Chitosan

• CAS: 9012-76-4
• Catalog Number: ACM9012764-55
• Category: Main Products
• Molecular Weight: 1526.5g/mol
• Molecular Formula: C6H13NO4
• Description: Active ingredient chitosan is de-acylated chitin. Derived from crustacean shells. Used as film-former and hair-fixative. Also used as deodorising agent. It possesses antimicrobial and excellent skin care properties. It prevents the excessive generation of odor-forming substances.
• Synonyms: Chitin, deacylated
• 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
• Canonical 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
• InChI: InChI=1S/C56H103N9O39/c1-87-56(86)65-28-38(84)46(19(10-74)96-55(28)104-45-18(9-73)95-49(27(64)37(45)83)97-39-12(3-67)88-47(85)20(57)31(39)77)103-54-26(63)36(82)44(17(8-72)94-54)102-53-25(62)35(81)43(16(7-71)93-53)101-52-24(61)34(80)42(15(6-70)92-52)100-51-23(60)33(79)41(14(5-69)91-51)99-50-22(59)32(78)40(13(4-68)90-50)98-48-21(58)30(76)29(75)11(2-66)89-48/h11-55,66-85H,2-10,57-64H2,1H3,(H,65,86)/t11-,12-,13-,14-,15-,16-,17-,18-,19-,20-,21-,22-,23-,24-,25-,26-,27-,28-,29-,30-,31-,32-,33-,34-,35-,36-,37-,38-,39-,40-,41-,42-,43-,44-,45-,46-,47-,48+,49+,50+,51+,52+,53+,54+,55+/m1/s1
• InChI Key: FLASNYPZGWUPSU-SICDJOISSA-N
• Melting Point: 102.5 °C
• Density: 1.0g/ml
• Appearance: Fine, off-white powder, characteristic odor
• Application: In the agricultural sector: as growth promoters, bio-pesticides, feed additives, seed treatment.
• Storage: Store light-protected at a cool and dry place
• Active Content: 80%
• Complexity: 2630
• Covalently-Bonded Unit Count: 1
• EC Number: 618-480-0
• Exact Mass: 1525.635315g/mol
• Form: Powder
• Formal Charge: 0
• Hazard Codes: Xn
• H-Bond Acceptor: 47
• H-Bond Donor: 29
• Heavy Atom Count: 104
• HS Code: 2936210000
• LogP: -1.52550
• Loss On Drying: 0.5 ppm
• Monoisotopic Mass: 1525.635315g/mol
• Odor: Odorless
• pH: 7.0-8.0
• Physical State: Solid
• PSA: 95.94
• Refractive Index: 1.7
• Rotatable Bond Count: 27
• Solubility In Water: Insoluble
• Stability: Stable. Incompatible with strong oxidizing agents.
• Storage Conditions: Store in a tightly closed container. Store in a cool, dry, well-ventilated area away from incompatible substances.
• XLogP3: -21.4

Case Study

Chitosan in 3D Chitin/Chitosan Scaffold Fabrication for Biomedical Applications

Dziedzic I, et al. Carbohydrate Polymer Technologies and Applications, 2024, 8, 100587.

In recent research, a 3D chitin/chitosan composite scaffold was developed using a natural framework derived from the marine sponge Aplysina aerophoba, aiming to retain the unique tubular architecture of chitin while adding the functional advantages of chitosan. This scaffold design capitalizes on chitosan's solubility in acidic solutions, which opens pathways for further chemical modifications beneficial for biomedical applications.
The scaffold was fabricated by first deacetylating sponge-derived chitin samples to create a composite chitin/chitosan structure. Deacetylation was conducted at 95°C using sodium hydroxide (NaOH) solutions of varying concentrations (25%, 38%, and 50%) across different treatment durations (15, 30, 60, and 180 minutes) to optimize the balance between scaffold stability and chitosan functionality. However, samples treated with 50% NaOH exhibited instability, losing their 3D structure upon neutralization, while those treated with 25% NaOH showed discoloration during iodine testing, indicating incomplete deacetylation. As a result, subsequent work focused on deacetylating in 38% NaOH, which preserved the structural integrity and functionality of the scaffold.
The final 3D chitin/chitosan scaffold combines the structural robustness of chitin with the chemical adaptability of chitosan, making it a promising material for advanced tissue engineering and drug delivery systems.

Chitosan-Coated Liposomes for Enhanced Stability and Delivery of ACE Inhibitory Peptides

Wang P, et al. Journal of Food Engineering, 2025, 388, 112363.

Chitosan-coated liposomes (CS-CPH-Lip) offer a promising solution for the stable delivery of bioactive ACE inhibitory peptides, enhancing their potential applications in the food and nutraceutical industries. This study demonstrates the effectiveness of chitosan as a coating agent for liposomes loaded with peptides derived from camellia seed cake (CPH). The chitosan-coated liposomes improve peptide stability during gastrointestinal digestion-a key challenge limiting the bioactivity of ACE inhibitory peptides in food applications.
Preparation of the CPH-liposomes (CPH-Lip) involved dissolving phosphatidylcholine, cholesterol, and Tween-80 in ethanol, followed by solvent removal, hydration with CPH-loaded phosphate-buffered saline (PBS), and sonication to reduce particle size. For coating, chitosan was dissolved in 1% acetic acid to form solutions of varying concentrations (0.1%, 0.5%, and 1.0%). The optimal chitosan concentration of 0.5% produced CS-CPH-Lip-0.5% with the highest encapsulation efficiency (82.67%) and superior stability.
The CS-CPH-Lip-0.5% liposomes demonstrated enhanced thermal and storage stability due to electrostatic interactions between chitosan and CPH-Lip. Notably, the chitosan layer also enabled a controlled peptide release, essential for targeted bioactivity, and retained 52.76% of the ACE inhibitory activity after simulated gastrointestinal digestion. This controlled release profile and preserved bioactivity highlight the role of chitosan in improving the functional delivery of ACE inhibitory peptides, which could benefit formulations targeting blood pressure regulation.

