9012-76-4 Usage
Uses
Used in Tissue Engineering, Biomedical, Cosmetics, and Industrial Applications:
Chitosan is used as an electrospun fiber for tissue engineering, biomedical, cosmetics, and various industrial applications due to its antimicrobial activity, hemostatic agent, metal-chelating, molecular affinity, and wound-healing agent properties.
Used in Medicine, Health Care, and Food Fields:
Chitosan is used as an ingredient in medicine, health care, and food fields for its various effects, such as improving immunity, activation of cells, preventing cancer, lowering blood pressure, anti-aging, and regulating body environment.
Used in Environmental Protection:
Chitosan is used as a component in sewage treatment, protein recovery, and water purification due to its high adsorption capacity and selectivity provided by many -NH2 and -OH groups that can chelate heavy metal ions.
Used in Functional Materials:
Chitosan is used as a film material, carrier, adsorbent, fiber, and medical material in functional materials applications.
Used in Light Textile:
Chitosan is used for fabric finishing, health underwear, and paper additives in the light textile field.
Used in Agriculture:
Chitosan is used as a feed additive, seed treatment, soil improvement, and preservation of fruit in agriculture.
Used in Tobacco:
Chitosan is used as an excellent sheet gel in tobacco and can also improve the taste with being non-toxic and odorless upon burning.
Used in Wound Healing, Hemostasis, Biosurgery, Ophthalmology, Scaffold and Cell Therapy, and Drug Delivery and Vaccines:
Chitosan is used as a film-forming polysaccharide in wound healing and hemostasis, biosurgery and ophthalmology, scaffold and cell therapy, and drug delivery and vaccines due to its ideal properties for these applications.
Used in Cosmetics:
Chitosan is used as a skin conditioner in cosmetics, improving skin softness and suppleness, aiding the skin's moisture content and moisture-retention capacity by preventing transepidermal water loss, and enhancing the microbiological stability of a preparation. It also has anti-bacterial properties and can help improve the water-resistance properties of sun protection creams and lotions, and the longevity of a fragrance's scent. Chitosan can be found in moisturizers, sunscreens, acne preparations, and hair care products.
Physical and Chemical Properties
Chitosan is the second most abundant (only next to cellulose) biopolymer and is widely distributed. It is mainly distributed in many lower animals particularly the shells of arthropods such as shrimp, crabs and insects. It is also presented in the cell wall of in lower plants such as algae and fungus.
Chitosan can be obtained through the deacetylation of chitin. Under the conditions of 40% NaOH and 100 ℃, chitin is subject to deacetylation reaction and give chitosan. It appears as a white or off-white translucent sheet-like gray solid. It is insoluble in water and alkali, but can be dissolved in most kinds of dilute acid including formic acid, acetic acid and hydrochloric acid. The molecular structure of chitosan is similar to that of the cellulose with the only difference being that the C2-position connects the amino group (-NH2). So it has affinity to the paper fibers, evolving strong ionic bonding and hydrogen bonding. Moreover, the chitosan has film-forming property that can help to improve the surface strength of the paper, thus becoming one of enhancers applied to specialty paper.
Chitosan appears as powder state and is tasteless, odorless with its aqueous solution having some spicy sense. Adding chitosan to the food for making soup and accompanied with a certain degree of cooking, frying, baking and other heat treatment will have its structure be not changed. Under the protection of nitrogen gas, even upon being heated to 250 ℃, the decomposition phenomenon does not occur.
At room temperature, placing chitosan powder in natural place free of sunshine for preservation of 181d causes no significant changes in aspects including appearance, solubility, and the degree of deacylation. The biscuits supplemented with chitosan, when packaged in a state with the temperature of 40 ℃, the relative humidity of 75% environment for preservation of 80d, have their content of dietary fiber and chitosan remain not changed.
The chemical structure of chitin, chitosan and cellulose
Physiological role and efficacy
Chitosan is a dietary fiber with various efficacies such as lowering serum cholesterol, regulation of intestinal flora and reducing blood pressure and other effects. After the human intake of chitosan, fecal analysis has showed that it is hardly digested and absorbed, and therefore belonging to a dietary fiber.
