Chitosan

Base Information

• Chemical Name: Chitosan
• CAS No.: 9012-76-4
• Molecular Formula: (C6H11NO4)n
• Molecular Weight: 161.16
• Hs Code.: 39139000
• Mol file: 9012-76-4.mol

Synonyms:Flonac C;Chitosan H;Marinkaito F 05N;Marinkaito F 05S;KW 5;TKS 250N;Sea Cure 123;FCM 117;SK 10 (polysaccharide);HC 1 (polysaccharide);North Chitosan MC 1;OTS 2;Sea Cure 143;SK 200;Sea Cure 340;HI-DENSITY CHITOSAN;Chitopearl BCW 3505;Chiton (molluscan common name)Chitopearl 3510;Chitopearl BCW 3507;Hiset KW 5;WOT Recovery Floc T;Kytex M;Sea Cure 243;Chitosan EL;Hydagen HCMF;Profloc 320;

Chemical Property of Chitosan

Chemical Property:

• Appearance/Colour: white Powder
• Melting Point: 88oC
• Refractive Index: 1.7
• PSA: 95.94000
• Density: 1.75g/cm3
• LogP: -1.52550
• Storage Temp.: room temp
• Solubility.: dilute aqueous acid (pH <6.5).: soluble

Purity/Quality:

99% ^*data from raw suppliers

Chitosan, Medium Molecular Weight ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 20/21/22-36/37/38
• Safety Statements: 24/25-36-26

MSDS Files:

SDS file from LookChem

Useful:

• Biomedical Attributes: Chitosan, derived from chitin, possesses desirable biomedical attributes. It is considered one of the most ideal antibacterial materials due to its inherent antibacterial properties, wide source, and high yield.
• Chemical Composition and Properties: Chitosan is a copolymer of glucosamine and N-acetyl glucosamine, derived from chitin. It is composed of varying amounts of (尾1鈫?4) linked residues of N-acetyl-2 amino-2-deoxy-D-glucose (glucosamine) and 2-amino-2-deoxy-D-glucose (N-acetyl-glucosamine) residues. Chitosan is soluble in aqueous acidic media via primary amine protonation.; Reactive groups in chitosan include the primary amino group (C2) and primary and secondary hydroxyl groups (C6, C3), allowing for various modifications and producing polymers with new properties.
• Sources and Production: Chitosan is mainly derived from crustaceans, especially crab, prawns, and shrimp shells, which are readily available as waste from the food processing industry. Commercial chitosan samples were historically produced from the chemical deacetylation of chitin from crustacean sources, but chitosan from fungi is gaining interest, particularly due to vegan demands.
• Market and Industrial Applications: In 2019, the global chitosan market size was valued at USD 6.8 billion. Chitosan serves as a raw material for a wide range of products used in food, medical, pharmaceutical, health care, agriculture, industry, and environmental pollution protection.
• Solubility and Derivatives: The solubility of chitosan depends on the acetylation degree and molecular weight.; Chitosan oligomers are soluble over a wide pH range, while samples with higher molecular weight are only soluble in acidic aqueous media.; Many chitosan derivatives with enhanced solubility have been synthesized to overcome limitations in neutral physiological conditions.
• Biological Activities and Health Benefits: Chitosan exhibits inhibitory effects on bacteria, fungi, and tumor cells. It can induce apoptosis in tumor cells and enhance immune function by promoting the proliferation of T lymphocytes. Chitosan also has reported effects on lowering blood pressure and cholesterol, inhibiting fat absorption, promoting small intestine peristalsis, and improving immunity.
• Applications and Formulation: Chitosan can chemically react with organic reagents and be prepared into various shapes, such as sponge materials, nanoparticles, and gel particles. It is utilized in conventional methods for various applications due to its versatility and ability to form different formulations.
• General Description: Chitosan is a biodegradable, biocompatible polysaccharide widely used as a green catalyst in organic synthesis and as a polymeric carrier in drug delivery systems. It demonstrates high catalytic efficiency in reactions such as the Michael addition, offering an environmentally friendly alternative to traditional catalysts. Additionally, chitosan serves as a versatile platform for prodrug development, enabling the controlled release of therapeutic agents like anti-HIV compounds (e.g., chitosan-d4T conjugates), enhancing drug efficacy while minimizing side effects. Its water solubility, modifiable structure, and ability to form nanoparticles further highlight its utility in pharmaceutical and biomedical applications.

