. The pelargonic and azelaic acids are recovered by vacuum distillation. The acids are then esterified to yield a plasticizer for vinyl compounds or for the production of lubricants. Azelaic acid is also a starting material in the production of a nylon type of polymer. 

Polyunsaturated fatty acids pose a slightly more complicated situation for the cell. Consider, for example, the case of linoleic acid shown in Figure 24.24. As with oleic acid, /3-oxidation proceeds through three cycles, and enoyl-CoA isomerase converts the cA-A double bond to a trans-b double bond to permit one more round of /3-oxidation. What results this time, however, is a cA-A enoyl-CoA, which is converted normally by acyl-CoA dehydrogenase to a trans-b, cis-b species. This, however, is a poor substrate for the enoyl-CoA hydratase. This problem is solved by 2,4-dienoyl-CoA reductase, the product of which depends on the organism. The mammalian form of this enzyme produces a trans-b enoyl product, as shown in Figure 24.24, which can be converted by an enoyl-CoA isomerase to the trans-b enoyl-CoA, which can then proceed normally through the /3-oxidation pathway. Escherichia coli possesses a... 

---