Urea-Based Low-Molecular-Weight Pseudopeptidic Organogelators for the Encapsulation and Slow Release of (R)-Limonene

J Agric Food Chem. 2020 Jul 1;68(26):7051-7061. doi: 10.1021/acs.jafc.0c01184. Epub 2020 Jun 19.

Abstract

Low-molecular-weight compounds containing alkylurea fragments attached to the amino end of different miminalistic pseudopeptidic structures have been shown to be excellent organogelators in a variety of organic solvents and liquid organic compounds of different nature. The formation of gels in this work is defined through rheological measurements for those cases where G' > G''. Both the topology and the symmetry of the corresponding urea compounds play a role in defining their organogelator behavior. This can also be tuned by the presence of additional supramolecular guests, as is the case for suberic acid. These compounds also achieve the gelation of relevant active substances such as terpene natural oils and complex mixtures of flavors and fragrances. This provides a simple and mass-efficient supramolecular system for the quantitative encapsulation of active substances, without the need for any additional solvent or complex processes, and their consequent controlled release.

Keywords: (R)-limonene; flavor and fragrance release; low-molecular-weight gelators (LMWGs); tripodal pseudopeptides; urea derivatives.

MeSH terms

  • Delayed-Action Preparations / chemistry*
  • Drug Compounding
  • Drug Liberation
  • Gels / chemistry
  • Limonene / chemistry*
  • Molecular Weight
  • Peptides / chemistry*
  • Rheology
  • Terpenes / chemistry

Substances

  • Delayed-Action Preparations
  • Gels
  • Peptides
  • Terpenes
  • Limonene