Dodecanoic acid, fatty acids

The transesterification of sucrose has been performed with a fatty acid ester of a volatile alcohol in the presence of an alkaline catalyst in a dipolar, aprotic solvent.142 The reaction of sucrose (293 mmoles) with methyl dodecanoate (293 mmoles) in A/,N-dimethylformamide in the presence of sodium methoxide in a pressure bomb for 8 h at 130° gave, after solvent extraction and crystallization, sucrose mono(dodecanoate) (m.p. 72-80° [a]D+52°) in 50% yield.142 Commercialization of these sucrose esters has so far been limited, in part because of the use of expensive solvents, and, in part, because solvent remaining in the product makes it unsuitable for use as a food emulsifier. In view of this situation, methods have been developed in which the use of toxic and expensive solvents has been avoided. 

A. T. James and A. J. P. Martin. Gas-Liquid Partition Chromatography The Separation and Micro-Estimation of Volatile Fatty Acids from Formic Acid to Dodecanoic Acid. Biochem. J., 50(1952) 679-690. 

Crooks et al. reported the transfer of amine-functionalized poly(amidoamine) dendrimers into toluene containing dodecanoic acid [198], The method is based on the formation of ion pairs between the fatty acids and the terminal amine-groups. These dendrimer-fatty acid complexes resemble unimolecular inverted micelles and could be used as phase transfer vehicles for the transport of Methyl Orange, an anionic dye molecule, into an organic medium. 

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... 

There are two general systems of nomenclature for fatty acids, as well as a few useful shorthand designations. Common names have their origins in history and are frequently used. Several examples are provided in table 18.1. Systematic names derive from the number of carbon atoms in the fatty acid for example, lauric acid is systematically known as dodecanoic acid. The parent hydrocarbon dodecane has 12 carbon atoms as does lauric acid. Several other examples are provided in table 18.1. 

As reported for all pentasaccharides from sweet potato (64, 86), pure compounds 232 and 233 were also submitted to sapoiufication yielding simonic acid B (87). The liberated fatty acids were identified as isobutyric, (25)-methyIbutanoic, -decanoic, -dodecanoic, and cinnamic acids. The site of lactonization by the aglycone in the macrocyclic unit was placed at C-2 of the second saccharide. The position of the ester linkage on the macrocyclic unit was C-2 of the terminal rhamnose. The acylations were identified as follows for the macrocyclic unit at C-2 of the third saccharide (n-dodecanoic acid), and at C-3 and C-4 of the branched... 

The prefix n- indicates the normal unbranched structure, For instance, dodecanoic simply indicates 12 carbon atoms, which could be arranged in a variety of branched forms n-dodecanoic specifies the linear, unbranched form, For unsaturated fatty acids, the configuration of each double bond is indicated in biological fatty acids the configuration is almost always cis. 

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. 

Another anionic surfactant is sodium dodecanoate, CnH23C02Na. It belongs to the class of sodium alkylcarboxylates, also called fatty acids or soaps. Just as with SDS in water at neutral pH, the alkali metal dissociates as a cation so that the surfactant becomes... 

Figure 12.22 gives the most common saturated fatty acids. The IUPAC names are given first. For dodecanoic acid, C12F12402, the parent chain has twelve carbons (do = 2 + deca = 10). The common names of the fatty acids are roughly derived from fats and oils that are rich in that fatty acid. For example, palm and palm kernel oils are rich in palmitic acid. Beef tallow is rich in stearic acid. Although stearic sounds a little bit like steers, it is derived from the Greek word for tallow. 

Dodecanoic acid 60, 73, 43 Dry, metallic, weak, fatty, waxy 10,000... 

This case study investigates the possibility of applying reactive distillation to the synthesis of fatty-acid esters as a generic multiproduct process. As representative species we consider the lauric (dodecanoic) acid and some alcohols the series Q-C8, such as methanol, n-propanol and 2-ethyl-hexanol (isooctanol). The generic reversible chemical reaction is ... 

James, A.T. and Martin, A.J.P. (1952) Gas-liquid partition chromatography the separation and microestimation of volatile fatty acids from formic acid to dodecanoic acid. Biochem. J., 50, 679-690. 

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 hydrogenation of fatty acids or fatty esters is of industrial importance for the production of fatty alcohols. Usually, the hydrogenation is performed in slurry-phase or fixed-bed reactors over copper-chromium oxide catalyst at elevated temperature and pressure.37 Rieke et al. investigated the hydrogenation of methyl dodecanoate over copper-chromium oxide at 280°C and 13.8 MPa H2, in order to study the side reactions that occur during hydrogenation.37 On the basis of the potential reaction routes described by Rieke et al., the pathways leading to C12 alcohol and various byproducts are summarized in Scheme 10.2, with exclusion of the formation and reactions of acetals. It has been found that both catalytic activity and selectivity correlated well with the crystallinity of the copper-chromium ox-... 

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.)...

The presence of medium chain fatty acids and glycerides in food products has stimulated interest in their potential utility as absorption enhancers. Some fatty acids and glycerides have been shown to increase drug absorption under a variety of conditions, almost always in animals and in most cases after rectal dosing. However, some studies have yielded positive results after oral dosing. Oral insulin bioavailability was increased to 9-13% relative to IM administration by a mixture of sodium dodecanoate and cetyl alcohol. Aftiraxone absorption was enhanced by glyceryl-1-monooctanoate after oral, duodenal, and rectal administration to animals. 

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