Kinetic study of the quenching reaction of singlet oxygen by common synthetic antioxidants (tert-Butylhydroxyanisol, tert-di-Butylhydroxytoluene, and tert-Butylhydroquinone) as compared with α-Tocopherol

Ji In Kim, Jun Hyun Lee, Dong Seong Choi, Bo Mi Won, Mun Yhung Jung, Jiyong Park

Research output: Contribution to journalArticle

29 Citations (Scopus)

Abstract

Effects of synthetic phenolic antioxidants (BHA, BHT, and TBHQ) on the methylene blue (MB) sensitized photooxidation of linoleic acid as compared with that of α-tocopherol have been studied. Their antioxidative mechanism was studied by both ESR spectroscopy in a 2,2,6,6-tetramethylpiperidone (TMPD)-methylene blue (MB) system and spectroscopic analysis of rubrene oxidation induced by a chemical source of singlet oxygen. Total singlet oxygen quenching rate constants (kox-Q + kq) were determined using a steady state kinetic equation. TBHQ showed the strongest protective activity against the MB sensitized photooxidation of linoleic acid, followed by BHA and BHT. TBHQ (1 × 10-3 M) exhibited 86.5% and 71.4% inhibition of peroxide and conjugated diene formations, respectively, in linoleic acid photooxidation after 60-min light illumination. The protective activity of TBHQ against the photosensitized oxidation of linoleic acid was almost comparable to that of α-tocopherol. The data obtained from ESR and rubrene oxidation studies clearly showed the strong singlet oxygen quenching ability of TBHQ. The kox-Q + kq of BHA, BHT, and TBHQ were determined to be 3.37 × 107, 4.26 × 106, and 1.67 × 108 M-1 s-1, respectively. The kox-Q + kq of TBHQ was within the same order of magnitude of that of α-tocopherol, a known efficient singlet oxygen quencher. There was a high negative correlation (r2 = -0.991) between log (k ox-Q + kq) and reported oxidation potentials for the synthetic antioxidants, indicating their charge-transfer mechanism for singlet oxygen quenching. This is the 1st report on the kinetic study on k ox-Q + kq of TBHQ in methanol as compared with other commonly used commercial synthetic antioxidants and α-tocopherol.

Original languageEnglish
JournalJournal of Food Science
Volume74
Issue number5
DOIs
Publication statusPublished - 2009 Jun 1

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Butylated Hydroxytoluene
Singlet Oxygen
hydroquinone
singlet oxygen
butylated hydroxytoluene
Tocopherols
tocopherols
Antioxidants
photooxidation
linoleic acid
methylene blue
antioxidants
kinetics
oxidation
Linoleic Acid
Butylated Hydroxyanisole
oxen
Methylene Blue
peroxides
lighting

All Science Journal Classification (ASJC) codes

  • Food Science

Cite this

@article{d9fae1d41ead443ba96bf2ae8d555815,
title = "Kinetic study of the quenching reaction of singlet oxygen by common synthetic antioxidants (tert-Butylhydroxyanisol, tert-di-Butylhydroxytoluene, and tert-Butylhydroquinone) as compared with α-Tocopherol",
abstract = "Effects of synthetic phenolic antioxidants (BHA, BHT, and TBHQ) on the methylene blue (MB) sensitized photooxidation of linoleic acid as compared with that of α-tocopherol have been studied. Their antioxidative mechanism was studied by both ESR spectroscopy in a 2,2,6,6-tetramethylpiperidone (TMPD)-methylene blue (MB) system and spectroscopic analysis of rubrene oxidation induced by a chemical source of singlet oxygen. Total singlet oxygen quenching rate constants (kox-Q + kq) were determined using a steady state kinetic equation. TBHQ showed the strongest protective activity against the MB sensitized photooxidation of linoleic acid, followed by BHA and BHT. TBHQ (1 × 10-3 M) exhibited 86.5{\%} and 71.4{\%} inhibition of peroxide and conjugated diene formations, respectively, in linoleic acid photooxidation after 60-min light illumination. The protective activity of TBHQ against the photosensitized oxidation of linoleic acid was almost comparable to that of α-tocopherol. The data obtained from ESR and rubrene oxidation studies clearly showed the strong singlet oxygen quenching ability of TBHQ. The kox-Q + kq of BHA, BHT, and TBHQ were determined to be 3.37 × 107, 4.26 × 106, and 1.67 × 108 M-1 s-1, respectively. The kox-Q + kq of TBHQ was within the same order of magnitude of that of α-tocopherol, a known efficient singlet oxygen quencher. There was a high negative correlation (r2 = -0.991) between log (k ox-Q + kq) and reported oxidation potentials for the synthetic antioxidants, indicating their charge-transfer mechanism for singlet oxygen quenching. This is the 1st report on the kinetic study on k ox-Q + kq of TBHQ in methanol as compared with other commonly used commercial synthetic antioxidants and α-tocopherol.",
author = "Kim, {Ji In} and Lee, {Jun Hyun} and Choi, {Dong Seong} and Won, {Bo Mi} and Jung, {Mun Yhung} and Jiyong Park",
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language = "English",
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Kinetic study of the quenching reaction of singlet oxygen by common synthetic antioxidants (tert-Butylhydroxyanisol, tert-di-Butylhydroxytoluene, and tert-Butylhydroquinone) as compared with α-Tocopherol. / Kim, Ji In; Lee, Jun Hyun; Choi, Dong Seong; Won, Bo Mi; Jung, Mun Yhung; Park, Jiyong.

