Abstract
Sinapoyl malate, naturally present in plants, has proved to be an exceptional UV filter and molecular heater for plants. Although there are nowadays industrially relevant sustainable synthetic routes to sinapoyl malate, its incorporation into certain cosmetic formulations, as well as its adsorption on plant leaves, is limited by its hydrophilicity. To overcome these obstacles, it is important to find a way to effectively control the hydrophilic–lipophilic balance of sinapoyl malate to make it readily compatible with the cosmetic formulations and stick on the waxy cuticle of leaves. To this end, herein, we describe a highly regioselective chemo-enzymatic synthesis of sinapoyl malate analogues possessing fatty aliphatic chains of variable length, enabling the lipophilicity of the compounds to be modulated. The potential toxicity (i.e., mutagenicity, carcinogenicity, endocrine disruption, acute and repeated-dose toxicity), bioaccumulation, persistence and biodegradability potential of these new analogues were evaluated in silico, along with the study of their transient absorption spectroscopy, their photostability as well as their photodegradation products.
Original language | English |
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Journal | Chemical Science |
Early online date | 21 Nov 2023 |
DOIs | |
Publication status | E-pub ahead of print - 21 Nov 2023 |
Bibliographical note
Acknowledgments:The authors acknowledge the FET-Open grant BoostCrop (grant agreement 828753) and the entire BoostCrop (https://boostcrop.eu/) team for their interest in the work. T. T. A. thanks the University of Warwick for a PhD studentship through the Chancellor Scholarship. B. R., L. M. M. M., M. M. M., A. A. M. P., F. B. and F. A. thank the Agence Nationale de la Recherche (grant number ANR-17-CE07-0046), as well as the Grand Reims, Conseil Départemental de la Marne, and the Grand Est region for financial support. V. G. S. thanks the Royal Society for a Royal Society Industry Fellowship. M. J. A. V., G. B., and J. O. acknowledge the Nederlandse Organisatie voor Wetenschappelijk Onderzoek (NWO) for the support of the FELIX laboratory and the NWO domain Science for computational time (grant number 2021.055). Additionally, we would like to acknowledge Marise Borja, Dirk Schulz, and Verena Wanders for their contribution to formulation development, coordination and sampling of the field trials enabling analysis of the crops with LC-MS.