- Synthesis, computational evaluation and pharmacological assessment of acetylsalicylic esters as anti-inflammatory agents
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A convenient approach to the synthesis of alkyl esters of aspirin (ASA-OR) has been developed. The synthesis of ASA-OR has been realized in two steps: (1) direct esterification of salicylic acid with alcohols in the presence of dicyclohexylcarbodiimide to give alkyl salicylates (SAL-OR); (2) acetylation of SAL-OR with acetyl chloride to yield ASA-OR. Molecular mechanics simulations, performed to calculate the kinetic radii of several ASA-OR, indicated that the pentyl and hexyl acetylsalicylates possess the best properties to cross cell membranes. The in vitro biological tests demonstrate their anti-inflammatory activity, superimposable to that of aspirin. The results of our study suggest that ASA-OR may be used as anti-inflammatory drugs for topical application.
- Mancuso, Raffaella,Ferlazzo, Nadia,De Luca, Giorgio,Amuso, Roberta,Piccionello, Antonio Palumbo,Giofrè, Salvatore V.,Navarra, Michele,Gabriele, Bartolo
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p. 292 - 299
(2019/01/09)
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- SO3H-functionalized Bronsted acidic ionic liquids as efficient catalysts for the synthesis of isoamyl salicylate
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Six Bronsted acidic ionic liquids (BAILs) composed of [HSO 4] were prepared, characterized, and used as catalysts of low dosage in the synthesis of isoamyl salicylate. The effects of various parameters such as the kind of BAILs, temperature, catalyst loading, and molar ratio of the reactants on the conversion of salicylic acid were also examined in detail. The results suggested that the catalytic performances of BAILs were of close relevance to their Hammett acidities. The SO3H-functionalized BAILs 1-(4-sulfonic acid) butyl-3-methylimidazolium hydrogen sulfate ([BSmim][HSO 4]) and N-(4-sulfonic acid) butyl triethylammonium hydrogen sulfate ([BSEt3N][HSO4]) of strong acidities exhibited excellently catalytic activities and selectivities in the esterification of salicylic acid with isoamyl alcohol. The fully optimized geometries of [BSmim][HSO4] and [BSEt3N][HSO4] further manifest that their strong acidities are derived from the strong interactions between the anion with the sulfonic acid group. In addition, it was found that [BSmim][HSO4] could be also recovered easily and used repetitively at least six times without obvious decline in activity and quantity.
- Tao, Duan-Jian,Wu, Jing,Wang, Zhen-Zhen,Lu, Zhang-Hui,Yang, Zhen,Chen, Xiang-Shu
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- Esterification of salicylic acid using Br?nsted acidic ionic liquid based on Keggin heteropoly acid
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For the first time, a newwater stable Br?nsted acidic ionic liquid based on Keggin heteroployacid (HPA) was used as environmentally benign catalytic medium in the esterfication of salicylic acid with aliphatic alcohols, CnH2n+1OH (n = 1-5) and benzylic alcohols, RC6H4CH2OH (R = H, NO2, OCH3). This ionic liquid (IL) afforded excellent yield in both thermal conditions and microwave irradiation. Maximum yields were observed under microwave irradiation. Different reaction runs were conducted by varying the reaction parameters such as molar ratio of reactants, weight of the IL, and reaction period in order to optimize the reaction. The IL was easily recovered and reused many times. No significant loss in catalytic activity was observed on recycling.
- Bamoharram, Fatemeh F.,Heravi, Majid M.,Ebrahimi, Javad,Tavakoli-Hoseini, Nilofar
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- Esterification of salicylic acid using Ce4+ modified cation-exchange resin as catalyst
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The esterification of salicylic acid with methanol was carried out over a series of Ce4+ modified cation-exchange resins. The effect of different reaction conditions was studied on the conversion of salicylic acid, and the optimal reaction parameters were obtained. The experimental results indicated that Ce(SO4)2/001×7 was an effective catalyst for the synthesis of methyl salicylate. The conversion of salicylic acid could reach 93.3% while its selectivity was more than 99.0%. SEM-EDS and TG-DSC analysis were employed to characterize the structure and property of the catalyst. Besides, the catalytic performance of Ce(SO4) 2/001×7 in the esterification of salicylic acid with different alcohols was compared. The reusability of Ce(SO4)2/ 001×7 was also studied by using salicylic acid and methanol as model substrates. The mechanism was proposed for the esterification of salicylic acid with methanol over Ce4+ modified cation-exchange resins.
