chitosan

Also known as poliglusam

Chitosan is a linear polysaccharide composed of randomly distributed β-(1→4)-linked D-glucosamine (deacetylated unit) and N-acetyl-D-glucosamine (acetylated unit). It is made by treating the chitin shells of shrimp and other crustaceans with an alkaline substance, such as sodium hydroxide.

Chemical data

Formula: C56H103N9O39
Molecular weight: 1526.5 g/mol
IUPAC name: methyl N-[(2S,3R,4R,5S,6R)-5-[(2S,3R,4R,5S,6R)-3-amino-5-[(2S,3R,4R,5S,6R)-3-amino-5-[(2S,3R,4R,5S,6R)-3-amino-5-[(2S,3R,4R,5S,6R)-3-amino-5-[(2S,3R,4R,5S,6R)-3-amino-5-[(2S,3R,4R,5S,6R)-3-amino-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4-hydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4-hydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4-hydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4-hydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4-hydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-2-[(2R,3S,4R,5R,6S)-5-amino-6-[(2R,3S,4R,5R,6R)-5-amino-4,6-dihydroxy-2-(hydroxymethyl)oxan-3-yl]oxy-4-hydroxy-2-(hydroxymethyl)oxan-3-yl]oxy-4-hydroxy-6-(hydroxymethyl)oxan-3-yl]carbamate
SMILES: COC(=O)N[C@@H]1[C@H]([C@@H]([C@H](O[C@H]1O[C@@H]2[C@H](O[C@H]([C@@H]([C@H]2O)N)O[C@@H]3[C@H](O[C@H]([C@@H]([C@H]3O)N)O)CO)CO)CO)O[C@H]4[C@@H]([C@H]([C@@H]([C@H](O4)CO)O[C@H]5[C@@H]([C@H]([C@@H]([C@H](O5)CO)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O[C@H]7[C@@H]([C@H]([C@@H]([C@H](O7)CO)O[C@H]8[C@@H]([C@H]([C@@H]([C@H](O8)CO)O[C@H]9[C@@H]([C@H]([C@@H]([C@H](O9)CO)O)O)N)O)N)O)N)O)N)O)N)O)N)O
InChIKey: FLASNYPZGWUPSU-SICDJOISSA-N
XLogP: -21.4
Polar surface area: 808 Å²
H-bond donors: 29
H-bond acceptors: 47
Formal charge: 0

via PubChem

Research

59,041 papers

Chitosan-Based Nanoparticles as Effective Drug Delivery Systems-A review.Molecules (Basel, Switzerland) · 2023
Chitosan scaffolds: Expanding horizons in biomedical applications.Carbohydrate polymers · 2024
Tuning chitosan's chemical structure for enhanced biological functions.Trends in biotechnology · 2023
Modified chitosan: Insight on biomedical and industrial applications.International journal of biological macromolecules · 2024
Hydrophilic Chitosan Derivatives: Synthesis and Applications.Chemistry (Weinheim an der Bergstrasse, Germany) · 2022

via PubMed

Wikidata facts

Mass: 1525.635315
Image: Chitosan.jpg

Show 4 more facts

chemical formula: C₅₆H₁₀₃N₉O₃₉
isomeric SMILES: COC(=O)N[C@@H]1[C@H]([C@@H]([C@H](O[C@H]1O[C@@H]2[C@H](O[C@H]([C@@H]([C@H]2O)N)O[C@@H]3[C@H](O[C@H]([C@@H]([C@H]3O)N)O)CO)CO)CO)O[C@H]4[C@@H]([C@H]([C@@H]([C@H](O4)CO)O[C@H]5[C@@H]([C@H]([C@@H]([C@H](O5)CO)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O[C@H]7[C@@H]([C@H]([C@@H]([C@H](O7)CO)O[C@H]8[C@@H]([C@H]([C@@H]([C@H](O8)CO)O[C@H]9[C@@H]([C@H]([C@@H]([C@H](O9)CO)O)O)N)O)N)O)N)O)N)O)N)O)N)O
canonical SMILES: COC(=O)NC1C(C(C(OC1OC2C(OC(C(C2O)N)OC3C(OC(C(C3O)N)O)CO)CO)CO)OC4C(C(C(C(O4)CO)OC5C(C(C(C(O5)CO)OC6C(C(C(C(O6)CO)OC7C(C(C(C(O7)CO)OC8C(C(C(C(O8)CO)OC9C(C(C(C(O9)CO)O)O)N)O)N)O)N)O)N)O)N)O)N)O
Commons category: Chitosan

Sources (2)

via Wikidata · CC0

~22 min read

Article

27 sections

Contents

History
Manufacture
Chemical modifications
Phosphorylated chitosan
Thiolated chitosan
Ionic chitosan
Properties
Solution
Gel
Noncovalent interactions
Biological properties
Uses
Agricultural and horticultural use
Natural biocontrol and elicitor
Filtration
Winemaking and fungal source chitosan
Wound management
Wound dressings
Other forms
Temperature-sensitive hydrogels
Research
Bioprinting
Weight loss
Food packaging
Battery electrolyte
References
External links

Chitosan has a number of commercial and possible biomedical uses. It can be used in agriculture as a seed treatment and biopesticide, helping plants to fight off fungal infections. In winemaking, it can be used as a fining agent, also helping to prevent spoilage. In industry, it can be used in a self-healing polyurethane paint coating. In medicine, it is useful in bandages to reduce bleeding and as an antibacterial agent; it can also be used to help deliver drugs through the skin.