Methyl anthranilate as generator and quencher of reactive oxygen species: a photochemical study
- Autores
- Gambetta, Carolina; Natera, Jose Eduardo; Massad, Walter Alfredo; Garcia, Norman Andino
- Año de publicación
- 2013
- Idioma
- inglés
- Tipo de recurso
- artículo
- Estado
- versión publicada
- Descripción
- Methyl anthranilate (MA) is a naturally occurring aromatizer and flavorant agent frequently employed in food industry and in personal care products. Due to the property of MA of being a UV-A radiation-absorber it is incorporated to topical sunscreen formulations. Within the framework of the wide variety of practical uses and applications, the photodegradation of MA becomes a topic of interest from health to an economic point of view. In this context, kinetics and mechanistic aspects of its photo-oxidation has been studied, in order to know the degradation pathways of MA under natural-like photoirradiation. The assays were performed in the absence and in the presence of riboflavin (Rf, vitamin B2) acting the later as a native photosensitizer. The results showed that MA is capable to generate singlet molecular oxygen (O2(1Δg)) upon direct UV-A irradiation, with a quantum yield value of 0.13 ± 0.02. The anthranilate also quenches the oxidative species with an overall rate constant value kt = 2.1 ± 0.2 × 107 M−1 s−1 while the reactive interaction between MA and O2(1Δg) showed a rate constant value in the range of 5.9–6.8 × 106 M−1 s−1. The kr/kt ratio, lower than 0.35 indicates that only one third of the O2(1Δg)-quenching events effectively lead to oxidation of the scavenger, being this an acceptable property for a sunscreen component. Regarding the Rf-photosensitized visible-light irradiation of MA–Rf mixtures, the anthranilate quenches the electronically excited singlet and triplet states of the vitamin. As a result the oxidative species O2− and H2O2, are generated, being the later effectively deactivated by MA. At first, the described results would show MA as a candidate for UV-A and visible-light mediated degradation. Nevertheless, at the same time MA acts as a moderate physical scavenger of photogenerated oxidative species in a sort of self-protector against photoinduced degradation and protector of oxidizable surrounding compounds.
Fil: Gambetta, Carolina. Universidad Nacional de Río Cuarto. Facultad de Ciencias Exactas Fisicoquímicas y Naturales. Departamento de Química; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina
Fil: Natera, Jose Eduardo. Universidad Nacional de Río Cuarto. Facultad de Ciencias Exactas Fisicoquímicas y Naturales. Departamento de Química; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina
Fil: Massad, Walter Alfredo. Universidad Nacional de Río Cuarto. Facultad de Ciencias Exactas Fisicoquímicas y Naturales. Departamento de Química; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina
Fil: Garcia, Norman Andino. Universidad Nacional de Río Cuarto. Facultad de Ciencias Exactas Fisicoquímicas y Naturales. Departamento de Química; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina - Materia
-
Methyl Anthranilate
Singlet Oxygen
Reactive Oxygen Species
Photochemistry - Nivel de accesibilidad
- acceso abierto
- Condiciones de uso
- https://creativecommons.org/licenses/by-nc-nd/2.5/ar/
- Repositorio
- Institución
- Consejo Nacional de Investigaciones Científicas y Técnicas
- OAI Identificador
- oai:ri.conicet.gov.ar:11336/23309
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Methyl anthranilate as generator and quencher of reactive oxygen species: a photochemical studyGambetta, CarolinaNatera, Jose EduardoMassad, Walter AlfredoGarcia, Norman AndinoMethyl AnthranilateSinglet OxygenReactive Oxygen SpeciesPhotochemistryhttps://purl.org/becyt/ford/1.4https://purl.org/becyt/ford/1Methyl anthranilate (MA) is a naturally occurring aromatizer and flavorant agent frequently employed in food industry and in personal care products. Due to the property of MA of being a UV-A radiation-absorber it is incorporated to topical sunscreen formulations. Within the framework of the wide variety of practical uses and