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Monitoring 2-ethylhexyl-4-methoxycinnamate Photoisomerization on Skin Using Attenuated Total Reflection Fourier Transform Infrared Spectroscopy

Monitoring 2-ethylhexyl-4-methoxycinnamate Photoisomerization on Skin Using Attenuated Total Reflection Fourier Transform Infrared Spectroscopy

P Pangnakorn, R Nonthabenjawan, S Ekgasit, C Thammacharoen, S Pattanaargson Wanichwecharungruang

Appl Spectrosc. 2007 Feb;61(2):193-8.

PMID: 17331311

Abstract:

Photoisomerization and photodimerization of a widely used UVB filter, 2-ethylhexy-4-methoxycinnamate (EHMC) on a ZnSe surface and baby mouse (Mus musculus Linn.) skin were monitored using attenuated total reflection Fourier transform infrared spectroscopy (ATR-FT-IR). Differentiation between the E- and the Z-EHMC could be achieved by examining the infrared (IR) peak at 981 cm(-1) (b peak), which corresponds to the CH rocking deformation vibration of Ph-CH=CH- detected only in the E configuration. By plotting the ratios of the peak area of the b peak and an internal standard peak (1060-998 cm(-1)) against mole percentage of Z-isomer in the E-Z mixtures, a linear calibration plot was obtained. Thus, a simple estimation of the mole percentage of each configuration in a sample was obtained. At the same UVB exposure, photostationary equilibrium of the E/Z isomerization on the surface varied with the applied amounts of EHMC. Photoisomerizations on ZnSe and on baby mouse skin were comparable. Less than 10% of E-EHMC changed configuration when the mouse skins applied with 1.0-4.0 mg/cm(2) E-EHMC were exposed to sunlight for 60 min (UVB radiant exposure of approximately 0.30 J/cm(2)). This corresponded to less than 5% loss in UV filtering efficiency. However, at a typical EHMC skin coverage ( approximately 0.2 mg/cm(2)), 0.30 J/cm(2) UVB exposure induced approximately 50% photoisomerization resulting in 25% loss of UV filtering efficiency. No photodimerization was detected even at the extreme EHMC coverage of 4.0 mg/cm(2) after a UVB exposure of 0.90 J/cm(2).

Chemicals Related in the Paper:

Catalog Number	Product Name	Structure	CAS Number	Price
AP5466773-A	2-Ethylhexyl 4-methoxycinnamate		5466-77-3	Price

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