Analysis of photokinetics of 2’-ethylhexyl-4-methoxycinnamate in sunscreens

Herzog, Bernd; Amorós-Galicia, Lola; Sohn, Myriam; Hofer, Matthias; Quass, Katja; Giesinger, Jochen

doi:10.1039/c9pp00084d

Cited by 12 publications

(16 citation statements)

References 13 publications

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“…Therefore, OMC and AVO were not considered photostable in formulations without photostabilizers (F1 and F1 RP), which are in agreement with the reports from literature (10,14,39,41) since they are known as photounstable UV‐filters that must be formulated with photostabilizers to produce stable sunscreen formulations. In addition, OMC and AVO have been studied regarding their mechanism of photodegradation and photoproducts using both diluted solutions and formulations.…”

Section: Resultssupporting

confidence: 82%

“…In a previous study, in ethanolic solution OMC showed no degradation after irradiation, but in the irradiated formulations OMC was significantly degraded (47). Thus, in diluted solutions (µM) the photoinstability of OMC might be related predominantly to the unimolecular photoisomerization trans/cis , but at higher concentrations in cosmetic formulations the concentration‐dependent bimolecular [2 + 2]‐cycloaddition can be detected (14,47). Meanwhile, it is well‐known that the photodegradation of AVO is induced by the keto‐enol tautomerization, followed by photodegradation reactions via triplet state leading to the loss of its effectiveness (10,48).…”

Section: Resultsmentioning

confidence: 99%

“…In addition, AVO may affect the photostability of other UV‐filters, and for instance, the photodegradation of the UVB‐filter octyl methoxycinnamate (OMC) is accelerated in the presence of avobenzone by [2 + 2]‐cycloaddition (14). This known photounstable combination is often used in many sunscreen products combined with photostabilizers, because both of them have a high molar extinction coefficient (AVO: 26 000 m −1 cm −1 ; OMC: 24 000 m −1 cm −1 ) and consequently a high absorption in the UVA and UVB region (15).…”

Section: Introductionmentioning

confidence: 99%

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Effects of UV‐filter Photostabilizers in the Photostability and Phototoxicity of Vitamin A Palmitate Combined with Avobenzone and Octyl Methoxycinnamate

Scarpin

Kawakami

Rangel

et al. 2021

Photochem & Photobiology

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A challenge for cosmetic and dermatologic products is to develop new high‐performance and safer anti‐aging products based on new compounds to enhance the stability of retinyl palmitate combined with broad‐spectrum UV‐filters. Consequently, the aim of this work was to evaluate the effects of three often used avobenzone photostabilizers—ethylhexyl methoxycrylene (EHMCR), tris(tetramethylhydroxypiperidinol) citrate (TTMHP) and tris‐biphenyl triazine (TBPT)—on the photostability and phototoxicity of the combination of avobenzone (AVO), octyl methoxycinnamate (OMC) and retinyl palmitate (RP). The photostability studies were performed by the exposure of formulations to UVA radiation. The phototoxicity was evaluated by the 3T3 neutral red uptake phototoxic assay (OECD TG 432). The addition of EHMCR, TBPT, and TTMHP in the formulations, with/or without RP, improved the photostability of AVO and RP, but EHMCR was the most effective in stabilizing RP. In the phototoxicity assay, the combinations AVO‐OMC containing or not RP showed phototoxic potential. EHMCR and TTMHP reduced the phototoxicity of the combination AVO‐OMC, whereas EHMCR also decreased the phototoxicity of the combination containing RP. Therefore, EHMCR might be used to the photostabilization of formulations of AVO‐OMC with/or not RP, while TTMHP can be added to this photounstable UV‐filter combination.

