Synthesis and biological properties of choline esters of amino acids

Topuzyan, V. O.; Gerasimyan, D. A.; Bagdasaryan, A. L.; Mndzhoyan, O. L.

doi:10.1007/bf00765209

Cited by 3 publications

(5 citation statements)

References 2 publications

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“…S8-S11, ESI [3,6,9,47,63,[72][73][74][75] Other methods of derivatization of carboxylic acids pp. S11-S16, ESI [56,57,62,[76][77][78][79][80][81][82] Utilization of biologically active compounds pp. S17-S20, ESI [9,47,57,83,84]…”

Section: Synthetic Proceduresmentioning

confidence: 99%

“…Two types of esterquats (choline-type and betaine-type), exhibit different physicochemical properties [ 3 , 6 ]. As demonstrated in Figure 8 , the presence of an ester bond within esterquats structure makes them susceptible to hydrolysis, and these compounds are even more reactive than conventional esters [ 56 , 62 , 76 , 77 ]. The quaternary positively charged nitrogen atom in betaines pulls electron density from the neighboring atoms, resulting in carbonyl carbon becoming more electrophilic.…”

Section: Susceptibility To Hydrolysis Of Choline-type and Betaine-typ...mentioning

confidence: 99%

“…Refs. [ 3 , 9 , 10 , 11 , 14 , 15 , 16 , 17 , 18 , 19 , 20 , 29 , 47 , 48 , 49 , 55 , 56 , 57 , 61 , 62 , 64 , 64 , 65 , 66 , 67 , 68 , 69 , 70 , 71 , 72 , 73 , 74 , 75 , 76 , 77 , 78 , 79 , 80 , 81 , 82 , 83 , 84 , 98 , 99 , 100 , 101 , 102 , 103 , 104 , 105 , 106 , 107 , 108 , 109 , 110 , 111 , 112 , 113 , ...…”

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Rethinking the Esterquats: Synthesis, Stability, Ecotoxicity and Applications of Esterquats Incorporating Analogs of Betaine or Choline as the Cation in Their Structure

Wysocki,

Stachowiak,

Smolibowski

et al. 2024

IJMS

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Esterquats constitute a unique group of quaternary ammonium salts (QASs) that contain an ester bond in the structure of the cation. Despite the numerous advantages of this class of compounds, only two mini-reviews discuss the subject of esterquats: the first one (2007) briefly summarizes their types, synthesis, and structural elements required for a beneficial environmental profile and only briefly covers their applications whereas the second one only reviews the stability of selected betaine-type esterquats in aqueous solutions. The rationale for writing this review is to critically reevaluate the relevant literature and provide others with a “state-of-the-art” snapshot of choline-type esterquats and betaine-type esterquats. Hence, the first part of this survey thoroughly summarizes the most important scientific reports demonstrating effective synthesis routes leading to the formation of both types of esterquats. In the second section, the susceptibility of esterquats to hydrolysis is explained, and the influence of various factors, such as the pH, the degree of salinity, or the temperature of the solution, was subjected to thorough analysis that includes quantitative components. The next two sections refer to various aspects associated with the ecotoxicity of esterquats. Consequently, their biodegradation and toxic effects on microorganisms are extensively analyzed as crucial factors that can affect their commercialization. Then, the reported applications of esterquats are briefly discussed, including the functionalization of macromolecules, such as cotton fabric as well as their successful utilization on a commercial scale. The last section demonstrates the most essential conclusions and reported drawbacks that allow us to elucidate future recommendations regarding the development of these promising chemicals.

