Synthesis and properties of gallate ionic liquids

Czerniak, Kamil; Biedziak, Agnieszka; Krawczyk, Krzysztof; Pernak, Juliusz

doi:10.1016/j.tet.2016.09.007

Cited by 8 publications

(8 citation statements)

References 49 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…The obtained ILs containing anions were derived from acids showing antioxidant activity: L‐ascorbic (AscH), protocatechuic (ProH), gentisic (GenH), gallic (GalH), syringic (SyrH), coumaric (CouH), caffeic (CafH), ferulic (FerH), and sinapic (SinH) acids. Until now, the protonation method has only been used for synthesis of salts and ILs based on various types of betaine [29,41–43] . This method is characterized by simplicity, the possible use of low‐cost solvents such as short‐chain alcohols (e. g., methanol), and the absence of byproducts compared to the metathesis reaction [44] …”

Section: Resultsmentioning

confidence: 99%

“…Until now, the protonation method has only been used for synthesis of salts and ILs based on various types of betaine. [29,[41][42][43] This method is characterized by simplicity, the possible use of low-cost solvents such as short-chain alcohols (e. g., methanol), and the absence of byproducts compared to the metathesis reaction. [44] The synthesized ILs containing the L-carnitine cation are depicted in Table 1, and the structures of the ILs anions are specified in Figure 1.…”

Section: Resultsmentioning

confidence: 99%

“…The papers published by our group thus far describe antioxidant ILs based on phenolic acids such as caffeic, ellagic, gallic, ferulic, protocatechuic and gentisic acids or antioxidant compounds such as abietic acid, L‐ascorbic acid or 2‐furoic acid [28–35] . Moreover, ILs were used in the production of iongels based on e. g. gelatin or carbon nanotubes and exhibiting antioxidant properties [36–38] .…”

Section: Introductionmentioning

confidence: 99%

“…[27] The papers published by our group thus far describe antioxidant ILs based on phenolic acids such as caffeic, ellagic, gallic, ferulic, protocatechuic and gentisic acids or antioxidant compounds such as abietic acid, L-ascorbic acid or 2-furoic acid. [28][29][30][31][32][33][34][35] Moreover, ILs were used in the production of iongels based on e. g. gelatin or carbon nanotubes and exhibiting antioxidant properties. [36][37][38] The purpose of this work was to determine the characteristics of bio-based ILs containing only anions derived from naturally occurring L-ascorbic acid and phenolic acids and cations based on L-carnitine.…”

Section: Introductionmentioning

confidence: 99%

See 3 more Smart Citations

L‐Carnitine‐Based Bio‐Ionic Liquids as Antioxidants

Czerniak

Pernak

2021

ChemistrySelect

Self Cite

View full text Add to dashboard Cite

The purpose of this research was to determine the antioxidant properties of ionic liquids containing an anion showing antioxidant activity and a cation of natural origin derived from L‐carnitine. Formation methods of ionic liquids based on direct protonation of an L‐carnitine zwitterion form were evaluated with the selected phenolic acids and L‐ascorbic acid. All received compounds were characterized, and the physicochemical properties significant to ionic liquid uses were measured (thermal stability and phase transitions). All research on antioxidant activity was conducted using commonly applied spectrophotometric methods, allowing for assessment of the neutralization ability of compounds regarding various radicals. The ferrous and cupric ion reduction ability and ferrous ion chelation of the ionic liquids were also examined. Furthermore, ionic liquid activity toward the enzyme xanthine oxidase responsible for the formation of reactive oxygen species in the body was determined.

show abstract

Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

See 2 more Smart Citations

L‐Carnitine‐Based Bio‐Ionic Liquids as Antioxidants

Czerniak

Pernak

2021

ChemistrySelect

Self Cite

View full text Add to dashboard Cite

show abstract

“…Czerniak et al synthesized gallate-based ILs to enhance the performance of the antioxidant. From their finding, the antioxidant activity of the synthesized ILs were seen affected by the intermolecular hydrogen bond that present due to the linear chain and stearic effect of the structure [34]. The same research group has then studied the dicationic based ILs and found that as the number of the active group increases on the structure, the antioxidant activity of the synthesized compound increased [35].…”

Section: Introductionmentioning

confidence: 99%

A Kinetic Approach of DPPH Free Radical Assay of Ferulate-Based Protic Ionic Liquids (PILs)

et al. 2018

View full text Add to dashboard Cite

The antiradical efficiency (AE) and kinetic behavior of a new ferulate-based protic ionic liquids (PILs) were described using 2,2-diphenyl-1-picrylhydrazyl (DPPH) free radical assay. The reduction of the DPPH free radical (DPPH•) was investigated by measuring the decrease in absorbance at 517 nm. The time to reach steady state for the reaction of parent acid (ferulic acid) and synthesized PILs with DPPH• was continuously recorded for 1 h. Results revealed that the AE of 2-butylaminoethanol ferulate (2BAEF), 3-dimethylaminopropanol ferulate (3DMAPF) and 3-diethylaminopropanol ferulate (3DEAPF) PILs have improved compared to ferulic acid (FA) as the reaction class changes from low to medium. This attributed to the strong hydrogen abstraction occurred in the PILs. Furthermore, these PILs were found to have a good kinetic behavior compared to FA due to the high rate constant (k2) (164.17, 242.84 and 244.73 M−1 s−1, respectively). The alkyl chain length and more alkyl substituents on the nitrogen atom of cation were believed to reduce the cation-anion interaction and speed up the hydrogen atom transfer (HAT) and electron transfer (ET) mechanisms; hence, increased rate constant was observed leading to a strong antioxidant activity of the synthesized PILs.

show abstract

Effect of Choline Cation Derivatives on the Efficacy of Plant Resistance Inducers

Czerwoniec

2022

ChemistrySelect

View full text Add to dashboard Cite

This article presents the synthesis, physical properties, phytotoxicity, and SAR induction activity of 48 new ionic liquids composed of cations which are choline derivatives and anions of inducers such as salicylic acid, 2,6‐dichloroisonicotinic acid, and benzo[1.2.3]thiadiazole‐7‐carboxylic acid. The cations from which the reported salts were obtained differ in the length of the aliphatic chain bonded to the N,N‐dimethylethanolamine, N,N‐diethylethanolamine, and N,N‐dibutylethanolamine groups. Examination of the obtained series of compounds determined the correlation between the structure of the cation and the biological action of the resistance inducer and investigated the relationship between the structure of the cation and its phytotoxic effect on the plant. Systemic acquired resistance efficacy tests were performed on tobacco Nicotiana tabacum var. Xanthi infected by tobacco mosaic virus (TMV) and phytotoxic tests were performed on Agrimonia eupatoria seeds. The results indicate that the phytotoxicity of salts composed of the same cation increases with the introduction of anions in the following order: salicylate<2,6‐dichloroisonicotinate

show abstract

Synthesis and properties of gallate ionic liquids

Cited by 8 publications

References 49 publications

L‐Carnitine‐Based Bio‐Ionic Liquids as Antioxidants

L‐Carnitine‐Based Bio‐Ionic Liquids as Antioxidants

A Kinetic Approach of DPPH Free Radical Assay of Ferulate-Based Protic Ionic Liquids (PILs)

Effect of Choline Cation Derivatives on the Efficacy of Plant Resistance Inducers

Contact Info

Product

Resources

About