Product recovery of an enzymatically synthesized (−)-menthol ester in a deep eutectic solvent

Pätzold, Magdalena; Burek, Bastien O.; Liese, Andreas; Bloh, Jonathan Z.; Holtmann, Dirk

doi:10.1007/s00449-019-02125-6

Cited by 21 publications

(8 citation statements)

References 16 publications

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“…In the case of menthol/hesperetin mixtures, the liquidus line could not be measured in an extensive composition region since its temperatures approached the normal boiling temperature of menthol (485 K [36]). Therefore, only a few points could be obtained for x menthol ≥ 0.75.…”

Section: Resultsmentioning

confidence: 99%

Liquefying Flavonoids with Terpenoids through Deep Eutectic Solvent Formation

et al. 2022

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The formation of deep eutectic solvents (DES) is tied to negative deviations to ideality caused by the establishment of stronger interactions in the mixture than in the pure DES precursors. This work tested thymol and menthol as hydrogen bond donors when combined with different flavonoids. Negative deviations from ideality were observed upon mixing thymol with either flavone or flavanone, two parent flavonoids that only have hydrogen bond acceptor (HBA) groups, thus forming non-ionic DES (Type V). On the other hand, the menthol systems with the same compounds generally showed positive deviations from ideality. That was also the case with the mixtures containing the more complex hydroxylated flavonoid, hesperetin, which resulted in positive deviations when mixed with either thymol or menthol. COSMO-RS successfully predicted the behavior of the solid-liquid phase diagram of the studied systems, allowing for evaluation of the impact of the different contributions to the intermolecular interactions, and proving to be a good tool for the design of DES.

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Section: Resultsmentioning

confidence: 99%

Liquefying Flavonoids with Terpenoids through Deep Eutectic Solvent Formation

et al. 2022

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“…Closer investigation of the reaction system revealed that water addition and stirring speed are interacting parameters. Furthermore, a product recovery strategy from the DES (−)-menthol/dodecanoic acid 3:1 was later demonstrated [ 101 ]. The product (−)-menthyl dodecanoate ester was separated from the DES reaction mixture and a second esterification reaction could be performed with the recovered (−)-menthol.…”

Section: Esterifications and Transesterificationmentioning

confidence: 99%

Combination of Enzymes and Deep Eutectic Solvents as Powerful Toolbox for Organic Synthesis

et al. 2023

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During the last decade, a wide spectrum of applications and advantages in the use of deep eutectic solvents for promoting organic reactions has been well established among the scientific community. Among these synthetic methodologies, in recent years, various examples of biocatalyzed processes have been reported, making use of eutectic mixtures as reaction media, as an improvement in terms of selectivity and sustainability. This review aims to show the newly reported protocols in the field, subdivided by reaction class as a ‘toolbox’ guide for organic synthesis.

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“…Notably, after 7 days of reaction, 50, 71, and 83% of octanoic acid, dodecanoic acid, and decanoic acid yielded their respective menthyl esters. To improve the esterification of menthol:DodecaA HDES, Pätzold and co-workers further examined the requisite enzyme quantity, thermodynamic water activity, and temperature of the esterification reaction, respectively . Under optimal reaction conditions, the group observed that 95% of the acid converted to ester within a day.…”

Section: Future Scope and Challengesmentioning

confidence: 99%

“…To improve the esterification of menthol:DodecaA HDES, Pätzold and co-workers further examined the requisite enzyme quantity, thermodynamic water activity, and temperature of the esterification reaction, respectively. 80 Under optimal reaction conditions, the group observed that 95% of the acid converted to ester within a day. Furthermore, a 1.36 mol/L concentration of the product was generated in 2.25 days.…”

Section: Future Scope and Challengesmentioning

confidence: 99%

Hydrophobic Deep Eutectic Solvents as Greener Substitutes for Conventional Extraction Media: Examples and Techniques

et al. 2023

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Deep eutectic solvents (DESs) are multicomponent designer solvents that exist as stable liquids over a wide range of temperatures. Over the last two decades, research has been dedicated to developing noncytotoxic, biodegradable, and biocompatible DESs to replace commercially available toxic organic solvents. However, most of the DESs formulated until now are hydrophilic and disintegrate via dissolution on coming in contact with the aqueous phase. To expand the repertoire of DESs as green solvents, hydrophobic DESs (HDESs) were prepared as an alternative. The hydrophobicity is a consequence of the constituents and can be modified according to the nature of the application. Due to their immiscibility, HDESs induce phase segregation in an aqueous solution and thus can be utilized as an extracting medium for a multitude of compounds. Here, we review literature reporting the usage of HDESs for the extraction of various organic compounds and metal ions from aqueous solutions and absorption of gases like CO 2 . We also discuss the techniques currently employed in the extraction processes. We have delineated the limitations that might reduce the applicability of these solvents and also discussed examples of how DESs behave as reaction media. Our review presents the possibility of HDESs being used as substitutes for conventional organic solvents.

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Product recovery of an enzymatically synthesized (−)-menthol ester in a deep eutectic solvent

Cited by 21 publications

References 16 publications

Liquefying Flavonoids with Terpenoids through Deep Eutectic Solvent Formation

Liquefying Flavonoids with Terpenoids through Deep Eutectic Solvent Formation

Combination of Enzymes and Deep Eutectic Solvents as Powerful Toolbox for Organic Synthesis

Hydrophobic Deep Eutectic Solvents as Greener Substitutes for Conventional Extraction Media: Examples and Techniques

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