Chitin dipentanoate as the new technologically usable biomaterial.

Karolina Skołucka-Szary, Aleksandra Ramięga, Wanda Piaskowska, Bartosz Janicki, Magdalena Grala, Piotr Rieske, Ewelina Stoczyńska-Fidelus, Sylwester Piaskowski

Index: Mater. Sci. Eng. C. Mater. Biol. Appl. 55 , 50-60, (2015)

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Abstract

In this article, the synthesis of novel biopolymer, chitin dipentanoate (Di-O-Valeryl Chitin, DVCH) has been described. DVCH is a chitin derivative esterified with two valeryl groups at positions 3 and 6 of the N-acetylglucosamine units and it is soluble in common organic solvents like ethanol, methanol, acetone, dichloromethane, 1,2-dichloroethane, N,N-dimethylmethanamide, N,N-dimethylacetamide and ethyl acetate. Highly efficient synthesis (degree of esterification close to 2) of DVCH was achieved by employing a huge excess of valeric anhydride used as both the acylation agent and the reaction medium in the presence of perchloric acid as catalyst. Studies on the DVCH synthesis were aimed at finding optimal conditions (temperature, reaction time) to obtain DVCH with high reaction yield and desirable physicochemical properties. Biological data demonstrate that DVCH is non-cytotoxic in vitro and doesn't exert irritating or allergic effects to animal skin. Thanks to its filmogenic properties, it can be used to manufacture threads, foils, foams and non-woven materials. Moreover, DVCH can be easily processed by salt-leaching method to prepare highly porous structures exhibiting open-cell architecture, that can be further employed in wound dressing therapies and scaffolds for tissue engineering. Copyright © 2015 Elsevier B.V. All rights reserved.