eprintid: 17059
rev_number: 2
eprint_status: archive
userid: 1
dir: disk0/00/01/70/59
datestamp: 2023-12-19 03:23:31
lastmod: 2023-12-19 03:23:31
status_changed: 2023-12-19 03:07:23
type: article
metadata_visibility: show
creators_name: Shimul, I.M.
creators_name: Moshikur, R.M.
creators_name: Minamihata, K.
creators_name: Moniruzzaman, M.
creators_name: Kamiya, N.
creators_name: Goto, M.
title: Amino Acid Ester based Phenolic Ionic Liquids as a Potential Solvent for the Bioactive Compound Luteolin: Synthesis, Characterization, and Food Preservation Activity
ispublished: pub
keywords: Amino acids; Biocompatibility; Dissolution; Esters; Flavonoids; Food preservation; Food preservatives; Hydrogen bonds; Positive ions; Solubility; Solvents, Amino acid esters; Bioactive compounds; Bioactives; Conductor-like screening model for real solvents; Ethyl esters; Flavonoid; Natural bioactives; Phenolic acids; Phenolics; Synthesised, Ionic liquids
note: cited By 13
abstract: Ionic liquids (ILs) have gained great attention as potent solubilizing agents of poorly soluble bioactive compounds. The use of Luteolin (LUT) � a natural bioactive compound � is limited because of its poor aqueous solubility. To address this issue, this study reports potential ILs for effectively solubilizing LUT at ambient temperature. First, promising ILs were screened from a potential 180 ILs that were proposed by the combination of 20 standard amino acid ethyl esters cations and nine phenolic acids anions using the conductor-like screening model for real solvents (COSMO-RS); the activity coefficients of LUT at infinite dilution in ILs were used as the screening criteria. Four proline ethyl ester phenolate ILs (PEEP-ILs) composed of a biocompatible proline ethyl ester and bioactive phenolic acids (trans-ferulic, vanillic, p-coumaric, and 4-hydroxybenzoic acid) were selected and synthesized. The synthesized PEEP-ILs were characterized through 1H NMR, FT-IR, elemental analysis, TGA, and DSC. The experimental solubility of LUT in PEEP-ILs (60 IL in water) showed excellent solubility. Among the PEEP-ILs, proline ethyl ester ferulate (ILProEtFer) exhibited the best LUT solubility, followed by ILs with p-coumarate (ILProEtCou), vanillate (ILProEtVan), and 4-hydroxybenzoate (ILProEtBen). 1H NMR assessment and COSMO-RS prediction confirmed that the ILs facilitated the solubilization of LUT through multiple hydrogen bonding, � � �, and cation � � interactions between the LUT and the ILs. The biocompatibility study revealed that PEEP-ILs were relatively harmless and low toxicity compared with conventional imidazolium, pyridinium, pyrrolidinium, piperidinium, and morpholinium-based ILs. The LUT dissolved in the newly-synthesized PEEP-ILs and demonstrated better organoleptic properties on red apple slices. These results indicate that PEEP-ILs can be potential green alternatives to conventional toxic solvents for dissolving poorly water-soluble bioactive natural preservatives. © 2021 Elsevier B.V.
date: 2022
publisher: Elsevier B.V.
official_url: https://www.scopus.com/inward/record.uri?eid=2-s2.0-85119397295&doi=10.1016%2fj.molliq.2021.118103&partnerID=40&md5=7015c3aed2438d4652c76d68a3251bd7
id_number: 10.1016/j.molliq.2021.118103
full_text_status: none
publication: Journal of Molecular Liquids
volume: 349
refereed: TRUE
issn: 01677322
citation:   Shimul, I.M. and Moshikur, R.M. and Minamihata, K. and Moniruzzaman, M. and Kamiya, N. and Goto, M.  (2022) Amino Acid Ester based Phenolic Ionic Liquids as a Potential Solvent for the Bioactive Compound Luteolin: Synthesis, Characterization, and Food Preservation Activity.  Journal of Molecular Liquids, 349.   ISSN 01677322