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Synthesis of Organosoluble Chitosan Derivatives With Polyphenolic Side Chains

Synthesis of Organosoluble Chitosan Derivatives With Polyphenolic Side Chains

Minoru Morimoto, Takahiro Nakajima, Masayuki Ishikura, Yoshihiro Shigemasa, Shinsuke Ifuku, Hiroyuki Saimoto

Carbohydr Polym. 2012 Oct 15;90(3):1259-64.

PMID: 22939339

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 (9.8mg mL(-1)) and 2-methoxyethanol (> 10mg mL(-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.

Chemicals Related in the Paper:

Catalog Number	Product Name	Structure	CAS Number	Price
AP27360072	Poly(vinyl butyral-co-vinyl alcohol-co-vinyl acetate)		27360-07-2	Price

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