Photodegradation of avobenzone: Stabilization effect of antioxidants

Afonso, Sandra; Horita, Kiyoshi; Silva, José P.; Almeida, Isabel F.; Amaral, Maria Helena; Lobão, Paulo; Costa, Paulo; Miranda, Margarida S.; Silva, Joaquim C. G. Esteves da; Lobo, José Manuel Sousa

doi:10.1016/j.jphotobiol.2014.07.004

Cited by 152 publications

(115 citation statements)

References 24 publications

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“…The use of Butyl Methoxydibenzoylmethane (Avobenzone) is almost essential to reach high UVA protection, but it has to be adequately stabilized in order to avoid the undesired photo-ketonisation reaction (Figure 2): The stabilization of Avobenzone could be reached by using different strategies [28,29]:…”

Section: Formulation Solutionsmentioning

confidence: 99%

The New Sunscreens among Formulation Strategy, Stability Issues, Changing Norms, Safety and Efficacy Evaluations

Lionetti¹,

Rigano

2017

Cosmetics

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Abstract:The sun-and-skin interactions have controversial sides. Besides important beneficial effects, we need to take into consideration also some serious harmful results. In particular, these are connected to the portion of the solar spectrum traditionally identified as ultraviolet type A and B. The topical application of sunscreens (and the avoidance of extreme exposure to sun rays) is worldwide recognized as the best strategy to avoid sunburn and oedema. Moreover, such strategy can efficiently prevent the onset of skin cancer. Therefore, the first aim of sunscreen products is to efficiently minimize all damage of sun exposure, while, at the same time, keeping good skin tolerability, avoiding safety problems and developing pleasant sensorial properties. Sunscreens, i.e., substances able to reflect and/or absorb, at a partial or complete extent, UV radiation are the key actors in skin protection. They are used to implement the level of primary photoprotection against UV rays. This means that when they absorb the radiation energy, their molecules pass to an excited state and successively re-emit energy in other forms (vibrational, rotational, infrared radiation) to come back to the ground state.

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Section: Formulation Solutionsmentioning

confidence: 99%

The New Sunscreens among Formulation Strategy, Stability Issues, Changing Norms, Safety and Efficacy Evaluations

Lionetti¹,

Rigano

2017

Cosmetics

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“…The photochemical behavior of this filter has been extensively studied and its photostability has been found to be highly dependent on the polarity and proticity of the solvent. In solution, avobenzone enol forms photoisomerized keto forms, revealing a great photoinstability [15,16,17,18]. …”

Section: Introductionmentioning

confidence: 99%

Stability Study of Sunscreens with Free and Encapsulated UV Filters Contained in Plastic Packaging

et al. 2017

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Sunscreens play a fundamental role in skin cancer prevention and in protection against photo-aging. UV filters are often photo-unstable, especially in relation to their vehicles and, being lipophilic substances, they are able to interact with plastic packaging. Finally, UV filter stability can be significantly affected by the routine use of the product at high temperatures. This work aims to study the stability of sunscreen formulations in polyethylene packaging. Butyl methoxydibenzoylmethane and octocrylene, both in a free form and as encapsulated filters were chosen as UV filters. Stability evaluations were performed both in the packaging and on the formulations. Moreover, a further two non-destructive techniques, near-infrared (NIR) spectroscopy and a multiple light scattering technique, were also used to evaluate the stability of the formulation. Results demonstrated clearly that all of the pack underwent significant changes in its elastic/plastic behavior and in external color after solar irradiation. From the evaluation of the extractable profile of untreated and treated packaging material an absorption of 2-phenoxyethanol and octocrylene were shown. In conclusion, the results highlighted clearly that a reduction of the UV filter in the formulation packed in high-density polyethylene/low-density polyethylene (HDPE/LDPE) material can occur over time, reducing the protective effect of the product when applied to the skin.

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“…[11][12][13] In particular, some reports have highlighted the possibility that certain photoexcited sunscreen molecules may produce harmful reactive oxygen species (ROS). 14,15 This has led to the concept of including molecules with antioxidant properties within sunscreen products either to increase the photostability of sunscreen molecules, or to ''mop up'' any ROS. [15][16][17] A particularly potent set of antioxidants are hydroxycinnamic acids, which include: ferulic acid (3-(4-hydroxy-3-methoxyphenyl)-2-propenoic acid) and caffeic acid (3-(3,4-dihydroxyphenyl)-2-propenoic acid), shown in Fig.…”

Section: Introductionmentioning

confidence: 99%

Photodynamics of potent antioxidants: ferulic and caffeic acids

Baker

Quan

Greenough

et al. 2016

Phys. Chem. Chem. Phys.

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The dynamics of ferulic acid (3-(4-hydroxy-3-methoxyphenyl)-2-propenoic acid) and caffeic acid (3-(3,4-dihydroxyphenyl)-2-propenoic acid) in acetonitrile, dioxane and water at pH 2.2 following photoexcitation to the first excited singlet state are reported. These hydroxycinnamic acids display both strong ultraviolet absorption and potent antioxidant activity, making them promising sunscreen components. Ferulic and caffeic acids have previously been shown to undergo trans-cis photoisomerization via irradiation studies, yet time-resolved measurements were unable to observe formation of the cis-isomer. In the present study, we are able to observe the formation of the cis-isomer as well as provide timescales of relaxation following initial photoexcitation.

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Photodegradation of avobenzone: Stabilization effect of antioxidants

Cited by 152 publications

References 24 publications

The New Sunscreens among Formulation Strategy, Stability Issues, Changing Norms, Safety and Efficacy Evaluations

The New Sunscreens among Formulation Strategy, Stability Issues, Changing Norms, Safety and Efficacy Evaluations

Stability Study of Sunscreens with Free and Encapsulated UV Filters Contained in Plastic Packaging

Photodynamics of potent antioxidants: ferulic and caffeic acids

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