43016-78-0Relevant academic research and scientific papers
Design, synthesis, antibacterial activity and toxicity of novel quaternary ammonium compounds based on pyridoxine and fatty acids
Agafonova, Mariya N.,Chirkova, Milana N.,Druk, Anastasia Y.,Grishaev, Denis Y.,Kayumov, Airat R.,Kazakova, Renata R.,Krylova, Elena S.,Nikishova, Tatyana V.,Nikitina, Elena V.,Sabirova, Alina E.,Sapozhnikov, Sergey V.,Shtyrlin, Nikita V.,Shtyrlin, Yurii G.
, (2021/01/06)
A diverse series of 43 novel “soft antimicrobials” based on quaternary ammonium pyridoxine derivatives which include six-membered acetals and ketals of pyridoxine bound via cleavable linker moieties (amide, ester) with a fragment of fatty carboxylic acid was designed. Nine compounds exhibited in vitro promising antibacterial activity against Gram-positive and Gram-negative bacterial strains with MIC values comparable with reference antiseptics miramistin, benzalkonium chloride and chlorohexidine. On various clinical isolates, the lead compounds 6i and 12a exhibited antibacterial activity comparable with that of benzalkonium chloride while higher than that of miramistin. Moreover, 6i and 12a were able to kill bacteria embedded into the matrix of mono- and dual species biofilms. The treatment of bacterial cells by either 6i and 12a lead to fast depolarization of the membrane suggesting that the membrane is an apparent molecular target of compounds. 6i and 12a were non mutagenic neither in SOS-chromotest nor in Ames test and non-toxic in vivo at acute oral (LD50 > 2000 mg/kg) and cutaneous administration (LD50 > 2500 mg/kg) on mice. Taken together, our data allow suggesting described active compounds as promising starting point for the new antibacterial agents development.
Synthesis and characterization of gemini ester surfactant and its application in efficient fabric softening
Liu, Dantong,Yang, Xin,Liu, Peng,Mao, Taoyan,Shang, Xiaoqin,Wang, Liming
, (2019/12/24)
Cationic surfactants with ester groups are considered as an important class of hydrolyzable and biodegradable materials utilized in multiple fields. In this work, a new type of gemini cationic surfactant containing two ester groups, N1,N1,N4,N4-tetramethyl-N1,N4-bis(2-(hexadecanoyloxy)ethyl)butane-1,4-diammonium bromide (TBDB), an 18-4-18 type gemini surfactant, has been successfully synthesized in a three-step reaction from natural palmitic acid, thionyl chloride, N,N-dimethylethanolamine and 1,4-dibromobutane. The maximum yield reaches about 94% under the optimum reaction conditions. The structures of the final product were characterized by FT-IR, 1H NMR and mass spectra. The critical micelle concentration (CMC) and surface tension of its aqueous solution are ~3.09 × 10? 5 M and 38.4 mN/m at 25 °C, respectively, and the gemini ester surfactant shows high benzene solubilization capacity. When treating cotton fabric, it can effectively retain the whiteness and surface hydrophilicity of the fabric while exhibiting a higher fabric-softening ability than the corresponding monomeric surfactants, due to its more efficient adsorption onto the fabric surface. The discovery suggests that this kind gemini ester surfactant is promising with potential applications in the fields of surfactants and coatings.
Thermal behavior of long-chain alkanoylcholine soaps
Tolentino, Ainhoa,Alla, Abdelilah,Martinez De Ilarduya, Antxon,Font-Bardia, Merce,Leon, Salvador,Munoz-Guerra, Sebastian
, p. 10738 - 10750 (2014/03/21)
Long-chain alkanoylcholines prepared from fatty acids (nACh) are fully sustainable cationic surfactants that are known for their biological and medicinal properties. In the present work the thermal behavior of the homologous series of alkanoylcholine iodides with n = 12, 14, 16 and 18, has been examined within the 25-200 °C range of temperatures. Up to three thermotropic phases have been identified, and the thermal transitions implied in their interconversion have been characterized by DSC and simultaneous WAXS and SAXS analysis carried out in real-time. All three phases consist of a bilayered structure with alkanoyl chains confined in the space between the head group layers and interdigitated to a greater or lesser extent. Melting-crystallization of either the polymethylene segments or the choline iodide groups is involved in such transitions. Additionally, a crystal phase consisting also of a bilayered structure but excluding side chain interdigitation was observed upon crystallization from solution and its structure was elucidated by single-crystal X-ray diffraction direct methods. The close correlation existing between thermal properties, phase structure and n has been brought into evidence.
Effect of hofmeister series anions on the thermotropic phase behavior of bioactive O -acylcholines
Tarafdar, Pradip K.,Reddy, S. Thirupathi,Swamy, Musti J.