Chitosan for the Preparation of Chitosan Foam via Emulsion Templates

Zhang Z, et al. International Journal of Biological Macromolecules, 2024, 136870.

Chitosan foams, with their porous 3D structures, are ideal for applications requiring high surface area and active functional groups, such as in tissue engineering or filtration. This study outlines an innovative method for preparing chitosan foam using an emulsion template, followed by a biomimetic dopamine (DA) and polyethyleneimine (PEI) co-deposition to enhance surface amine functionality.
The chitosan foam was prepared by dissolving chitosan powder in acetic acid to form a chitosan sol, followed by the addition of Span 80 as an emulsifier and n-octane as a porogen. The mixture was vigorously stirred to create a stable emulsion, then poured into molds and frozen. The frozen samples were freeze-dried at -60°C under vacuum for 24 hours, resulting in a 3D porous chitosan foam structure.
To achieve amine functionalization, a DA-PEI co-deposition strategy was employed. The chitosan foam was immersed in a Tris-HCl buffer solution (pH 8.5) containing DA and PEI. This immersion triggered DA self-polymerization, which was cross-linked with PEI, resulting in a stable coating on the foam's surface. The DA-PEI co-deposition significantly increased the surface amine content, transforming the foam into an amine-functionalized chitosan foam (ACF).
The amine-rich surface of ACF provides additional reactive sites for further modification, enhancing the foam's potential for applications in adsorption, catalysis, or biomedical engineering.

Chitosan for the Preparation of Chitosan-graft-PVAc Adhesives

Todorovic T, et al. International Journal of Adhesion and Adhesives, 135, 103818.

This study focuses on the sequential hydrolysis of chitosan followed by emulsion polymerization to prepare chitosan-grafted PVAc adhesives with enhanced adhesion properties.
Hydrolysis Process: Initially, chitosan (6 g, 9% moisture) was dissolved incrementally in 0.5 M HCl, stirred vigorously at 25 °C for an hour. To enhance hydrolysis, concentrated HCl was then added to bring the solution to 2 M HCl, and the mixture was heated to 60 °C for 1 hour. The solution was quenched using an ice-water bath, followed by neutralization with 30 wt% NaOH. The hydrolyzed chitosan (H-CS) was precipitated in ethanol, filtered, and washed to remove salts, then freeze-dried for subsequent polymerization.
Emulsion Polymerization: For grafting, both hydrolyzed chitosan (H-CS) and non-hydrolyzed chitosan (NH-CS) were utilized. H-CS was dissolved in 10 wt% acetic acid for 2 hours, while NH-CS required overnight stirring. Following dissolution, an initiator (cerium ammonium nitrate) was added, initiating polymerization of vinyl acetate (VAc). The mixture was heated in an oil bath at 60 °C, followed by the addition of AIBN to complete the reaction at 75 °C, ensuring complete VAc polymerization.
This synthesis method yielded a chitosan-grafted PVAc adhesive with high binding efficiency and water resistance, suitable for applications demanding durable, biocompatible adhesives.

Chitosan for the Preparation of Graphene-chitosan Composites

Briceño S, et al. Carbon Trends, 2024, 17, 100405.

Chitosan can be used to prepare graphene-chitosan composites. The specific synthesis method is as follows:
We dissolved 0.1 g of chitosan (CS) in 100 mL of acetic acid (2%) and ultrasonicated for 30 min. At the same time, 0.1 g of graphene Elicarb flakes (GR ) was sonicated in 2 mL of acetic acid (2%) for 30 min. The two samples were mixed in a 4:1 ratio, i.e., 8 mL chitosan and 2 mL graphene in acetic acid. The resulting GR-CS composites were sonicated for 30 min. Au/CTAB and Ag/CTAB NPs were added to the G R -C S composites in a 1:2 molar ratio and stirred at 45 °C for 30 minutes. The samples were then dried at 60 °C for 12 hours.

Custom Q&A

What is the PubChem CID of chitosan?

The PubChem CID of chitosan is 71853.

What is the molecular formula of chitosan?

The molecular formula of chitosan is C56H103N9O39.

What is the molecular weight of chitosan?

The molecular weight of chitosan is 1526.5 g/mol.

What is the structure of chitosan?

The structure of chitosan is a linear polysaccharide consisting of D-glucosamine and N-acetyl-D-glucosamine.

Where is naturally-occurring chitosan found?

Naturally-occurring chitosan is found in the cell walls of fungi, soil, and sediments.

How is commercial chitosan derived?

Commercial chitosan is derived from the deacetylation of chitin contained in the shells of various sea crustaceans such as shrimps.

What are the reported effects of chitosan?

Chitosan is reported to have effects on protein aggregation, emulsification capacity, film-forming ability, clarifying ability, and fatty acid absorption capability.

What additional activities does chitosan exhibit?

Chitosan also exhibits antimicrobial and antioxidant activities.

Where else can chitosan be found in nature?

Chitosan is found in Didymella pinodes, a natural product.

How does chitosan potentially reduce the development and progression of certain cancers?

Chitosan may reduce advanced glycation end product (AGE) levels, which can limit the interaction between AGEs and the receptor for advanced glycation end products (RAGE). This interaction is associated with poor patient outcomes in some tumor types.