- Selenated and Sulfurated Analogues of Triacyl Glycerols: Selective Synthesis and Structural Characterization
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The synthesis of sulfur- and selenium-containing isosters of triacyl glycerols is herein described. Regioselective fluoride-induced ring-opening reaction of suitable substituted thiiranes with bis(trimethyl)silyl selenide, followed by in situ S- and Se-acylation with fatty acid acyl chlorides, enables the one pot synthesis of mixed chalcogeno esters in good yield. The key step of this methodology is the functionalization of S?Si and Se?Si bonds of silyl chalcogenides, generated in situ under mild conditions. A related procedure for the synthesis of functionalized selenides, bearing two thiol ester and two ester moieties, was also developed through a fine tuning of the reaction conditions. The physico-chemical properties of these novel fatty acid chalcogeno esters have been investigated through DSC, SAXS, WAXS, FTIR and polarized optical microscopy, and compared to those of the common triglycerides in order to highlight the effect of the replacement of oxygen with other chalcogen elements in the polar head of the lipid.
- Ambrosi, Moira,Capperucci, Antonella,D'Esopo, Veronica,Lo Nostro, Pierandrea,Tanini, Damiano,Tatini, Duccio
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supporting information
p. 2719 - 2725
(2020/03/04)
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- OLEIC ACID DERIVATIVES, PHARMACEUTICAL COMPOSITION OR FOOD COMPOSITION COMPRISING SAID OLEIC ACID DERIVATIVES, AND THEIR USES
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This invention relates to oleic acid derivative comprising a hydrophobic part C17H33 linked to a particular polar head part "A", especially for use as a medicament, for instance, for the treatment of a disorder caused by the GPR120 receptor and/or the CD36 receptor, comprising administering to a subject in need thereof a therapeutically effective amount of said oleic acid derivative or of said pharmaceutical composition. The invention also relates to the use of said oleic acid derivative as a food composition.
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- Fatty acid monomer, preparation method and thermoplastic macromolecule synthesized through application
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The invention discloses a fatty acid monomer, a preparation method and a thermoplastic macromolecule synthesized through application. Tetramethyl guanidine and other catalysts are mainly utilized to catalyze a monomer containing halogen elements (Cl, Br and I) or halogen element and fatty acid, and the fatty acid monomer and thermoplastic macromolecule are obtained through efficient reaction. The application range can be thus widened by functionally improving the obtained fatty acid monomer and thermoplastic macromolecule. The reaction process is mild in condition, the catalytic efficiency of the catalysts is very high, few side reactions is produced, products are easy to separate and purify, and the fatty acid monomer and the thermoplastic macromolecule have a very high industrial application prospect.
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Paragraph 0028
(2017/09/02)
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- Super-toughened glycidol ester modified amine hardener and preparation method thereof
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The invention discloses a super-toughened glycidol ester modified amine hardener and a preparation method thereof. The preparation method comprises the following steps: (1) subjecting oleic acid and epoxy chloropropane to a reaction in the presence of a catalyst, so as to obtain a chlorohydrine intermediate; (2) adding a sodium hydroxide solution into the chlorohydrine intermediate obtained in the step (1), and carrying out a cyclization reaction; (3) then, collecting glycidyl oleate from a reaction product; (4) adding the obtained glycidyl oleate into isophorondiamine, carrying out a reaction, and then, carrying out depressurization to remove excessive isophorondiamine, thereby obtaining the glycidyl oleate modified isophorondiamine hardener. The hardener has the characteristics of large epoxy number, low chlorinity, low viscosity and the like, and the toughness and impact strength of epoxy resin cured products are greatly improved.
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Paragraph 0039; 0040-0043; 0047-0050; 0053-0056; 0059-0062
(2017/12/27)
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- Efficient synthesis of 3-O-thia-cPA and preliminary analysis of its biological activity toward autotaxin
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The efficient synthesis of 3-O-thia-cPAs (4a-d), sulfur analogues of cyclic phosphatidic acid (cPA), has been achieved. The key step of the synthesis is an intramolecular Arbuzov reaction to construct the cyclic thiophosphate moiety. The present synthetic route enables the synthesis of 4a-d in only four steps from the commercially available glycidol. Preliminary biological experiments showed that 4a-d exhibited a similar inhibitory effect on autotaxin (ATX) as original cPA.