, p. 9900 - 9909 (2013/09/23)
O-Acylcholines (OACs), which are true cationic lipids due to the quaternary ammonium functionality in the headgroup, exhibit interesting biological activities and medicinal properties. In the present study, a homologous series of OACs with even chain lengths (n = 12-20) have been synthesized, and their thermotropic and chaotropic phase transitions have been characterized. The role of various anions (Cl-, Br-, I-, NO 3-, SO42-, ClO3 -, ClO4-) on the phase behavior of O-stearoylcholine was investigated by calorimetric, spectroscopic, and turbidimetric approaches. The results obtained revealed that in aqueous dispersion O-stearoylcholine undergoes a cooperative phase transition from a gel phase to a micellar structure and that the transition temperature increases when the counterions are changed in the Hofmeister series. Single-crystal X-ray diffraction studies showed that O-stearoylcholine iodide forms an interdigitated bilayer structure, with the polymethylene chain adopting an all-trans conformation. The Hofmeister effect and phase behavior were explained using the concepts of matching water affinities, water penetration into the bilayer, and electrostatic repulsion. It was also observed that one counterion per molecule is sufficient to strongly modulate the phase properties of the lipid/surfactant.
Synthesis and properties of dissymmetric gemini surfactants
Xu, Qun,Wang, Liyan,Xing, Fenglan
experimental part, p. 85 - 90 (2012/01/13)
A series of novel dissymmetric gemini cationics surfactants was synthesized by three-step reactions. The dissymmetric gemini surfactants contain a dodecanoic acid dimethylethylamine ester as the constant cationic part on one side of the hydroxypropyl center and a similar other cationic part, but with a different acid length (from octanoic to palmitic), on the other side. The critical micelle concentration (CMC) and the effectiveness of surface tension reduction (γ CMC) were determined. The surface tension measurements of dissymmetric gemini surfactants showed good water solubility, and low CMC had great efficiency in lowering the surface tension and a strong adsorption at the air/water interface. The CMC was observed to increase initially with the increase of the ester bond alkyl group. They also showed good foaming properties and wetting capabilites.
Improved LC-MS method for the determination of fatty acids in red blood cells by LC-orbitrap MS
Li, Xingnan,Franke, Adrian A.
, p. 3192 - 3198 (2011/11/04)
We report a new method for fast and sensitive analyses of biologically relevant fatty acids (FAs) in red blood cells (RBC) by liquid chromatography mass spectrometry (LC-MS). A new chemical derivatization approach was developed forming picolylamides from FAs in a quantitative reaction. Fourteen derivatized FA standards, including saturated and unsaturated FAs from C14 to C22, were efficiently separated within 15 min. In addition, the use of a recently introduced benchtop orbitrap mass spectrometer under positive electrospray ionization (ESI) full scan mode showed a 2-10-fold improvement in sensitivity compared with a conventional tandem MS method, with a limit of detection in the low femtomole range for saturated and unsaturated FAs. The developed method was applied to determine FA concentrations in RBC with intra- and interday coefficients of variation below 10%.
Dimer poly-quaternary ester compounds
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Page/Page column 5, (2009/10/06)
The present invention relates to a novel class of polymeric compounds having specific quaternized amine based upon a dimer acid reacted with an alkanolamine to make an ester quaternary compound. Dimer acid is a C-36 diacid having a cyclic structure and two amine groups that allow for the synthesis of a high molecular weight cationic compound which is extremely substantitive to human skin and are well tolerated by human tissue making them suitable for use preparation of barrier products for personal care applications. These materials are dimethylaminopropyl amine free, which is highly desirable in personal care applications.
ADJUVANT AND DISPERSANT FORMULATIONS FOR PESTICIDAL APPLICATIONS
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Page/Page column 22, (2008/12/07)
There is provided is an adjuvant/dispersant for pesticide formulations (among other formulated uses) comprising at least one dialkyl alkanolamine such as dimethyl ethanolamine, at least one derivative thereof, or a combination thereof. Pesticide compositions comprising a pesticide, such as glyphosate, and the adjuvant/dispersant of the present technology and methods for enhancing the effectiveness of the pesticide, such as glyphosate, in an aqueous composition through the addition of the adjuvant/dispersant of the present technology are also disclosed. Solid pesticidal formulations comprising a pesticidal active ingredient and the adjuvant/dispersant of the present technology are also provided.
Dimer poly-quaternary ester compounds
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Page/Page column 8-9, (2008/06/13)
The present invention relates to a novel class of polymeric compounds having specific quaternized amine based upon a dimer acid reacted with an alkanolamine to make an ester quaternary compound. Dimer acid is a C-36 diacid having a cyclic structure and two amine groups that allow for the synthesis of a high molecular weight cationic compound which is extremely substantitive to human skin and are well tolerated by human tissue making them suitable for use preparation of barrier products for personal care applications. These materials are dimethylaminopropyl amine free, which is highly desirable in personal care applications.
SYNTHESIS AND THERMAL STABILITY OF CATIONIC SURFACE-ACTIVE DIMETHYLAMINOETHANOL DERIVATIVES
Ryzhkov, Yu. A.,Voronchikhina, L. I.
, p. 734 - 736 (2007/10/02)
Syntheses are reported for individual cationic surface-active quaternary derivatives of dimethylaminoethanol, differing in structures of hydrophilic and hydrophobic moieties and also in the nature of the anion.The thermal stability of the surfactans has been studied by thermal analysis.A mechanism of thermal decomposition of these compounds has been proposed, in relation to their structure.Recommendations are given for using these surfactants at elevated temperatures.
