Myristic acid, synthesis

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) ... 

MYRISTIC ACID. [CAS 544-63-8]. Also called tetradecanoic acid, formula CHjlCHiJnCOOH, At room temperature, it is an oily, white crystalline solid. Soluble in alcohol and ether insoluble in water. Specific gravity 0.8739 (80°C) mp 54.4°C bp 326.2°C. Combustible. The acid is derived by the fractional distillation of coconut oil. Myristic ucid is used in soaps cosmetics in the synthesis of esters for flavorings and perfumes and as a component of food-grade additives, Myristic acid is a constituent of several vegetable oils. See also Vegetable Oils (Edible). 

Following the study of the simple coupling of radicals derived from the salt of a single carboxylic acid, it was found that the electrolysis of a mixture of carboxylate anions or of the salts of half esters of dicarboxylic acids increased the synthetic value of the method. This arises from the possibility of the formation of symmetrical and unsymmetrical coupled products of the derived radicals. These anodic syntheses are illustrated in the synthesis of hexacosane (Expt 5.11), sebacic acid (decanedioic acid), octadecanedioic acid and myristic acid (tetra-decanoic acid), in Expt 5.131. 

Jallon, 1984). The HC polymorphism between populations of this species was mapped to the desat locus (Coyne et al., 1999), which contains two A9-desaturase genes, desatl and desat2, located in tandem. We found that desat2 is not expressed at all in Canton-S (7,11-HC strain), but is expressed in Tai females (5,9-HC strain) (Dallerac et al., 2000). Desat2 desaturates myristic acid (C14 0) to myristoleic acid (A9 C14 1), leading to the synthesis of 5,9-HC in Tai females. A deficiency of 16 nucleotides present in 7,11-HC flies is responsible for the lack of desat2 transcription in these females (Takahashi et al., 2001). 

The activities of the immobilized lipase components in ester synthesis have also been tested. Myristic acid was esterified with propanol, isopropanol, and oleic alcohol, respectively (Table X). 

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). 

Gosalbo, L., M. Barrot, G. Fahrias, G. ArsequeU, and F. Camps, Synthesis of Deuterated Cyclopropene Fatty Esters Structurally Related to Palmitic and Myristic Acids, Lipids 28 1125-1130 (1993). 

Several studies have examined the effects of PA supplementation on milk FA profile. Grummer (1991) demonstrated that de novo FA synthesis decreased linearly as supplementation of dietary fat increased, and that the changes in stearic acid and PA were dependent on the ratio in the added fat. Steele and Moore (1968) reported reductions in yield and concentration of short and medium-chain FAs (from butyric to myristic acids) and dramatic increases in PA with increased dietary intake of PA the concentration of PA in milk increased from 38.7% of total FA in controls to 60.7% of total FA in cows supplemented with PA. Noble et al. (1969) reported similar changes in milk FAs when diet was supplemented with PA at 10%, they foimd that short- and medium-chain FAs decreased when compared with a no-fat control, while milk PA increased from 36.4% of total FA in controls to 49.8% of total FA in PA-treated cows. Banks et al. (1976) also observed decreases in short- and medium-chain FAs in milk, with increases observed in concentrations of PA, palmitoleic, and oleic acids. Using duodenal infusions of 500 g of PA, Enjalbert et al. (2000) reported that concentrations of PA in milk increased 30% compared with controls. Mosley et al. (2007) determined the optimmn feeding level of a by-product rich in PA (86.6%) on dry matter intake, milk yield, milk components, and milk FA profile in dairy cattle. They formd that milk FA concentrations were affected by the addition of this by-product. As the intake of PA increased with the supplemented diets, milk PA concentrations increased. When 1.5 kg/d of this by-product was consumed, milk PA concentration increased by 50% compared with the... 

There is also a link between PA and myristic acid (14 0) and insulin synthesis. These SFA (in particular PA) have been demonstrated to stimulate P-cells in panereas. When SFA content in pancreatic islets increases, nitrie oxide and ceramide are synthesized. A link between serum ceramides, IR and inflammation is related to the inflammatory marker IL-6 [87]. As a consequence increased oxidative stress, inflammation and endoplasmic reticulmn stress are occurred, that lead to P-cell apoptosis [88]. At the same time, insulin gene expression is inhibited [89]... 

The increase in the saturated fatty acids (myristic and palmitic) found in lean and myristic acid in subcutaneous fat are very likely due to the inhibition of stearoyl-CoA desaturase activity, a key enzyme involved in the synthesis of monounsaturated fatty acids (MUFA) by CLA. Studies by Lee el al. (22) and Bretillon el al. (23) demonstrated that CLA isomers inhibited A9 desaturase activity, and thus this inhibition caused an inaease in the saturated fatty add content. Changes in the unsaturated fatty acid profile of subcutaneous fat could result from the increase of 18 1 and 18 2 due to the contribution of CLA 60 in the diet. CLA 60 was substituted for com in the study by Thiel-Cooper el al. (3) therefore, because CLA 60 contains high concentrations of unsaturated fatty acids, the diet would be higher in unsaturated fatty acids than a com diet alone, hi earlier work, Banni el al. (24) and Sdbedio el al. (25) suggested that... 

---