Chitosan oligosaccharide(COS) - Molecular weight≤2000 , CAS No.148411-57-8

CAS: 148411-57-8 Cat. No.: C302935 EC Number: 604-631-8

GRADE & PURITY Molecular weight≤2000

Synonyms

A-D-glucopyranose | (2R,3S,4R,5R,6S)-5-amino-6-[(2R,3S,4R,5R,6R)-5-amino-4,6-dihydroxy-2-(hydroxymethyl)oxan-3-yl]oxy-2-(hydroxymethyl)oxane-3,4-diol | beta-D-glucosaminyl-(1->4)-beta-D-glucosamine | Q27122179 | (2R,3R,4R,5S,6R)-3-amino-5-{[(2S,3R,4R,5S,6

Storage

Room temperature

Shipped In

Normal

Specifications

Synonyms

A-D-glucopyranose | (2R, 3S, 4R, 5R, 6S)-5-amino-6-[(2R, 3S, 4R, 5R, 6R)-5-amino-4, 6-dihydroxy-2-(hydroxymethyl)oxan-3-yl]oxy-2-(hydroxymethyl)oxane-3, 4-diol | beta-D-glucosaminyl-(1->4)-beta-D-glucosamine | Q27122179 | (2R, 3R, 4R, 5S, 6R)-3-amino-5-{[(2S, 3R, 4R, 5S, 6

Specifications & Purity

Molecular weight≤2000

Storage

Room temperature

Shipped In

Normal

Names and Identifiers

• Pubchem Sid: 488199203
• Pubchem Sid Url: https://pubchem.ncbi.nlm.nih.gov/substance/488199203
• Canonical Smiles: C(C1C(C(C(C(O1)OC2C(OC(C(C2O)N)O)CO)N)O)O)O
• IUPAC Name: (2R,3S,4R,5R,6S)-5-amino-6-[(2R,3S,4R,5R,6R)-5-amino-4,6-dihydroxy-2-(hydroxymethyl)oxan-3-yl]oxy-2-(hydroxymethyl)oxane-3,4-diol
• InChIKey: QLTSDROPCWIKKY-PMCTYKHCSA-N
• INCHI: 1S/C12H24N2O9/c13-5-9(19)10(4(2-16)21-11(5)20)23-12-6(14)8(18)7(17)3(1-15)22-12/h3-12,15-20H,1-2,13-14H2/t3-,4-,5-,6-,7-,8-,9-,10-,11-,12+/m1/s1
• Isomeric SMILES: C([C@@H]1[C@H]([C@@H]([C@H]([C@@H](O1)O[C@@H]2[C@H](O[C@H]([C@@H]([C@H]2O)N)O)CO)N)O)O)O
• Reaxy-Rn: 25642292
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=25642292&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Organic oxygen compounds
    • Class Organooxygen compounds
      • Subclass Carbohydrates and carbohydrate conjugates
        • Level5 Aminosaccharides
          • Level6 Aminoglycosides

• Kingdom: Organic compounds
• Superclass: Organic oxygen compounds
• Class: Organooxygen compounds
• Subclass: Carbohydrates and carbohydrate conjugates
• Intermediate Tree Nodes: Aminosaccharides
• Direct Parent: Aminoglycosides
• Alternative Parents: O-glycosyl compounds Disaccharides Oxanes Secondary alcohols Hemiacetals 1,2-aminoalcohols Oxacyclic compounds Acetals Primary alcohols Organopnictogen compounds Monoalkylamines Hydrocarbon derivatives
• Molecular Framework: Aliphatic heteromonocyclic compounds
• Substituents: Aminoglycoside core - Disaccharide - Glycosyl compound - O-glycosyl compound - Oxane - 1,2-aminoalcohol - Hemiacetal - Secondary alcohol - Organoheterocyclic compound - Acetal - Oxacycle - Organonitrogen compound - Alcohol - Primary aliphatic amine - Hydrocarbon derivative - Organopnictogen compound - Organic nitrogen compound - Amine - Primary alcohol - Primary amine - Aliphatic heteromonocyclic compound
• Description: This compound belongs to the class of organic compounds known as aminoglycosides. These are molecules or a portion of a molecule composed of amino-modified sugars.
• External Descriptors: beta-D-glucosaminyl-(1->4)-D-glucosamine

Data sources

1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.