Studies have shown that chitosan has some characteristics of dietary fiber, such as water retention, swelling property, adhesion property and difficult for digestion and absorbing, etc. It can promote gastrointestinal peristalsis, adhesion of toxic substances, increase stool volume, lower abdominal and intestinal pressure, improve constipation and prevent colorectal cancer.
Chitosan has similar physical and chemical property as gastric mucin with effects of inhibiting gastric acid, anti-ulcer and anti-inflammatory effect. It is an anti-gastric acid polysaccharide with swelling into sticky syrup with adhesion property upon coming across water. It can form protective film in the stomach to reduce the stimulation of gastric acid on the ulcer surface.
Food safety: when the dose of chitosan feeding animal reaches 20% of the feed, cases of animal deaths have been reported. It is believed that it is due to the gel formation in animal offal caused by high concentrations of the chitosan that inhibit the nutrient absorption by animal. At present, we need to systematically study the physiological roles of the high viscosity chitosan macromolecules and small molecules of low viscosity as well as conduct long-term chronic toxicology test on the safety and metabolism of the chitosan of clear source.
The main resource chitin, chitosan
Antibacterial activity
Chitosan has broad antibacterial activity, but with different concentrations of chitosan having different antibacterial capability. For example, when the chitosan concentration is 0.1%, it can completely inhibit the reproduction of all kinds of fungi Fusarium genus within 8d but this concentration has no effect on Rhizopus, Penicillium, Aspergillus and other fungus. At a concentration of 0.4%, it also has strong inhibitory effect against Escherichia coli, Proteus vulgaris, Bacillus subtilis, and Staphylococcus aureus. In addition, chitosan of different degrees of deacylation have their antibacterial properties being also different with mold of high level of deacylation having strong anti-mold effect. One reason is that the chitosan interacts with the surface portion of mold cells, increasing the cell permeability. Preservatives with chitosan being combined with sodium acetate, adipic acid have more significant antibacterial effect without affecting the flavor of food.Antibacterial effect of chitosan mainly includes the following two mechanisms: one is that chitosan adhere to the cell surface and form a layer of polymer film, preventing the transport of the nutrients into the cells, thus playing the role of antimicrobial sterilization; the other mechanism is that: chitosan enters into the cell body through penetration into the cell body, adhering the anion-containing cytoplasm inside cells and cause flocculation, disrupting the normal physiological activities of cells, thus killing the bacteria. Because the cell wall structure of gram-positive bacteria and gram-negative bacteria are different with the two actions having different effects, so chitosan of different molecular weight has different antibacterial mechanism.The above information is edited by the lookchem of Dai Xiongfeng.
preparation
Chitosan is prepared by a degree of acetylation. Acetyl groups are removed during the deacetylation process and Mw changes due to the depolymerization reaction. There are two processes, that is, the enzymatic process and chemical process, and chitosan is produced by chemical process. It is preferable for large-scale production.Glycosidic bonds are attracted toward acids and alkalis. Chitin is processed homogeneously or heterogeneously. In the homogeneous method, chitin is diffused in concentrated alkali at 25℃ for 3h and allowed to disperse in compressed ice at around 0℃. In the heterogeneous process the chitin is treated with hot high-concentration alkali and then washed with distilled water until the pH is neutral. It is difficult to produce higher deacetylated chitosan. The addition of thiophenol as a catalyst during the process would minimize the degradation by trapping oxygen and enhance the effective deacetylation. The effective deacetylation process of chitin achieves the preparation of chitosan if the alkali concentration is four times greater than the total amino group in the polysaccharide at a temperature around 100℃ for the duration of 1 h. It is recommended to use low concentration alkali and a short contact time between alkali and polymer.Chemical deacetylation has many disadvantages like high energy consumption and environmental pollution problems. An alternative method of enzyme deacetylation has been developed to overcome these drawbacks. Chitin deacetylation enzyme acts as a catalysis to hydrolyze N-acetamide bonds. This enzyme is extracted from the fungi Mucor rouxii, Absidia coerulea, Aspergillus hidulans, and two strains of Celletotrichum lindemuthianum. This enzyme is thermally stable and has a binding affinity toward β-(1, 4)-linked N-acetyl-D-glucosomine polymers. Most of the time the enzyme process is carried out in both batch and continuous culture. In the batch process the Mw of chitosan is lower with respect to time. Moreover, chitosan of higher Mw is obtained in a specific culture even though the yield is comparatively low.
