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Article Dans Une Revue Journal of Agricultural and Food Chemistry Année : 2020

Sustainable Straightforward Synthesis and Evaluation of the Antioxidant and Antimicrobial activity of Sinapine and Analogs

Louis Mouterde
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Matthieu Mention
Fanny Brunissen
Florent Allais

Résumé

Naturally occurring sinapine was successfully synthesized through a proline-mediated Knoevenagel–Doebner condensation in ethanol. This synthetic process involving biobased syringaldehyde, Meldrum’s acid, and choline chloride offers a sustainable alternative to the existing low-yield pathways. This two-step strategy gives access to sinapine in a 52% overall yield and has been implemented in the synthesis of sinapine analogues, using 4-hydroxybenzaldehyde, 3,4-dihydroxybenzaldehyde, and vanillin as precursors, giving target molecules with 34–61% overall isolated yields. The purity of synthetic sinapine and its analogues (ca. 95%) was assessed by NMR and high-performance liquid chromatography—mass spectrometry analyses. Furthermore, the antioxidant and antimicrobial activities were assessed, and the potential of this series of molecules was confirmed.
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Dates et versions

hal-02876020 , version 1 (20-06-2020)

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Louis Mouterde, Aurélien Peru, Matthieu Mention, Fanny Brunissen, Florent Allais. Sustainable Straightforward Synthesis and Evaluation of the Antioxidant and Antimicrobial activity of Sinapine and Analogs. Journal of Agricultural and Food Chemistry, 2020, 68 (26), pp.6998-7004. ⟨10.1021/acs.jafc.0c02183⟩. ⟨hal-02876020⟩

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