Evaluation of antioxidant activity and electronic structure of aspirin and paracetamol

Motozaki, W.; Nagatani, Y.; Kimura, Yukio; Endo, Kazunaka; Takemura, Tamiko; Kurmaev, E.Z.; Moewes, A.

doi:10.1016/j.molstruc.2010.10.021

Cited by 6 publications

(3 citation statements)

References 35 publications

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“…9, on high H 2 O 2 concentration such as induced lipid peroxidation, the hydroxylated phenol derivatives can be formed (Diniz et al, 2004;Alves et al, 2006;Motozaki et al, 2011). The reaction mechanisms are related to electron or hydrogen transfer mediated by HO Á radical (Teismann and Ferger, 2000) in accordance with theoretically proposed mechanism for other phenol derivatives (Leopoldini et al, 2011a, b;Iuga et al, 2012;Marino et al, 2014;Alberto et al, 2013).…”

Section: Resultssupporting

confidence: 63%

A computational study for the antioxidant capacity increases in hydroxy-derivatives of paracetamol and salicylic acid

et al. 2015

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Paracetamol is a more potent antioxidant than salicylic acid on the several oxidative stress-forced models. A possible mechanism of hydroxylation by the hydroxyl radicals and their antioxidant properties was performed by molecular modeling using quantum chemical calculations at the B3LYP level of theory. The calculation was made in gas phase and water using PCM method. The electron abstraction for hydroxylated paracetamol derivatives is more favored than hydroxylated salicylic acid derivatives. The increase in antioxidant capacity is more observed for hydroxylated derivatives of the paracetamol than salicylic acid. Some hydroxylated derivatives of paracetamol and salicylic acid were more reactive than trolox by hydrogen transfer. Their antioxidant capacity can be increased by number and position of the hydroxyl group.

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Section: Resultssupporting

confidence: 63%

A computational study for the antioxidant capacity increases in hydroxy-derivatives of paracetamol and salicylic acid

et al. 2015

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“…AAP is also an important antioxidant as it is known to quench the formation of radicals that attack proteins and thus suppresses oxidative damage. 14 Chemically, AAP is a well-conjugated molecule (Fig. 1), whose methyl-capped peptide group may provide important sites for molecular recognition.…”

mentioning

confidence: 99%

Conformationally resolved structures of jet-cooled acetaminophen by UV–UV hole-burning spectroscopy

Lee

Min

Kim

et al. 2011

Phys. Chem. Chem. Phys.

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The conformational structures of jet-cooled acetaminophen were investigated in the gas phase by resonant 2-photon ionization and UV-UV hole-burning spectroscopy. In contrast to the results from a previous study, two nearly isoenergetic conformers were distinctly found in a supersonic molecular beam expansion and positively identified as the cis and trans isomers of acetaminophen by UV-UV hole-burning spectroscopy. The 0-0 bands of the cis and trans isomers were found at 33518.7 and 33485.6 cm(-1), respectively. The vibronic bands of the two isomers are close-lying and/or partially overlapping due to the small energy difference (33 cm(-1)) between the two 0-0 bands. As a consequence, the recorded resonant 2-photon ionization spectrum is highly congested in the low excitation energy region, which develops continuously into a featureless, broadened spectrum in the high energy region.

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“…In fact, the spin density calculation reveals that the semiquinone free-radical of paracetamol has more resonance structures in the aromatic ring than that of the salicylic acid. Therefore, DFT calculations indicated that the paracetamol presents larger stability for the semiquinone free-radical formation compared to the salicylic acid [26] [36]- [40].…”

Section: Structure and Activity Relationshipmentioning

confidence: 99%

A Structure and Antioxidant Activity Study of Paracetamol and Salicylic Acid

Borges¹,

Barros²,

Pereira³

et al. 2014

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The paracetamol has more antioxidant properties than the salicylic acid on the several oxidative stress-forced models and one possible mechanism is due to electron or hydrogen transfer by the evaluated hydroxyl radicals. The antioxidant mechanism for the compounds studied here was performed by molecular modeling using quantum chemical calculations at the B3LYP level of theory. Our results show that the paracetamol has more antioxidant properties than the salicylic acid in experimental and theoretical studies. The theoretical mechanism show that the hydrogen transfer is more favorable than the electron transfer. From the study it was concluded that the electron abstraction for paracetamol is more favored than salicylic acid.

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Evaluation of antioxidant activity and electronic structure of aspirin and paracetamol

Cited by 6 publications

References 35 publications

A computational study for the antioxidant capacity increases in hydroxy-derivatives of paracetamol and salicylic acid

A computational study for the antioxidant capacity increases in hydroxy-derivatives of paracetamol and salicylic acid

Conformationally resolved structures of jet-cooled acetaminophen by UV–UV hole-burning spectroscopy

A Structure and Antioxidant Activity Study of Paracetamol and Salicylic Acid

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