Comparison of two computational methods for solvent screening in countercurrent and centrifugal partition chromatography

Vilas-Boas, Sérgio M.; Cordova, Isabella W.; Kurnia, Kiki A.; Almeida, Heloísa H.S.; Gaschi, Priscilla S.; Coutinho, J.; Pinho, Simão P.; Ferreira, Olga

doi:10.1016/j.chroma.2022.462859

Cited by 9 publications

(13 citation statements)

References 87 publications

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“…The log P O/W for ferulic acid is 1.643 ± 0.0033, which means that almost 98% of ferulic acid is partitioned to n -octanol. Similar values of partition coefficient for ferulic acid were determined by other authors, i.e., 1.69 [ 49 ] using reversed-phase HPLC analysis and 1.77 [ 49 ] and 1.32 ± 0.01 [ 50 ] using the shake flask method. The prepared salts of ferulic acid with amino acid propyl esters are distinctly more hydrophilic than the unmodified acid.…”

Section: Discussionsupporting

confidence: 83%

New Ferulic Acid and Amino Acid Derivatives with Increased Cosmeceutical and Pharmaceutical Potential

et al. 2022

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Ferulic acid (FA) has been widely used in the pharmaceutical and cosmetics industry due to its, inter alia, antioxidant, antiaging and anti-inflammatory effects This compound added to cosmetic preparations can protect skin because of its photoprotective activity. However, the usefulness of FA as a therapeutic agent is limited due to its low solubility and bioavailability. The paper presents the synthesis, identification, and physicochemical properties of new FA derivatives with propyl esters of three amino acids, glycine (GPr[FA]), L-leucine (LPr[FA]), and L-proline (PPr[FA]). The NMR and FTIR spectroscopy, DSC, and TG analysis were used as analytical methods. Moreover, water solubility of the new conjugates was compared with the parent acid. Both ferulic acid and its conjugates were introduced into hydrogel and emulsion, and the resulting formulations were evaluated for stability. Additionally, in vitro penetration of all studied compounds from both formulations and for comparative purposes using Franz diffusion cells was evaluated from the solution in 70% (v/v) ethanol. Finally, cytotoxicity against murine fibroblasts L929 was tested. All of the analyzed compounds permeated pig skin and accumulated in it. LPr[FA] and PPr[FA] were characterized by much better permeability compared to the parent ferulic acid. Additionally, it was shown that all the analyzed derivatives are characterized by high antioxidant activity and lack of cytotoxicity. Therefore, they can be considered as an interesting alternative to be applied in dermatologic and cosmetic preparations.

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Section: Discussionsupporting

confidence: 83%

New Ferulic Acid and Amino Acid Derivatives with Increased Cosmeceutical and Pharmaceutical Potential

et al. 2022

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“…For a better comparison, the solubilities in water were excluded from Figure and are presented separately in Figure S1 in the SI. The solvent’s molecular parameters were retrieved from the literature. ,, …”

Section: Resultsmentioning

confidence: 99%

“…The semipredictive NRTL-SAC model has been extensively applied to describe the solubility of biomolecules in water and organic solvents ,− and was described in detail by Chen and co-authors. , In this approach, the activity coefficient of solute i is calculated as the sum of the combinatorial (γ i C ) and the residual (γ i R ) contributions ln ( γ i ) = ln ( γ i C ) + ln ( γ i R ) …”

Section: Modelingmentioning

confidence: 99%

“…In summary, the model characterizes the solute and solvent molecules by four conceptual segments representing different surface interactions: hydrophilicity ( X ), hydrophobicity ( Z ), polar-attractive ( Y – ), and polar-repulsive ( Y + ). These parameters are available in the literature for many solvents, ,,, including those addressed in this work. Therefore, only the solute descriptors are required to estimate the solubilities with the NRTL-SAC, which will be regressed using a small set of the experimental solubility data.…”

Section: Modelingmentioning

confidence: 99%

“…The solvent's molecular parameters were retrieved from the literature. 32,45,50 A very good description of the available solubility data for the monoterpenoids is obtained using the NRTL-SAC model, with global ARDs obtained in the correlation (15%) and prediction (14%). Excellent results were obtained for L-(−)-menthol and thymol (ARD lower than 8%) during correlation, and even lower for the predictions, where ARD is close to 4% for both solutes.…”

Section: Nrtl-sacmentioning

confidence: 99%

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Modeling the Solubility of Monoterpenoids with Hybrid and Predictive Thermodynamic Tools

Vilas-Boas

Cordova

Abranches

et al. 2023

Ind. Eng. Chem. Res.

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The Abraham and NRTL-SAC semipredictive models were employed to represent the solubility of (−)-borneol, (1R)-(+)-camphor, L-(−)-menthol, and thymol in water and organic solvents, using data measured in this work and collected from the literature. A reduced set of solubility data was used to estimate the model parameters of the solutes, and global average relative deviations (ARDs) of 27% for the Abraham model and 15% for the NRTL-SAC model were obtained. The predictive capability of these models was tested by estimating the solubilities in solvents not included in the correlation step. Global ARDs of 8% (Abraham model) and 14% (NRTL-SAC model) were obtained. Finally, the predictive COSMO-RS model was used to describe the solubility data in organic solvents, with ARD of 16%. These results show the overall better performance of NRTL-SAC in a hybrid correlation/prediction approach, while COSMO-RS can produce very satisfactory predictions even in the absence of any experimental data.

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“Sweet space” strategy for solvent system selection in countercurrent chromatography: A case study on separation of polyunsaturated fatty acids from borage oil

Han,

Fu,

Yang

et al. 2024

J of Separation Science

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This study presents a comprehensive strategy for the selection and optimization of solvent systems in countercurrent chromatography (CCC) for the effective separation of compounds. With a focus on traditional organic solvent systems, the research introduces a “sweet space” strategy that merges intuitive understanding with mathematical accuracy, addressing the significant challenges in solvent system selection, a critical bottleneck in the widespread application of CCC. By employing a combination of volume ratios and graphical representations, including both regular and trirectangular tetrahedron models, the proposed approach facilitates a more inclusive and user‐friendly strategy for solvent system selection. This study demonstrates the potential of the proposed strategy through the successful separation of gamma‐linolenic acid, oleic acid, and linoleic acid from borage oil, highlighting the strategy's effectiveness and practical applicability in CCC separations.

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Comparison of two computational methods for solvent screening in countercurrent and centrifugal partition chromatography

Cited by 9 publications

References 87 publications

New Ferulic Acid and Amino Acid Derivatives with Increased Cosmeceutical and Pharmaceutical Potential

New Ferulic Acid and Amino Acid Derivatives with Increased Cosmeceutical and Pharmaceutical Potential

Modeling the Solubility of Monoterpenoids with Hybrid and Predictive Thermodynamic Tools

“Sweet space” strategy for solvent system selection in countercurrent chromatography: A case study on separation of polyunsaturated fatty acids from borage oil

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