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• 88-26-6 3,5-di-tert-butyl-4-hydroxybenzyl alcohol 

Relevant academic research and scientific papers

Synthesis of the hydrazones of 2-((3,5-di-tert-butyl-4-hydroxybenzyl) thio) acetohydrazide and the study of their radical scavenging activity by the DPPH assay and the computational method

The synthesis of antioxidant compounds bearing pharmacologically active groups has become a research interest in the last decade.Aseries of hydrazones containing a butylated hydroxyl group were synthesized from 2-((3,5-di-tert-butyl-4-hydroxybenzyl)thio)acetohydrazide and various benzaldehyde derivatives, and their radical scavenging activity was explored by 2,2-diphenyl-1-picrylhydrazyl (DPPH) assay and computational calculations. Based on the results, the effects of different substituents on the DPPH IC50 values were discussed. The bond dissociation enthalpies (BDE) of O H and N Hbonds and the spin density (SD) values of the compounds were calculated using the density functional theory (DFT) to determine the theoretical capability of the hydrazones as radical scavengers. Based on the results, the effects of the thioether group and the substituent groups next to the N H bond on the BDE values were also discussed.

Semicarbazide and thiosemicarbazide containing butylated hydroxytoluene moiety: new potential antioxidant additives for synthetic lubricating oil

New multipotent antioxidants (MPAOs), namely semicarbazides and thiosemicarbazides bearing thiolated butylated hydroxytoluene (BHT), were synthesized. The antioxidant activity of the synthesized compounds was evaluated usingin vitroDPPH assay. Compounds containing thiosemicarbazides (5a′-h′) were found more active in free radical scavenger than semicarbazides (5a-h). Among the other compounds, compound5f′(IC50of 25.47 ± 0.42 μM) showed the best antioxidant activity against DPPH radicals compared to standard antioxidant butylated hydroxytoluene (BHT). Based on DPPH results, compound5f′and its corresponding semicarbazide5fwere blended into trimethylolpropane trioleate (TMPTO) and isothermal differential scanning calorimetry (DSC) was carried out for the investigation of oxidative stability. At 125 °C isothermal DSC, TMPTO with 0.25 wt% of5f′showed 1.5 times higher oxidation stability than its corresponding semicarbazide5fand was 2 times better than BHT. It was anticipated that due to the strong auto-synergistic effect, compound5f′showed promising oxidative stability to TMPTO by protecting from pre-mature oxidative degradation.

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

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. Graphic abstract: [Figure not available: see fulltext.]