The role of direct photolysis and indirect photochemistry in the environmental fate of ethylhexyl methoxy cinnamate (EHMC) in surface waters

Vione, Davide; Calza, Paola; Galli, F.; Fabbri, Debora; Santoro, V.; Medana, Claudio

doi:10.1016/j.scitotenv.2015.08.002

Cited by 38 publications

(31 citation statements)

References 40 publications

(52 reference statements)

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“…This stabilization effect by Vit.E is in line with reported studies performed on other type of UV filters . In addition to the identified photoproduct Z‐isomer, distinct researchers have reported the formation of additional photoproducts in aqueous environment, such as EHMC cyclodimer isomers . Due to their polarity and chemical structure, these dimers are eluted at higher retention times than EHMC.…”

Section: Resultssupporting

confidence: 89%

“…These preliminary results show not only that the encapsulation of EHMC with alginate MP promotes the photostabilization of the UV filter, but also that this effect is more evident in the presence of Vit.E. As an antioxidant, Vit.E is capable of scavenging the free radicals and the reactive oxygen species that are formed during the photodegradation process and known to participate in the mechanism of EHMC degradation in water matrix . This stabilization effect by Vit.E is in line with reported studies performed on other type of UV filters .…”

Section: Resultsmentioning

confidence: 99%

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Alginate microparticles as carriers for the UV filter 2‐ethylhexyl 4‐methoxycinnamate: Influence on photostability

Duarte

Almeida

Silva

et al. 2019

Intern J of Cosmetic Sci

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OBJECTIVE: The organic ultraviolet UVB filter 2-ethylhexyl 4methoxycinnamate (EHMC) was encapsulated in microparticles (MPs) of sodium alginate and co-loaded with vitamin E (Vit.E) by an extrusion process using an aerodynamically assisted jetting (AAJ) methodology. The aim was to assess the effect of encapsulation concerning UVB filter release from the MPs and its photochemical stability. METHODS: The EHMC photostability was analysed by exposing the samples (both MPs in aqueous dispersion and incorporated in a cream preparation) during 1 h to simulated solar light. For the MPs (empty-MP, EHMC-MP and EHMC + Vit.E-MP), the morphology and size were characterized; while in the case of the encapsulated samples, the amount of EHMC-loading was determined. The release of EHMC was evaluated by adding EHMC-MP or EHMC + Vit.E-MP to 65% ethanol in water under mechanical stirring at 32°C. RESULTS: All MPs showed a homogeneous size distribution with a median of 90.5 AE 2.5 lm for EHMC-MP and 70.4 AE 1.14 lm for EHMC + Vit.E-MP. The encapsulation efficiency was 92.9% and 99.4% for EHMC-MP and EHMC + Vit.E-MP, respectively. The observed release from the MPs was lower than the dissolution of the pure UV filter. EHMC-MP and EHMC + Vit.E-MP were successfully incorporated into a cream formulation, with no evidence of phase separation or colour modification. Upon simulated light exposure, the photoisomerization/phototransformation of EHMC encapsulated in MPs and Vit.E-MP decreased as compared to free EHMC, both in aqueous dispersion and as a cream. The conformational ratio of the isomers (Z-/E-EHMC) was found to be the lowest in the presence of Vit.E. CONCLUSION:This work demonstrates that use of these alginate microparticulate carriers could enhance the effectiveness of sunscreen preparations containing this UVB filter. R esum e OBJECTIF: Le filtre ultraviolet organique D'UVB 2-ethylhexyl 4methoxycinnamate (EHMC) a et e encapsul e dans des microparticules (MPs) d'alginate de sodium et co-charg e avec la vitamine E (Vit.E) par un processus d'extrusion utilisant une m ethode de jet assist e a erodynamique (AAJ). L'objectif etait d' evaluer l'effet de l'encapsulation concernant la lib eration du filtre UVB par les MPs et sa stabilit e photochimique. M ETHODES: La photostabilit e EHMC a et e analys ee en exposant les echantillons (les deux MPs en dispersion aqueuse et incorpor es dans une pr eparation de type cr eme) pendant 1 h a la lumi ere solaire simul ee. Pour les MPs (MP-vide, EHMC-MP et EHMC -Vit.E-MP), la morphologie et la taille ont et e caract eris ees; tandis que dans le cas des echantillons encapsul es, la quantit e de charge EHMC a et e d etermin ee. Le relargage de l'EHMC a et e evalu e en ajoutant EHMC-MP ou EHMC -Vit.E-MP a 65% d' ethanol dans l'eau sous agitation m ecanique a 32°C. R ESULTATS: Tous les MP ont montr e une distribution homog ene de taille avec une m ediane de 90,5 +-2,5 lm pour EHMC-MP et de 70,4 +-1,14 lm pour l'EHMC et Vit.E-MP. L'efficacit e de l'encapsulation etait de 92,9 % et 99,4 % pour EHMC-MP et ...