Technology Process of Chitosan

There total 6 articles about Chitosan which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 98.0%

chitin, average molecular weight 70 kDa → chitosan (9012-76-4)

Guidance literature:

With sodium hydroxide; In water; for 120h; Reflux;

DOI:10.1002/hlca.200890064

Reference yield: 92.6%

chitin (1398-61-4) → chitosan (9012-76-4)

Guidance literature:

With sodium hydroxide; at 60 ℃; for 72h;

DOI:10.1039/c5ra27489c

Reference yield:

chitosan acetate → chitosan (9012-76-4)

Guidance literature:

With sodium hydroxide; water; for 5h;

upstream raw materials:

chitin

Downstream raw materials:

Deloxan ASP I/7

acetyl 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl-(1->4)-2-acetamido-3,6-di-O-acetyl-2-deoxy-β-D-glucopyranosyl-(1->4)-2-acetamido-3,6-di-O-acetyl-2-deoxy-β-D-glucopyranosyl-(1->4)-2-acetamido-3,6-di-O-acetyl-2-deoxy-α-D-glucopyranose

(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl)-(1→4)-(2-acetamido-3,6-di-O-acetyl-2-deoxy-β-D-glucopyranosyl)-(1→4)-2-acetamido-1,3,6-tri-O-acetyl-2-deoxy-α-D-glucopyranose

chitobiose octaacetate

Refernces

Regioorientation in the Addition Reaction of α-Substituted Cinnamonitrile to Enamines Utilizing Chitosan as a Green Catalyst: Unambiguous Structural Characterization Using 2D-HMBC NMR Spectroscopy

10.1002/jhet.2341

This research investigates the synthesis of hexahydroquinolines and their fused derivatives through the reaction of enamines with substituted cinnamonitriles, using DABCO, piperidine, or chitosan as catalysts. The purpose is to develop an efficient and environmentally benign method for synthesizing these biologically significant compounds, which have applications in the pharmaceutical field, particularly for their antibacterial and anticancer activities. The study concludes that DABCO and chitosan are highly effective catalysts, with chitosan being a green alternative. The structures of the synthesized compounds were unambiguously determined using 2D-HMBC NMR spectroscopy, confirming the regioorientation of the Michael addition reaction.

Synthesis, nanosizing and in vitro drug release of a novel anti-HIV polymeric prodrug: Chitosan-O-isopropyl-5′-O-d4T monophosphate conjugate

10.1016/j.bmc.2009.11.013

The research describes the development of a novel anti-HIV polymeric prodrug: chitosan-O-isopropyl-50-O-d4T monophosphate conjugate. The study aims to improve the antiviral efficacy of nucleoside reverse transcriptase inhibitors (NRTIs) and reduce their side effects by constructing a nanosized NRTI monophosphate-polymer conjugate using d4T as a model NRTI. Key chemicals involved in the research include chitosan, a biodegradable and biocompatible polysaccharide used as the polymeric vehicle, and d4T (stavudine), an NRTI used in the treatment of HIV infection. The synthesis of the chitosan-d4T conjugate was achieved through the Atherton–Todd reaction under mild conditions, resulting in a water-soluble prodrug with a degree of substitution (DS) of 17.0%. Other chemicals used in the synthesis process include O-isopropyl-5-H-phosphonate of d4T, synthesized using phosphorus trichloride as a phosphorylation reagent, and various reagents such as triethylamine, tetrachloromethane, and sodium tripolyphosphate (TPP) for the preparation of nanoparticles. The study evaluated the anti-HIV activity and cytotoxicity of the conjugate in MT4 cells, prepared nanoparticles for enhanced delivery to viral reservoirs, and conducted in vitro drug release studies to assess the controlled release of d4T monophosphate derivatives.