Of myristic acid

An excellent synthesis of myristic acid is thus achieved from readily accessible starting materials. An alternative synthesis of myristic acid utilises hexanoic acid (M-caproic acid n-hexoic acid) (X) (2 mols) and methyl hydrogen sebacate (XI) (1 mol) the products, after hydrolysis, are Ji-decane (XII), myristic acid (XIII) and hexadecane-1 16-dlcarboxylic acid (XIV) ... 

Reflux a mixture of 7 3 g. of methyl myristate with a solution of 4 8 g. of sodium hydroxide in 200 ml. of 90 per cent, methanol for 2 hours, distil off the methanol on a water bath, dissolve the residue in 400 ml. of hot water, add 15 ml. of concentrated hydrochloric acid to the solution at 50° in order to precipitate the organic acid, and cool. Collect the acid by suction filtration, wash it with a little water and dry in a vacuum desiccator. The yield of myristic acid (tetradecanoic acid tetradecoic acid), m.p. 57-58°, is 5 9 g. 

Orris. Orris is produced from rhi2omes of Ins pallida and Ins germanica. The plants are found and cultivated mosdy ia Italy, but also ia Morocco and China. It is used ia perfumery as an absolute, a steam-distilled essential oil, and a concrete. The last material, which is a low melting soHd (due to a high content of myristic acid) and therefore erroneously called a concrete, is by far the most used. Orris has a violet-like odor useful ia fine perfumes, luxury soaps, and fragrances for powders and other cosmetic products. Its most important odor contributors are the irones, of which the most important isomer... 

Endothelial NOS was found to be associated with cell membranes and this property was associated with the finding that the cDNA contained the structure for binding myristic acid55. Busconi and Michel56 used bovine aortic endothelial cells to demonstrate that the myristoylated protein was found. When the second amino acid, glycine, was converted to alanine, the addition of myristic acid was prevented and the enzyme remained soluble. Sessa and coworkers51 carried out the same experiments simultaneously and found the same results. However, in both cases the enzyme was not purified, although the protein... 

The apparent similarity of the F, A curves of myristic acid to the F, V curves for an easily liquefiable gas such as carbon dioxide has led Adam to suggest that the molecules in the expanded films of these substances are in a similat state to those of say carbon dioxide in the vapour state. He adduces as further argument in support of this hypothesis, the much greater coefficient of compression of expanded films. Again it is evident that the molecules are not lying down flat in the expanded state, for the increased area even under low compressions is only 50 A., whilst for stearic acid of length 21 A. and of cross-section 5 2 A. a horizontal molecule would occupy at least 109 A. of area at the same time the area per molecule decreases somewhat as the length of the hydrocarbon chain increases. 

Inflvsnce of temperature on time required to cover an area of 56 9 sq. cm. of water with a unimolecular film under zero compression of myristic acid. Length ofwaier acid interface 0 251 cm. 

The extract produced an inhibition of 5-aRl and 5-aR2 activities in the presence of free fatty (oleic, lauric, linoleic, and myris-tic) acids only. Esterified fatty acids, alcohols, and sterols assayed were inactive. A specificity of the fatty acids in 5-aRl or 5-aR2 inhibition has been found. Palmitic and stearic acids were inactive on the two isoforms. Lauric acid was active on 5-aRl (lC5o= 17 + 3 iig/mL) and5-aR2 (lC5o= 19 + 9 p,g/mL). The inhibitory activity of myristic acid was evaluated on 5-aR2 only and found active on this isoform (IC50 = 4 2 p,g/mL) ° . LSESr markedly inhibited both isozymes (Kj [type 1] = 8.4 nM and 7.2 p,g/mL, respectively Kj [type 2] = 7.4 nM and 4.9 iig/mL, respectively). Results indicated that LSESr displayed non-competitive inhibition of the type 1 isozyme and uncompetitive inhibition of the type 2 isozyme . 

The myristoyl moiety attached to VP4 is observed in the poliovirus structures. This moiety is in close association with the cylinder formed by VP3 [19]. In HRVs, density consistent with the myristoyl moiety is also seen near the P cylinder [25]. In the HRVs, structural disorder of the first 25-28 N-terminal residues of VP4 obscures the connection between VP4 and the myristoyl group. The addition of myristic acid to protein is seen in many viral and cellular... 

