Chain Fatty Acid Derivatives Research Articles

Pheromone Bouquet of the Mandibular Glands in Andrena haemorrhoa F. (Hym., Apoidea)

Abstract The complex volatile secretion from the mandibular glands of Andrena haemorrhoa (Hym., Apoidea) has been analysed by GC/M S. It is composed primarily of three groups of compounds: 1. Spiroacetals of five different systems: two 1,6-dioxyspiro[4.4]nonanes, four 1,6-dioxaspiro[4.5] decanes, two 1,7-dioxaspiro[5.5]undecanes, one 1,6-dioxaspiro[4.6]undecane and one 1,7-dioxa-spiro[5.6]dodecane. 2. Straight chain fatty acid derivatives: methyl ketones, primary and secondary alcohols, acetates and hydrocarbons. 3. Isoprenoids: geraniol and geranyl acetate. Mass spectral fragmentation patterns have been studied for several synthesized spiroacetals.

Aminimides: II. Antimicrobial effect of short chain fatty acid derivatives.

AbstractA new family of surfactants, aminimides, has been screened forin vitro antimicrobial activity. These compounds are active against both bacteria and yeast, activity being a function of chain length. Maximum activity for acetimide and acrylimide amine derivatives was extablished with chain lengths of C14–C16. Homologous compounds with lower or higher chain lengths were less active. While showing low antimicrobial activity against gram negative bacteria, mixtures containing C12 and C16 gave good activity against gram negative strains without losing gram positive activity. Aminimides gave low acute LD50’s (200–400 mg/kg) when tested in mice by intraperitoneal injection.

Aminimidesi I. Antimicrobial effect of some long chain fatty acid derivatives.

AbstractAminimides are a new class of surface active agents which have antimicrobial activity. These bipolar compounds have activity against both gran‐positive and yeast organisms. Their activity against gram‐negative organisms is low or absent. The acyl derivatives tested showed maximum activity at chain lengths of C14 and C16. Fatty acid derivatives, shorter (<C14) or longer (>C16), were less active. Unsaturation was an important factor contributing to aminimide activity. Their low toxicity and wide spectrum of antimicrobial activity make aminimides ideal candidates for further investigation.

Correlation of solubility data: III. The isopleth reference method for predicting solubility data for long chain homologous and analogous compounds

AbstractA new graphical method for correlating and predicting solubility data for homologous and analogous compounds is described. It complements the isotherm and isopleth methods which are applicable only to long chain homologous compounds. This method is based upon the linear relationship, derived from the approximate freezing point depression equation in which T and T′ are the primary freezing points of two analogous compounds at the same molar concentration in a given solvent. The basic assumption that ΔH′f/ΔHf remains essentially constant for homologous and analogous compounds in the same solvent over wide ranges of temperature was validated by construction of isopleth reference plots using both published and new experimental solubility data for a number of long chain fatty acids and fatty acid derivatives in a variety of solvents. Complete solubility data are reported for behenic, stearic, palmitic, heptadecanoic, brassidic, erucic, petroselaidic and petroselinic acid in acetone, methanol, toluene and isopropyl ether. Complete solubility data are also included for elaidic acid in acetone, toluene and isopropyl ether and oleic acid in isopropyl ether.

Non‐volatilea‐branched chain fatty acid derivatives: IV. Addition of aryl esters to long chain olefins

AbstractThe di‐tertiary butyl peroxide initiated free radical addition of methyl phenylacetate, methylp‐tolylacetate and methylp‐methoxyphenylacetate to 1‐decene gives two types of products. In addition to the expecteda‐branched esters, dehydrodimer (bothmeso anddl) esters were also obtained. The highest yield ofa‐branched ester was obtained from methyl phenylacetate. Higher yields of the dehydrodimer esters were obtained from the substituted phenyl esters. Attempts to add methylp‐nitrophenylacetate to 1‐decene were not successful and no evidence for the formation of a dehydrodimer product was observed.