- Tanaka, Ryo,Kato, Masaru,Suzuki, Takahiro,Nakazaki, Atsuo,Nozaki, Emi,Gotoh, Mari,Murakami-Murofushi, Kimiko,Kobayashi, Susumu
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scheme or table
p. 4180 - 4182
(2011/08/06)
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- Direct determination of MCPD fatty acid esters and glycidyl fatty acid esters in vegetable oils by LC-TOFMS
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Analysis of MCPD esters and glycidyl esters in vegetable oils using the indirect method proposed by the DGF gave inconsistent results when salting out conditions were varied. Subsequent investigation showed that the method was destroying and reforming MCPD during the analysis. An LC time of flight MS method was developed for direct analysis of both MCPD esters and glycidyl esters in vegetable oils. The results of the LC-TOFMS method were compared with the DGF method. The DGF method consistently gave results that were greater than the LC-TOFMS method. The levels of MCPD esters and glycidyl esters found in a variety of vegetable oils are reported. MCPD monoesters were not found in any oil samples. MCPD diesters were found only in samples containing palm oil, and were not present in all palm oil samples. Glycidyl esters were found in a wide variety of oils. Some processing conditions that influence the concentration of MCPD esters and glycidyl esters are discussed.
- Haines, Troy D.,Adlaf, Kevin J.,Pierceall, Robert M.,Lee, Inmok,Venkitasubramanian, Padmesh,Collison, Mark W.
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experimental part
p. 1 - 14
(2011/10/04)
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- Structure-activity relationship of a series of inhibitors of monoacylglycerol hydrolysis - Comparison with effects upon fatty acid amide hydrolase
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A series of 32 heterocyclic analogues based on the structure of 2-arachidonoylglycerol (2-AG) were synthesized and tested for their ability to inhibit monoacylglycerol lipase and fatty acid amide hydrolase activities. The designed compounds feature a hydrophobic moiety and different heterocyclic subunits that mimic the glycerol fragment. This series has allowed us to carry out the first systematic structure-activity relationship study on inhibition of 2-AG hydrolysis. The most promising compounds were oxiran-2-ylmethyl (5Z,8Z,11Z,14Z)-icosa-5,8,11,14-tetraenoate (1) and tetrahydro-2H-pyran-2- ylmethyl (5Z,8Z,11Z,14Z)-icosa-5,8,11,14-tetraenoate (5). They inhibited cytosolic 2-oleoylglycerol (2-OG) hydrolysis completely (IC50 values of 4.5 and 5.6 μM, respectively). They also blocked, albeit less potently, 2-OG hydrolysis in membrane fractions (IC50 values of 19 and 26 μM, respectively) and anandamide hydrolysis (IC50 values of 12 and 51 μM, respectively). These compounds will be useful in delineating the importance of the cytosolic hydrolytic activity in the regulation of 2-AG levels and, hence, its potential as a target for drug development.
- Cisneros, José Antonio,Vandevoorde, Séverine,Ortega-Gutiérrez, Silvia,Paris, Clément,Fowler, Christopher J.,López-Rodríguez, María L.
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p. 5012 - 5023
(2008/03/12)
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- Regioselective opening of an oxirane system with trifluoroacetic anhydride. A general method for the synthesis of 2-monoacyl- and 1,3-symmetrical triacylglycerols
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A trifluoroacetic anhydride-catalyzed opening of the oxirane system of glycidyl esters with a simultaneous migration of the acyl group provides a new, efficient entry to either 2-monoacylglycerols (2-MAG) or 1,3-symmetrical triglycerides (1,3-STG) as potential prodrug frameworks.
- Stamatov, Stephan D.,Stawinski, Jacek
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p. 3659 - 3669
(2007/10/03)
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- Synthesis of Aniline Derivatives with Potential Toxicological Implications to the Spanish Toxic Oil Syndrome
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The synthesis of anilides 2 from several saturated and unsaturated fatty acids 1 required for toxicological studies related to the Spanish Toxic Oil Syndrome is reported.In addition, a simple procedure for the determination of the position of a carbon-carbon double bond of a fatty acid residue is described.This procedure involves epoxidation of the sample with 3,3-dimethyldioxirane followed by oxidative cleavage with periodic acid to yield the corresponding carbonyl derivatives which are easily identifiable by GC-MS analysis.Finally, the synthesis of anilino derivatives 5-8 formally derived from glycerol is also reported.For this purpose, a common precursor, i.e. 3-(phenylamino)propane-1,2-diol (4) is prepared, and convenient procedures for its chemoselective acylation at either the hydroxy or the amino group have been developed. Key Words: Toxic oil syndrome / Aniline / Fatty acids, synthesis of
- Ferrer, Marta,Galceran, Montserrat,Sanchez-Baeza, Francisco,Casas, Josefina,Messeguer, Angel
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p. 507 - 512
(2007/10/02)
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