Tetradecanoic acid, fatty acids

The production of fatty acid-capped silver nanoparticles by a heating method has been reported [115]. Heating of the silver salts of fatty acids (tetradecanoic, stearic, and oleic) under a nitrogen atmosphere at 250°C resulted in the formation of 5-20-nm-diameter silver particles. Monolayers of the capped particles were spread from toluene and transferred onto TEM grids. An ordered two-dimensional array of particles was observed. The oleic acid-capped particle arrays had some void regions not present for the other two fatty acids. 

Isoprenoid fatty acids (4,8,12 trimethyl tetradecanoic acid and phytanic acid), acids with 16, 18 and 20 carbon atoms Heated marine lipids [42,43]... 

In total, 185 substances were found in the wing-sac liquid of male S. bilineata from a Costa Rican population. For a more detailed analysis the relative peak area of thirteen focus compounds was compared (Table 14.1). Of these nine were male-specific substances (indole, indol-3-carboxaldehyde, indole-3-carboxylic acid, 2-aminoacetophenon, anthranilic acid, SHJOH-dipyrrolofl -aT -dJpyrazine-5,10-dione (pyrocoll), indolo[2,l-b]quinazoline-6,12-dione (tryptanthrin), 2,6,10-trimethyl-3-oxo-6,10-dodecadienolide, and a compound C15H24O2 of unknown structure), three were fatty acids (tetradecanoic acid, hexadecanoic acid, and octadecanoic acid), and one a steroid (cholesterol). On average, the cumulative peak area of these substances made up 62.5 20.7% of the whole chromatogram area. 

The traditional major source for the nonionic surfactant industry is fatty acid triglycerides from both animal and vegetable sources as the saturated or unsaturated acids. The saturated acids include lauric acid (w-dodecanoic), myristic acid (n-tetradecanoic), palmitic acid ( -hexadecanoic),and stearic acid (n-octadecanoic). The unsaturated acids include oleic acid (Z-9-octadecenoic) and linoleic acid (Z,Z-9,12-octadecadienoic). Of the 200 non-ionic surfactants... 

Despite the large variety of potential fatty acid components in natural-occurring phosphodiglycerides, only three major fatty acid derivatives of synthetic phospholipids are commonly used in liposome preparation (1) myristic acid (w-tetradecanoic acid containing 14 carbons), (2) palmitic acid (w-hexadecanoic acid containing 16 carbons), and (3) stearic acid (w-octadccanoic acid containing 18 carbons) (Fig. 334). 

Total fatty acids were liberated by subjecting Salmonella minnesota Re lipopolysaccharide (or free lipid A) to acidic (4 N HC1, 5 h, 100°C) followed by alkaline (1 N NaOH, 1 h, 100°C) hydrolysis. After extraction (chloroform), the free fatty acids were converted into their methyl esters (diazomethane) and analysed by combined gas-liquid chromatography/mass spectrometry. Alternatively, the fatty acids of lipid A are transesterified by treatment of lipopolysaccharide with methanolic HC1 (2 N HC1 in water-free CHaOH, 18 h, 85°C). By these procedures the following fatty acids were identified (in approximate amounts relative to 2 moles glucosamine) dodecanoic (12 0, 1.1 mole), tetradecanoic (14 0, 0.8 mole), hexadecanoic (16 0, 0.9 mole), 2-hydroxytetradecanoic (2-OH-l4 0, 0.1 mole), and 3-hydroxytetradecanoic acid (3-OH-14 0, 4 moles). In total, therefore, approximately 7 moles of fatty acids are present per mole of lipid A backbone. The stereochemistry of the hydroxylated fatty acids was determined by gas-liquid chromatography of their diastereomeric methoxyacyl-L-phenylethylamide derivatives (24). It was found that 2-hydroxyte-tradecanoic acid possesses the-Ts), and the predominating 3-hydroxytetradecanoic acid the (R) configuration. 

Therefore, of the 2 moles of ester-bound 3-OH-14 0 one is 3-0-acylated by tetradecanoic acid the other should carry a free 3-hydroxyl group. This latter assumption was proven to be correct by the following experiment. Lipid A was treated with t-butyldimethylsilylchloride, ester-bound fatty acids were trans-esterified by NaOCH3 and analysed by gas-liquid chromatography. Besides the other expected fatty acid methyl esters (12 0, 16 0, 3-OCH3-14 0) approximately 1 mole (per 2 moles glucosamine) of the t-butyldimethylsilylether of 3-hydroxytetradecanoic acid me-thylester could be identified (26). 

Quantitative changes in lipid compounds on the silk and cuticle of females correlate significantly with changes in female sexual receptivity in spiders. For example, female T. atrica attach a contact sex pheromone to their web (Trabalon et al., 1997,2005 Prouvost et al., 1999). This pheromone consists of a complex mixture of saturated hydrocarbons, methyl esters (methyl tetradecanoate, methyl pentadecanoate, methyl hexadecanoate, and methyl octadecanoate) and their fatty acids (tetradecanoic, pentadecanoic, hexadecanoic, and cis,cis-9,12-octadecadienoic acids). The female uses cuticular compounds, which are applied to the silk in substantial amounts during web construction. Modification of chemical profiles makes the female attractive to males (Trabalon et al., 2005). Receptive females are different to unreceptive ones with respect to three fatty acids (hexadecanoic, octadeca-dienoic and octadecenoic acids) and three methyl esters (linoleate, oleate, and stearate) present on both the web and the cuticle. Our combined results from chemical analyses and behavioral assays demonstrate clearly that these contact compounds are quantitatively correlated with the behavior of spiders. 

