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
CONICET Digital (CONICET)
Institución
Consejo Nacional de Investigaciones Científicas y Técnicas
OAI Identificador
oai:ri.conicet.gov.ar:11336/23309
Acceder
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oai_identifier_str oai:ri.conicet.gov.ar:11336/23309
network_acronym_str CONICETDig
repository_id_str 3498
network_name_str CONICET Digital (CONICET)
spelling 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 Técnicas2025-10-22T11:21:11Zoai: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:34982025-10-22 11:21:11.892CONICET 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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score 12.982451

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