Myristate and Methyl Palmitate

Of the early references to the preparation of methyl myristate and methyl palmitate, few are of preparative value. Methyl myristate can be prepared by the fractional distillation of the methyl esters from ucuhuba fat4 and from cocoanut oil.5-6 Methyl palmitate can be prepared in a similar manner from cocoanut oil6 and from bayberry wax.7... 

METHYL MYRISTATE AND METHYL PALMITATE AND THE CORRESPONDING ACIDS... 

Similar investigations with the related species Tegenaria pagana and Tegenaria domestica (Trabalon et al., 1997) determined that males of both species reacted to attractive females with longer contact times compared with that for unattractive or solvent-washed females. The response was species specific, and when pentane extracts were partitioned between pentane and methanol, most of the activity was found in the methanol fraction. The methanol fractions contained fatty acids and their methyl esters and showed quantitative differences between the two physiological states of the females with respect to myristic acid, methyl palmitate,... 

Eight binary systems are reported. Six include cholesterol as one component of the mixed film. The second components in these six films were myristic acid, methyl palmitate, ethyl palmitate, 1,2-dimyristin, 1,2-dimyristoyl-3-lecithin, and l,2-didecanoyl-3-lecithin. In addition, the systems trilaurin-dimyristoyl lecithin and triolein-dimyristoyl lecithin... 

Fujiwara et al. studied the precipitation phase boundary diagrams of the sodium salts of a-sulfonated myristic and palmitic acid methyl esters in the presence of calcium ions [61]. The time dependency of the precipitation showed that the calcium salts have an extremely slow crystallization rate at room temperatures. This is the reason for the good hardness tolerance of the a-sulfonated fatty acid methyl esters. 

A soap-based powder can be produced in combination with ester sulfonates. Thirty-five percent of a sodium soap mixture (5% lauric acid, 5% myristic acid, 52% palmitic acid, 21% stearic acid, 12% oleic acid, and 5% linoleic acid) is mixed with 15% sodium a-sulfo palm oil fatty acid methyl ester, 3% lauric acid ethoxylate, 5% sodium silicate, 17% sodium carbonate, 20% Na2S04- 10H2O, and 5% water [79]. 

Myristic and palmitic acids can be obtained from their esters by the procedure in Org. Syn. Coll. Vol. 1, 371. From roo g. of methyl myristate is obtained 85-89 g. (90-95 per cent of the theoretical amount) of colorless myristic acid melting at 52-53°. From 100 g. of methyl palmitate is obtained 84-88 g. (90-95 per cent of the theoretical amount) of colorless palmitic acid melting at 62-63°. 

The basic fish oil (27) also included a generous amount of saturated fatty acids. As can be seen from Figure 5 and Table 1, the saturated fatty acids are dominated by the 16 0 (palmitic acid), usually accompanied by about half as much or less of 14 0 (myristic acid) and much less of 18 0 (stearic acid). Usually the saturated fatty acid totals are at least 20%, especially as the odd chain (15 0, 17 0) and methyl-branched (iso, anteiso, pristanic, phytanic) fatty acids (compare Figure 4) are sam-rated and will total around 2-3%. An unsaturated peak that is often observed is 17 ln-8, which is roughly equal to 17 0. The details of these peaks are discussed in other publications, but those researchers attempting modern open-tubular gas chromatography analyses should be aware of their presence and influence on peak identification and quantitation. As can be seen from Figure 6, there is an... 

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. 

Lockemann CA, Schliinder EU. High-pressure mass transfer coefficients in the liquid phase of the binary systems carbon dioxide-methyl myristate and carbon dioxide-methyl palmitate. Chem Eng Proc 1996 35 121-129. 

Substitution of a methyl group at the a-methylene carbon of methyl esters of laurate, myristate, and palmitate results in characteristic infrared spectra that readily distinguish them from the straight-chain homologs and facilitate their unequivocal identification when separated from complex lipid mixtures by gas-liquid partition chromatography (Napier, 1966). Spectral changes observed with the methyl esters are also evident in the cholesterol esters of 2-methylalkanoates and also serve in their identification. 

The synthesis of a novel cyclopropyl analog of arachidonic acid [7] via a convergent synthesis that employed methyl (lR,25)-2-formylcyclopropane-carboxylate in conjunction with the ylide from (3Z,6Z)-pentadeca-3,6-dienyl(triphenyl)-phosphonium iodide was reported (62). A new approach to cyclopropene fatty acids has been developed for the synthesis of methyl sterculate [8] and methyl 2-hydroxy-sterculate this involves the 1,2-deiodination of 1,2-diiodocyclopropanes with butyllithium at low temperature (63). The synthesis of deuterated cyclopropene fatty esters structurally related to palmitic and myristic acids has been reported (64). 

While it is believed that solute-solute interactions are not as large as solute-solvent interactions, there is clear evidence that some type of solute-solute interaction is present in SCF/high molecular mass systems. Lockemann [49] studied the phase behaviour of the ternary system C02/methyl myristate/methyl palmitate and found that these two components can be separated using SC CO2. However, the separation factor, which dictates the degree or difficulty of separation, is dependent on the composition of the feed to be separated and the operating pressure and temperature. They found that while the composition does not significantly affect the separation factor, better separation can be achieved at lower composition of the component to be extracted. 