Nonvolatile α‐branched chain fatty acid derivatives: III. Addition of acid chlorides, anhydrides and amides to terminal olefins

AbstractAt‐butyl peroxide initiated free radical reaction was employed for the preparation of α‐branched fatty acid chlorides, which were then converted in situ to methyl esters. Similarly prepared were an α‐branched fatty acid amide and an α‐branched acid anhydride. The latter was converted to the methyl ester. The use of the acid chloride and acid anhydride permitted reduction in the molar ratio of reactants to half or less than that used in the addition of esters to terminal olefins without affecting the yield. The resulting increase of α‐branched product concentration in the reaction mixture also made isolation of the product easier. The direct addition of a variety of stearic acid derivatives to 1‐decene under the same conditions (20:4:1.2 molar ratio of reactants at 160 C) gave the following olefin based yield order: stearoyl chloride > stearic anhydride > stearamide and methyl stearate > stearic acid.

An experimental approach to the problem of disordered lipid metabolism

The nature of lipid biosynthesis is considered in relation to the branched chain fatty acid derivatives which were selected for experimental studies. Substituted a-oxyisobutyric acids were uniquely active in preliminary tests in rats. Subsequent examination of the preferred compound ethyl-α-(p-chlorophenoxy)isobutyrate (CPIB or clofibrate) in this and other species revealed that its effects were by no means consistent, but could be made more so by administering androsterone at the same time. An important factor contributing to variations in serum lipids was found to be a seasonal variation in adrenal and thyroid function. In man this was evidenced by the close correlation between variation in pre-treatment levels of serum cholesterol in 600 patients (in the multicentre Atromid trial) and the variation in Achilles tendon reflex time (a measure of thyroid function) in 30 normal men studied over the same period. The mode of action of Atromid is discussed in terms of the hypothesis that the chlorophenoxyisobutyrate anion displaces serum albumin-bound acidic substrates, co-enzymes, or hormones (including thyroxine, 17-ketosteroid sulphates, and pyridoxal-5-phosphate). The effects of the displaced acids are predominantly localized in the liver, causing a reduction in lipid synthesis. The extent of the alteration in lipid metabolism due to the CPIB or androsterone components of Atromid probably depends upon species and other differences in serum albumin and in endocrine function. L'auteur considère la nature de la biosynthèse lipidique par rapport aux dérivés des acides gras à chaîne ramifiée qu'il a sélectionnés en vue d'études expérimentales. Les acides a-oxyisobutyriques substitués ont été uniquement actifs dans des tests préliminaires. Un examen consécutif du composé préféré, le α-p-chlorophénoxyisobuty-rate d'éthyle (CPIB, clofibrate) a révélé chez ces rats et chez d'autres espèces que ses effets n'étaient nullement solides, mais pouvaient l'être davantage par l'administration simultanée en même temps d'androstérone. Il a été constaté qu'un facteur important susceptible de contribuer aux variations des lipides sérrques était constitué par les variations saisonnières des fonctions surrénalienne et thyroïdienne. Chez l'homme ce fait s'est montré évident en raison de l'étroite corrélation entre les variations des chiffres du cholestérol sérique avant traitement chez 600 sujets (dans l'essai de l'Atromide effectué à plusieurs centres) et les variations du temps de réflexe du tendon d'Achille (une mesure de la fonction thyroïdienne) chez 30 hommes normaux observés pendant la meme période. Le mode d'action de l'Atromide a été discuté dans le cadre de l'hypothèse selon laquelle l'anion du chlorophénoxyisobutyrate déplacerait les substrats acides liés à l'albumine sérique, coenzymes ou hormones (y compris la thyroxine, les sulfates de 17-cétostéroïde et le phosphate de pyridoxal-5). Les effets des acides déplacés sont principalement localisés dans le foie où ils provoquent une réduction de la synthèse lipidique. Le degré d'altération du métabolisme lipidique due au CPIB ou aux composants de l'androstérone de l'Atromide est probablement dépendant de l'espèce, ainsi que d'autres différences d'albumine sérique et de fonction endocrine. Der Charakter der Lipoid-Biosynthese wird betrachtet mit Bezug auf einige für Versuchszwecke ausgewählte verzweigt-kettige Fettsäure-Derivate. Substituierte α-Hydroxyisobuttersäuren waren in einleitenden Untersuchungen bei Ratten besonders aktiv. Eine weitere Untersuchung bei Ratten and anderen Tieren mit dem mit Vorzug verwendeten Gemisch äthyl-p-chlorophenoxy-isobutyrat (CPIB oder Clofibrate) zeigte, dass seine Wirkungen bei weitem nicht übereinstimmend waren, doch konnten sie durch das gleichzeitige Zufügen von Androsteron einheitlicher gemacht werden. Eine jahreszeitliche Variation der Nebennieren- and Thyroid-Funktion erwies sich als ein wichtiger Faktor in den Veränderungen der Serum-Lipoide. Beim Menschen wurde dies ausgedrückt in dem engen Zusammenhang zwischen den Veränderungen des Serumcholesterinspiegels vor der Behandlung bei 600 Patienten (in der parallelen Atromid-Untersuchung) einerseits, and den Veränderungen der Achillessehnen-Reflexzeit (ein Mass der Thyroidfunktion) bei 30 normalen Männern andererseits, die während der selben Zeit untersucht wurden. Die Wirkungsweise des Atromids wird aufgrund der Hypothese erörtert, dass das chlorophenoxy-isobuttersäure Anion, serumalbumin-gebundene säurebildende Substrate, Coenzyme, oder Hormone (Thyroxin, 17-Hydroxysteroid-sulphat and Pyridoxal-5-phosphat einbegriffen) verdrängt. Die Wirkung der verdrängten Säuren ist vorwiegend in der Leber lokalisiert and verursacht eine Verminderung in der Lipoid- Synthese. Der Umfang der Veränderung im Lipoidsstoffwechsel – dank derv CPIB oder derv Androsteron-Komponenten des Atromids – hängt wahrscheinlich von den Spezies- and anderen Unterschieden im Serumalbumin and in den endokrinen Funktionen ab.

