BIS-ETHYLHEXYLOXYPHENOL METHOXYPHENYL TRIAZINE

Bis-ethylhexyloxyphenol methoxyphenyl triazine (BEMT) is a highly efficient organic UV filter characterized by a broad ultraviolet absorption spectrum, exceptional photothermal stability and minimal skin penetration, which make it a core component in high-SPF sunscreen formulations. However, systematic research on the molecular photophysical behaviour of BEMT across various solvents-particularly its anomalous solvatochromism effect-remains scarce. This limited understanding results in the empirical selection of oil-based matrices during formulation development and hinders the targeted optimization of BEMT performance. Herein, we systematically investigate the spectral characteristics, excited-state relaxation pathways and photostability of BEMT in solvents with varying polarities and protonic properties. The ground-state-specific stability mechanism associated with the unique solvatochromism of BEMT is elucidated. In addition, this anomalous solvatochromism effect and the rapid excited-state relaxation process synergistically inhibit BEMT from photodegradation in polar media, reduce the generation of reactive oxygen species (ROS) and improve ultraviolet absorption efficiency, which provides both theoretical foundations and experimental support for the efficient formulation and performance optimization of BEMT in sunscreen preparations.

Understanding the processes that organic UV filters undergo in coastal and marine environments is crucial for assessing their long-term environmental risks. One key process is degradation by microorganisms in sediments. This study aimed to determine whether coastal marine sediments harbor microorganisms capable of degrading organic UV filters. Sediment from Toulon Harbor was tested for its degradation potential with respect to 12 different organic UV filters. Sediment microcosms showed degradation activity towards benzophenone-3 (BP3), 2-ethylhexyl salicylate (ES), and homosalate (HS) after 12 days. However, no degradation was observed for butyl methoxydibenzoylmethane (BM), octocrylene (OC), diethylamino hydroxybenzoyl hexyl benzoate (DHHB), drometrizole trisiloxane (DTS), phenylene bis-diphenyltriazine (TriAsorB), bis-ethylhexyloxyphenol methoxyphenyl triazine (BEMT), methylene bis-benzotriazolyl tetramethylbutylphenol (MBBT), diethylhexyl butamido triazone (DBT), or ethylhexyl triazone (ET), even after 100 days of incubation. Two degrading strains were isolated from the microcosms: a Rhodococcus strain degrading ES and a Microbacterium strain capable of degrading HS. Despite substantial efforts, the microorganism thought to be responsible for BP3 degradation could not be isolated. This work demonstrates that microorganisms in coastal sediments can degrade a limited range of organic UV filters.

Protection against sunburn, skin damage and the carcinogenic effects of ultraviolet light are the primary health benefits associated with UV filters used in topical sunscreen drug products. Countries such as Europe have 30+ UV filters approved for sunscreen products while the US has about 10, greatly reducing the options to provide diverse, effective sun protection products. Bemotrizinol (BEMT) is the first new sunscreen active ingredient to be evaluated for inclusion in the Over-The-Counter (OTC) sunscreen monograph using FDA's new Generally Recognized as Safe and Effective (GRASE) testing guidelines. An in vitro skin permeation test (IVPT) and clinical pilot pharmacokinetic Maximum Usage Trial (MUsT) were completed to support the GRASE determination for 6% BEMT. IVPT results indicated an oil +10% ethanol as the model sunscreen intervention for the pilot MUsT. The open-label trial revealed: BEMT concentrations rarely exceeded FDA's defined threshold (0.5 ng/mL) in plasma; no evidence for BEMT accumulation or steady-state concentrations above threshold; only one moderate and few mild treatment emergent adverse events (TEAEs). Therefore, maximal topical applications of 6% BEMT in a model sunscreen formulation did not contribute to meaningful systemic exposure. These results support the safety of BEMT 6% for human sunscreen use.

There is now unequivocal evidence that sunscreen can severely affect marine ecosystems. However, so far, most studies have focused on the impact of single sunscreen ingredients rather than on the whole sunscreen products, which are released into the marine environment. In the present work, we investigated the ecological impact of six formulations, which represent the "new generation" organic UV filters such as diethylamino hydroxybenzoyl hexyl benzoate (DHHB), methylene bis-benzotriazolyl tetramethylbutylphenol (MBBT), ethylhexyl triazone (EHT), and bis-ethylhexyloxyphenol methoxyphenyl triazine (BEMT), which are progressively replacing the "old generation" organic UV filters (e.g., oxybenzone, octinoxate) banned in several countries of the world. The six formulations tested were characterized by a different combination of ingredients, on a model species particularly sensitive to environmental alterations: the sea urchin, Paracentrotus lividus. We investigated the sea urchin responses both in terms of gene expression and anomalies in embryonic development. We found that all sunscreen products containing only MBBT, DHHB, BEMT, and EHT as UV filters, are more eco-compatible than those also containing also ES, or other ingredients such as emollients and texturizing compounds, which may act synergistically causing molecular stress, morphological anomalies, and ultimately possible death. Overall, the results presented here provide new insights on the effects of sunscreen products based on "new generation" UV filters, and highlights the urgency of testing complete formulations, rather than just specific UV filters to ascertain the eco-compatibility of sunscreen products, to effectively minimize their impact on marine ecosystems.

