7459-29-2

Upstream product

• 506-33-2 Brassidic acid 
• 79-37-8 oxalyl dichloride 
• 112-86-7 cis-13-docosenoic acid 
• 1072-39-5 docos-13-enoic acid 

Downstream Products

• 128389-74-2 1,3-Dierucin 
• 23848-79-5 Erucasaeure-p-kresylester 
• 23848-78-4 Erucasaeure-m-kresylester 
• 23848-77-3 Erucasaeure-o-kresylester 
• 23848-76-2 Erucasaeurephenylester 
• 112-84-5 Unislip 1753 
• 106-02-5 pentadecanolide 

Relevant academic research and scientific papers

Studies on the synthesis, surface activity and the ability to form pH-regulated wormlike micelles with surfactant containing carboxyl group

In this article, a series of pH regulated surfactants with different hydrophobic chain length and carboxyl group molecular structure positions were designed and synthesized. The molecular structure of pH regulated surfactants was analyzed by mass spectrometry and 1H NMR spectroscopy. The results of the surface activity test show that the pH regulated surfactants have lower surface tension, which indicates that it is easier to adsorb directionally at the gas-liquid interface and to aggregate in solution. Both inorganic and organic counterions can improve the viscosity of the system to some extent, but the viscosity-increasing ability of organic counterions is much higher than that of inorganic counterions. The results of rheology and dynamic light scattering show the transition from spherical micelles to wormlike micelles was observed when pH increased from 5 to 8 in the Docos-13-enoylamino-acetic acid (Gly-22)/Trimethylstearylammonium chioride (ODAC) system. The results of Cryo-transmission electron microscopy verify this result directly. Also, the experimental results show that the Gly-22/ODAC system has excellent pH cycle regulation performance, which can significantly reduce the application cost of the system.

Antiproliferative 3-deoxysphingomyelin analogs: Design, synthesis, biological evaluation and molecular docking of pyrrolidine-based 3-deoxysphingomyelin analogs as anticancer agents

Sphingomyelins and glycerophospholipids are structurally related phospholipids. Nevertheless, glycerophospholipids analogs are known as antitumor agents while sphingomyelin analogs were reported as cytoprotective agents. Herein, we have addressed the development of 3-deoxysphingomyelin analogs as cytotoxic agents possessing modified sphingobases. Thus, pyrrolidine-based 3-deoxysphingomyelin analogs were synthesized and evaluated against a panel of cell lines representing four major types of cancers. Compounds 3d, 4d and 6d elicited better GI50 values than the FDA approved drug miltefosine. Investigation of their impact on Akt phosphorylation as a possible mechanism for the antiproliferative activity of this class of compounds revealed that these compounds might elicit a concentration-dependent mechanism via inhibition of Akt phosphorylation at the lower concentration. Molecular docking predicted their binding modes to Akt to involve polar head binding to the Pleckstrin homology domain and hydrophobic tail extension into a hydrophobic pocket connecting the Pleckstrin homology domain and the kinase domain. As a whole, the described work suggests compounds 3d, 4d and 6d as promising pyrrolidine-based 3-deoxysphingomyelin analogs for development of novel cancer therapies.

Synthesis and biological evaluation of 5-fatty-acylamido-1, 3, 4-thiadiazole-2-thioglycosides

In the present study, the synthesis of 1, 3, 4-thiadiazole-based thioglycosides were accomplished in good yields with employing a convergent synthetic route. The starting material 5-amino-1, 3, 4-thiadiazole-2-thiol and followed by a series of 5-fatty-acylamido-1, 3, 4-thiadiazole-2-thiols (4a–4j) were synthesized with different fatty acid chlorides. The glycosylation of compounds 4a–4j were achieved with trichloroacetimidate methodology. Antimicrobial and cytotoxicity activities of title compounds were evaluated. Among the entire compounds lauric acid and myristic acid derivatives showed good and moderate antimicrobial activity. In case of cytotoxicity results of compounds 8a–8j and 9a–9j, the acetate protected short chain (C6:0, C8:0, C10:0) compounds and the free hydroxyl long chain saturated (C16:0, C18:0) and unsaturated (C18:1, C22:1) compounds exhibited good activity against different cancer cell lines. Further, the free hydroxyl compounds 9a, 9c–9j did not show any toxicity towards normal CHO-K1 cell line whereas acylated compounds 8a–8j exhibited toxicity.