The composition of essential oil extracted using SC-C02 has been compared with that of steam-distilled oil by GC-MS (Gopalan et al., 2000b). Out of the 21 components identified, ar-turmerone and turmerone constituted about 60% of the total oil. Analysis of the cyclohexane extract of turmeric by GC-MS coupled with Pseudo Sadtler retention indices reveals a series of saturated and unsaturated fatty acids, along with sesquiterpenes. The fatty acids reported are tetradecanoic... 

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. 

The saturated fatty acid tetradecanoic acid (also known as myristic acid) is manufactured commercially from coconut oil by base-catalysed hydrolysis. You may be surprised to learn that coconut oil contains more saturated fat than butter, lard, or beef dripping much of it is the trimyristate ester of glycerol. Hydrolysis with aqueous sodium hydroxide, followed by reprotonation of the sodium carboxylate salt with acid, gives myristic acid. Notice how much longer it takes to hydrolyse this branched ester than it did to hydrolyse a methyl ester (p. 291). 

Fig. 45.—Decomposition to glucose by alpha amylase of complexes of starch with various fatty acids given as the function of time. 1, behenic acid 2, arachic acid 3, octadecanoic acid 4, hexadecanoic acid tetradecanoic acid decanoic acid 7, hexoctanoic acid 8, pure amylose. (By permission from Acker and Brauner-Glaesner.746)...

Fig. 56.—Water solubility of tapioca starch and chemically modified starch extruded without and with 2% addition of fatty acids. C2, acetic acid C 2, dodecanoic acid C 4, tetradecanoic acid C,A, hexadecanoic acid C18, octadecanoic acid C18 i, oleic acid C 8 2, linoleic acid CaSL, calcium octadecanoyl lactate GMS glyceryl monooctadecanoate GMP, glyceryl mono-hexadecanoate Am, Amidan and Dm, Dimodan (mixtures of GMS and GMP). (Reprinted with permission of C. Mercier, R. Charbonniere, J. Grebaut, and J. F. de la Gueriviere, Cereal Chem., 57 (1980) 4-9.)...

It is evident from stability-constant measurements that the monoglyceride of tetradecanoic acid forms the most stable complex. Enthalpies of melting of the complex increase proportionally with the length of the carbon chain of the fatty acid residue. Binding parameters (Table LII)717 show that the complexes are weak and they can be readily decomposed by other competing agents. As shown by Kim and Hill,863 cyclomaltoheptaose forms binary complexes with lysolecithin and ternary complexes with lysolecithin and amylose. The complex of lysolecithin with amylose is disrupted by cyclomaltoheptaose. 

The list of compounds given in Table 7.13.1 contain some long chain fatty acids (tetradecanoic acid, pentadecanoic acid, hexadecanoic acid) that probably are not generated from chitin itself but from associated materials present in the chitin sample (chitin purification is difficult due to its insolubility). The main pyrolysis mechanism seems to be similar to that of cellulose. 1,6-Anhydro-2-acetamido-2-deoxyglucose seems to be a major component in the pyrolysate as are further dehydrated hexosamines. 

A series of ethyl esters of fatty acids, from butanoate to tetradecanoate, were identified in the EMB. Two esters, ethyl oc-tanoate and ethyl nonanoate, were found in Romano cheese. Esters are important flavor compounds in cheeses however, a high concentration of esters may cause a "fruity" defect in cheese flavor, y- and 6-dodecalactone were identified in the EMB sample as well as in Romano cheese. Lactones are well distributed in food flavors. 

Under ideal conditions the C10 —C14 fatty acids were converted, palladium-catalysed, to 100% the isolated yields of 9-oxo-decanoic, 10-oxo-undecanoic and 13-oxo-tetradecanoic acid methylester were about 70%. RhCl3/FeCl3 as catalyst was more selective but the yields were lower. 

Calculate the number of ATP molecules produced by complete p-oxidation of the fourteen-carbon saturated fatty acid tetradecanoic acid (common name myristic acid). 

Dodecanoic and tetradecanoic acids are almost odorless when purified. The flavor is fatty, weak for (E.ll) (Chemisis, 1998). 

Isopropyl Myrlstate. Tetradecanoic add l-meth-ylethyl ester. C,7H,4( >, mol wt 270.44. C 75.50%, H 12.67%, O 11,83%, CH,(CHj),jCOOCH(CHj)2. The commercial product usually appears as a mixture of myris-tate with small amounts of esters of palmitic and other satd fatty acids. Physical properties Bonhorst et al, Ind. Eng. Chem. 40, 2379 (1948). 

---