Fatty methyl linoleate

Figure 1.7 Typical zero-order and corresponding second-derivative electronic absorption spectra of ethanol-reconstituted lipid/chloroform extracts of autoxidized model polyunsaturated fatty-acid compounds and inflammatory synovial fluid obtained after (1) reduction with NaBH4 and (2) dehydration with alcoholic H2S04- (a) Methyl linoleate subsequent to autoxidation in air at ambient temperature for a period of 72 h (—), or exposure to a Fenton reaction system containing EDTA (5.75 x 10 mol/dm ), H2O2 (1.14 X 10 mol/dm ) and Fe(ll) (5.75 x IO mol/dm ) as an aqueous suspension (—) (b) as (a) but with methyl linolenate (c) untreated rheumatoid knee-joint synovial fluid.

C12 to C20, primarily Ci6 to ( is), used as surface lubricants in the manufacture of food-contact articles. The method, which uses ethyl palmitate (Eastman Chemicals No. 1575 Red Label) as an internal standard, has been validated at 200 ppm total FAME [185]. Other FAME standards (methyl palmitate, methyl stearate, methyl oleate, methyl linoleate and methyl linolenate) are available (Applied Science Laboratories) [116], Worked out examples of additive determinations are given in the Food Additives Analytical Manual [116], which also describes a great many of indirect food additives, such as BHA, BHT, TBHQ, l-chloro-2-propanol, DLTDP, fatty acid methyl esters, w-heptyl-p-hydroxybenzoate, propyl-gallate, sodium benzoate, sodium stearoyl-2-lactylate, sorbitol and phenolic antioxidants. EPA methods 606 and 8060 describe the CGC separation of phthalate esters (direct injection) (cf. Figure 4.2). 

Low levels of nitrogen dioxide react with the polyunsaturated fatty acids under anaerobic conditions to give allylic nitro and allylic nitrite derivatives of methyl linoleate and methyl linolenate. These were identified by NICI-MS558. 

Methyl linoleate, methyl oleate from methyl linoleate, methyl oleate, methyl esters of saturated fatty acids KY Toluene [184]... 

The partial synthesis of a Ci8 dimethyl furanoid ester (29) from methyl linoleate and from methyl 10,13-epoxy-ll-methyloctadeca-10,12-dienoate has been described (Scheme 5) (81CC1110). Treatment of methyl linoleate (23) with MCPBA gave the methyl 9,12-diepoxystearate (24), which was easily converted to a mixture of the two C18 furanoid fatty ester isomers (25). TTie corresponding methyl dioxostearates (26) were methylated to... 

Because conjugated fatty esters are potential intermediates, alkali-conjugated methyl linoleate [mixture of mainly cis,trans-( 9,11- and 10,12)-octadecadienoate] was catalytically hydrocar boxy lated. Under comparable conditions, these conjugated dienes were more difficult to... 

A significant portion of the neutral ethyl ether extract from the salts of carboxylated methyl linoleate consists of ,/3-unsaturated cyclic ketones. This material is produced in small but significant amounts (4-10%) (Table I) from the carboxylation of polyunsaturates but not from the corresponding monounsaturated fatty acids and esters (19). These ,/ -unsaturated cyclic ketones were identified spectroscopically (IR, UV, and NMR) as 4. This structural assignment was firmly established by mass spectral analyses before and after hydrogenation of the carbon-carbon double bond. 

Further studies have extended this promotion of auxin and gibberellin action to other fat-soluble substances, in particular some isoprenoid vitamins and related compounds (I). For instance, vitamin E, vitamin Kl9 and phytol are quite comparable in their growth-promoting ability to the fatty acid ester, methyl linoleate. But some fat-soluble vitamins are not active—for instance, vitamin A, -carotene, and vitamin D2. 

Fatty acid esters Ethyl acetate, methyl methacrylate, trimethylolpropane trimethacrylate, decyl methacrylate, 2-hydroxyethyl methacrylate, ethoxy ethyl acetate, methyl palmitate, ethyl palmitate, isopropyl palmitate, butyl palmitate, isobutyl palmitate, methyl margarate, butyl margarate, methyl stearate, ethyl stearate, butyl stearate, isobutyl stearate, methyl oleate, bis(2-ethylhexyl) adipate, bis(2-ethylhexyl) sebacate, methyl linoleate, methyl laurate, octyl laurate, methyl myristate, isobutyl myristate, butyl myristate, dihydroisopimaric add methyl ester... 

The use of isolated fatty acids as substrates for epoxidations has already been reported in 1990 with the epoxidation of methyl oleate and methyl linoleate by MT0/H202 in ferf-butanol. After respectively 24 and 2 h, good yields of either the corresponding diol (methyl oleate) or the monoepoxide (methyl linoleate) are obtained (respectively 92% and 80%) [48]. Under biphasic conditions, the MTO-catalyzed epoxidation of methyl linoleate yields a mixture of mono- and diepoxide (approximately 1 1) at complete conversion after 6 h [79]. Finally, a conjugated methyl linoleate is treated with the MT0/H202 system in biphasic conditions, but here, poor results are obtained after 24 h at room temperature, yielding 26% of the 11,12-monoepoxide and 20% of the 9,10-epoxide [80]. 

