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Butylated hydroxy benzylidene ring: an important moiety for antioxidant synergism of semicarbazones

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Abstract

The compounds having two or more antioxidant functions in their structure exhibit antioxidant synergism that generally increase the antioxidant activity of these compounds. In this study, two series of semicarbazone (7a–j and 7a′–j′) bearing butylated ortho and para hydroxy benzylidene ring were prepared for the investigation of antioxidant synergism. This study found that intramolecular hydrogen bond can form in semicarbazones due to the inappropriate position of hydroxyl group on benzylidene ring, which adversely affects the antioxidant synergism. As consequence, butylated para hydroxyl benzylidene phenyl semicarbazone (7a) (IC50 12.27 µM) showed ~ 4.3 times and ~ 2.7 times better antioxidant activity than compounds 7a′ (IC50 53.30 µM) and BHT (IC50 32.63 µM), respectively, in DPPH assay. In addition, based on the solubility in trimethylolpropane trioleate (TMPTO) as synthetic base oil and obtained IC50 results, oxidation stability of synthesized compounds was also evaluated by two kinds of differential scanning calorimeter (DSC) test, namely temperature ramping DSC and programmed temperature DSC. Thermogravimetric analysis is also performed for the thermal stability assessment. TMPTO incorporated with 0.25 mass% of 7c and 7e were found better oxidative (around 2 times) and thermal resistance than BHT. This DSC results showed another important aspect of semicarbazones that proper modification of semicarbazones can be used in the synthetic lubricant oil as a potential antioxidant. Thus, the results of this study are promising which can be taken under consideration to design and prepare more efficient multipotent semicarbazones.

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Acknowledgements

The authors would like to thank Grand Challenge (GC001C-14AET), PPP Grant PG208-2015B and RU2018 provided by the University of Malaya and Ministry of Higher Education, Malaysia (MOHE) for their cordial support in completing this work.

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  1. Nanotechnology and Catalysis Research Centre (NANOCAT), Block 3A, Institute for Advanced Studies, University of Malaya, 50603, Kuala Lumpur, Malaysia

    Amit R. Nath, Wageeh A. Yehye & Mohd Rafie Bin Johan

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  1. Amit R. Nath
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Correspondence to Wageeh A. Yehye.

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Nath, A.R., Yehye, W.A. & Johan, M.R. Butylated hydroxy benzylidene ring: an important moiety for antioxidant synergism of semicarbazones. J Therm Anal Calorim 146, 2101–2114 (2021). https://doi.org/10.1007/s10973-020-10199-8

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