In: Journal of Food Science, Vol. 74, No. 5, 01.06.2009.

Research output: Contribution to journalArticle

TY - JOUR

T1 - Kinetic study of the quenching reaction of singlet oxygen by common synthetic antioxidants (tert-Butylhydroxyanisol, tert-di-Butylhydroxytoluene, and tert-Butylhydroquinone) as compared with α-Tocopherol

AU - Kim, Ji In

AU - Lee, Jun Hyun

AU - Choi, Dong Seong

AU - Won, Bo Mi

AU - Jung, Mun Yhung

AU - Park, Jiyong

PY - 2009/6/1

Y1 - 2009/6/1

N2 - Effects of synthetic phenolic antioxidants (BHA, BHT, and TBHQ) on the methylene blue (MB) sensitized photooxidation of linoleic acid as compared with that of α-tocopherol have been studied. Their antioxidative mechanism was studied by both ESR spectroscopy in a 2,2,6,6-tetramethylpiperidone (TMPD)-methylene blue (MB) system and spectroscopic analysis of rubrene oxidation induced by a chemical source of singlet oxygen. Total singlet oxygen quenching rate constants (kox-Q + kq) were determined using a steady state kinetic equation. TBHQ showed the strongest protective activity against the MB sensitized photooxidation of linoleic acid, followed by BHA and BHT. TBHQ (1 × 10-3 M) exhibited 86.5% and 71.4% inhibition of peroxide and conjugated diene formations, respectively, in linoleic acid photooxidation after 60-min light illumination. The protective activity of TBHQ against the photosensitized oxidation of linoleic acid was almost comparable to that of α-tocopherol. The data obtained from ESR and rubrene oxidation studies clearly showed the strong singlet oxygen quenching ability of TBHQ. The kox-Q + kq of BHA, BHT, and TBHQ were determined to be 3.37 × 107, 4.26 × 106, and 1.67 × 108 M-1 s-1, respectively. The kox-Q + kq of TBHQ was within the same order of magnitude of that of α-tocopherol, a known efficient singlet oxygen quencher. There was a high negative correlation (r2 = -0.991) between log (k ox-Q + kq) and reported oxidation potentials for the synthetic antioxidants, indicating their charge-transfer mechanism for singlet oxygen quenching. This is the 1st report on the kinetic study on k ox-Q + kq of TBHQ in methanol as compared with other commonly used commercial synthetic antioxidants and α-tocopherol.

AB - Effects of synthetic phenolic antioxidants (BHA, BHT, and TBHQ) on the methylene blue (MB) sensitized photooxidation of linoleic acid as compared with that of α-tocopherol have been studied. Their antioxidative mechanism was studied by both ESR spectroscopy in a 2,2,6,6-tetramethylpiperidone (TMPD)-methylene blue (MB) system and spectroscopic analysis of rubrene oxidation induced by a chemical source of singlet oxygen. Total singlet oxygen quenching rate constants (kox-Q + kq) were determined using a steady state kinetic equation. TBHQ showed the strongest protective activity against the MB sensitized photooxidation of linoleic acid, followed by BHA and BHT. TBHQ (1 × 10-3 M) exhibited 86.5% and 71.4% inhibition of peroxide and conjugated diene formations, respectively, in linoleic acid photooxidation after 60-min light illumination. The protective activity of TBHQ against the photosensitized oxidation of linoleic acid was almost comparable to that of α-tocopherol. The data obtained from ESR and rubrene oxidation studies clearly showed the strong singlet oxygen quenching ability of TBHQ. The kox-Q + kq of BHA, BHT, and TBHQ were determined to be 3.37 × 107, 4.26 × 106, and 1.67 × 108 M-1 s-1, respectively. The kox-Q + kq of TBHQ was within the same order of magnitude of that of α-tocopherol, a known efficient singlet oxygen quencher. There was a high negative correlation (r2 = -0.991) between log (k ox-Q + kq) and reported oxidation potentials for the synthetic antioxidants, indicating their charge-transfer mechanism for singlet oxygen quenching. This is the 1st report on the kinetic study on k ox-Q + kq of TBHQ in methanol as compared with other commonly used commercial synthetic antioxidants and α-tocopherol.

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