Photo-antioxidant abilities of 2-hydroxybenzoyl compounds

Dobashi, Yoshiyuki; Kondou, Jun-ichi; Ohkatsu, Yasukazu

doi:10.1016/j.polymdegradstab.2005.01.010

Cited by 33 publications

(20 citation statements)

References 15 publications

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“…It is plain that the extension of the conjugation system containing a 4-oxo-5-hydroxy benzene moiety through the double bond is necessary for the increase in the photo-antioxidant activity. Table 5 shows photo-antioxidant activities of another series of 2-hydroxybenzoyl compounds 5) . Comparison of the groups connected to the 2-hydroxybenzoyl shows that unsaturated hydrocarbon groups control photo-oxidation better than saturated groups.…”

Section: Antioxidant and Photo-antioxidant Activitiesmentioning

confidence: 99%

“…Comparison of the groups connected to the 2-hydroxybenzoyl shows that unsaturated hydrocarbon groups control photo-oxidation better than saturated groups. In particular, a group giving a more enlarged conjugation system, such as styryl, seems to improve photoantioxidant activity much more 5) . This fact may be explained by the resonance stabilization of a photoexcited species with the C2 _ C3 double bond of the flavonoid C ring.…”

Section: Antioxidant and Photo-antioxidant Activitiesmentioning

confidence: 99%

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Relationship between Chemical Structure and Antioxidant Function of Flavonoids

Ohkatsu

Sakurai

Sato

2010

J. Jpn. Petrol. Inst.

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Antioxidant activities (including photo-antioxidant activities) of flavonoids were evaluated fundamentally and kinetically for the potential to produce plastic food packages with high antioxidant performance and food safety. Chalcones with two aromatic rings acquire additional another ring by ring-closure in the metabolic pathway of chalcones and form a flavanone (naringenin), with dramatically decreased antioxidant activities. As further metabolism proceeds, naringenin produces various flavonoids, which gradually acquire antioxidant activities comparable to and finally higher than those of chalcones. Therefore, a plant can again form an enhanced antioxidant, especially with photo-antioxidant activities. In general, flavonoids are present in the concentration of 1-10 mmol/dm 3 in plants. The metabolite with the highest antioxidant activities, quercetin, was found to protect a plant almost completely in the concentration of 0.5 mmol/dm 3 from harmful UV radiation. The complex metabolic pathway of tyrosine or phenylalanine to flavonoids will be partly necessary for the safe photo-synthesis of plants without suffering UV damage. Such flavonoids are expected to be useful for the safe stabilization of petro chemicals, especially food packages.

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Section: Antioxidant and Photo-antioxidant Activitiesmentioning

confidence: 99%

Section: Antioxidant and Photo-antioxidant Activitiesmentioning

confidence: 99%

Relationship between Chemical Structure and Antioxidant Function of Flavonoids

Ohkatsu

Sakurai

Sato

2010

J. Jpn. Petrol. Inst.

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“…2-Hydroxy-4-methoxybenzophenone, 2-hydroxybenzophenone, 2-hydroxy-5-methylbenzophenone, 2 0 -hydroxy-5 0 -methoxyacetophenone, phenyl salicylate, 4-tert-butylphenyl salicylate, 4-nitrophenyl salicylate, benzyl salicylate, and n-propyl salicylate were purchased from Tokyo Kasei Kogyo Ltd. The other benzophenone-type UVA and homologs were synthesized by procedures reported in a paper [10,11]. The other salicylate-type UVA were synthesized by the following general procedures.…”

Section: Commercial Uvamentioning

confidence: 99%

“…Supposing that the essence of UVA performance is to inhibit the photo-oxidation of polymeric materials, we tried to connect the 3 with photo-antioxidant ability of UVA, but our effort ended in failure [10,11]. Instead, we have just found the fairly good correlation between photo-antioxidant ability and maximum absorption wavelength (l max ) of UVA.…”

Section: Introductionmentioning

confidence: 99%

Dependence of ultraviolet absorbers' performance on ultraviolet wavelength

Dobashi

Ohkatsu

2008

Polymer Degradation and Stability

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“…Introduction 2,4-dihydroxy benzophenone is one of the most commonly used UV absorbers (UVA) suitable [1][2][3]. It can transform absorbed radiation energy into less harmful thermal energy via a photophysical process involving ground-state and excited-state molecules [4,5], and has been used as compounding agents for sun-screening cosmetics and medicals or as additives in various plastics, resins, anti-UV coatings, functional textile finishing, and many other fields to prevent the undesirable photooxidation and photodegradation from sunlight [6][7][8].…”

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confidence: 99%

Synthesis, characterization, and crystal structure of modified benzophenone UV-absorber containing reactive group

Shen

Zhu²,

Chen³

et al. 2015

Res Chem Intermed

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A modified benzophenone UV-absorber containing reactive group (4-(4,6-dichloro-1,3,5-triazin-2-yloxy)-2-hydroxyphenyl)phenyl)methanone (UV-DTHM) has been prepared in good yield from the nucleophilic substitution reaction of 2,4-dihydroxy benzophenone with 2,4,6-trichlorotriazine, catalyzed by 1.3 equiv. NaOH. The most favorable reaction conditions (the catalyst dosage, the mole ratio of the reactants, and reactive time) were selected. The compound was characterized by IR spectroscopy, 1 H NMR, 13 C NMR, mass spectrometry, elemental analysis, and single crystal X-ray diffraction. The crystal monoclinic, space group C c with the unit cell parameters a = 3.987(2), b = 30.688(16), c = 12.423(6) Å and a = 90.00, b = 92.117(15), c = 90.008, Z = 4, R = 0.0620. wR(F 2 ) = 0.1589. The crystal structure reveals that 2,4,6-trichlorotriazine is boned to 4-seat hydroxyl of 2,4-dihydroxy benzophenone and a intramolecular hydrogen bond is formed with hydrogen of 2-hydroxyl and oxygen of carbonyl group. Moreover, thermogravimetric analysis (TGA) of UV-DTHM was studied, showing two distinct endothermic peaks at temperatures of 281.5 and 358.5°C. The molar absorption coefficient of UV-DTHM is 1.6 9 10 4 and 6.3 9 10 3 at 268 and 330 nm, respectively, and shows excellent ultraviolet absorption property.Electronic supplementary material The online version of this article (

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Photo-antioxidant abilities of 2-hydroxybenzoyl compounds

Cited by 33 publications

References 15 publications

Relationship between Chemical Structure and Antioxidant Function of Flavonoids

Relationship between Chemical Structure and Antioxidant Function of Flavonoids

Dependence of ultraviolet absorbers' performance on ultraviolet wavelength

Synthesis, characterization, and crystal structure of modified benzophenone UV-absorber containing reactive group

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