Terpenoid-capric acid based natural deep eutectic solvent: Insight into the nature of low viscosity

Fan, Chun‐Lin; Sebbah, Tarik; Liu, Yang; Cao, Xueli

doi:10.1016/j.clet.2021.100116

Cited by 18 publications

(6 citation statements)

References 42 publications

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Section: Introductionmentioning

confidence: 99%

“…[12] These solvents show hydrophobicity and low viscosity, but despite the interest of these novel mixtures, a deep understanding of these compounds and their mixtures is necessary as the nature of their unique properties still remains largely unknown. [15,16] In this sense, of all the works published so far on the use of hydrophobic eutectic mixtures as extracting solvents for hydrophobic compounds (see Table 1), only a few of them report partially the extracting capacity of the eutectic mixtures compared to that of the precursor compounds of the mixtures. [17,18] Although the separate precursor components are typically solids at room temperature and they have to be heated to be used as extracting solvents, it is important for their evaluation whether there are advantages in the use of hydrophobic eutectic mixtures in comparison to the use of their precursor components alone.…”

Section: Introductionmentioning

confidence: 99%

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A comparative study of lupeol extraction from a by‐product of lupin processing by hydrophobic natural deep eutectic solvents and their precursor components

Bañares,

Baréa,

Chabni

et al. 2023

Euro J Lipid Sci & Tech

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A series of hydrophobic natural deep eutectic solvents (HNADESs) have been employed to extract lupeol from lupin seed coat at 30 and 70°C. The extraction yields have been compared with those obtained with conventional organic solvents. In general, lupeol extraction yields (LEYs) obtained when using HNADES are somewhat smaller than those obtained if organic solvents are used. However, the nature of the HNADES mixtures as green solvents represents a superior performance in terms of sustainability of the extraction process. Additionally, an investigation has been carried out in order to compare the LEYs obtained when using the HNADES mixtures with those obtained if the isolated precursor compounds are employed at a temperature (70°C) where both HNADES and the corresponding precursor compounds are liquids. Surprisingly, LEYs for lupeol at 70°C were found to be, in some cases, slightly higher if the precursor compounds are used in comparison with the proper HNADES mixtures. It seems that the unique properties of the HNADES mixtures are not enough to perform better as extractants in comparison with the isolated precursor compounds at moderate temperatures, at least for the case of lupeol from lupin seed coat. Some hints are presented to explain these results.

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Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

A comparative study of lupeol extraction from a by‐product of lupin processing by hydrophobic natural deep eutectic solvents and their precursor components

Bañares,

Baréa,

Chabni

et al. 2023

Euro J Lipid Sci & Tech

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“…Recently, natural and biorenewable sources have been utilized to produce natural DESs, which have better environmental and operational properties with low toxicity and high biodegradability. An excellent candidate for the formation of natural DESs is terpenoids, which additionally promote the hydrophobicity of the obtained solvent, allowing the use of eutectic mixtures in the applications that require direct contact with water [ 30 ]. Although DESs have found wide application in analytical chemistry for sample preparation, their combination with the most sensitive detection method — mass spectrometry — remains a challenge.…”

Section: Introductionmentioning

confidence: 99%

Plant-based meat substitute analysis using microextraction with deep eutectic solvent followed by LC-MS/MS to determine acrylamide, 5-hydroxymethylfurfural and furaneol

Osiecka,

Vakh,

Makoś-Chełstowska

et al. 2023

Anal Bioanal Chem

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For the analysis of plant-based meat substitutes and the determination of Maillard reaction products such as acrylamide, 5-hydroxymethylfurfural and furaneol, a novel and effective procedure based on hydrophobic natural deep eutectic solvent and liquid chromatography coupled with tandem mass spectrometry was developed for the first time. The 49 compositions of the deep eutectic solvents were designed and screened to select the most suitable option. The terpenoids eugenol and thymol in a molar ratio of 2:1 were selected as precursors for solvent formation, allowing effective extraction of the target analytes. The developed procedure comprised two main steps: extraction — in which the analytes are isolated from the solid sample due to the salting-out effect and pre-concentrated in the deep eutectic solvent, and back-extraction — in which the analytes are re-extracted into the formic acid solution for subsequent mass spectrometric detection. As the density of the aqueous phases changed during the extraction and back-extraction steps, the phenomenon of inversion of the coalesced organic phase was observed, which simplified the withdrawing of the phases. The linear range was 1–50 ng/mL for acrylamide, 10–1000 ng/mL for 5-hydroxymethylfurfural and 200–1000 ng/mL for furaneol with coefficients of determination above 0.9952. The developed method was fully validated and found recoveries were in the range 83–120%, with CVs not exceeding 4.9%. The method was applied to real sample analysis of pea-based meat substitutes. Graphical abstract

