Vorkommen ungeradzahliger Fettsäuren in Organlipiden des Schweines in pränatalen und postnatalen Lebensphasen

Occurrence of Odd Number Fatty Acids in Organ Lipids of Pig in Prenatal and Postnatal Phases Numerous studies in recent years have rejected the view regarding the absence of odd number fatty acids in animal organism. Using improved analytical methods, 1-2% fatty acids having an odd number of carbon atoms have been found in various animal fats. The relative amount of odd number fatty acids in a few organ lipids in prenatal and postnatal phases are determined from the fatty acid composition, and the results are discussed.     

Alkylendiamide und Alkylendiisoimide von Äthyleniminocarbonsäuren und -dicarbonsäuren

Alkylenediamides and Alkylenediisoimides from Ethyleneimino Carboxylic Acids and Ethyleneimino Dicarboxylic Acids Preparation and properties of some alkylenediamides from β-ethyleneiminopropionic acid and ethyleneiminosuccinic acid as well as of two alkylenediisoimides of ethyleneiminosuccinic acid are described.     

Synthese von N-Maleoyl-aminosäuren und -peptiden

Synthesis of N-Maleoyl-aminoacids and -peptides N-Maleoyl-aminoacid-N′-hydroxysuccinimidesters 3 or N-maleoyl-aminobenzoic acids 5 are synthesized from N-maleyl-aminoacids 1 on different ways. N-maleoyl-aminobenzoic-4-nitro-phenyl-,-2-nitro-phenyl-or 2,4-dinitro-phenylesters 6 , 7 and 8 will be obtained from 1 or 5 . o-Mercapto-aniline, thiourea or cysteine react with 5 to benzothiazines 9 , thiazolidines 10 and 1,4-thiazines 11 . from 5 the peptides 12 are yielded. The pentapeptide 13 are formed from 12 by addition of glutathione.     

Produkte der Dimerisierung ungesättigter Fettsäuren III: Trennung dimerer Fettsäuren mittels GC und HPLC — Nachweis aliphatischer und verzweigter Dicarbonsäuren

Products of the Dimerisation of Unsaturated Fatty Acids III: Separation of Dimeric Fatty Acids with the Aid of GC and HPLC — Identification of Branched Aliphatic Dicarboxylic Acids From dimers produced by dimerisation of pure oleic acid we obtain by freezing small amounts of compounds, which can be separated further by GC. The separated compounds are isomers with a molecular weight of 594. They are saturated branched aliphatic dicarboxylic acid esters. They are obviously produced by en-reaction followed by hydrogenation. A much more effective separation than by GC is possible by HPLC, using a detector based on light scattering. Thus the dimeric fatty esters can be separated into four fractions: the first fraction consists of aromatics, the second obviously of alicyclic and unsaturated dicarboxylic acids, the third and fourth consist of aliphatic dicarboxylic acid esters of MW 594. Fatty acids obtained by dimerisation of a starting material rich in linoleic acid contain large amounts of aromatic compounds, those which are obtained by dimerisation of starting material rich in oleic acid contain rather high amounts of aliphatic dicarboxylic acids and practically no aromatic compounds.     

Regioselektive C-H-Funktionalisierung von Fettsäuren und Fettsäuremethylestern

Regioselective C-H-Functionalization of Fatty Acids and their Methyl Esters Fatty acids and thier methyl esters can be chlorinated preferentially at the terminal methylene groups with N-alkylchloroamines in sulfuric acid. With capric acid and its methyl ester the optimal reaction conditions for the selective chlorination were elaborated and then transferred to longer fatty acids up to stearic acid. The influence of the solvent, the temperature and the nature of different chlorinating reagents on the selectivity was studies. The capillary GC/MS-analysis of the isomeric chlorinated fatty acids is described.     

Darstellung neuer substituierter 1,2,4-Triazin-6-carbonsäuren und 1,2,4-Triazin-6-yl-alkancarbonsäuren

Synthesis of New Substituted as-Triazine-6-carboxylic Acids and as-Triazine-6-yl-alkanoic Acids New substituted 3-amino-, 5-amino- and 3,5-diamino-as-triazine-6-carboxylic acids 4a , b , 5a , b and 6 were obtained by the hydrolysis 6-azalumazine derivatives 3a – e . Corresponding acids of the structure 10a – d , 11a , b and 12 were synthesized from 5-chlor-3-methylthio-astriazine-6-carboxylic-ester 8 . The synthesis of new 3-alkylthioderivatives of as-triazine-6-yl-acetic acid 16a – c and -propionic acid 18 and its hydrolysis to 3,5-dioxotetrahydro-as-triazine-6-yl-propionic acid 19 is reported.     