Production Methods
Chitosan is manufactured commercially by chemically treating the
shells of crustaceans such as shrimps and crabs. The basic
manufacturing process involves the removal of proteins by
treatment with alkali and of minerals such as calcium carbonate
and calcium phosphate by treatment with acid. Before these
treatments, the shells are ground to make them more accessible. The
shells are initially deproteinized by treatment with an aqueous
sodium hydroxide 3–5% solution. The resulting product is
neutralized and calcium is removed by treatment with an aqueous
hydrochloric acid 3–5% solution at room temperature to precipitate
chitin. The chitin is dried so that it can be stored as a stable
intermediate for deacetylation to chitosan at a later stage. NDeacetylation
of chitin is achieved by treatment with an aqueous
sodium hydroxide 40–45% solution at elevated temperature
(1108℃), and the precipitate is washed with water. The crude
sample is dissolved in acetic acid 2% and the insoluble material is
removed. The resulting clear supernatant solution is neutralized
with aqueous sodium hydroxide solution to give a purified white
precipitate of chitosan. The product can then be further purified and
ground to a fine uniform powder or granules. The animals from
which chitosan is derived must fulfil the requirements for the health
of animals suitable for human consumption to the satisfaction of the
competent authority. The method of production must consider
inactivation or removal of any contamination by viruses or other
infectious agents.
benefits
Chitosan is a fibrous substance that might reduce how much fat and cholesterol the body absorbs from foods. It also helps blood clot when applied to wounds.
Pharmaceutical Applications
Chitosan is used in cosmetics and is under investigation for use in a
number of pharmaceutical formulations. The suitability and
performance of chitosan as a component of pharmaceutical
formulations for drug delivery applications has been investigated
in numerous studies. These include controlled drug delivery
applications, use as a component of mucoadhesive dosage
forms, rapid release dosage forms, improved peptide
delivery, colonic drug delivery systems, and use for gene
delivery. Chitosan has been processed into several pharmaceutical
forms including gels, films, beads, microspheres, tablets, and coatings for liposomes.
Furthermore, chitosan may be processed into drug delivery systems
using several techniques including spray-drying, coacervation, direct compression, and conventional granulation
processes.
Safety
Chitosan is being investigated widely for use as an excipient in oral
and other pharmaceutical formulations. It is also used in cosmetics.
Chitosan is generally regarded as a nontoxic and nonirritant
material. It is biocompatible with both healthy and infected
skin. Chitosan has been shown to be biodegradable.
LD50 (mouse, oral): >16 g/kg
storage
Chitosan powder is a stable material at room temperature, although
it is hygroscopic after drying. Chitosan should be stored in a tightly
closed container in a cool, dry place. The PhEur 6.5 specifies that
chitosan should be stored at a temperature of 2–88℃.
Incompatibilities
Chitosan is incompatible with strong oxidizing agents.
Regulatory Status
Chitosan is registered as a food supplement in some countries.
Check Digit Verification of cas no
The CAS Registry Mumber 9012-76-4 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 9,0,1 and 2 respectively; the second part has 2 digits, 7 and 6 respectively.
Calculate Digit Verification of CAS Registry Number 9012-76:
(6*9)+(5*0)+(4*1)+(3*2)+(2*7)+(1*6)=84
84 % 10 = 4
So 9012-76-4 is a valid CAS Registry Number.
InChI:InChI=1/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
9012-76-4Relevant articles and documents
Surface functionalization of chitosan isolated from shrimp shells, using salicylaldehyde ionic liquids in exploration for novel economic and ecofriendly antibiofoulants
Elshaarawy, Reda F. M.,Mustafa, Fatma H. A.,Herbst, Annika,Farag, Aida E. M.,Janiak, Christoph
, p. 20901 - 20915 (2016)
Since the use of organotin as antifouling additives was prohibited in 2003, many researchers have endeavored to design and develop novel economic environment-friendly marine antifouling additives. This work reports the successful functionalization of biop
Synthesis and characterization of N-propyl-N-methylene phosphonic chitosan derivative
Zu?iga, Adriana,Debbaudt, Adriana,Albertengo, Liliana,Rodríguez, María Susana
, p. 475 - 480 (2010)
A simple methodology for the preparation of a new chitosan derivative called N-propyl-N-methylene phosphonic chitosan (PNMPC) is proposed. Introduction of a propyl chain onto a modified chitosan (N-methylene phosphonic chitosan) offers the presence of hydrophobic and hydrophilic branches for controlling solubility properties of the new derivative. Its chemical identity was determined by FT-IR, 1H, 13C and 31P NMR spectroscopy. The degree of propyl substitution estimated by elemental analysis was 0.64. Furthermore derivative molecular weight is about 60 × 103, X-ray diffraction and SEM showed certain degree of crystallinity and homogeneous surface with a rather packed structure. This derivative opens new perspectives in food, pharmaceutical and cosmetic fields.
