Synthesis, characterisation, and performance evaluation of tri-armed phenolic antioxidants

Higgins, Clare L.; Filip, Sorin V.; Afsar, Ashfaq; Hayes, Wayne

doi:10.1016/j.tetlet.2020.152127

Cited by 11 publications

(10 citation statements)

References 30 publications

(31 reference statements)

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“…It can be explained by the increased lipophilicity and stability aroused by esterified phenolic hydroxyl in AHE. Similarly, it was also reported that phenolic compounds with modified functional groups had a stronger antioxidant effect than themselves (Higgins et al ., 2020; Yu et al ., 2021). Importantly, covalently binding two antioxidant‐active molecules is an effective way to obtain new compounds with high antioxidant activity.…”

Section: Resultsmentioning

confidence: 99%

Synthesis of acetyl ferulic 7‐hydroxyisoflavone ester and evaluating its antioxidant activity on improving fish oil thermal stability

Wang,

Xue,

Yao

et al. 2023

Int J of Food Sci Tech

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SummaryAcetyl ferulic 7‐hydroxyisoflavone ester (AHE) was synthesized and its antioxidant capacity in vitro was evaluated by free radical scavenging assay and thermo‐oxidative stability analysis of fish oil in this study. The formation of primary and secondary oxidation products can be effectively inhibited by AHE, tert‐butylhydroxyquinone (TBHQ), ferulic acid and 7‐hydroxyisoflavone. The intensity of UV‐Vis absorption spectra increased significantly, whereas the intensity of fluorescence spectra decreased obviously with the deepening of oxidation degree of fish oil. AHE significantly alleviated the degradation of unsaturated fatty acids in fish oil. The results demonstrated that AHE was more effective than TBHQ, ferulic acid and 7‐hydroxyisoflavone in retarding the oxidative degradation of fish oil during high temperature storage (80 °C). Moreover, the formation of oxidation products in fish oil followed a first‐order kinetic model, and AHE effectively reduced reaction rate constant and delayed secondary lipid oxidation process. As a result, AHE is an effective antioxidant that can stabilise fish oil.

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Section: Resultsmentioning

confidence: 99%

Synthesis of acetyl ferulic 7‐hydroxyisoflavone ester and evaluating its antioxidant activity on improving fish oil thermal stability

Wang,

Xue,

Yao

et al. 2023

Int J of Food Sci Tech

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“…ðsolventÀ eÞ À . solv (14) where solvent solv is the molecule of solvent in the same solvent, and (solventÀ e) À * means that electron is attached to the molecule of solvent.…”

Section: Dft Study: Calculations Of Bde and Ipmentioning

confidence: 99%

“…Generally, increasing the numbers of the antioxidant fragments in one molecule represents an attractive approach to improve the antioxidative efficiency and thermal stability. But if the active moieties are the same such as multiple phenol, [8][9][10][11][12][13][14] polydiphenylamine [15] or polysulfides, [16] the improvement of the antioxidative efficiency is very limited. In view of the intermolecular synergism between hindered phenol and diphenylamine in the formula, [17][18][19][20] combining the active functions into one molecule could be an advanced strategy (Scheme 2).…”

Section: Introductionmentioning

confidence: 99%

A New Antioxidant with Higher Activity at Elevated Temperature Based on Multiple Intramolecular Synergisms

2023

ChemistrySelect

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A new type of multifunctional antioxidant RSSPD was designed through combining four different antioxidant fragments. Pressure differential scanning calorimetry (PDSC) tests show that RSSPD has outstanding antioxidative activity especially at high temperature compared with both the traditional antioxidants and our reported antioxidant SSPD. From the comparison with different related formulations and the density func-tional theory (DFT) calculations, a complicated intramolecular synergism mechanism is proposed. The intramolecular synergism between different primary antioxidants and the intramolecular synergism between primary antioxidants and secondary antioxidants can be considered as the main reasons for the high antioxidative activity of RSSPD.

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“…Among them, the antioxidants 1-13 were purchased in Wuhan, Hubei Province, China, with a purity of 98%, and their OOTs were obtained by experiment. The OOTs of antioxidants 14-30 in the same base oil were derived from the literature [19][20][21]. polyalphaolefin (PAO4) was employed as the lubricating base oil, and phenolic antioxidants were used as the research object, whose structures are shown in Table 1.…”

Section: Data Sources Of Antioxidantsmentioning

confidence: 99%

Evaluation of Antioxidant Properties and Molecular Design of Lubricant Antioxidants Based on QSPR Model

Liu,

Zhang,

et al. 2023

Lubricants

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Two quantitative structure–property relationship (QSPR) models of hindered phenolic antioxidants in lubricating oils were established to help guide the molecular structure design of antioxidants. Firstly, stepwise regression (SWR) was used to filter out essential molecular descriptors without autocorrelation, including electronic, topological, spatial, and structural descriptors, and multiple linear regression (MLR) was used to construct QSPR models based on the screened variables. The two models are statistically sound, with R2 values of 0.942 and 0.941, respectively. The models’ reliability was verified by the frontier molecular orbital energy gaps of the antioxidants. A hindered phenolic additive was designed based on the models. Its antioxidant property is calculated to be 20.9% and 11.0% higher than that of typical commercial antioxidants methyl 3-(3,5-di-tert-butyl-4-hydroxyphenyl) propionate and 2,2′-methylenebis(6-tert-butyl-4-methylphenol), respectively. The structure–property relationship of hindered phenolic antioxidants in lubricating oil obtained by computer-assisted analysis can not only predict the antioxidant properties of existing hindered phenolic additives but also provide theoretical basis and data support for the design or modification of lubricating oil additives with higher antioxidant properties.

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Synthesis, characterisation, and performance evaluation of tri-armed phenolic antioxidants

Cited by 11 publications

References 30 publications

Synthesis of acetyl ferulic 7‐hydroxyisoflavone ester and evaluating its antioxidant activity on improving fish oil thermal stability

Synthesis of acetyl ferulic 7‐hydroxyisoflavone ester and evaluating its antioxidant activity on improving fish oil thermal stability

A New Antioxidant with Higher Activity at Elevated Temperature Based on Multiple Intramolecular Synergisms

Evaluation of Antioxidant Properties and Molecular Design of Lubricant Antioxidants Based on QSPR Model

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