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chitosan
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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.
OverviewAI-generated
Chitosan is a chemical compound with the formula C₅₆H₁₀₃N₉O₃₉. Its mass is listed as 1525.635315, while its weight is recorded as 1526.5. The substance has a charge of 0.
Chemical properties include an xlogp value of -21.4 and a topological polar surface area of 808. The molecule contains 29 hydrogen bond donors and 47 hydrogen bond acceptors.
The subject is associated with a Commons category titled "Chitosan." It has been referenced by 243 other encyclopedia articles. A search for chitosan in PubMed yields a count of 59041.
Synthesized by Vinony from 14 facts across 4 sources: Wikidata, PubMed, PubChem, Vinony graph. Generated from structured data (not the Wikipedia text) and checked against those facts — may still contain errors.
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 Ų
- 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
- Subclass of
- polysaccharide
- Has part
- nitrogen
- Mass
- 1525.635315
- Image
- Chitosan.jpg
Show 6 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
- subject has role
- antihemorrhagic
- found in taxon
- Mycosphaerella pinodes
Sources (2)
via Wikidata · CC0
~22 min read
Encyclopedic overview
27 sectionsContents
- 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 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.
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.
Excerpted from Wikipedia’s “chitosan” article, available under the CC BY-SA 4.0 licence.