applications, the photodegradation of MA becomes a topic of interest from health to an economic point of view. In this context, kinetics and mechanistic aspects of its photo-oxidation has been studied, in order to know the degradation pathways of MA under natural-like photoirradiation. The assays were performed in the absence and in the presence of riboflavin (Rf, vitamin B2) acting the later as a native photosensitizer. The results showed that MA is capable to generate singlet molecular oxygen (O2(1Δg)) upon direct UV-A irradiation, with a quantum yield value of 0.13 ± 0.02. The anthranilate also quenches the oxidative species with an overall rate constant value kt = 2.1 ± 0.2 × 107 M−1 s−1 while the reactive interaction between MA and O2(1Δg) showed a rate constant value in the range of 5.9–6.8 × 106 M−1 s−1. The kr/kt ratio, lower than 0.35 indicates that only one third of the O2(1Δg)-quenching events effectively lead to oxidation of the scavenger, being this an acceptable property for a sunscreen component. Regarding the Rf-photosensitized visible-light irradiation of MA–Rf mixtures, the anthranilate quenches the electronically excited singlet and triplet states of the vitamin. As a result the oxidative species O2− and H2O2, are generated, being the later effectively deactivated by MA. At first, the described results would show MA as a candidate for UV-A and visible-light mediated degradation. Nevertheless, at the same time MA acts as a moderate physical scavenger of photogenerated oxidative species in a sort of self-protector against photoinduced degradation and protector of oxidizable surrounding compounds.Fil: Gambetta, Carolina. Universidad Nacional de Río Cuarto. Facultad de Ciencias Exactas Fisicoquímicas y Naturales. Departamento de Química; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas; ArgentinaFil: Natera, Jose Eduardo. Universidad Nacional de Río Cuarto. Facultad de Ciencias Exactas Fisicoquímicas y Naturales. Departamento de Química; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas; ArgentinaFil: Massad, Walter Alfredo. Universidad Nacional de Río Cuarto. Facultad de Ciencias Exactas Fisicoquímicas y Naturales. Departamento de Química; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas; ArgentinaFil: Garcia, Norman Andino. Universidad Nacional de Río Cuarto. Facultad de Ciencias Exactas Fisicoquímicas y Naturales. Departamento de Química; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas; ArgentinaElsevier Science2013-07info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionhttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdfapplication/pdfapplication/pdfhttp://hdl.handle.net/11336/23309Gambetta, Carolina; Natera, Jose Eduardo; Massad, Walter Alfredo; Garcia, Norman Andino; Methyl anthranilate as generator and quencher of reactive oxygen species: a photochemical study; Elsevier Science; Journal of Photochemistry and Photobiology A: Chemistry; 269; 7-2013; 27-331010-6030CONICET DigitalCONICETenginfo:eu-repo/semantics/altIdentifier/doi/10.1016/j.jphotochem.2013.06.013info:eu-repo/semantics/altIdentifier/url/http://www.sciencedirect.com/science/article/pii/S1010603013002803info:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc-nd/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-09-29T09:51:47Zoai:ri.conicet.gov.ar:11336/23309instacron:CONICETInstitucionalhttp://ri.conicet.gov.ar/Organismo científico-tecnológicoNo correspondehttp://ri.conicet.gov.ar/oai/requestdasensio@conicet.gov.ar; lcarlino@conicet.gov.arArgentinaNo correspondeNo correspondeNo correspondeopendoar:34982025-09-29 09:51:47.942CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse |
dc.title.none.fl_str_mv |
Methyl anthranilate as generator and quencher of reactive oxygen species: a photochemical study |
title |
Methyl anthranilate as generator and quencher of reactive oxygen species: a photochemical study |
spellingShingle |
Methyl anthranilate as generator and quencher of reactive oxygen species: a photochemical study Gambetta, Carolina Methyl Anthranilate Singlet Oxygen Reactive Oxygen Species Photochemistry |
title_short |
