Synthesis and studies on gelation ability of phenol based maleate amphiphile and its application in nutraceutical release

Kumar, Bijari Anil; Chowdhury, Sabyasachi Roy; Mishra, Sabyashachi; Nayak, Rati Ranjan

doi:10.1016/j.colsurfa.2017.08.031

Cited by 6 publications

(4 citation statements)

References 50 publications

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“…Four gelator molecules with different alkyl chain lengths, 6‐PAM, 8‐PAM, 10‐PAM, and 12‐PAM were synthesized under mild reaction conditions (Scheme S1, Supporting Information) . The phenoxy‐alkyl maleates form gels efficiently in numerous edible oils namely, corn, olive, gingelly, canola, soybean, groundnut, rice bran, sunflower, coconut, and palm oils (Figure S13, Supporting Information).…”

Section: Resultsmentioning

confidence: 99%

“…To address the issue of edible oil gelation, we designed and synthesized the phenoxy alkyl derivatives with maleic anhydride in the terminal head group, phenoxy moiety at the other terminal. It should be noteworthy to mention, the polar maleic anhydride group may facilitate intermolecular hydrogen bonding, and the phenoxy group will help in the formation of π–π stackings . Furthermore, the alkyl chain is responsible for van der Wall interaction.…”

Section: Introductionmentioning

confidence: 99%

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Phenoxy‐Alkyl Maleates as Phase‐Selective Organogelators for Gelation of Edible Oils

Kumar

Nayak

2018

Euro J Lipid Sci & Tech

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Phase selective gelation may solve environmental problems such as water pollution and fire accidents during oil storage, a major problem for aquatic bodies. The objective of this work is to synthesize a series of phenoxy‐alkyl maleates (n‐PAM) oleogelators with homologous alkyl chain lengths for efficient phase selective gelation. The n‐PAM molecules are found to form oleogel in various edible oils among which sunflower oil shows best gelation. The gelation behavior increases with an increase in alkyl chain length of the n‐PAM gelators as observed from their low minimum gelation concentration (MGC) values. Oleogels thermal stability is examine through tube inversion method and differential scanning calorimetry (DSC). The rheological studies suggest that the oleogel of sunflower oil is mechanically stable and show typical viscoelastic properties. The field emission scanning electron microscopy (FE‐SEM) study of the gels shows sheet‐like morphology. Furthermore, the n‐PAM gelators exhibit quick phase selective gelation of edible oils at low MGC. Both the edible oil and gelator are quantitatively regained from recovered oleogel by employing the vacuum distillation. It is believed that these n‐PAMs could aid in reducing the environmental impacts of oil spills. Practical Applications: The phenoxy‐alkyl maleates gelators present in the MS show gelation ability in various edible oils at low minimum gelation concentration. These molecules also form efficient phase selective gelation with edible oils. Both oil and gelator can be recovered through vacuum distillation and gelator can be reused multiple times. Thus, all these advantages strongly point that out their bright future, in particular in edible oil spill recovery, could aid in reducing the environmental impacts from oil spills. Herein, the synthesized phenoxy alkyl maleate derivatives are reported as separators of edible oil from the oil‐water biphasic mixture. Initially, the gelator is solubilized in the biphasic mixture by heating. Later, gelation ability is observed by tube inversion method. From the phase selective gel, oil and gelator are separated through a distillation method. The recovered gelator can be reused in oil recovery process. This application may find use in oil recovery from waste plant of edible oil industries.

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Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Phenoxy‐Alkyl Maleates as Phase‐Selective Organogelators for Gelation of Edible Oils

Kumar

Nayak

2018

Euro J Lipid Sci & Tech

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“…As observed, glycolipids 12M , 12D , and 16D formed organogels in the presence of water only. The hydrogen bonding induced due to the presence of water preferred the gel formation . From this observation, the connection between the gelation ability with respect to the volume of water used was established.…”

Section: Resultsmentioning

confidence: 95%

“…The hydrogen bonding induced due to the presence of water preferred the gel formation. 41 From this observation, the connection between the gelation ability with respect to the volume of water used was established. With the change in water volume, the maximum quantity of solvent utilized to form stable organogels was studied and is presented in Figure S1.…”

Section: Resultsmentioning

confidence: 99%

Supramolecular Glycolipid-Based Hydro-/Organogels with Enzymatic Bioactive Release Ability by Tuning the Chain Length and Headgroup Size

Holey

Sekhar

Swain

et al. 2022

ACS Biomater. Sci. Eng.

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Designing of supramolecular hydro-/organogels having desired properties, biocompatibility, and stimuli responsiveness is a challenging task. Herein, the gelation ability of amphiphilic glycolipid-based gelators in a wide range of solvents is explored. The structure–function relationship was established by varying the chain length and polar headgroup size of amphiphilic gelators. The prepared hydro-/organogels were characterized by employing several techniques such as differential scanning calorimetry (DSC), rheology, field emission scanning electron microscopy (FE-SEM), high-resolution transmission electron microscopy (HR-TEM), X-ray diffraction (XRD), etc. The thermal stability of hydro-/organogels increased with an increase in chain length. Rheological analysis depicted that variation in chain length and headgroup size of amphiphilic gelators significantly affected the gel strength and stability. The self-assembled morphology of hydro-/organogel samples revealed the compact entangled fibrillar network structures. After comparing the energy-minimized molecular length with the d-spacing value obtained by XRD, interdigitated bilayer packing in the gel network was established. The bioactive encapsulation and enzymatic release study of hydro-/organogels portrayed their potential application in the biomedical field. To our delight, glycolipid 16M (C16 chain length) formed a molecular hydrogel with injectable and thixotropic behaviors. High critical strain value, thixotropy, injectability, thermoreversibility, and faster bioactive release for the 16M-W hydrogel proved crucial to predict its future applications. Overall, glycolipid amphiphiles designed by upholding proper hydrophilic–lipophilic balance can form multifunctional supramolecular hydrogels with excellent implementation in the drug delivery system.

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Supramolecular phenoxy-alkyl maleate-based hydrogels and their enzyme/pH-responsive curcumin release

Kumar

Nayak

2019

New J. Chem.

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Synthesis and studies on gelation ability of phenol based maleate amphiphile and its application in nutraceutical release

Cited by 6 publications

References 50 publications

Phenoxy‐Alkyl Maleates as Phase‐Selective Organogelators for Gelation of Edible Oils

Phenoxy‐Alkyl Maleates as Phase‐Selective Organogelators for Gelation of Edible Oils

Supramolecular Glycolipid-Based Hydro-/Organogels with Enzymatic Bioactive Release Ability by Tuning the Chain Length and Headgroup Size

Supramolecular phenoxy-alkyl maleate-based hydrogels and their enzyme/pH-responsive curcumin release

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