Kinetic study of the quenching reaction of singlet oxygen by biological hydroquinones and related compounds

Mukai, Kazuo; Itoh, Shintaro; Daifuku, Koji; Morimoto, H.; Inoue, Kenzo

doi:10.1016/0005-2728(93)90234-7

Cited by 22 publications

(34 citation statements)

References 25 publications

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“…Thomas and Foote (1978) reported that a plot of log ( k ox−Q + k q ) compared with oxidation potential for the phenol was linear over most of the range (with the correlation coefficient = 0.96). Similar relations were also observed for the hydroquinons (Mukai and others 1993), aliphatic amines (Monroe 1977), and catechins (Mukai and others 2005). The high relationship between the log ( k ox−Q + k q ) and E ° for BHA, BHT, and TBHQ clearly suggested that the transition state in the singlet oxygen quenching reaction by synthetic phenols has a property of a charge‐transfer mechanism.…”

Section: Resultssupporting

confidence: 75%

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

Lee

Choi

et al. 2009

Journal of Food Science

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Effects of synthetic phenolic antioxidants (BHA, BHT, and TBHQ) on the methylene blue (MB) sensitized photooxidation of linoleic acid as compared with that of alpha-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 (k(ox-Q)+k(q)) 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 x 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 alpha-tocopherol. The data obtained from ESR and rubrene oxidation studies clearly showed the strong singlet oxygen quenching ability of TBHQ. The k(ox-Q)+k(q) of BHA, BHT, and TBHQ were determined to be 3.37 x 10(7), 4.26 x 10(6), and 1.67 x 10(8) M(-1) s(-1), respectively. The k(ox-Q)+k(q) of TBHQ was within the same order of magnitude of that of alpha-tocopherol, a known efficient singlet oxygen quencher. There was a high negative correlation (r(2) = -0.991) between log (k(ox-Q)+k(q)) 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)+k(q) of TBHQ in methanol as compared with other commonly used commercial synthetic antioxidants and alpha-tocopherol.

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Section: Resultssupporting

confidence: 75%

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

Lee

Choi

et al. 2009

Journal of Food Science

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“…By using eq , the second-order rate constants ( k Q values) of the 1 O 2 quenching by AYAAQs have been determined from the slopes of the k versus [Q] plots, and are listed in Table , together with SOAC values (measures of 1 O 2 quenching) . The k Q value of TFAQ is close to that of vitamin E (α-tocopherol, 1.2 × 10 8 M –1 s –1 in ethanol), which is well-known as an efficient 1 O 2 quencher. , …”

Section: Resultsmentioning

confidence: 99%

Correlation between Excited-State Intramolecular Proton-Transfer and Singlet-Oxygen Quenching Activities in 1-(Acylamino)anthraquinones

et al. 2014

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Excited-state intramolecular proton-transfer (ESIPT) and singlet-oxygen ((1)O2) quenching activities of intramolecularly hydrogen-bonded 1-(acylamino)anthraquinones have been studied by means of static and laser spectroscopies. The ESIPT shows a substituent effect, which can be explained in terms of the nodal-plane model. The ESIPT activity positively and linearly correlates with their (1)O2 quenching activity. The reason for this correlation can be understood by considering ESIPT-induced distortion of their ground-state potential surface and their encounter complex formation with (1)O2. Intramolecularly hydrogen-bonded hydroxyanthraquinones found in aloe also show a similar positive and linear correlation, which can be understood in the same way.

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“…Related nitrogen-containing functional groups also quench O 2 ( 1 Δ g ). Hydrazines are known as excellent physical charge-transfer quenchers, but sulfenamides (R−S−NR 2 ) quench singlet oxygen through reactive pathways. , In addition to nitrogen-based functionalities, various hydroquinones, phenols, and methoxybenzenes also physically quench O 2 ( 1 Δ g ) with rate constants that depend on ease of oxidation. ,, …”

Section: Introductionmentioning

confidence: 99%

“…18,19 In addition to nitrogen-based functionalities, various hydroquinones, phenols, and methoxybenzenes also physically quench O 2 ( 1 ∆ g ) with rate constants that depend on ease of oxidation. 16,20,21 The key intermediates in the quenching pathways, exciplexes of singlet oxygen, are not very well characterized. Some years ago, Foote estimated that the 1 (O 2 δ-‚‚‚phenol δ+ ) exciplex in methanol involves 44% of the charge transfer expected for full electron transfer.…”

Section: Introductionmentioning

confidence: 99%

Charge-Transfer Quenching of Singlet Oxygen O₂(¹Δ_g) by Amines and Aromatic Hydrocarbons

1998

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The quenching rate constants of singlet oxygen O2(1Δg) luminescence at 1.27 μm by 29 amines and aromatic hydrocarbons were measured in acetonitrile and benzene. Quenching occurs via reversible charge transfer with the formation of an exciplex with a partial (δ ≈ 0.2 esu) electron transfer. An estimate of the intersystem-crossing rate constant for the exciplex of ca. 1010 s-1 is obtained, and a modest decrease with increasing exciplex energy is noted. The data predict and it is confirmed that charge transfer plays a significant role in the nonradiative decay of singlet oxygen in solvents as difficult to oxidize as toluene-d 8 and mesitylene. It is also confirmed that N,N,N‘,N‘-tetramethyl-p-phenylene diamine quenches O2(1Δg) nearly exclusively by full electron transfer in D2O, but electron transfer is not observed in other solvents.

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Kinetic study of the quenching reaction of singlet oxygen by biological hydroquinones and related compounds

Cited by 22 publications

References 25 publications

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

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

Correlation between Excited-State Intramolecular Proton-Transfer and Singlet-Oxygen Quenching Activities in 1-(Acylamino)anthraquinones

Charge-Transfer Quenching of Singlet Oxygen O₂(¹Δ_g) by Amines and Aromatic Hydrocarbons

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Kinetic study of the quenching reaction of singlet oxygen by biological hydroquinones and related compounds

Cited by 22 publications

References 25 publications

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

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

Correlation between Excited-State Intramolecular Proton-Transfer and Singlet-Oxygen Quenching Activities in 1-(Acylamino)anthraquinones

Charge-Transfer Quenching of Singlet Oxygen O2(1Δg) by Amines and Aromatic Hydrocarbons

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Charge-Transfer Quenching of Singlet Oxygen O₂(¹Δ_g) by Amines and Aromatic Hydrocarbons