Methyl anthranilate as generator and quencher of reactive oxygen species: a photochemical study |
title_full |
Methyl anthranilate as generator and quencher of reactive oxygen species: a photochemical study |
title_fullStr |
Methyl anthranilate as generator and quencher of reactive oxygen species: a photochemical study |
title_full_unstemmed |
Methyl anthranilate as generator and quencher of reactive oxygen species: a photochemical study |
title_sort |
Methyl anthranilate as generator and quencher of reactive oxygen species: a photochemical study |
dc.creator.none.fl_str_mv |
Gambetta, Carolina Natera, Jose Eduardo Massad, Walter Alfredo Garcia, Norman Andino |
author |
Gambetta, Carolina |
author_facet |
Gambetta, Carolina Natera, Jose Eduardo Massad, Walter Alfredo Garcia, Norman Andino |
author_role |
author |
author2 |
Natera, Jose Eduardo Massad, Walter Alfredo Garcia, Norman Andino |
author2_role |
author author author |
dc.subject.none.fl_str_mv |
Methyl Anthranilate Singlet Oxygen Reactive Oxygen Species Photochemistry |
topic |
Methyl Anthranilate Singlet Oxygen Reactive Oxygen Species Photochemistry |
purl_subject.fl_str_mv |
https://purl.org/becyt/ford/1.4 https://purl.org/becyt/ford/1 |
dc.description.none.fl_txt_mv |
Methyl anthranilate (MA) is a naturally occurring aromatizer and flavorant agent frequently employed in food industry and in personal care products. Due to the property of MA of being a UV-A radiation-absorber it is incorporated to topical sunscreen formulations. Within the framework of the wide variety of practical uses and applications, the photodegradation of MA becomes a topic of interest from health to an economic point of view. In this context, kinetics and mechanistic aspects of its photo-oxidation has been studied, in order to know the degradation pathways of MA under natural-like photoirradiation. The assays were performed in the absence and in the presence of riboflavin (Rf, vitamin B2) acting the later as a native photosensitizer. The results showed that MA is capable to generate singlet molecular oxygen (O2(1Δg)) upon direct UV-A irradiation, with a quantum yield value of 0.13 ± 0.02. The anthranilate also quenches the oxidative species with an overall rate constant value kt = 2.1 ± 0.2 × 107 M−1 s−1 while the reactive interaction between MA and O2(1Δg) showed a rate constant value in the range of 5.9–6.8 × 106 M−1 s−1. The kr/kt ratio, lower than 0.35 indicates that only one third of the O2(1Δg)-quenching events effectively lead to oxidation of the scavenger, being this an acceptable property for a sunscreen component. Regarding the Rf-photosensitized visible-light irradiation of MA–Rf mixtures, the anthranilate quenches the electronically excited singlet and triplet states of the vitamin. As a result the oxidative species O2− and H2O2, are generated, being the later effectively deactivated by MA. At first, the described results would show MA as a candidate for UV-A and visible-light mediated degradation. Nevertheless, at the same time MA acts as a moderate physical scavenger of photogenerated oxidative species in a sort of self-protector against photoinduced degradation and protector of oxidizable surrounding compounds. Fil: Gambetta, Carolina. Universidad Nacional de Río Cuarto. Facultad de Ciencias Exactas Fisicoquímicas y Naturales. Departamento de Química; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina Fil: Natera, Jose Eduardo. Universidad Nacional de Río Cuarto. Facultad de Ciencias Exactas Fisicoquímicas y Naturales. Departamento de Química; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina Fil: Massad, Walter Alfredo. Universidad Nacional de Río Cuarto. Facultad de Ciencias Exactas Fisicoquímicas y Naturales. Departamento de Química; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina Fil: Garcia, Norman Andino. Universidad Nacional de Río Cuarto. Facultad de Ciencias Exactas Fisicoquímicas y Naturales. Departamento de Química; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina |
description |
