Abstract

With the increasing demand for antimicrobial agents and the spread of antibiotic resistance in pathogens, the exploitation of plant oils to partly replace antibiotic emerges as an important source of fine chemicals, functional food utility and pharmaceutical industries. This work introduces a novel catalytic method of plant oils hydroxylation by Fe(III) citrate monohydrate (Fe3+-cit.)/Na2S2O8 catalyst. Methyl (9Z,12Z)-octadecadienoate (ML) was selected as an example of vegetable oils hydroxylation to its hydroxy-conjugated derivatives (CHML) in the presence of a new complex of Fe(II)-species. Methyl 9,12-di-hydroxyoctadecanoate 1, methyl-9-hydroxyoctadecanoate 2 and methyl (10E,12E)-octadecanoate 3 mixtures is produced under optimized condition with oxygen balloon. The specific hydroxylation activity was lower in the case of using Na2S2O8 alone as a catalyst. A chemical reaction has shown the main process converted of plantoils hydroxylation and (+ 16 Da) of OH- attached at the methyl linoleate (ML-OH). HPLC and MALDI-ToF-mass spectrometry were employed for determining the obtained products. It was found that adding oxidizing agents (Na2S2O8) to Fe3+ in the MeCN mixture with H2O would generate the new complex of Fe(II)-species, which improves the C-H activation. Hence, the present study demonstrated a new functional method for better usage of vegetable oils.Producing conjugated hydroxy-fatty acids/esters with better antipathogenic properties. CHML used in food industry, It has a potential pathway to food safety and packaging process with good advantages, fundamental to microbial resistance. Lastly, our findings showed that biological monitoring of CHML-minimum inhibitory concentration (MIC) inhibited growth of various gram-positive and gram-negative bacteria in vitro study. The produced CHML profiles were comparable to the corresponding to previousstudies and showed improved the inhibition efficiency over the respective kanamycin derivatives.

Highlights

  • Diverse functions of vegetable oils have attracted their attention for fossil feedstock and industrial applications as renewable biomass to partly replace theSenan et al BMC Chemistry (2021) 15:20 fatty acid is based on the reaction of isomerization and/ or oxidation to corresponding keto-fatty acids/esters isomers with Pd(II)/Lewis acid catalyst [13, 14]

  • The chemical reaction was carried out in acetonitrile mixture with water at 80 °C in presence of oxygen balloon, offering 95.3 ± 3.2% neither of the conjugated hydroxy methyl linoleate (CHML) mixture product, while neither Fe (III) ­C6H7O8 nor of sodium persulfate alone is inactive for methyl linoleate hydroxylation

  • The hydroxylation of plant oils exhibited the significant role of ­Na2S2O8 in promoting the Fe(III)-catalyzed methyl linoleate hydroxylation

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Summary

Introduction

Diverse functions of vegetable oils have attracted their attention for fossil feedstock and industrial applications as renewable biomass to partly replace theSenan et al BMC Chemistry (2021) 15:20 fatty acid is based on the reaction of isomerization and/ or oxidation to corresponding keto-fatty acids/esters isomers with Pd(II)/Lewis acid catalyst [13, 14]. The iron (III) citrate is significantly activated N­ a2S2O8 and, it promotes the hydroxylation of methyl linoleate to the corresponding hydroxy-conjugates under simple conditions.

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