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Article Dans Une Revue Beilstein Journal of Organic Chemistry Année : 2022

Cyclodextrin-based Schiff base pro-fragrances: Synthesis and release studies

Attila Palágyi
  • Fonction : Auteur
Jindřich Jindřich
Juraj Dian

Résumé

A simple method for the preparation of β-cyclodextrin derivatives containing covalently bonded aldehydes via an imine bond was developed and used to prepare a series of derivatives from 6 I -amino-6 I -deoxy-β-cyclodextrin and the following volatile aldehydes – cinnamaldehyde, cyclamen aldehyde, lilial, benzaldehyde, anisaldehyde, vanillin, hexanal, heptanal, citral, and 5-methylfurfural. Subsequently, the rate of release of the volatile compound from selected pro-fragrances, as a function of the environment (solvent, pH), was studied by 1 H NMR spectroscopy (for benzaldehyde) and static headspace-gas chromatography (for benzaldehyde, heptanal, and 5-methylfurfural). The aldehyde release rate from the imine was shown to depend substantially on the pH from the solution and the air humidity from the solid state.

Domaines

Chimie
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Dates et versions

hal-04242254 , version 1 (14-10-2023)

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Attila Palágyi, Jindřich Jindřich, Juraj Dian, Sophie Fourmentin. Cyclodextrin-based Schiff base pro-fragrances: Synthesis and release studies. Beilstein Journal of Organic Chemistry, 2022, 18, pp.1346-1354. ⟨10.3762/bjoc.18.140⟩. ⟨hal-04242254⟩
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