55584-26-4Relevant academic research and scientific papers
Comparative biocompatibility and antimicrobial studies of sorbic acid derivates
Nemes, Dániel,Kovács, Renátó,Nagy, Fruzsina,Tóth, Zoltán,Herczegh, Pál,Borbás, Anikó,Kelemen, Viktor,Pfliegler, Walter P.,Rebenku, István,Hajdu, Péter B.,Fehér, Pálma,Ujhelyi, Zoltán,Fenyvesi, Ferenc,Váradi, Judit,Vecsernyés, Miklós,Bácskay, Ildikó
, (2020)
Nowadays, the sorbates are the third largest group of antimicrobial preservatives in food and pharmaceutical industries, following the parabens and benzoates whose safety is questioned by recent publications. A disadvantage of sorbates is their pH dependence, as their antimicrobial effect is greatly reduced in alkaline environment. The main, widely used sorbate derivatives are sorbic acid and potassium sorbate, no sorbic acid esters are involved in current industrial application. We aimed to test whether the esters of sorbic acid are capable to extend the antimicrobial spectrum of the original molecule while maintaining its advantageous biocompatibility profile. A comparative biocompatibility study of different derivatives (sorbic acid, potassium sorbate, isopropyl sorbate and ethyl sorbate) was carried out. In vitro cell viability assays of MTT (2-(4,5-dimethyl-2-thiazolyl)-3,5-diphenyl-2H-tetrazolium bromide), Neutral Red (3-amino-7-dimethylamino-2-methylphenazine hydrochloride) and flow cytometry with propidium iodide and annexin were performed on Caco-2 cells. In case of in vivo toxicity study, G. mellonella larvae were injected with different concentrations of the test compounds. Time-kill tests were executed on reference strains of C. albicans, E. coli, and S. aureus. According to the MTT-assay, the IC50 values were the following: ethyl sorbate, sorbic acid w/w, isopropyl sorbate 0.32% w/w, potassium sorbate >0.75% w/w, while Neutral Red values were >0.75% w/w for the esters and potassium sorbate and 0.66% w/w for sorbic acid. Flow cytometry results indicated the higher cell damage in case of isopropyl sorbate. However, the cytotoxic results of isopropyl sorbate, in vivo toxicity study on G. mellonella larvae did not show significant mortality. It was found, that the antimicrobial properties of isopropyl sorbate were outstanding compared to sorbic acid and potassium sorbate. These results indicate, that the use of sorbate esters can be advantageous, hence, further toxicity studies are needed to prove their safety.
Direct Formic Acid Mediated Z-Selective Reductive Coupling of Dienes and Aldehydes
Cooze, Christopher,Dada, Raphael,Lundgren, Rylan J.
supporting information, p. 12246 - 12251 (2019/08/01)
Methods for the addition of unsaturated nucleophiles to carbonyls to generate Z-olefin products remain rare and often require either alkyl borane or zinc reductants, limiting their utility. Demonstrated here is that formic acid mediates the Rh-catalyzed,
Quantitative structure-activity relationship studies for prediction of antimicrobial activity of synthesized 2,4-hexadienoic acid derivatives
Narasimhan, Balasubramanian,Judge, Vikramjeet,Narang, Rakesh,Ohlan, Ruchita,Ohlan, Sucheta
, p. 5836 - 5845 (2008/03/18)
A new series of 2,4-hexadienoic acid derivatives (S1-S42) has been synthesized and evaluated as antimicrobial agents against Staphylococcus aureus, Bacillus subtilis, Escherichia coli, Candida albicans, and Aspergillus niger. Quantitative structure-activity relationship (QSAR) investigation using Hansch analysis was applied to find out correlation between antimicrobial activities with physicochemical properties of the synthesized compounds. Various physicochemical descriptors and experimentally determined minimum inhibitory concentration values for different microorganisms were used as independent and dependent variables, respectively. The QSAR revealed that topological parameters especially molecular connectivity indices (χ2, 0χv, 2χv) were found to have overall significant correlation with antimicrobial activity of 2,4-hexadienoic acid derivatives. The statistical results of training set, cross-validated r2 and conventional r values gave reliability to the prediction of molecules with activity using QSAR models.
A Simple and Efficient Esterification Method
Ming-Yi, Chen,Lee, Adam Shih-Yuan
, p. 103 - 108 (2007/10/03)
A convenient and practical esterification was realized and this reaction proceeded without a dehydrating reagent or water removal equipment. The synthesis of esters by reaction of carboxylic acids with various alcohols such as methyl, ethyl, isopropyl, isobutyl, allyl, benzyl, propargyl and decanyl alcohols were achieved with a catalytic amount of CBr4 under refluxing reaction condition.
Polyenic acids. I. Antifungal and bacteriostatic activities of hexa-2,4 dienoic acid derivatives
Le Baut,Sparfel,Clairc,et al.
, p. 441 - 445 (2007/10/02)
Synthesis of esters and amides of 2,4-(2 E, 4 E) hexadienoic acid are reported. The authors have tried to modulate the polarity of these compounds by introducing sequences with hydroxyl, amino groups, ether, thioether functions and halogen atoms or heterocycles. A gain in bacteriostatic activity, compared with sorbic acid has been stated in some cases, it is accompanied by either a breakdown (compounds 3, 38, 51, and 54) or a maintenance of fungistatic activity (compounds 5, 10 and 17).