2-Azido-2-deoxycellulose: Synthesis and 1,3-dipolar cycloaddition
Zhang, Fuyi,Bernet, Bruno,Bonnet, Veronique,Dangles, Olivier,Sarabia, Francisco,Vasella, Andrea
, p. 608 - 617 (2008)
Chitosan (1) was prepared by basic hydrolysis of chitin of an average molecular weight of 70000 Da, 1H-NMR spectra indicating almost complete deacetylation. N-Phthaloylation of 1 yielded the known N-phthaloylchitosan (2), which was tritylated to provide 3a and methoxytritylated to 3b. Dephthaloylation of 3a with NH2NH 2·H2O gave the 6-O-tritylated chitosan 4a. Similarly, 3b gave the 6-O-methoxytritylated 4b. CuSO4-Catalyzed diazo transfer to 4a yielded 95% of the azide 5a, and uncatalyzed diazo transfer to 4b gave 82% of azide 5b. Further treatment of 5a with CuSO4 produced 2-azido-2-deoxycellulose (7). Demethoxytritylation of 5b in HCOOH gave 2-azido-2-deoxy-3,6-di-O-formylcellulose (6), which was deformylated to 7. The 1,3-dipolar cycloaddition of 7 to a range of phenyl-, (phenyl)alkyl-, and alkylmonosubstituted alkynes in DMSO in the presence of CuI gave the 1,2,3-triazoles 8-15 in high yields.
Continuous production of oligofructose syrup from Jerusalem artichoke juice by immobilized endo-inulinase
Nguyen, Quang D.,Rezessy-Szabó, Judit M.,Czukor, Bálint,Hoschke, ágoston
, p. 298 - 303 (2011)
A commercially available endo-inulinase from Aspergillus niger was successfully immobilized onto a chitin carrier with 66% yield. The immobilized endo-inulinase showed maximal activity at 65 °C that was 5 °C higher than the optimum temperature of the free
Oral administration with chitosan hydrolytic products modulates mitogen-induced and antigen-specific immune responses in BALB/c mice
Chang, Shun-Hsien,Wu, Guan-James,Wu, Chien-Hui,Huang, Chung-Hsiung,Tsai, Guo-Jane
, p. 158 - 166 (2019)
The aim of this study was to investigate whether oral administration in BALB/c mice with chitosan hydrolytic products including chitosan hydrolysate, LMWC and a chitooligosaccharide mixture (oligomixture), modulates mitogen-induced and antigen-specific immune responses. A water-soluble chitosan hydrolysate was obtained via cellulase degradation of chitosan, and a LMWC and the oligomixture were separated from this hydrolysate. In non-immunized mice, both the chitosan hydrolysate and oligomixture significantly increased the phagocytic activity of peritoneal macrophages. Three chitosan hydrolytic products significantly increased the mitogen-induced proliferation of splenocytes and Peyer's patch (PP) lymphocytes. LMWC and oligomixture up-regulated IFN-γ secretion, and induced predominantly Th1 cytokine secretion in splenocytes. In antigen-specific immunity, similar effects of the chitosan hydrolytic products were observed on augmenting ovalbumin (OVA)-, as well as mitogen-, induced proliferation of splenocytes harvested from OVA-immunized mice. Interestingly, oligomixture was the most potent chitosan hydrolytic product to elicit OVA-specific IgM, IgG, and IgA production, while LMWC was the most potent one to elevate splenic IFN-γ production and IFN-γ/IL-4 (Th1/Th2) ratio. These results provide the distinct immunomodulatory properties of chitosan hydrolytic products in response to mitogens and specific antigen, paving the way for further development and application of dietary chitosan hydrolytic products against immune disorders and infection.