- Zhang, Ming,Zhu, Wen Shuai,Li, Hua Ming,Shi, Hua,Yan, Yong Sheng,Wang, Zhi Gao
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p. 1477 - 1481
(2013/07/19)
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- LILIAN SURROGATE
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Due to toxicological concerns, it may be desirable to replace the fragrance compound lilial with less problematic compounds without losing the creative power and quality regarding perfumes. The present invention addresses this need by using selected oxazolidines described herein.
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- Catalytic performance of nano-SiO2-supported Preyssler heteropolyacid in esterification of salicylic acid with aliphatic and benzylic alcohols
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An efficient and environmentally benign procedure for the catalytic esterification of salicylic acid with aliphatic alcohols, CnH 2n+1OH (n = 1-5) and benzylic alcohols, RC6H 4CH2OH (R = H, NO2, OCH3, Br, Cl, Me) was developed using nano-SiO2-supported Preyssler heteropolyacid both under thermal conditions and microwave irradiation. Silica nanostructures were obtained through a sol-gel method and were characterized by transmission electron microscopy and powder X-ray diffraction. The effects of various parameters such as solvent type, molar ratio of substrates, Preyssler heteropolyacid loading on silica, catalyst amount, temperature, and reaction time were studied and the optimum conditions were obtained. It has been found that the catalyst with 30 wt loading is highly active and shows high yields in esterification reactions. The use of nano-SiO2-supported Preyssler heteropolyacid coupled with microwave irradiation allows a solvent-free, rapid (3 min), and high-yielding reaction. This catalyst can be easily recovered and reused for many times without a significant loss in its activity.
- Bamoharram, Fatemeh F.,Heravi, Majid M.,Ebrahimi, Javad,Ahmadpour, Ali,Zebarjad, Mojtaba
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experimental part
p. 782 - 788
(2012/05/04)
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- Microwave-accelerated esterification of salicylic acid using Br?nsted acidic ionic liquids as catalysts
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A variety of Br?nsted acidic ionic liquids were screened as catalysts for the esterification of salicylic acid. The experimental results indicated that SO3H-functionalized ionic liquids with HSO4- performed high catalytic activity under microwave irradiation, and the yields can reach 91.9-93.6%. Furthermore, ionic liquids can be easily separated by simple decantation and have a fair reusability. The Br?nsted acidity-catalytic activity relationships were also investigated and the results showed that the activity of the acidic ionic liquids is in excellent agreement with their acidity order. Crown Copyright
- Shi, Hua,Zhu, Wenshuai,Li, Huaming,Liu, Hua,Zhang, Ming,Yan, Yongsheng,Wang, Zhigao
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experimental part
p. 588 - 591
(2010/11/05)
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- PERFUME COMPOSITION
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A perfume composition contains specified ketones, salicylates and alcohols/acetates/propionates. Use of such a perfume composition inhibits development of human body malodour. The combination of specified materials makes it possible to avoid inclusion of individual components with powerful, unacceptable odours. The perfume composition may be used in various products notably in a fabric conditioning product used during the rinsing or tumble drying of fabrics after washing to soften the fabrics.
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- Perfume compositions
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A perfume composition contains at least 50% by weight of materials which fall into five categories defined by structure, and molecular weight. Amounts of material within each category fall within specified ranges of percentage of the whole composition. Two categories, ethers and salicylates, must be present. At least two of the remaining three categories, which are alcohols, acetate/propionate esters and methyl aryl ketones, must also be present. The compositions enable good levels of deodorant activity to be achieved along with consumer-acceptable fragrance.
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- Transparent cosmetic composition that reflects infrared radiation and its use for protecting the human epidermis against infrared radiation
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Transparent cosmetic composition that reflects infrared radiation and its use for protecting the human epidermis against infrared radiation. The invention relates to a transparent cosmetic composition comprising, by way of an agent that reflects infrared radiation for protecting the human epidermis, a substance which is dispersible in the cosmetic medium used, possessing a reflectance (R) of infrared radiation equal to at least 45%, and of which a 2% strength dispersion in vaseline possesses an optical transmission in the visible of at least 85%, chosen from a diatom of particle size less than 100 microns, hollow glass microspheres of size less than 100 microns, a bismuth oxychloride of particle size less than 75 microns and zirconium powder covered ceramic microparticles of particle size less than 8 microns. This cosmetic composition can also contain 0.5 to 20% by weight of UV-A, UV-B or broad-band screening agents.
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