Antioxidant properties of two novel lipophilic derivatives of hydroxytyrosol

• Published in: Food chemistry 2020-06, Vol.315, p.126197-126197, Article 126197
• Main Authors: Olajide, Tosin M., Liu, Tao, Liu, Haian, Weng, Xinchu
• Format: Article
• Language: English
• Subjects: 3,4-Dihydroxyphenylacetic Acid - chemistry; Antioxidant activity; Antioxidants - chemical synthesis; Antioxidants - chemistry; Cooking; Hydroquinones - chemistry; Hydroxytyrosol derivatives; Kinetic parameters; Kinetics; Lipophilicity; Olive Oil - chemistry; Phenylethyl Alcohol - analogs & derivatives; Phenylethyl Alcohol - chemistry; Rancimat test; Soybean Oil - chemistry; Structure-Activity Relationship; Temperature
• ISSN: 0308-8146; 1873-7072
• DOI: 10.1016/j.foodchem.2020.126197

[Display omitted] •Butylated hydroxytyrosol (HT) derivatives are excellent lipophilic antioxidants.•HT derivatives are better antioxidants than HT and TBHQ at high temperatures.•Bulky alkyl group was added to the ortho-diphenolic structure of HT.•DPPH scavenging activity decreased in the presence of bulky alkyl moiety.•Arrhenius kinetic parameters were evaluated. Two novel lipophilic derivatives of the natural olive oil phenol, hydroxytyrosol (HT), were synthesized using 3,4-dihydroxyphenylacetic acid as starting material. Their antioxidant activities and kinetics compared to HT and TBHQ were assessed by Rancimat, Schaal Oven, 2,2-diphenyl-1-picrylhydrazyl (DPPH) and deep-frying methods. All experiments, including kinetic data analysis based on the Arrhenius equation, utilized in assessing antioxidant activity except the DPPH assay revealed that the new lipophilic HT derivatives exhibited much stronger antioxidant activity than hydroxytyrosol. Tert-butylhydroquinone exhibited stronger antioxidant activity in bulk oil at 65 °C than the new HT derivatives, but showed much lower activity at higher temperatures (>110 °C). This demonstrates that the introduction of bulky alkyl moiety to the ortho-diphenolic structure of HT increased its antioxidant activity. It can be concluded that the new lipophilic HT derivatives satisfy industrial demands for bioactive compounds with strong antioxidant potential at high temperatures.