Association of antioxidant monophenolic compounds with β-cyclodextrin-functionalized cellulose and starch substrates

Carbohydr Polym. 2021 Sep 1:267:118189. doi: 10.1016/j.carbpol.2021.118189. Epub 2021 May 12.

Abstract

Polysaccharide substrates loaded with antioxidant and antimicrobial compounds, effectively protected by cyclodextrin moieties, can be a long-lasting solution to confer certain properties to fabrics, paper and other materials. β-Cyclodextrin was attached to α-cellulose, bleached pulp and starch by a two-step esterification with a tetracarboxylic acid. The resulting derivatives were characterized by spectroscopy, thermal degradation analysis and capability of phenolphthalein inclusion. The carriers, containing between 89 and 171 μmol of β-cyclodextrin per gram, were loaded with carvacrol, cuminaldehyde, cinnamaldehyde and hydroxytyrosol. From a stoichiometric addition, the percentage of compound retained ranged from 49% (hydroxytyrosol in pulp-cyclodextrin) to 92% (carvacrol in starch-cyclodextrin). Finally, the release rate to aqueous ethanol was measured over eight days and fitted to kinetic models. From the analysis of the mean dissolution time, it can be concluded that inserting β-cyclodextrin units enhanced the long-term holding of phenolic active compounds in carbohydrate matrices.

Keywords: Carbohydrate chemistry; Cellulose; Crosslinking; Phenolics; Release kinetics; Starch; β-Cyclodextrin.

MeSH terms

  • Acrolein / analogs & derivatives
  • Acrolein / chemistry
  • Antioxidants / chemistry*
  • Benzaldehydes / chemistry
  • Butanes / chemistry
  • Carboxylic Acids / chemistry
  • Cellulose / analogs & derivatives*
  • Cellulose / chemical synthesis
  • Cross-Linking Reagents / chemistry
  • Cymenes / chemistry
  • Drug Liberation
  • Kinetics
  • Phenols / chemistry*
  • Phenylethyl Alcohol / analogs & derivatives
  • Phenylethyl Alcohol / chemistry
  • Starch / analogs & derivatives*
  • Starch / chemical synthesis
  • beta-Cyclodextrins / chemical synthesis
  • beta-Cyclodextrins / chemistry*

Substances

  • Antioxidants
  • Benzaldehydes
  • Butanes
  • Carboxylic Acids
  • Cross-Linking Reagents
  • Cymenes
  • Phenols
  • beta-Cyclodextrins
  • 3,4-dihydroxyphenylethanol
  • 1,2,3,4-butanetetracarboxylic acid
  • Acrolein
  • Cellulose
  • Starch
  • carvacrol
  • Phenylethyl Alcohol
  • cuminaldehyde
  • cinnamaldehyde