A highly photostable UVA filter derived from avobenzone

IF 4.1 3区 化学 Q2 CHEMISTRY, PHYSICAL Journal of Photochemistry and Photobiology A-chemistry Pub Date : 2024-08-17 DOI:10.1016/j.jphotochem.2024.115972
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Abstract

Avobenzone was derivatized to avo-glycerol by replacing the p-methoxy group with glycerol at the ortho position. Avo-glycerol exhibited absorption in the UVA range (315–400 nm), similar to avobenzone, indicating good UVA coverage. Unlike avobenzone, a solution of avo-glycerol in an aprotic solvent demonstrates remarkable photostability, with no significant decrease in absorbance at the UVA range after 6 h irradiation. This suggests that the hydroxyl group in avo-glycerol functions as an efficient acid-base catalyst in enolization. Consequently, the rapid enolization of the photochemically generated keto form prevents its accumulation. This inherent photostability of avo-glycerol eliminates the need for photo stabilizers in sunscreen formulations and provides greater flexibility in selecting other sunscreen components.

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一种从阿伏苯宗提取的高度光稳定性 UVA 过滤器
通过在正交位置用甘油取代对甲氧基,将阿伏苯宗衍生为阿伏甘油。阿伏甘油在 UVA 波段(315-400 纳米)的吸收率与阿伏苯宗相似,表明其具有良好的 UVA 遮盖能力。与阿伏苯宗不同,阿伏甘油在无相溶剂中的溶液具有显著的光稳定性,在 UVA 范围内的吸光度在照射 6 小时后没有明显下降。这表明阿伏甘油中的羟基在烯醇化过程中起到了高效酸碱催化剂的作用。因此,光化学生成的酮形式的快速烯醇化可以防止其积累。牛油甘油的这种固有光稳定性使防晒配方中不再需要光稳定剂,并为选择其他防晒成分提供了更大的灵活性。
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来源期刊
CiteScore
7.90
自引率
7.00%
发文量
580
审稿时长
48 days
期刊介绍: JPPA publishes the results of fundamental studies on all aspects of chemical phenomena induced by interactions between light and molecules/matter of all kinds. All systems capable of being described at the molecular or integrated multimolecular level are appropriate for the journal. This includes all molecular chemical species as well as biomolecular, supramolecular, polymer and other macromolecular systems, as well as solid state photochemistry. In addition, the journal publishes studies of semiconductor and other photoactive organic and inorganic materials, photocatalysis (organic, inorganic, supramolecular and superconductor). The scope includes condensed and gas phase photochemistry, as well as synchrotron radiation chemistry. A broad range of processes and techniques in photochemistry are covered such as light induced energy, electron and proton transfer; nonlinear photochemical behavior; mechanistic investigation of photochemical reactions and identification of the products of photochemical reactions; quantum yield determinations and measurements of rate constants for primary and secondary photochemical processes; steady-state and time-resolved emission, ultrafast spectroscopic methods, single molecule spectroscopy, time resolved X-ray diffraction, luminescence microscopy, and scattering spectroscopy applied to photochemistry. Papers in emerging and applied areas such as luminescent sensors, electroluminescence, solar energy conversion, atmospheric photochemistry, environmental remediation, and related photocatalytic chemistry are also welcome.
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