A Study on the Photoisomerization of (<i>E</i>)-Dehydrozingerone, Its (<i>E</i>)-(<i>E</i>)-C₂ Symmetric Dimer, and Their <i>O</i>-Methylated Derivatives

A Study on the Photoisomerization of (<i>E</i>)-Dehydrozingerone, Its (<i>E</i>)-(<i>E</i>)-C₂ Symmetric Dimer, and Their <i>O</i>-Methylated Derivatives

In this study, UV-induced (<i>E</i>)-to-(<i>Z</i>) geometrical isomerizations of the curcumin degradation product (<i>E</i>)-dehydrozingerone, along with curcumin-inspired (<i>E</i>)-<i>O</i>-methylated dehydrozingerone and their correspond...

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Bibliographic Details
Main Authors: Maria Antonietta Dettori, Valeria Ugone, Davide Fabbri, Paola Carta
Format: Article
Language:English
Published: MDPI AG 2024-12-01
Series:Molecules
Subjects:
curcumin analogs
photoisomerization
NMR spectroscopy
UV light exposure
hydroxylated biphenyls
UV-Vis spectroscopy
Online Access:https://www.mdpi.com/1420-3049/29/24/5901
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Summary:In this study, UV-induced (<i>E</i>)-to-(<i>Z</i>) geometrical isomerizations of the curcumin degradation product (<i>E</i>)-dehydrozingerone, along with curcumin-inspired (<i>E</i>)-<i>O</i>-methylated dehydrozingerone and their corresponding C<sub>2</sub>-symmetric dimers, were investigated. All compounds produced corresponding (<i>Z</i>) isomers in varying yields upon UV irradiation in deuterated solvents. The efficiency of these photoisomerizations depended on the solvent and wavelength used. While (<i>Z</i>) dehydrozingerone and its corresponding (<i>Z</i>)-(<i>Z</i>) dimer proved to be highly unstable during purification, the <i>O</i>-methylated derivatives were successfully isolated, fully characterized by NMR spectroscopy, and further analyzed by UV-Vis spectroscopy and computational methods.
ISSN:1420-3049

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