Organic UV filters are present in wastewater treatment plants (WWTPs) due to the use of these compounds in many personal care products (PCPs) and their subsequent release into the wastewater system from showering/bathing. Once in the wastewater system, organic UV filters generally partition into the solid phase but might also undergo other processes, such as degradation by microorganisms. To further understand the fate of organic UV filters in WWTPs, the degradation of 7 UV filters by WWTP sludge was investigated The UV filters 2-ethylhexyl salicylate (ES), homosalate (HS), butyl methoxydibenzoylmethane (BM) and octocrylene (OC) were degraded after 20-60 days. The rest of the filters tested, namely, bis-ethylhexyloxyphenol methoxyphenyl triazine (BEMT), methylene bis-benzotriazolyl tetramethylbutylphenol (MBBT) and diethylhexyl butamido triazone (DBT), did not degrade even after 120 days of incubation. The microbial community from the microcosms degrading ES, HS, OC and BM was transferred every 30 days into new microcosms to enrich for microorganisms capable of utilizing the individual UV filters for growth. The enrichment cultures continued to degrade throughout 20 transfers. The microbial community was clearly different between the enrichments degrading ES, HS, OC and BM, meaning that the microbial community was strongly influenced by the UV filter present. Furthermore, several strains were isolated from OC-degrading cultures and two of these strains, Gordonia sp. strain OC_S5 and Sphingopyxis sp. strain OC_4D, degraded OC with and without other carbon sources present. These experiments show that several organic UV filters can be degraded by a specific set of microorganisms. The lack of degradation observed for BEMT, MBBT and DBT is probably due to limited bioavailability. Indeed, this is the first biodegradation study of these filters, in addition to being the first description of ES and HS degradation in microcosm experiments.

A fast and simple ultra-high-performance liquid chromatography using diode array detector (UHPLC-DAD) technique has been developed for the simultaneous determination of 22 sunscreen agents (UV filters), viz. phenylbenzimidazole sulfonic acid (PBS), terephthalydene dicamphor sulfonic acid (TDS), benzophenone-4 (BZ4), camphor benzalkonium methosulfate (CBM), benzophenone-2 (BZ2), benzylidene camphor sulfonic acid (BCS), benzophenone-3 (BZ3), 3-benzylidene camphor (3BC), isoamyl p -methoxycinnamate (IMC), 4-methylbenzylidene camphor (MBC), diethylamino hydroxybenzoyl hexyl benzoate (DHHB), octocrylene (OCR), butyl methoxydibenzoyl methane (BDM), ethylhexyl dimethyl PABA (EDP), ethylhexyl methoxycinnamate (EMC), homosalate (HS), ethylhexyl salicylate (ES), diethylhexyl butamido triazone (DBT), ethylhexyl triazone (ET), drometrizole trisiloxane (DRT), methylene bis-benzotriazolyl tetramethylbutylphenol (MBP), and bis-ethylhexyloxyphenol methoxyphenyl triazine (EMT) in cosmetic products. Different parameters, such as column type, oven temperature, mobile phase composition, and detection wavelength, were studied. The best chromatographic separation was obtained under the following conditions: Poroshell 120 EC-C 18 (100 mm×4.6 mm, 2.7 μm) column set at 25 ℃ and gradient acetonitrile-isopropanol-water (containing 50 mmol/L ammonium acetate and 0.05% (v/v) formic acid) as the mobile phase, pumped at a flow rate of 0.5 mL/min, with a wavelength of 311 nm. The proposed UHPLC-DAD technique provided separation of the 22 target sunscreen agents within 35 min, with the optimized sample pretreatment procedure below. First, samples were mixed thoroughly by adding 2 mL or 5 mL tetrahydrofuran, followed by vortex and dispersal. If the wax samples were still not homogenized completely, an ultrasonic dispersal protocol with heating to 50 ℃ was adopted. Second, the homogeneous samples were ultrasonically extracted with ethanol containing 0.1% (v/v) formic acid. The developed method showed good linear relationships, with correlation coefficients of no less than 0.998. Two kinds of samples with different matrix types were fortified at three levels. The average spiked recoveries of 22 UV filters ranged from 85.2% to 112.3%, with the relative standard deviations (RSDs) ranging from 0.5% to 6.5%. The limits of detection were between 0.7 and 64 mg/kg, and the limits of quantification ranged from 2.4 mg/kg to 215 mg/kg. Moreover, the stabilities of the mixed standard solutions at the levels of 2, 10, and 50 mg/L were tested. The stability results showed that drometrizole trisiloxane was stable for 12 h, while the others were stable for 36 h. The reliability of the developed method was demonstrated by applying it to 16 commercial sunscreen-containing cosmetic samples obtained from the Chinese market. The levels determined in this study agreed well with those of five commercial samples (such as emulsion and cream). The method developed was remarkably different from the standard method, which is mentioned in the Safety and Technical Standards for Cosmetics (2015 edition), especially in terms of mobile phase composition and extraction solvent. Compared to the standard method, this method bypassed the use of large amounts of corrosive solvents like tetrahydrofuran and perchloric acid, thus improving the extraction efficiency of low-polarity components like drometrizole trisiloxane, methylene bis-benzotriazolyl tetramethylbutylphenol, and bis-ethylhexyloxyphenol methoxyphenyl triazine, and the analytes were well separated with better stability. Benzophenone-2 was added to this method as another detection component. The good analytical features, as well as their environment-friendly characteristics, make the presented method suitable not only for routine analysis in cosmetics industries, but also as a candidate reference method for sunscreen analysis. 建立了一种超高效液相色