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“…These terpenes-based DESs are often referred to as natural deep eutectic solvents (NADES). 20 The abundance of these natural resources accompanied by their high hydrophobicity and low viscosity has rendered them exceedingly advantageous for widespread use in drug delivery, biomass extraction, chemical reactions, separation, and processing, among others. 21−30 Moreover, NADESs are relatively novel and underutilized.…”

Section: ■ Introductionmentioning

confidence: 99%

“…A wide array of DESs composed of n -decanoic acid (DA), a common and popular long chain fatty acid, combined with five (5) different terpenoids (thymol (Thy), geraniol (Ger), linalool (Lin), eugenol (Eug), and β-citronellol (Cit)) are investigated. These terpenes-based DESs are often referred to as natural deep eutectic solvents (NADES) . The abundance of these natural resources accompanied by their high hydrophobicity and low viscosity has rendered them exceedingly advantageous for widespread use in drug delivery, biomass extraction, chemical reactions, separation, and processing, among others. − Moreover, NADESs are relatively novel and underutilized.…”

Section: Introductionmentioning

confidence: 99%

Decanoic Acid Based Deep Eutectic Solvents: Constituent-Controlled Physicochemical Properties and Solvatochromic Probe Behavior

Patra

Khokhar

Pandey

2022

Ind. Eng. Chem. Res.

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The search for environmentally benign sustainable replacements for volatile organic compounds (VOCs) has resulted in advent of deep eutectic solvents (DESs) that have exhibited enormous application potential. Apart from the fact that their constituents could be inexpensive and naturally occurring, the physicochemical properties of the DESs can be easily tailored by judicious and systematic alteration of their constituents. Physicochemical properties and solute solvation environment afforded by five so-called "hydrophobic" natural DESs (NADESs) prepared by mixing n-decanoic acid (DA) with terpenoids thymol (Thy), geraniol (Ger), linalool (Lin), eugenol (Eug), and βcitronellol (Cit), respectively, in 1:1 mol ratio are investigated. Significantly low water miscibility in the DA-based DESs renders them viable nonaqueous media in lieu of currently used organic solvents. Their densities are lower than that of water and higher than most of the common "hydrophilic" DESs. The refractive index of the DESs scale with the density. The dynamic viscosity of these DESs are relatively lower as compared to the common tetralkylammonium salt-and metal-salt-based DESs thus enhancing their utility due to faster diffusion and dynamics. Their surface tension values are similar to those of several common organic solvents but lower than those of common "hydrophilic" DESs. Kamlet−Taft parameters, obtained using UV−vis absorbance probes, reveal the dipolarity/polarizability (π*) to be much higher for phenyl group containing DESs (DA with Eug and Thy) in comparison to the others, whereas H-bond-donating acidity (α) does not vary much for the DESs. The H-bond-accepting basicity (β) spans wide range depending on the position of the hydroxyl group on the constituents. The solvation milieu of the ratiometric fluorescence probe pyrene is more polar for the phenyl-containing DESs as compared to the others. Five different fluorescence wavelength-shift solvatochromic probes reveal the solvation environment afforded by these DAbased DESs to be considerably nonpolar in nature. The outcomes reported here establish the DA-based NADESs as possible replacements for nonpolar organic solvents.

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Terpenoid-capric acid based natural deep eutectic solvent: Insight into the nature of low viscosity

Cited by 18 publications

References 42 publications

A comparative study of lupeol extraction from a by‐product of lupin processing by hydrophobic natural deep eutectic solvents and their precursor components

A comparative study of lupeol extraction from a by‐product of lupin processing by hydrophobic natural deep eutectic solvents and their precursor components

Plant-based meat substitute analysis using microextraction with deep eutectic solvent followed by LC-MS/MS to determine acrylamide, 5-hydroxymethylfurfural and furaneol

Decanoic Acid Based Deep Eutectic Solvents: Constituent-Controlled Physicochemical Properties and Solvatochromic Probe Behavior

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