Synthesis of organosoluble chitosan derivatives with polyphenolic side chains |
| |
Authors: | Minoru Morimoto Takahiro Nakajima Masayuki Ishikura Yoshihiro Shigemasa Shinsuke Ifuku Hiroyuki Saimoto |
| |
Institution: | Research Center for Bioscience and Technology, Tottori University, Koyama, Tottori 680-8550, Japan. |
| |
Abstract: | A one-pot synthesis was used to produce chitosan derivatives with polyphenolic side chains via a regioselective phenolic coupling reaction. Under Mannich reaction conditions, treatment of chitosan with formaldehyde and methyl 2,4-dihydroxybenzoate gave N-(2,6-dihydroxy-3-methoxycarbonylphenyl)methylated chitosan in good yield (87%). Formation of a CC bond occurred regioselectively at the C(3) position of methyl 2,4-dihydroxybenzoate. Chitosan derivatives having various phenolic compounds as a side chain were easily synthesized in a similar manner. The chitosan derivatives showed good biodegradability and improved their solubility in methanol (9.8mgmL(-1)) and 2-methoxyethanol (> 10mgmL(-1)). The UV protection provided by the derivatives with phenolic benzophenone side chain was evaluated using UV spectra of polyethylene terephthalate and poly(vinyl butyral-co-vinyl alcohol-co-vinyl acetate) films coated with the derivatives and the derivatives absorbed effectively in the UV-A region (<60%). Self-aggregation of the chitosan derivatives with the phenolic side chain was observed by using a fluorescent probe in aqueous solution. |
| |
Keywords: | |
本文献已被 ScienceDirect PubMed 等数据库收录! |
|