Extraction and physicochemical characterization of chitin and chitosan from Zophobas morio larvae in varying sodium hydroxide concentration
Soon, Chu Yong,Tee, Yee Bond,Tan, Choon Hui,Rosnita, Abdul Talib,Khalina, Abdan
, p. 135 - 142 (2018)
Large amount of sodium hydroxide (NaOH) is consumed to remove the protein content in chitin biomass during deproteinization. However, excessive NaOH concentration used might lead to the reduction of cost effectiveness during chitin extraction. Hence, the
Chitin and chitosan preparation from shrimp shells using optimized enzymatic deproteinization
Younes, Islem,Ghorbel-Bellaaj, Olfa,Nasri, Rim,Chaabouni, Moncef,Rinaudo, Marguerite,Nasri, Moncef
, p. 2032 - 2039 (2012)
Different crude microbial proteases were applied for chitin extraction from shrimp shells. A Box-Behnken design with three variables and three levels was applied in order to approach the prediction of optimal enzyme/substrate ratio, temperature and incubation time on the deproteinization degree with Bacillus mojavensis A21 crude protease. These optimal conditions were: an enzyme/substrate ratio of 7.75 U/mg, a temperature of 60 °C and an incubation time of 6 h allowing to predict 94 ± 4% deproteinization. Experimentally, in these optimized conditions, a deproteinization degree of 88 ± 5% was obtained in good agreement with the prediction and larger than values generally given in literature. The deproteinized shells were then demineralized to obtain chitin which was converted to chitosan by deacetylation and its antibacterial activity against different bacteria was investigated. Results showed that chitosan dissolved at 50 mg/ml markedly inhibited the growth of most Gram-negative and Gram-positive bacteria tested.
Novel hybrid chitosan blended MoO3-TiO2 nanocomposite film: Evaluation of its solar light photocatalytic and antibacterial activities
Magesan,Sanuja,Umapathy
, p. 42506 - 42515 (2015)
In the present study, we report newly synthesized TiO2 and MoO3-TiO2 nanocomposites and chitosan and chitosan-blended MoO3-TiO2 nanocomposite films by sol-gel and solution cast methods, respectively. The synthesized nanocomposite films were characterized by XRD, FT-IR, TG-DTA and FESEM with EDAX. The antibacterial activities of the prepared nanocomposite films were tested against E. coli using the well diffusion method. The photocatalytic activities of the materials were investigated against methyl orange dye as a model organic pollutant under the irradiation of solar light. Furthermore, the mechanical properties (tensile strength and elongation) were determined using a Universal Testing Machine. From the obtained results, it was concluded that the chitosan-blended MoO3-TiO2 nanocomposite film exhibited higher photocatalytic, antibacterial and mechanical properties than the other materials.
Characteristics of deacetylation and depolymerization of β-chitin from jumbo squid (Dosidicus gigas) pens
Jung, Jooyeoun,Zhao, Yanyun
, p. 1876 - 1884 (2011)
This study evaluated the deacetylation characteristics of β-chitin from jumbo squid (Dosidicus gigas) pens by using strongly alkaline solutions of NaOH or KOH. Taguchi design was employed to investigate the effect of reagent concentration, temperature, time, and treatment step on molecular mass (MM) and degree of deacetylation (DDA) of the chitosan obtained. The optimal treatment conditions for achieving high MM and DDA of chitosan were identified as: 40% NaOH at 90 °C for 6 h with three separate steps (2 h + 2 h + 2 h) or 50% NaOH at 90 °C for 6 h with one step, or 50% KOH at 90 °C for 4 h with three steps (1 h + 1 h + 2 h) or 6 h with one step. The most important factor affecting DDA and MM was temperature and time, respectively. The chitosan obtained was then further depolymerized by cellulase or lysozyme with cellulase giving a higher degradation ratio, lower relative viscosity, and a larger amount of reducingend formations than that of lysozyme due to its higher susceptibility. This study demonstrated that jumbo squid pens are a good source of materials to produce β-chitosan with high DDA and a wide range of MM for various potential applications.
Kinetics of base deacetylation of chitin and chitosan as influenced by their crystallinity
Chebotok,Novikov,Konovalova
, p. 1753 - 1758 (2007)
Structural properties of the initial and reprecipitated chitin and chitosan samples in dry and wet states were studied.
