The Effect of Photoisomerization on the Antioxidant Properties of Sinapic Acid and Methyl Sinapate in Different Solvents: A DFT/TD-DFT Study
The impact of photoisomerization on antioxidant properties holds significant implications for fields such as medicine, chemistry, and consumer products. This investigation employs multistate complete active space second-order perturbation theory (MS-CASPT2), complemented by density functional theory...
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MDPI AG
2025-05-01
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| Series: | Antioxidants |
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| author | Lei Wang Chaofan Sun Lingling Wang |
| author_facet | Lei Wang Chaofan Sun Lingling Wang |
| author_sort | Lei Wang |
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| description | The impact of photoisomerization on antioxidant properties holds significant implications for fields such as medicine, chemistry, and consumer products. This investigation employs multistate complete active space second-order perturbation theory (MS-CASPT2), complemented by density functional theory (DFT) and time-dependent DFT (TD-DFT) methods, to examine the photoisomerization behavior of sinapic acid (SA) and methyl sinapate (MS) under ultraviolet (UV) irradiation, while systematically analyzing their antioxidant properties in the S<sub>1</sub> state. The computational results, validated by two independent theoretical approaches, confirm that both SA and MS can undergo photoisomerization through conical intersection pathways, providing crucial insights into their non-radiative transition mechanisms. In the S<sub>0</sub> state, cis-SA and cis-MS exhibit higher antioxidant activity, while in the S<sub>1</sub> state, antioxidant performance is strongly solvent-dependent: trans-SA outperforms in ethyl acetate (Eac) and water, whereas cis-SA is more effective in methanol (MeOH). Notably, the natural population analysis (NPA) charges of all four compounds increase upon photoexcitation, suggesting that photoexcitation enhances antioxidant properties. This study addresses a critical gap in our understanding of the relationship between photoisomerization and antioxidant activity in natural phenolic compounds. |
| format | Article |
| id | doaj-art-ed9c67b995c94e9f86a6a62e8f6e7e23 |
| institution | Matheson Library |
| issn | 2076-3921 |
| language | English |
| publishDate | 2025-05-01 |
| publisher | MDPI AG |
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| series | Antioxidants |
| spelling | doaj-art-ed9c67b995c94e9f86a6a62e8f6e7e232025-06-25T13:23:07ZengMDPI AGAntioxidants2076-39212025-05-0114663310.3390/antiox14060633The Effect of Photoisomerization on the Antioxidant Properties of Sinapic Acid and Methyl Sinapate in Different Solvents: A DFT/TD-DFT StudyLei Wang0Chaofan Sun1Lingling Wang2College of Science, Northeast Forestry University, Harbin 150040, ChinaCollege of Science, Northeast Forestry University, Harbin 150040, ChinaCollege of Chemistry, Chemical Engineering and Resource Utilization, Northeast Forestry University, Harbin 150040, ChinaThe impact of photoisomerization on antioxidant properties holds significant implications for fields such as medicine, chemistry, and consumer products. This investigation employs multistate complete active space second-order perturbation theory (MS-CASPT2), complemented by density functional theory (DFT) and time-dependent DFT (TD-DFT) methods, to examine the photoisomerization behavior of sinapic acid (SA) and methyl sinapate (MS) under ultraviolet (UV) irradiation, while systematically analyzing their antioxidant properties in the S<sub>1</sub> state. The computational results, validated by two independent theoretical approaches, confirm that both SA and MS can undergo photoisomerization through conical intersection pathways, providing crucial insights into their non-radiative transition mechanisms. In the S<sub>0</sub> state, cis-SA and cis-MS exhibit higher antioxidant activity, while in the S<sub>1</sub> state, antioxidant performance is strongly solvent-dependent: trans-SA outperforms in ethyl acetate (Eac) and water, whereas cis-SA is more effective in methanol (MeOH). Notably, the natural population analysis (NPA) charges of all four compounds increase upon photoexcitation, suggesting that photoexcitation enhances antioxidant properties. This study addresses a critical gap in our understanding of the relationship between photoisomerization and antioxidant activity in natural phenolic compounds.https://www.mdpi.com/2076-3921/14/6/633sinapic acidphotoisomerizationantioxidantdual descriptor potentialdensity function theory |
| spellingShingle | Lei Wang Chaofan Sun Lingling Wang The Effect of Photoisomerization on the Antioxidant Properties of Sinapic Acid and Methyl Sinapate in Different Solvents: A DFT/TD-DFT Study Antioxidants sinapic acid photoisomerization antioxidant dual descriptor potential density function theory |
| title | The Effect of Photoisomerization on the Antioxidant Properties of Sinapic Acid and Methyl Sinapate in Different Solvents: A DFT/TD-DFT Study |
| title_full | The Effect of Photoisomerization on the Antioxidant Properties of Sinapic Acid and Methyl Sinapate in Different Solvents: A DFT/TD-DFT Study |
| title_fullStr | The Effect of Photoisomerization on the Antioxidant Properties of Sinapic Acid and Methyl Sinapate in Different Solvents: A DFT/TD-DFT Study |
| title_full_unstemmed | The Effect of Photoisomerization on the Antioxidant Properties of Sinapic Acid and Methyl Sinapate in Different Solvents: A DFT/TD-DFT Study |
| title_short | The Effect of Photoisomerization on the Antioxidant Properties of Sinapic Acid and Methyl Sinapate in Different Solvents: A DFT/TD-DFT Study |
| title_sort | effect of photoisomerization on the antioxidant properties of sinapic acid and methyl sinapate in different solvents a dft td dft study |
| topic | sinapic acid photoisomerization antioxidant dual descriptor potential density function theory |
| url | https://www.mdpi.com/2076-3921/14/6/633 |
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