The Synthesis of Long Chain Fatty Acid Derivatives of the Vitamin B6 Group1,2

The Synthesis of Long Chain Fatty Acid Derivatives of the Vitamin B₆ Group^1,2

The Synthesis of Long Chain Fatty Acid Derivatives of Pantothenic Acid1

The Synthesis of Long Chain Fatty Acid Derivatives of Pantothenic Acid¹

Of the adjustment of a quadrilateral in a tertiary system of triangulation

Epicuticular and intracuticular waxes from both adaxial and abaxial surfaces of the leaves of Kalanchoe daigremontiana were analyzed. All wax mixtures were found to contain approximately equal amounts of triterpenoids and very long chain fatty acid (VLCFA) derivatives. The triterpenoid fraction consisted of glutinol (8–19% of the total wax) and friedelin (4–9%), together with smaller amounts of glutanol, glutinol acetate, epifriedelanol, germanicol and β-amyrin. The VLCFA derivatives comprised C27–C35 alkanes (19–37% of the total wax), C32–C34 aldehydes (3–7%), C32 and C34 fatty acids (0.2–3%), C26–C36 primary alcohols (4–8%), and C42–C52 alkyl esters (2–9%). The wax layers were found to differ in triterpenoid amounts, with the intracuticular wax containing higher percentages of most triterpenoids than the epicuticular wax. Friedelin, the only triterpenoid ketone present, showed the opposite distribution with higher proportions in the epicuticular wax. VLCFA derivatives also accumulated to higher percentages in the epicuticular than in the intracuticular wax layer. Epicuticular wax crystals were observed on both the adaxial and abaxial leaf surfaces.