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Section: Synthetic Proceduresmentioning

confidence: 99%

Section: Susceptibility To Hydrolysis Of Choline-type and Betaine-typ...mentioning

confidence: 99%

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Rethinking the Esterquats: Synthesis, Stability, Ecotoxicity and Applications of Esterquats Incorporating Analogs of Betaine or Choline as the Cation in Their Structure

Wysocki,

Stachowiak,

Smolibowski

et al. 2024

IJMS

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show abstract

“…Two types of esterquats (choline-type and betaine-type), exhibit different physicochemical properties [3,6]. As demonstrated in Figure 8, the presence of an ester bond within esterquats structure makes them susceptible to hydrolysis, and these compounds are even more reactive than conventional esters [55,61,75,76]. The quaternary positively charged nitrogen atom in betaines pulls electron density from the neighboring atoms, resulting in carbonyl carbon to become more electrophilic.…”

Section: Susceptibility To Hydrolysis Of Choline-type and Betaine-typ...mentioning

confidence: 99%

Rethinking the Esterquats: Synthesis, Stability, Ecotoxicity and Applications of Esterquats Incorporating Analogs of Betaine or Choline as the Cation in Their Structure

Wysocki,

Stachowiak,

Smolibowski

et al. 2024

Preprint

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Esterquats constitute a unique group of quaternary ammonium salts (QASs) that contain an ester bond in the structure of the cation. Despite the numerous advantages of this class of compounds, only two mini-reviews discuss the subject of esterquats: the first one (2007) briefly summarizes their types, synthesis, and structural elements required for a beneficial environmental profile and only briefly covers their applications whereas the second one only reviews the stability of selected betaine-type esterquats in aqueous solutions. The rationale for writing this review is to critically reevaluate the relevant literature and provide others with a “state-of-the-art” snapshot of choline-type esterquats and betaine-type esterquats. Hence, the first part of this survey thoroughly summarizes the most important scientific reports demonstrating effective synthesis routes leading to the formation of both types of esterquats. In the second section, the susceptibility of esterquats to hydrolysis is explained, and the influence of various factors, such as the pH, the degree of salinity or the temperature of the solution, was subjected to thorough analysis that includes quantitative components. The next two sections refer to various aspects associated with the ecotoxicity of esterquats. Consequently, their biodegradation and toxic effects on microorganisms are extensively analyzed as crucial factors that can affect their commercialization. Then, the reported applications of esterquats are briefly discussed, including functionalization of macromolecules, such as cotton fabric as well as their successful utilization on a commercial scale. The last section demonstrates the most essential conclusions and reported drawbacks that allow us to elucidate future recommendations regarding the development of these promising chemicals.

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“…An analysis of the reaction mixture of 2-(N-phthaloyl-13-alanyl)-l-oxybenzotriazole (IIIf) with DMAE 2 (1 : 2) performed by TLC (Silufol UV-254, chloroform-benzenemethanol, 9 : 1 : 1) showed that the "activated" amide IIIf is completely consumed within 45 rain. Such a high rate of the reaction between DMAE with III (as compared to that with p-nitrophenyl esters [3,4]) is quite expectable, since benzotriazole-l-oxy group exceeds the p-nitrophen0xy group 2 Besides the standard abbreviations recommended by the IUPAC-IUB Commission on biochemistry nomenclature [10, I 1] we use the following abbreviations: DMAE = 13-dimethylaminoethanol, 7-Abu = ~,-aminobutyric acid (GABA), ~-Aka = e-aminocaproic acid. …”

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confidence: 94%

Choline esters of N-substituted amino acids. IX. Synthesis and cholinergic properties of β-dimethylaminoethyl esters of N-substituted amino acids

et al. 1997

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Synthesis and biological properties of choline esters of amino acids

Cited by 3 publications

References 2 publications

Rethinking the Esterquats: Synthesis, Stability, Ecotoxicity and Applications of Esterquats Incorporating Analogs of Betaine or Choline as the Cation in Their Structure

Rethinking the Esterquats: Synthesis, Stability, Ecotoxicity and Applications of Esterquats Incorporating Analogs of Betaine or Choline as the Cation in Their Structure

Rethinking the Esterquats: Synthesis, Stability, Ecotoxicity and Applications of Esterquats Incorporating Analogs of Betaine or Choline as the Cation in Their Structure

Choline esters of N-substituted amino acids. IX. Synthesis and cholinergic properties of β-dimethylaminoethyl esters of N-substituted amino acids

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