Übergangsmetallkatalysierte Oxidationen ungesättigter Fettsäuren — Synthesen von Keto- und Dicarbonsäuren

Transition-metal Catalyzed Oxidation of Unsaturated Fatty Acids — Synthesis of Ketocarboxylic Acids and Dicarboxylic Acids Terminal unsaturated C₁₀–C₁₄-fatty acid methylesters (9-decenoic-, 10-un-decenoic-, 13-tetradecenoic methylesters) were converted to methylketocarboxylic methylesters (yields: 60–75%, isolated) by oxidation with O₂/H₂O at roomtemperature under catalysis of PdCl₂/CuCl₂. Using RhCl₃/FeCl₃ at 80°C yields of 40–60% were obtained. For the first time methyl oleate was converted directly to a mixture of 9-oxo- and 10-oxo-stearic acid methylester by palladium catalyzed oxidation. In DMF/H₂O the selectivity to these two ketoesters was 85% (15% isomers), in dioxane/H₂O the selectivity droped to 55% while the yield of the oxostearic acid esters climbed to 70%. The Mn-catalyzed oxidative cleavage of methylketocarboxylic acid esters with O₂ at 115°C led in each case to a mixture of two dicarboxylic acid esters in a molar ratio of 2 : 1. Starting with 9-oxodecanoic acid azelaic and suberic acid were obtained at a conversion rate of 90%. Analogous 10-oxoundecanoic acid led to C₁₀/C₉- and 13-oxotetradecanoic acid led to C₁₃/C₁₂-dicarboxylic acids. The oxidative cleavage of 9-/10-oxostearic acid methylester yielded mixtures of C₈–C₁₀-monocarboxylic acids and methylesters of C₈–C₁₀-dicarboxylic acids.     

Anionen-grenzflächenaktive Stoffe aus Aminosäuren und Glycidäthern

Anionic Interfacially Active Agents from Amino Acids and Glycid Ethers After referring to the preparation of interfacially active agents by using amino carboxylic acids, especially sarkosine, experiments on the reaction of alkylene oxides as well as glycid ethers with amino carboxylic acids are described. Saturation concentrations, critical micelle concentrations and corresponding surface tensions (dyn/cm) of the aqueous solutions (0° d. H.) at 20° C are given for the adducts from glycine or sarkosine with octylene-1,2-oxide and n-octyl- or lauryl glycid ether.     

Analytik und Biophysik von verzweigtkettigen Fettsäuren in Lipiden

Analytics and biophysics of branched fatty acids in lipids . Objects of our investigations are long chain fatty acids with methyl groups in different positions and fatty acids with a different length of the sidegroup in α-position. The separation of racemic branched fatty acid methyl esters by gas chromatography on a chiral column depends on the structure of the branched fatty acid. Diastereomeric amides and phosphatidylcholines with α-branched fatty acid residues were separated preparatively. The branched fatty acids were incorporated into 1,2-diacyl-, 1-acyl-2-hexadecyl- and 2-acyl-1-hexadecyl-glycerophosphocholines and characterized by differential scanning calorimetry and X-ray diffraction.     

Gaschromatographische und dünnschichtchromatographische Untersuchung von Fettsäuren: Die Anwendung von gepackten Glaskapillarsäulen zur Trennung von cis- und trans-ungesättigten Fettsäuren

Gas Chromatographic and Thin-Layer Chromatographic Studies on Fatty Acids: The Application of Packed Glass Capillary Columns for Separation of cis- and trans-Unsaturated Fatty Acids from Saturated Fatty Acids Packed glass capillary columns were used for the quantitative determination of trans- and cis-unsaturated fatty acids in the presence of saturated fatty acids by gas chromatography. The fatty acids were analyzed as methyl esters after interesterification of the triglyceride samples. The conversion of glyceryl esters of fatty acids into methyl esters could be followed using short GC columns and by thin-layer chromatography.     

Neuartige Imidazoline und ihre Derivate aus Fettsäuren und Hydroxyalkylaminen

Novel Imidazolines and Their Derivatives from Fatty Acids and Hydroxyalkylamines Epoxides, derived from terminal and internal olefins, were reacted with ethylenediamine to give N-(vic.-hydroxyalkyl)-ethylenediamines and condensed with fatty acids and aromatic as well as aliphatic mono- and dicarboxylic acids to give 2-imidazolines. Quaternation of the 2-imidazolines yields imidazolinium salts, which, according to their structure, show strong microbiocide properties; they are also of interest as textile auxiliary.