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Section: Resultssupporting

confidence: 89%

Section: Resultsmentioning

confidence: 99%

Alginate microparticles as carriers for the UV filter 2‐ethylhexyl 4‐methoxycinnamate: Influence on photostability

Duarte

Almeida

Silva

et al. 2019

Intern J of Cosmetic Sci

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“…EHMC is readily degradable [41,45] whereas BP3 was quite photostable in the aquatic environment [46,47]. Therefore, it's likely that EHMC and BP3 had similar sources rather than similar environmental fate in the sediment of the Pearl River and the PRE.…”

Section: Behavior and Fate Of The Emerging Contaminantsmentioning

confidence: 99%

Persistence, temporal and spatial profiles of ultraviolet absorbents and phenolic personal care products in riverine and estuarine sediment of the Pearl River catchment, China

Peng

Xiong

et al. 2017

Journal of Hazardous Materials

111

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“…S1), direct photodegradation is another potential pathway, which can occur under irradiation conditions. Noteworthy, both direct and indirect mechanisms were found to be a possible explanation of popular sunscreen agent, 2-ethylhexyl 4-methoxycinnamate degradation in surface waters (Vione et al 2015); however, direct photodegradation was found to be the main route.…”

Section: Resultsmentioning

confidence: 99%

“…It is worth to mention that according to some studies (Mopper and Stahovec 1986;Kieber et al 1990;Zhou and Mopper 1997;Reader and Miller 2011), there is a relationship between the presence of dissolved organic matter capable of absorbing UV light and formaldehyde contamination. Vione et al 2015;McNeill and Canonica 2016;Vione 2016). Noteworthy, the presence of ODPABA and p-aminobenzoic acid (PABA) significantly enhance singlet oxygen ( 1 O 2 ) generation in UV-irradiated water (Allen and Gossett 1996).…”

Section: Resultsmentioning

confidence: 99%

Studies on the formation of formaldehyde during 2-ethylhexyl 4-(dimethylamino)benzoate demethylation in the presence of reactive oxygen and chlorine species

Studziński

Gackowska

Przybyłek

et al. 2017

Environ Sci Pollut Res

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In order to protect the skin from UV radiation, personal care products (PCPS) often contain chemical UV-filters. These compounds can enter the environment causing serious consequences on the water ecosystems. The aim of this study was to examine, the effect of different factors, such as UV light, the presence of NaOCl and H2O2 on the formaldehyde formation during popular UV filter, 2-ethylhexyl 4-(dimethylamino)benzoate (ODPABA) demethylation. The concentration of formaldehyde was determined by VIS spectrophotometry after derivatization. The reaction mixtures were qualitatively analyzed using GC/MS chromatography. The highest concentration of formaldehyde was observed in the case of ODPABA/H2O2/UV reaction mixture. In order to describe two types of demethylation mechanisms, namely, radical and ionic, the experimental results were enriched with Fukui function analysis and thermodynamic calculations. In the case of non-irradiated system containing ODPABA and NaOCl, demethylation reaction probably proceeds via ionic mechanism. As it was established, amino nitrogen atom in the ODPABA molecule is the most susceptible site for the HOCl electrophilic attack, which is the first step of ionic demethylation mechanism. In the case of irradiated mixtures, the reaction is probably radical in nature. The results of thermodynamic calculations showed that abstraction of the hydrogen from N(CH3)2 group is more probable than from 2-ethylhexyl moiety, which indicates higher susceptibility of N(CH3)2 to the oxidation.Electronic supplementary materialThe online version of this article (doi:10.1007/s11356-017-8477-8) contains supplementary material, which is available to authorized users.

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The role of direct photolysis and indirect photochemistry in the environmental fate of ethylhexyl methoxy cinnamate (EHMC) in surface waters

Cited by 38 publications

References 40 publications

Alginate microparticles as carriers for the UV filter 2‐ethylhexyl 4‐methoxycinnamate: Influence on photostability

Alginate microparticles as carriers for the UV filter 2‐ethylhexyl 4‐methoxycinnamate: Influence on photostability

Persistence, temporal and spatial profiles of ultraviolet absorbents and phenolic personal care products in riverine and estuarine sediment of the Pearl River catchment, China

Studies on the formation of formaldehyde during 2-ethylhexyl 4-(dimethylamino)benzoate demethylation in the presence of reactive oxygen and chlorine species

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