Chitosan 6-(2-hydroxyethyl) ether
Glycol chitosan
CAS: 123938-86-3
Molecular Formula: C24H47N3O16
Chitosan 6-(2-hydroxyethyl) ether - Names and Identifiers
| Name | Glycol chitosan |
| Synonyms | Glycol chitosan HYDROXYETHYL CHITOSAN Glycol Chitosan DISCONTINUED Chitosan 6-(2-hydroxyethyl) ether |
| CAS | 123938-86-3 |
Chitosan 6-(2-hydroxyethyl) ether - Physico-chemical Properties
| Molecular Formula | C24H47N3O16 |
| Molar Mass | 633.64048 |
| Appearance | crystalline |
| Color | yellow |
| Storage Condition | -20°C |
| MDL | MFCD00131218 |
| Physical and Chemical Properties | Bioactive Glycol chitosan is a chitosan derivative with hydrophilic ethylene glycol branches. Glycol chitosan enhanced membrane permeability and leakage of Glycine max Harosoy 63W cells. Glycol chitosan is water-soluble, biocompatible and biodegradable. Glycol chitosan inhibited the growth of Escherichia coli, Staphylococcus aureus and Streptococcus enteritidis with MIC values of 4 μg/mL,32 μg/m L and <0.5 μg/mL, respectively. |
| Use | Overview Chitosan is a polymer compound composed of acetylglucosamine units that naturally exists in shrimps, crabs, insects and other crustaceans. Chitin is a polymer compound obtained by deacetylation or enzymatic deacetylation under strong alkali conditions. It is also a linear structure composed of a large number of glucosamine units and a small amount of acetylglucosamine units through 1,4-glycosidic bonds and the only natural polysaccharide biopolymer compound with alkaline characteristics. Compared with chitin, there are more polar amino groups that can be protonated in the molecular structure of chitosan. Therefore, when it maintains good biodegradability, biocompatibility and environmental friendliness of chitin, its solubility in acidic medium is also significantly improved compared with chitin, and its application performance is also significantly improved. |
Chitosan 6-(2-hydroxyethyl) ether - Risk and Safety
| WGK Germany | 3 |
Chitosan 6-(2-hydroxyethyl) ether - Reference
| Reference Show more | 1. Xu, Kaimeng, et al. "Green sustainable, facile nitrogen self-doped porous carbon derived from chitosan/cellulose nanocrystal biocomposites as a potential anode material for lithium-ion batteries." Journal of the Taiwan Institute of Chemical Engineers 109 ( |
Chitosan 6-(2-hydroxyethyl) ether - Uses and synthesis methods
Preparation
Hydroxyethyl chitosan (hydroxyethyl deacetylated chitosan) preparation: according to the mass ratio of the mixed alkali composed of sodium hydroxide, lithium hydroxide and/or potassium hydroxide to chitosan of 2.0~10: 1.0 to the chitosan to add a mass percentage of the concentration of 20 ~ 50% alkali aqueous solution, fully stirred and mixed, and then placed in the environment of -20~50 ℃ alkalization for 10~48 hours; according to the mass ratio of chitosan to isopropanol of 1.0: 10~100, the alkalized chitosan is dispersed in isopropanol, and then stirred at a constant temperature of 10~90 ℃ for 5~150min; According to the ratio of bromoethanol, ethylene oxide and/or chloroethanol to the substance of chitosan glucosamine unit of 0.1~20, the isopropanol solution of bromoethanol, ethylene oxide and/or chloroethanol is dripped into the alkalized chitosan-isopropanol system, after dropping, react at 10~100 ℃ for 2~48 hours; centrifuge or filter the reaction material, and dissolve or disperse the obtained solid with water to obtain hydroxyethyl chitosan (hydroxyethyl Deacetylated chitosan) aqueous solution or slurry; after evaporating and concentrating the aqueous solution or slurry containing hydroxyethyl chitosan (hydroxyethyl deacetylated chitosan) under negative pressure, then transfer the concentrated solution to a dialysis bag with a cut-off molecular weight of 500-50000, and dialyze in distilled water or deionized water for 12-72 hours to remove inorganic salts and excess alkali in the concentrated solution; After the dialysis concentrate for the second time, under stirring, the concentrated solution is slowly added to the absolute ethanol and/or acetone according to the volume ratio of the concentrated solution to absolute ethanol and/or acetone of 1.0: 1.0~50 to make the hydroxyethyl chitosan (Hydroxyethyl deacetylated chitosan) precipitate out in the form of precipitation, and finally filter the material and freeze-dry the obtained solid material, that is, hydroxyethyl chitosan (hydroxyethyl deacetylated chitosan) with an average grafting degree of hydroxyethyl of glucosamine unit of 5 ~ 300% was obtained.
Target
MIC: 4 μg/mL ( E. coli ), 32 μg/mL ( S. aureus ) and <0.5 μg/mL ( S. enteritidis )
in vitro studies
Glycol chitosan derivatives have been successfully applied to deliver antimicrobial agents and anticancer drugs such as chemodrugs, genes, and photosensitizers (PSs), either by physical encapsulation or chemical conjugation. Glycol chitosan can be directly linked with hydrophobic drugs to generate amphiphilic compounds that can also form nanoparticles (NPs) for cell imaging and drug delivery. The use of Glycol chitosan derivatives for cell imaging and drug delivery has several advantages, including superb tumor-homing ability in the case of Glycol chitosan NPs based on enhanced permeability and retention (EPR) effect, low cytotoxicity, ease of chemical modification, great biocompatibility, and biodegradability.
The hydrophobic modification of Glycol chitosan is already confirmed, such as Glycol chitosan bearing a 5β-cholanic acid moiety and deoxycholic acid-Glycol chitosan, could self-assemble into nanoparticles, acting as a promising vehicle for hydrophobic drugs and genes.
Last Update：2024-04-09 20:52:54
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