The esters of fatty acids and hydrocarbons (Table I, 11-17 with corresponding micrographs and laser diffraction patterns) have all assisted moderately to develop crazes in a stressed polystyrene. The effect of methyl linoleate helped to initiate more crazes than that of methyl oleate (see Figures 11 and 12). As shown in Figures 13 and 14 toluene and xylene assisted in developing more dense but finer crazes as compared with the first two. Note that these chemicals tend to cover the surface of the polystyrene and cause the central region of the diffraction... 

Again, it is important to note that methyl esters of lard and tallow are the sum of the methyl esters of fatty acids found in the original fat. Methyl lard for example, will contain methyl myristate, methyl palmitate, methyl stearate, methyl oleate, methyl linoleate, and methyl linolenate in the same percentages as the lard used as the raw material, unless the manufacturer fractionates the material, thereby selecting methyl esters of certain fatty acids over others. 

To elucidate the mechanism of homogeneous hydrogenation catalyzed by Fe(CO)s, kinetic studies were carried out with mixtures of unsaturated fatty esters containing a radioactive label. A C-labeled methyl octadecadienoate-Fe(CO)3 complex was prepared to serve as a catalytic intermediate. Hydrogenation of methyl oleate (m-9-octa-decenoate) and palmitoleate (cis-9-hexadecenoate) and of their mixtures with methyl linoleate was also studied to determine the selectivity of this system, the function of the diene-Fe(CO)3 complex, and the mechanism of homogeneous isomerization. Mixtures of reaction intermediates with a label helped achieve unique simulation of the kinetic data with an analog computer. 

In this paper, we describe the apparatus we use to make phase equilibrium measurements on mixtures of conqponents with greatly differing volatilities, putting particular emphasis on recent inqprove-ments over the previous version (6-7). We also describe quantitative measurements of the solubility of methyl oleate in supercritical fluids which can provide a basis for choosing a solvent to separate fatty acids in edible oils. In the following paper (JB.) we explore the utility of cubic equations of state to describe the results of supercritical fluid - liquid phase equilibrium measurements. Some additional experimental results on the mutual solubility of methyl linoleate and carbon dioxide are presented there also. 

Several cubic equations of state such as Redlich-Kwong, Soave-Redlich-Kwong, and Peng-Robinson have been used to calculate vapor liquid equilibria of fatty acid esters in supercritical fluids. Comparisons are made with experimental data on n-butanol, n-octane, methyl oleate, and methyl linoleate in carbon dioxide and methyl oleate in ethane. Two cubic equations of state with a non quadratic mixing rule were successful in modeling the experimental data. 

Figure 7. Methyl esters of unsaturated fatty acids as resolved on the 25%-cyanopropyl-25%-phenyl methyl siloxane DB-225. Split Injection to a 30m x 0.25mm column coated with a 0.25 m bonded film, hydrogen carrier at 46cm/sec, isothermal at 200 °C. Components 1, 14 1 methyl myristoleate 2, 16 1 trans methyl palmite-laidate 3, 16 1 cis methyl palmitoleate 4, 18 1 trans methyl elaidate 5, 18 1 cis methyl oleate 6, 18 2 trans methyl linolea-laidate 7, 18 2 cis methyl linoleate 8, 18 3 methyl linoleate ...

Various Pt(IV), Pt(II), and Pt(0) catalysts were screened for the hydrosilylation of fatty acid esters (Eq. 7) containing terminal as well as internal double bonds. The reaction of terminally unsaturated fatty acid esters proceeds smoothly with short reaction times for nearly all catalysts examined, whereas the Pt(IV) and Pt(II) or Pt(0) species with labile ligands are sufficiently active in the reaction of internally unsaturated compounds. For methyl linoleate, a conjugation of the two internal double bonds before the hydrosilylation was observed. The reaction can be carried out in solid as well as in solvent systems, permitting catalyst recycling and reuse. In these systems, however, hydrogenation and double-bond isomerization are found as side reactions [22]. 

A supercritical fluid extraction (SFE) method for analysis of CO2 extractables in cranberry seeds was investigated. The SFE operating conditions were optimized to maximize the extraction yields. Extraction yields obtained by SFE were comparable to conventional Soxhlet extraction. The extracts were derivatized and then analyzed by GC-MS. The extracts obtained via hexane and CO2 mostly contained methylated fatty acids. Linoleic acid and palmitic acid were the major compounds extracted. 

Methyl Linoleate. (Hart lYods. Cop.] Fatty acid esters base ftw super amides. 

Polyunsaturated fatty acids with double bonds three carbons from the methyl end (w3 fatty acids) and six carbons from the methyl end (w6 fatty acids) are required for the synthesis of eicosanoids (see Chapter 35). Because humans cannot synthesize these fatty acids de novo (i.e., from glucose via palmitate), they must be present in the diet or the diet must contain other fatty acids that can be converted to these fatty acids. We obtain w6 and w3 polyunsaturated fatty acids mainly from dietary plant oils that contain the w6 fatty acid linoleic acid (18 2, and the w3 fatty acid a-linolenic acid (18 3, In the body, linoleic acid can be converted by elongation and desatura-... 

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