Synthesis and high-performance of a new sarcosinate anionic surfactant with a long unsaturated tail

A new C22 tailed sarcosinate anionic surfactant, 2-(N-erucacyl-N-methyl amido) acetate (EMAA), has been synthesized by use of the erucic acid and a hydrotrope - sarcosine. In contrast to the common method, which blends the hydrotrope with a surfactant, the sarcosine has been introduced into the anionic surfactant through chemical modification. Interestingly, the resultant C22 tailed anionic surfactant shows excellent water solubility despite the ultra-long alkyl chain. Besides, the EMAA also exhibits high surface activity, and pH controllable micelles to vesicles transition (MVT). Rheology studies have revealed that the rheological properties of EMAA solutions are influenced by the concentration, temperature, salt, and pH dramatically. Aside from the excellent water solubility, the original feature highlighted in this work is that such a new C22 tailed sarcosinate anionic surfactant exhibits good temperature resistance. Compared to the potassium oleate (KOA), the zero-shear viscosity of the EMAA solution is nearly 3 orders of magnitude higher under the same conditions.

Screening of a selection of commercially available homogeneous Ru-catalysts in valuable olefin metathesis transformations

A library of thirteen different commercially available Ru-based catalysts was evaluated in valuable metathesis reactions for the production of fragrance and bioactive molecule precursors. Rigorous library screening clearly illustrated the different catalytic behaviour of the catalyst selection and highlighted its significant advantage to provide efficiency in specific metathesis applications. Interestingly, this strategy offered substantial improvement over the state of the art, with the efficient synthesis of the macrocyclic Exaltolide 2 at low catalyst loading and dilution conditions. The Royal Society of Chemistry 2013.

Electrospray ionization and collision induced dissociation mass spectrometry of primary fatty acid amides

Primary fatty acid amides are a group of bioactive lipids that have been linked with a variety of biological processes such as sleep regulation and modulation of monoaminergic systems. As novel forms of these molecules continue to be discovered, more emphasis will be placed on selective, trace detection. Currently, there is no published experimental determination of collision induced dissociation of PFAMs. A select group of PFAM standards, 12 to 22 length carbon chains, were directly infused into an electrospray ionization source Quadrupole Time of Flight Mass Spectrometer. All standards were monitored in positive mode using the [M + H]+ peak. Mass Hunter Qualitative Analysis software was used to calculate empirical formulas of the product ions. All PFAMs showed losses of 14 m/z indicative of an acyl chain, while the monounsaturated group displayed neutral losses corresponding to H2O and NH3. The resulting spectra were used to propose fragmentation mechanisms. Isotopically labeled PFAMs were used to validate the proposed mechanisms. Patterns of saturated versus unsaturated standards were distinctive, allowing for simple differentiation. This determination will allow for fast, qualitative identification of PFAMs. Additionally, it will provide a method development tool for selection of unique product ions when analyzed in multiple reaction monitoring mode.

Synthesis of 1-oxo-1-(3-pyridazinyl) derivatives - Potent inhibitors of Fatty Acid Amide Hydrolase (FAAH): An improved and optimized procedure

A greatly improved procedure for the preparation of long-chain α-ketopyridazines, a class of potent inhibitors of fatty acid amide hydrolase (FAAH), is described. This optimization study shows a great dependence of the yields of desired products on the pyrididazinyl lithium/Weinreb amide ratio and offers a general approach to this kind of compound. Georg Thieme Verlag Stuttgart.

Vanilloids. 1. Analogs of Capsaicin with Antinociceptive and Antiinflammatory Activity

As part of a program to establish structure-activity relationships for vanilloids, analogs of the pungent principle capsaicin, the alkyl chain portion the parent structure (and related compounds derived from homovanillic acid) was varied.In antinociceptive and antiinflammatory assays (rat and mouse hot plate and croton oil-inflamed mouse ear), compounds with widely varying alkyl chain structures were active.Short-chain compounds were active by systemic administration in the assays mentioned above but they retained the high pungency and acute toxicity characteristic of capsaicin.In contrast, the long chain cis-unsaturates, NE-19550 (vanillyloleamide) and NE-28345 (oleylhomovanillamide), were orally active, less pungent, and less acutely toxic than capsaicin.The potential of these compounds as antiinflammatory/analgesic agents is discussed in light of recent data on the mechanism of action of vanilloids on sensory nerve fibers.