Myristic acid (from decanoic acid and methyl hydrogen adipate). Dissolve 55-2 g. of pure decanoic acid (capric acid decoic acid), m.p. 31-32°, and 25 -6 g. of methyl hydrogen adipate in 200 ml. of absolute methanol to which 0-25 g. of sodium has been added. Electrolyse at 2-0 amps, at 25-35° until the pH of the electrolyte is 8-2 (ca. 9 hours). Neutralise the contents of the electrolytic cell with acetic acid, distil off the methanol on a water bath, dissolve the residue in about 200 ml. of ether, wash with three 50 ml. portions of saturated sodium bicarbonate solution, and remove the ether on a water bath. Treat the residue with a solution of 8 0 g. of sodium hydroxide in 200 ml. of 80 per cent, methanol, reflux for 2 hours, and distil off the methanol on a water bath. Add about 600 ml. of water to the residue to dissolve the mixture of sodium salts extract the hydrocarbon with four 50 ml. portions of ether, and dry the combined ethereal extracts with anhydrous magnesium sulphate. After removal of the ether, 23-1 g. of almost pure n-octadecane, m.p. 23-24°, remains. Acidify the aqueous solution with concentrated hydrochloric acid (ca. 25 ml.), cool to 0°, filter off the mixture of acids, wash well with cold water and dry in a vacuum desiccator. The yield of the mixture of sebacic and myristic acids, m.p. 52-67°, is 26 g. Separate the mixture by extraction with six 50 ml. portions of almost boiling light petroleum, b.p. 40-60°. The residue (5 2 g.), m.p. 132°, is sebacic acid. Evaporation of the solvent gives 20 g. of myristic acid, m.p. 52-53° the m.p. is raised slightly upon recrystallisation from methanol. 

When metals are available, the laminae are stabilized by bonding forces as shown in studies on phospholipid-water systems59. Even films of myristic acid and metal ions are solid up to a cross-section area of 50 A per molecule60,61. The numerous phase transitions of pure phospholipid-water systems62 and the polymorphism of phospholipid crystals63 suggest that even pure phospholipid bilayers — in their true nature — do not represent stable lattice structures but require metal ions for coordina-tive purposes. 

Dumont et al. (1991) Batch Esterification of myristic acid with ethanol Lipase from Mucor miehei... 

Internal diffusional limitations are possible any time that a porous immobilized enzymatic preparation is used. Bernard et al. (1992) studied internal diffusional limitations in the esterification of myristic acid with ethanol, catalyzed by immobilized lipase from Mucor miehei (Lipozyme). No internal mass diffusion would exist if there was no change in the initial velocity of the reaction while the enzyme particle size was changed. Bernard found this was not the case, however, and the initial velocity decreased with increasing particle size. This corresponds to an efficiency of reaction decrease from 0.6 to 0.36 for a particle size increase from 180 pm to 480 pm. Using the Thiele modulus, they also determined that for a reaction efficiency of 90% a particle size of 30 pm would be necessary. While Bernard et al. found that their system was limited by internal diffusion, Steytler et al. (1991) found that when they investigated the effect of different sizes of glass bead, 1 mm and 3 mm, no change in reaction rate was observed. 

Bryant, M. L., Heuckeroth, R. O., Kimata, J. T., Ratner, L., and Gordon, J. I. 1989. Replication of human immunodeficiency virus 1 and Moloney murine leukemia virus is inhibited by different heteroatom-containing analogs of myristic acid. Proc. Natl. Acad. Sci. USA 86 8655-8659. 

Parang, K., Wiebe, L. I., Knaus, E. E., Huang, J. S., Tyrrell, D. L., and Csizmadia, F. 1997. In vitro antiviral activities of myristic acid analogs against human immunodeficiency and hepatitis B viruses. Antiviral Res. 34 75-90. 

With the exception of sterols most membrane lipids are conformationally flexible molecules. The question arises whether the concept of conformational restriction can be extended from peptides to the field of sphingolipids. The observation that conformationally restricted derivatives of myristic acid have selective toxicity towards trypanosomes demonstrates that this strategy is also applicable... 

Prolonged storage of nutmeg oil leads to the loss of few volatile components and thereby changes in the oil composition. Sanford and Heinz (1971) observed that the content of myristic acid might serve as an indicator of the age of ground nutmeg. 

Palmitic and stearic acids are the major saturated fatty acid constituents of most animal and plant tissues. Much smaller amounts of other saturated fatty acids are present in most natural sources. Low concentrations of myristic acid (n-tetradecanoic acid 14 0) and lauric acid (n-dodecanoic acid 12 0) have been detected in certain tissues. 

Signs of elastic afterworking have been observed in a number of cases, though never so pronounced as in the above two. There seems to be a slight delay in reaching equilibrium in the films of myristic acid, especially in the transition region between the expanded and condensed states. A closer investigation of this phenomenon is needed. 

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