Antioxidant properties of butylatedhydroxytoluene refluxed in ferric chloride solution

• Published in: Food chemistry Vol. 61; no. 1; pp. 101 - 105
• Main Authors: Duan, S, Weng, X.C, Dong, X.W, Liu, Y.P, Li, H.P, Jin, J.R
• Format: Journal Article
• Language: English
• Published: Oxford Elsevier Ltd 1998; Elsevier
• Subjects: Chemistry; Exact sciences and technology; Noncondensed benzenic compounds; Organic chemistry; Preparations and properties; Induction period; Backfat; Enol; Phenols; Benzenic compound; Steric hindrance; Iron III Chlorides; Foodstuff; Quinonemethide; Toluene derivatives; Antioxidant; Animal fat
• ISSN: 0308-8146; 1873-7072
• DOI: 10.1016/S0308-8146(97)00122-2

1,2-Bis (3,5- di- tert-butyl-4-hydroxyphenyl)-ethane (BBH PE), 3,3′,5,5′- tetra- tert-butyl-stilbene-4,4′-quinone (TBSQ), 3,3′,5,5′- tetra- tert-butylhydroxy-stilbene-4,4′-quinone (TBHSQ) and 4-hydroxy-3,5- tert-butylbenzaldehyde (HBBA) were isolated from a mixture of butylatedhydroxytoluene (BHT) refluxed in ferric chloride solution by using TLC and identified by mass, NMR, IR and UV spectra. Their antioxidant properties were investigated individually and in comparison with BHT and butylatedhydroxyanisole (BHA) on the Oxidative Stability Instrument (OSI) at 95, 100 and 105°C, separately. This demonstrated that BBHPE was the strongest antioxidant of the compounds isolated, much stronger even than BHT and as strong as BHA. The phenolic compound, HBBA, structurally similar to BHT, had much weaker antioxidant effect than BHT and even weaker than the quinones, TBSQ and TBHSQ. The strength of the antioxidant activity of the compounds decreased in the order: BHA, BBHPE >> BHT > TBSQ, TBHSQ > HBBA. As temperature increased, the protection factors (Pf) of BHA and BHT increased, but those of BBHPE, TBSQ, TBHSQ and HBBA decreased slightly.