UV filters are widely used in many pharmaceutical and personal care products such as sunscreen and cosmetics to protect from UV irradiation. Due to their hydrophobic properties and relative stability, they have a high capacity to accumulate in sediment. Little information is available on their ecotoxicity on fish. In aquatic ecosystems, fish eggs could be directly affected by UV filters through contact with contaminated sediment. The aim of this study was to investigate the individual toxicity of four UV filters: benzophenone-3 (BP3), butyl methoxydibenzoylmethane (BM), bis-ethylhexyloxyphenol methoxyphenyl triazine (BEMT), and methylene bis-benzotriazolyl tetramethylbutylphenol (MBBT), in embryo-larval stages of zebrafish Danio rerio. Fish eggs were exposed to single UV filters by contact with spiked sediment during 96 h at a concentration of 10 μg g -1 . Among the four UV filters tested, BP3 was the more toxic, reducing cardiac frequency and increasing standard metabolic rate of larvae.

As several reports have raised a variety of environmental, health, and safety issues related to ultraviolet (UV) filters, it is crucial to understand the trends in the exposure of the population to UV filters. To determine the frequency of UV filter usage in sunscreens and other cosmetic products in Thai market. We surveyed the UV filter labelling on sunscreens and cosmetic products sold in the Thai market. In all, 312 sunscreens and 1350 other cosmetic products were investigated. Titanium dioxide was the most frequently used UV filter in both sunscreens (66.7%) and other cosmetic products (68.4%). Ethylhexyl methoxycinnamate was the most common organic UVB filter, whereas butyl methoxydibenzoylmethane was the most common organic UVA filter. In sunscreens aimed at children, bis-ethylhexyloxyphenol methoxyphenyl triazine was the most commonly used UV filter. The most frequent co-occurrence of UV filters was titanium dioxide and ethylhexyl methoxycinnamate. Titanium dioxide was the most commonly used UV filter, which differs from the findings of previous surveys. Knowing the availability and frequency of each UV filter provides valuable information about consumer exposure levels, facilitates refinements of the allergen series in patch testing, and enhances the monitoring of adverse effects of UV filters.

Here we demonstrate an animal-free skin permeation analytical approach suitable for testing pharmaceuticals, cosmetics, occupational skin hazards and skin allergens. The method aims to replace or significantly reduce existing in-vivo models and improve on already established in-vitro models. This by offering a more sensitive and flexible analytical approach that can replace and/or complement existing methods in the OECD guidelines for skin adsorption (no 427 and no 428) and measure multiple compounds simultaneously in the skin while being able to also trace endogenous effects in cells. We demonstrate this here by studying how active ingredients in sunscreen permeate through left-over human skin, from routine surgery, in a in a Franz-cell permeation model. Two common sunscreens were therefore applied to the human skin and Time of flight secondary ion mass spectrometry (ToF-SIMS) was used to trace the molecules through the skin. We show that that ToF-SIMS imaging can be applied in visualizing the distribution of Avobenzone, Bemotrizinol, Biscotrizole and Ethyl hexyl triazine at subcellular resolution in the skin. The UV-blockers could be visualized at the same time in one single experiment without any probes or antibodies used. The UV-blockers mostly remained in the stratum corneum. However, in certain features of the skin, such as sebaceous glands, the penetration of the UV-blockers was more prominent, and the compounds reached deeper into the epidermis.

Sunscreens are used to protect human skin against harmful UV radiation. Today there is a trend towards high sun protection factors (SPF) and good UVA protection. Methods for the assessment of SPF and UVA protection involve irradiation of the product, and the photostability properties of the sunscreen have an influence on its performance. Sunscreens often contain more than one UV filter. Some photolabile UV absorbers may be stabilized by the presence of other photostable UV-absorbers. Stabilization can be achieved just by a certain optical density due to the presence of such UV-filter substances. However, photostabilization may also be caused by quenching mechanisms, such as singlet-singlet or triplet-triplet energy transfer. Investigation of butyl methoxy dibenzoylmethane and ethylhexyl methoxycinnamate as photolabile sunscreens in the presence of either octocrylene or bis ethylhexyloxyphenol methoxyphenyl triazine showed that both mechanisms may apply. With the systems butyl methoxy dibenzoylmethane plus octocrylene and ethylhexyl methoxycinnamate plus bis ethylhexyloxyphenol methoxyphenyl triazine the quenching mechanism appears to be predominant.