Oleates methyl oleate

In an excellent study of neutral lipids by Foglia and Jones [836], a 100/0/0.4 (hold 5 min) -> 20/80/0.4 (at 15 min hold 2 min) hexane/MrBE/acetic acid gradient was used with a cyanopropyl column (ELSD, 40°C drift tube, and = 1.5 L/min). Two separations are shown, one involving neutral lipid standards (cholesterol, oleate, methyl oleate, oleic acid, triolein, 1,3- and 1,2-diolein, 1- and 2-monoolein) and the other IPA-transesterifled tallow separated into fractions (isopropylesters, free fatty acids, triglycerides, 1,3- and 1,2-diglycerides, and 1-monoglyceride). Area vs. concentration plots for these analytes were nonlinear over the 0-50 pg/mL range. Overall separations were excellent, as were peak shapes. 

Methyl oleate Methyl oleate Methyl lithocholate Methyl lithocholate Methyl lithocholate Methyl lithocholate Methyl deoxycholate Methyl deoxycholate Methyl deoxycholate Lithocholic acid Anasil B Silica gel G Silica gel G Silica gel G Silica gel G Anasil B Silica gel G AnasU B Silica gel G Silica gel G... 

Use the Non-Polar Lipid Mix-B, 25 mg/inl-1 ml standard from Matreya (catalog number 1130). This standard contains equal amounts of cholesteryl oleate, methyl oleate, triolein, oleic acid, and cholesterol. The standard is shipped in an ampoule containing a total of 25 mg of the neutral lipids in 1 ml of chloroform. Quantitatively transfer the 1 ml of chloroform to a 50-ml volumetric flask by rinsing with chloroform. Adjust the volume in the flask to 50 ml by the addition of chloroform to achieve a final total lipid concentration of exactly 0.5 4g/ 4l. The weight of cholesterol in this standard will be 0.1 fig/fil. 

Methyl oleate [112-62-9] M 296.5, f -19.9 , b 217 /16mm, d 0.874, n 1.4522. Purified by fracuonal distn under reduced pressure, and by low temperature crystn from acetone. 

Organisms differ with respect to formation, processing, and utilization of polyunsaturated fatty acids. E. coli, for example, does not have any polyunsaturated fatty acids. Eukaryotes do synthesize a variety of polyunsaturated fatty acids, certain organisms more than others. For example, plants manufacture double bonds between the A and the methyl end of the chain, but mammals cannot. Plants readily desaturate oleic acid at the 12-position (to give linoleic acid) or at both the 12- and 15-positions (producing linolenic acid). Mammals require polyunsaturated fatty acids, but must acquire them in their diet. As such, they are referred to as essential fatty acids. On the other hand, mammals can introduce double bonds between the double bond at the 8- or 9-posi-tion and the carboxyl group. Enzyme complexes in the endoplasmic reticulum desaturate the 5-position, provided a double bond exists at the 8-position, and form a double bond at the 6-position if one already exists at the 9-position. Thus, oleate can be unsaturated at the 6,7-position to give an 18 2 d5-A ,A fatty acid. 

Stork and Takahashi took -glyceraldehyde synthon from the chiral pool and condensed it with methyl oleate, using lithium diisopropyl amide as catalyst for the mixed aldol reaction, leading to The olefinic linkage is a latent form... 

Methyl oleate gives methyl 9,10-dideuterostearate on treatment with deuterium. Similarly, methyl linoleate gives 9,10,12,13-tetradeuterostearate. The products have bp 214-215715 mm. 

A similar reaction occurs with fatty acids (such as stearic acid) or methyl stearate, which undergo isomerization, cracking, dimerization, and oligomerization reactions. This has been used to convert solid stearic acid into the more valuable liquid isostearic acid [102] (Scheme 5.1-70). The isomerization and dimerization of oleic acid and methyl oleate have also been found to occur in chloroaluminate(III) ionic liquids [103]. 

The ability to disperse the calcium soap formed from a given amount of sodium oleate has been studied for a number of a-sulfo fatty acid esters with 14-22 carbon atoms [28,30]. In principle, the lime soap dispersion property increases with the number of C atoms and the dissymmetry of the molecule. Esters with 14 C atoms have no dispersion power and in the case of esters with 15-17 carbon atoms the least symmetrical are the better lime soap-dispersing agents. However this property does not only depend on the symmetry but on the chain length of the fatty acid group. For example, methyl and ethyl a-sulfomyristate have better dispersing power than dodecyl propionate and butyrate. The esters with 18 and more carbon atoms are about equal in lime soap dispersion power. Isobutyl a-sulfopalmitate is the most effective agent under the test conditions. 

The addition of an ester sulfonate of an unsaturated fatty acid improves the rinsing properties in washing tests. A mixture of 50% sodium methyl a-sulfostearate and 50% sodium salt of sulfonated methyl oleate (30 70 mono-sulfonate/polysulfonate ratio) was used [83]. 

This has been found to be a general reaction for many types of olefins. It has also been applied to highly branched structures, such as 2,4,4-trimethyl-2-pen-tane and propylene trimers and tetramers [177], to unbranched olefins with internal double bonds, such as methyl oleate [178] and tricosane, and to a-ole-fins [179], In all cases the data indicate that the reaction occurs at the double... 

Butyl cellosolve stearate Diamyl naphthalene Dibutyl tin laurate Dioctylphthalate Methyl cellosolve oleate Methyl phthalylethylglycola Phenylsalicylate Propylene stearate Stearic acid... 

C HgfC H2)7-C HCI-C H-(C H2)7-C02CH3 FIGURE 1.15 Product of reaction between DDT and methyl oleate. 

Schwack W (1988) Photoinduced additions of pesticides to biomolecules. 2. Model reactions of DDT and methoxychlor with methyl oleate. J Agric Eood Chem 36 645-648. 

In the case of functionalized olefins, heterogeneous catalysts have usually not performed well [84,85]. Methyl oleate is the typical test substrate the following order of stability towards the ester functional group for the different SOM catalysts has been observed (based on the number of turnovers) Re W > Mo, which is similar to what has been described for related homogeneous systems. In the specific case of Re, 900 TON can be reached, while TON for other Re-based heterogeneous catalysts do not exceed 200 [79,84]. 

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). 

Q-MG, CLG, DG, Retinue attraction of workers to mated queen QMP,methyl oleate 56, (2 )-3-(4-hydroxy-3-methoxy)-prop-2-en-1 -ol 57, hexadecan-1 -ol 58, linolenic acid 59 [96,99]... 

Larva Inhibits worker ovarian development Ten component blend of brood pheromone methyl ethyl palmitate 78 79, stearate 80 81, oleate 56 90,linoleate 82 83, linolenate 84 84a, specifically ethyl palmitate methyl linolenate [121,122]... 

Larva Trigger workers to cap larval cells Methyl linoleate 82, linolenate 84, oleate 56, palmitate 78 [147]... 

Larva Stimulate development of worker hypo-pharyngeal glands Ethyl oleate 90 methyl palmitate 78 [148]... 

In the Table 2 the methyl oleate content in the reaction system and the immobilized enzyme activity, towards the transesterification reaction, are reported. 

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