Perfluorinated fatty acids

Table 2 Physical/chemical properties of select perfluorinated fatty acids...

Jones, P. D., Hu, W., De Coen, W. Binding of perfluorinated fatty acids to serum proteins. Environ. Toxicol Chem., 22 2639-2649 (2003). 

Ikeda, T., Aiba, K., Fukuda, K., Tanaka, M. The induction of peroxisome proliferation in rat liver by perfluorinated fatty acids, metabolically inhert derivatives of fatty acids. J. Biochem., 98 475 82 (1985). 

Intrasuksri, U., Feller, D. R. Comparison of the effects of selected monocarboxyUc, dicarboxylic and perfluorinated fatty acids on peroxisome proliferation in primary cultured rat hepatocytes. Biochem. Pharm., 42 184-188 (1991). 

Upham, B. L., Deocamp, N. D., Wurl, B., Troskp, J. E. Inhibition of gap junction intercellular communication by perfluorinated fatty acids is dependent on the chain length of the fluorinated tail. Int. J. Cancer, 78 491 95 (1998). 

Several studies have used NMR spectroscopy to determine the number and identity of drug metabolites in bile. These include the use of NMR spectroscopy to study doxifluridine catabolites in human bile, and C NMR spectroscopy of perfluorinated fatty acids in rat bile and NMR for monitoring the formation of formaldehyde from demethylation of antipyrine. NMR spectroscopy of rat bile has been used to monitor the excretion of paracetamol metabolites. A combination of H and H- - C 2D NMR methods has allowed identification of 4-cyano-A,N-dimethylaniline, cefoperazone and benzyl chloride in rat bile. ... 

Vanden Heuvel, J. P., Thompson, J. T., Frame, S. R., and Gillies, P. J. (2006). Differential activation of nuclear receptors by perfluorinated fatty acid analogs and natural fatty acids a comparison of human, mouse, and rat peroxisome proliferator-activated receptor-alpha, -beta, and -gamma, liver X receptor-beta, and retinoid X receptor-alpha. Toxicol Sci 92, 476-489. 

Based on lysine as before, single chain derivatives (18) and bicatenar compounds (19) have been prepared by a strategy the inverse of that described earlier [46]. The products (18 and 19) are obtained with higher overall yields than 17. As before, no protection or deprotection steps are needed in this case [46,47]. The synthesis consists of a reaction between two moduU prepared beforehand, one representing the polar head group in the final product and the other the junction modulus. The preparation of this intermediate starts from aldoses or acids derived Irom them that are coupled with lysine in its basic form (Scheme 15). The yields for this step are quantitative. A subsequent amidation reaction with a hydrogenated or perfluorinated fatty acid (Scheme 16) leads to the monosubstituted compounds (18). Esterification of the free acid function of lysine (Scheme 17) yields in a final step the bicatenar structures (19). 

Fluorinated surfactants. Cg-Cg perfluorinated fatty acids, analyzed as their methyl esters, require a thick-film colunrn in order to show adequate retention time. The C4 compounds are too volatile for analysis without applying external cooling (37). 

Some special esters of isohexides (prepared conventionally, however) have been described, including diesters of several long-chain fatty acids121,122 and dicarboxylic acids,123 isomannide-mono-oleate,124 isosorbide dinicotin-ate,125 and perfluorinated long-chain fatty acid diesters of isosorbide and isomannide.126 Bis(chloroformate)s of isosorbide and isomannide, and the... 

An important number of esters of long-chain alcohols and amino acids have been described in the literature. The permethylation of the amino function (Scheme 7) leads to the ammonium salts (7) showing generally interesting surfactant properties [30], We have chosen a similar pathway by reacting a perfluorinated fatty alcohol with chloroacetic acid the subsequent substitution of the chlorine atom by trimethylamine leads to the corresponding ammonium salt (8) [31]. The latter is water soluble, but the hydrolysis of the ester function is rather rapid (<6 h), which renders this type of compound less interesting for possible applications. 

Emulsifiers such as fatty alcohol sulfates, alkane sulfonates, alkali salts of fatty acids, and others have been found to be slightly to marginally effective. Fluorinated surfactants, particularly perfluorinated carboxylic acids containing seven or eight fluorine atoms, have been especially effective in maintaining a high rate of polymerization after about 40% conversion. Fluorinated surfactants are characterized by low values of critical concentration of micelle formation, They are thermally and chemically stable, and their incorporation does not impair the polyvinyl fluoride properties. 

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