Methyl anthranilate (MA) is a naturally occurring aromatizer and flavorant agent frequently employed in food industry and in personal care products. Due to the property of MA of being a UV-A radiation-absorber it is incorporated to topical sunscreen formulations. Within the framework of the wide variety of practical uses and applications, the photodegradation of MA becomes a topic of interest from health to an economic point of view. In this context, kinetics and mechanistic aspects of its photo-oxidation has been studied, in order to know the degradation pathways of MA under natural-like photoirradiation. The assays were performed in the absence and in the presence of riboflavin (Rf, vitamin B2) acting the later as a native photosensitizer. The results showed that MA is capable to generate singlet molecular oxygen (O2(1Δg)) upon direct UV-A irradiation, with a quantum yield value of 0.13 ± 0.02. The anthranilate also quenches the oxidative species with an overall rate constant value kt = 2.1 ± 0.2 × 107 M−1 s−1 while the reactive interaction between MA and O2(1Δg) showed a rate constant value in the range of 5.9–6.8 × 106 M−1 s−1. The kr/kt ratio, lower than 0.35 indicates that only one third of the O2(1Δg)-quenching events effectively lead to oxidation of the scavenger, being this an acceptable property for a sunscreen component. Regarding the Rf-photosensitized visible-light irradiation of MA–Rf mixtures, the anthranilate quenches the electronically excited singlet and triplet states of the vitamin. As a result the oxidative species O2− and H2O2, are generated, being the later effectively deactivated by MA. At first, the described results would show MA as a candidate for UV-A and visible-light mediated degradation. Nevertheless, at the same time MA acts as a moderate physical scavenger of photogenerated oxidative species in a sort of self-protector against photoinduced degradation and protector of oxidizable surrounding compounds. |
publishDate |
2013 |
dc.date.none.fl_str_mv |
2013-07 |
dc.type.none.fl_str_mv |
info:eu-repo/semantics/article info:eu-repo/semantics/publishedVersion http://purl.org/coar/resource_type/c_6501 info:ar-repo/semantics/articulo |
format |
article |
status_str |
publishedVersion |
dc.identifier.none.fl_str_mv |
http://hdl.handle.net/11336/23309 Gambetta, Carolina; Natera, Jose Eduardo; Massad, Walter Alfredo; Garcia, Norman Andino; Methyl anthranilate as generator and quencher of reactive oxygen species: a photochemical study; Elsevier Science; Journal of Photochemistry and Photobiology A: Chemistry; 269; 7-2013; 27-33 1010-6030 CONICET Digital CONICET |
url |
http://hdl.handle.net/11336/23309 |
identifier_str_mv |
Gambetta, Carolina; Natera, Jose Eduardo; Massad, Walter Alfredo; Garcia, Norman Andino; Methyl anthranilate as generator and quencher of reactive oxygen species: a photochemical study; Elsevier Science; Journal of Photochemistry and Photobiology A: Chemistry; 269; 7-2013; 27-33 1010-6030 CONICET Digital CONICET |
dc.language.none.fl_str_mv |
eng |
language |
eng |
dc.relation.none.fl_str_mv |
info:eu-repo/semantics/altIdentifier/doi/10.1016/j.jphotochem.2013.06.013 info:eu-repo/semantics/altIdentifier/url/http://www.sciencedirect.com/science/article/pii/S1010603013002803 |
dc.rights.none.fl_str_mv |
info:eu-repo/semantics/openAccess https://creativecommons.org/licenses/by-nc-nd/2.5/ar/ |
eu_rights_str_mv |
openAccess |
rights_invalid_str_mv |
https://creativecommons.org/licenses/by-nc-nd/2.5/ar/ |
dc.format.none.fl_str_mv |
application/pdf application/pdf application/pdf |
dc.publisher.none.fl_str_mv |
Elsevier Science |
publisher.none.fl_str_mv |
Elsevier Science |
dc.source.none.fl_str_mv |
reponame:CONICET Digital (CONICET) instname:Consejo Nacional de Investigaciones Científicas y Técnicas |
reponame_str |
CONICET Digital (CONICET) |
collection |
CONICET Digital (CONICET) |
instname_str |
Consejo Nacional de Investigaciones Científicas y Técnicas |
repository.name.fl_str_mv |
CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicas |
repository.mail.fl_str_mv |
dasensio@conicet.gov.ar; lcarlino@conicet.gov.ar |
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1844613590442573824 |
score |
13.070432 |