Pyka and Bober separated methyl laureate, methyl myristate, methyl palmitate, methyl isostearate, methyl stearate, and methyl arachidate by RP-HPTLC on... 

Preparation of the Time Index Standard Mixture (FAMEs) Methyl caprylate, methyl pelargo-nate, methyl caprate, methyl laurate, methyl myristate, methyl palmitate, methyl stearate, methyl eicosanoate, methyl docosanoate, lignoceric acid methyl ester, methyl hexaco-sanoate, methyl octacosanoate, and triaconta-noic acid methylester. Alternatively, alkanes or fatty acids may also be used. The final concentration of each compound in the mixture should be between 0.4 and 0.8 mg/mL of chloroform. 

Certain saturated and unsaturated compounds migrate together in TLC on layers which have been rendered hydrophobic this is as found in other partition procedures such as liquid-liqtdd counter-current distribution and partition chromatography in columns or on impregnated paper. Thus, as seen from Fig. 148, methyl palmitate (C g, saturated) and methyl oleate (C g, monoolefine) appear together in one spot as do methyl myristate (Cj4, saturated) and methyl linoleate (Cjg, diolefine). Such critical pairs are likewise formed by the corresponding free acids or aldehydes and also by tripalmitin/triolein and trimyristin/trilinolein [78]. 

Column chromatography on silicic acid has also been used to isolate polar fatty acid esters, and as examples, methyl 9- and 13-hydroxy-stearate [224] and the acetate derivatives of methyl 9,10-dihydroxy-myristate and 9,10-dihydroxy-palmitate [178] have been resolved by this technique. A small-scale column procedure, with Florisil as adsorbent, has been described for separating normal from 2-hydroxy fatty acid esters, i.e. the component fatty acids of sphingoglycolipids [122]. 

Contains up to 1% (normally about 0.3%) of a viscous volatile oil, about half of which is composed of fatty acids, with palmitic, lino-leic, myristic, and linolenic acids predominant. Aromatic constituents present include terpenes, thymol, thymol methyl ether, 4-hydroxy-thymol dimethyl ether, and isobutyric... 

Schlunder, E.-U. and Lockemann, C.A. (1995) Liquid-phase viscosities of the binary systems carbon dioxide-oleic acid, carbon dioxide-methyl myristate, and carbon dioxide-methyl palmitate at high pressure. Chem. Eng. Process., 34, 487-493. 

Nystrom and co-workers (1959) applied the Wilzbach technique to H labeling of methyl esters of saturated fatty acids, and the anticipated substitution of hydrogen by tritium occurred. In this procedure, gram amounts of methyl esters of palmitic and stearic acids were exposed to 1 Ci of H2 at room temperature. The fatty acid esters were deposited as thin layers by solvent evaporation on the inside wall of 1- X 10-inch reaction tubes. Methyl laurate and methyl myristate, being liquid at room temperature, required sealed ampules equipped with break seals the ampules were rotated to provide a continuously renewed thin film during their exposure to 5 Ci of tritium gas. Purification of the tritiated methyl esters includes saponification and extraction of the free acid with diethyl ether. 

Chem. Descrip. Methyl laurate (49%), methyl myristate (18%), methyl caprylate (10%), methyl palmitate (8%), methyl oleate-stearate (8%), methyl caprate (7%) Uses Lubricant for metalworking, textiles, and agric. applies., cutting fluids and drawing compds., drawing lubricants in aluminum beverage cans solvent, cosolvent, crop oil, or carrier oil In agric. applies. 

TLC spots with marker reveal the presence of free fatty acids (FFA), diglyceride (DG), monoglyceride (MG) but negligible amount of TG. GCMS of fatty acid— methyl esters (FAME) from lion mane presented evidence for fatty acids ranging from C9-C24 (Figs. 5.3- 5.6). Low volatility molecules like nonanedioic acid (Fig. 5.3), tridecanoic acid (Fig. 5.4), 12-methyl tridecanoic acid were also present in lion hair lipids. In addition fatty acids such as myristic, pentadecanoic, palmitic, heptanoic, stearic and octadecenoic acids (Fig. 5.5) have also been detected. Erucic... 

Parrish (1977) reviewed the research and development of lactose ester-type surfactants carried out by Scholnick and his colleagues (Scholnick et al. 1974, 1975 Scholnick and Linfield 1977). Their initial attempts to form lactose esters followed the same transesterification procedures that had been used with sucrose (a fatty acid methyl ester in N,N-dimethylformamide with potassium carbonate as the catalyst). Their successful approach was the reaction of lactose in N-methyl-2-pyrrolidone as the solvent with fatty acid chlorides, resulting in yields of 88 to 95% for esters of lauric, myristic, palmitic, stearic, oleic, and tallow fatty acids. The principal product was the monoester, which is important for detergent use, since diesters and higher esters of lactose are not water soluble. 

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