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Section: Resultssupporting

confidence: 82%

Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Effects of UV‐filter Photostabilizers in the Photostability and Phototoxicity of Vitamin A Palmitate Combined with Avobenzone and Octyl Methoxycinnamate

Scarpin

Kawakami

Rangel

et al. 2021

Photochem & Photobiology

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“…Now a days, a number of different UV absorbing molecules nd their use in commercial sunscreens [19][20][21]. There are 27 registered compounds, which are used as UV-lter in Europe as sunscreens [8].…”

Section: Introductionmentioning

confidence: 99%

“…Protection against sunlight supports to avert skin damage from unnecessary and extended contact to the sunlight. Excessive exposure to the sunlight can perform a major role in degenerative variations in the skin like photoaging and skin cancer [7][8][9][10][11][12]. It has been proved that ultraviolet (UV) radiations cause erythema solare [13].…”

Section: Introductionmentioning

confidence: 99%

Elucidating the Photoluminescence Quenching in Ensulizole: An Artificial Water Soluble Sunscreen

Mubeen

Khalid

Mukhtar

et al. 2021

Preprint

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Employing natural or artificial sunscreens is essential to protect the skin from ultraviolet radiations that cause premature aging and develop melanoma and other forms of skin cancer. The 2-Phenylbenzimidazole-5-sulfonic acid, commonly known as ensulizole is a water-soluble artificial sunscreen that absorbs mostly UV-B (280 nm − 315 nm) radiations and protects the skin against the harmful effects of these radiations. Steady-state absorption indicates a strong absorption feature at 303 nm and a weak at 316 nm that have been identified as π → π* and n → π* transitions, respectively. The photoluminescence (PL) spectra indicate that the PL of ensulizole is less Stokes-shifted in polar solvents and more Stokes-shifted in non-polar solvents. The average PL lifetime of ensulizole is longer in non-polar solvents as compared to polar solvents and it exhibits the shortest PL lifetime in aqueous medium that signifies its efficiency in water. This suggests in non-polar solvents intersystem crossing is the dominant mode of relaxation of the excited ππ* state. Furthermore, an increase of pH of ensulizole solution decreases the PL intensity and the lifetime. Stern-Volmer equation is employed to evaluate bimolecular quenching rate constant kq that suggests the diffusional dynamic mode of PL quenching is operative.

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Elucidating the Photoluminescence Quenching in Ensulizole: an Artificial Water Soluble Sunscreen

et al. 2021

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Employing natural or arti cial sunscreens is essential to protect the skin from ultraviolet radiations that cause premature aging and develop melanoma and other forms of skin cancer. The 2-Phenylbenzimidazole-5-sulfonic acid, commonly known as ensulizole is a water-soluble arti cial sunscreen that absorbs mostly UV-B (280 nm − 315 nm) radiations and protects the skin against the harmful effects of these radiations. Steady-state absorption indicates a strong absorption feature at 303 nm and a weak at 316 nm that have been identi ed as π → π* and n → π* transitions, respectively. The photoluminescence (PL) spectra indicate that the PL of ensulizole is less Stokes-shifted in polar solvents and more Stokes-shifted in non-polar solvents. The average PL lifetime of ensulizole is longer in non-polar solvents as compared to polar solvents and it exhibits the shortest PL lifetime in aqueous medium that signi es its e ciency in water. This suggests in non-polar solvents intersystem crossing is the dominant mode of relaxation of the excited ππ* state. Furthermore, an increase of pH of ensulizole solution decreases the PL intensity and the lifetime.Stern-Volmer equation is employed to evaluate bimolecular quenching rate constant k q that suggests the diffusional dynamic mode of PL quenching is operative.

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Analysis of photokinetics of 2’-ethylhexyl-4-methoxycinnamate in sunscreens

Abstract: 2′-Ethylhexyl-4-Methoxycinnamate (EHMC), also designated as octinoxate, is one of the most employed UVB absorbers in sunscreens for the protection of human skin against solar UV-radiation.

Cited by 12 publications

References 13 publications

Effects of UV‐filter Photostabilizers in the Photostability and Phototoxicity of Vitamin A Palmitate Combined with Avobenzone and Octyl Methoxycinnamate

Effects of UV‐filter Photostabilizers in the Photostability and Phototoxicity of Vitamin A Palmitate Combined with Avobenzone and Octyl Methoxycinnamate

Elucidating the Photoluminescence Quenching in Ensulizole: An Artificial Water Soluble Sunscreen

Elucidating the Photoluminescence Quenching in Ensulizole: an Artificial Water Soluble Sunscreen

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