Solubility and structure of N-carboxymethylchitosan

https://doi.org/10.1016/0141-8130(94)90048-5Get rights and content

Abstract

N-Carboxymethylchitosan from crab and shrimp chitosans was obtained in water-soluble form by proper selection of the reactant ratio, i.e. using equimolar quantities of glyoxylic acid and amino groups. HPLC determinations of glyoxylic and glycolic acids, in conjunction with NMR analysis, permitted identification of the structure of the product, which is partly N-mono-carboxymethylated (0.3), N,N-dicarboxymethylated (0.3) and N-acetylated depending on the level of deacetylation of the starting chitosan (0.08–0.15). The preparation can be made successfully even in the presence of large concentrations of glycolic acid. The use of enzymes exerting hydrolysing activity on the high-molecular-weight fractions helps to avoid gel formation during storage and precipitate formation on addition of anti-microbial agents.

References (12)

  • R.A.A. Muzzarelli et al.

    Carbohydr. Res.

    (1982)
  • R.A.A. Muzzarelli

    Carbohydr. Polym.

    (1988)
  • M. Petrarulo et al.

    J. Chromatogr.

    (1988)
  • M. Petrarulo et al.

    Clin. Chim. Acta

    (1991)
  • M. Rinaudo et al.

    Int. J. Biol. Macromol.

    (1992)
  • R.A.A. Muzzarelli et al.

    Enzyme Microb. Technol.

    (1994)
There are more references available in the full text version of this article.

Cited by (124)

  • Solvent-less carboxymethylation-induced electrostatic crosslinking of chitosan

    2023, International Journal of Biological Macromolecules
  • Chitin and chitosan-based polymer blends, interpenetrating polymer networks, and gels

    2023, Handbook of Natural Polymers, Volume 1: Sources, Synthesis, and Characterization
  • Carboxymethyl chitosan has sensitive two-way CO<inf>2</inf>-responsive hydrophilic/hydrophobic feature

    2020, Carbohydrate Polymers
    Citation Excerpt :

    For instance, carboxymethyl chitosan (CMC), a CS derivative via carboxymethyl (CM) substitution on CS, is water soluble in neutral water (Chen & Park, 2003). CMC with different CM substitution positions including O-, N-, N, O-, and N, N-CMC could be prepared by different reaction conditions and reagents (Ge & Luo, 2005; Jayakumar et al., 2010; Kong, 2012; Lin & Lin, 2009; Muzzarelli, Ilari, & Petrarulo, 1994; Song, Zhang, Gao, & Ding, 2010). The water solubility of CMC is closely related with the degree of deacetylation (DD) and the degree of CM substitution (DS) (Chen, Du, Wu, & Xiao, 2002; Kittur, Prashanth, Sankar, & Tharanathan, 2002; Shi, Du, Yang, Zhang, & Sun, 2006).

View all citing articles on Scopus
View full text