Biology, Medicine, & Natural Product Chemistry
Vol 14, No 2 (2025)

Synthesis, Characterization, and Micellar Behavior of Amphiphilic Chitosan Bearing Sulfate and Anisaldehyde Imine Groups

Herayati, Herayati (Unknown)
Wahyuningrum, Deana (Unknown)
Bima, Damar Nurwahyu (Unknown)
Sari, Indah Puspita (Unknown)



Article Info

Publish Date
24 Oct 2025

Abstract

Amphiphilic chitosan derivatives bearing sulfate and anisaldehyde imine (anisimine) groups were successfully synthesized and characterized for potential applications as functional biomaterials. The synthesis involved two key steps: (1) sulfation of chitosan using chlorosulfonic acid to introduce O-sulfate groups, and (2) Schiff base formation via reaction with p-anisaldehyde to generate N-anisimine functionalities. Structural modifications were confirmed by Fourier-transform infrared (FTIR) spectroscopy, which showed characteristic absorption bands at ~1250 cm-¹ and ~820 cm-¹ corresponding to O=S=O stretching of sulfate, and a C=N stretch at ~1640 cm-¹ indicating imine formation. Proton nuclear magnetic resonance (1H-NMR) spectra further verified the successful attachment of aromatic protons from p-anisaldehyde and the disappearance of primary amine peaks, confirming imination. The amphiphilic behavior and micelle-forming ability of the N-anisimine-O-sulfated (NAOS) chitosan were evaluated using pyrene as a hydrophobic fluorescent probe for determining the critical micelle concentration (CMC), which was found to be 0.012 mg/mL. The observed low CMC value indicates strong self-assembly capability in aqueous media. These results suggest that NAOS chitosan possesses promising structural and surface-active properties suitable for advanced applications in drug delivery and cosmetic formulations.

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Journal Info

Abbrev

BIOMEDICH

Publisher

Subject

Biochemistry, Genetics & Molecular Biology Medicine & Pharmacology Public Health

Description

BIOLOGY, MEDICINE, & NATURAL PRODUCT CHEMISTRY, this journal is published to attract and disseminate innovative and expert findings in the fields of plant, animal, and microorganism secondary metabolite, and also the effect of natural product on biological system as a reference source for ...