DOI: 10.1186/s13321-016-0174-y

Chemical and Physical Properties

• Molecular Weight: 340.330 g/mol
• XLogP3: -5.200
• Hydrogen Bond Donor Count: 8
• Hydrogen Bond Acceptor Count: 11
• Rotatable Bond Count: 4
• Exact Mass: 340.148 Da
• Monoisotopic Mass: 340.148 Da
• Topological Polar Surface Area: 201.000 Ų
• Heavy Atom Count: 23
• Formal Charge: 0
• Complexity: 390.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 10
• Undefined Atom Stereocenter Count: 0
• Defined Bond Stereocenter Count: 0
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 0
• Covalently-Bonded Unit Count: 1

References

1. Jinhui Tang, Guangye Tu, Zongshuo Tao, Yu Yan.  (2023)  New Insights into the Dissolution Kinetics of Alite Powder and the Effects of Organic Toughening Materials.  Materials,  16  (22): (7242).  [PMID:38005173] [10.3390/ma16227242]

2. Hongmei Yu, Yuanrong Zheng, Changyu Zhou, Lianliang Liu, Libin Wang, Jinxuan Cao, Yangyin Sun, Jun He, Daodong Pan, Zhendong Cai, Qiang Xia.  (2023)  Tunability of Pickering particle features of whey protein isolate via remodeling partial unfolding during ultrasonication-assisted complexation with chitosan/chitooligosaccharide.  CARBOHYDRATE POLYMERS,      [PMID:38008470] [10.1016/j.carbpol.2023.121583]

3. Pierre Dramou, Yiyang Sun, Xu Ni, Fangqi Wang, Hua He.  (2023)  In-depth descriptive investigation of composite sorbent based self-assembled magnetic halloysite nanotube-graphene oxide: Actual use case study for rutin.  APPLIED CLAY SCIENCE,      [PMID:] [10.1016/j.clay.2023.107193]

4. Rui Wang.  (2023)  Bi-layer graphite felt as the positive electrode for zinc-bromine flow batteries: Achieving efficient redox reaction and stable mass transport.  Journal of Energy Storage,      [PMID:] [10.1016/j.est.2023.109487]

5. Kaibo Xu, Liqin Cao, Zhouyu Wang, Liu-ping Chen.  (2023)  Heparin-Mimetic Chitooligosaccharides-Based Monoliths Obtained from C/W Emulsions: Hemocompatibility and Toxin Removal Ability.  ACS Biomaterials Science & Engineering,      [PMID:37703897] [10.1021/acsbiomaterials.3c00833]

6. Li-wei Liu, Zheng-hao Ding, Ganggang Ren, Guang-di Wang, Xin Pan, Guo-hai Wei, Xiang Zhou, Zhi-bing Wu, Zhi-chao Jin, Yonggui Robin Chi, Song Yang.  (2023)  Inorganic Nanoparticles–Driven Self–Assembly of natural small molecules in water for constructing multifunctional nanocapsules against plant diseases.  CHEMICAL ENGINEERING JOURNAL,      [PMID:] [10.1016/j.cej.2023.146041]

7. Kaibo Xu, Liqin Cao.  (2023)  Sulfonated Hydrogel Formed via CO2-in-Water Emulsion: Potential in Antibiotic Removal.  Gels,  9  (9): (703).  [PMID:37754384] [10.3390/gels9090703]

8. Mengqi Jia, Ruilin Lu, Caikun Liu, Xiaodong Zhou, Pengfei Li, Shiyong Zhang.  (2023)  In Situ Implantation of Chitosan Oligosaccharide-Doped Lipoic Acid Hydrogel Breaks the “Vicious Cycle” of Inflammation and Residual Tumor Cell for Postoperative Skin Cancer Therapy.  ACS Applied Materials & Interfaces,      [PMID:37358539] [10.1021/acsami.3c03355]

9. Zhe Luo, Yang Zhang.  (2022)  Construction of a Chitosan/ZnO-Based Light-Resistant Coating System to Protect Dyed Wood from Ultraviolet Irradiation via Layer-by-Layer Self-Assembly.  INTERNATIONAL JOURNAL OF MOLECULAR SCIENCES,  23  (24): (15735).  [PMID:36555382] [10.3390/ijms232415735]

10. Xinlong Wang, Huahui Zeng, Xin Zhu, Duanjie Xu, Qikang Tian, Can Wang, Lingzhou Zhao, Junwei Zhao, Mingsan Miao, Xiangxiang Wu.  (2022)  TP-CSO: A Triptolide Prodrug for Pancreatic Cancer Treatment.  MOLECULES,  27  (12): (3686).  [PMID:35744811] [10.3390/molecules27123686]

11. Chun-Xia Zhang, Yu Wang, Xinhe Duan, Kai Chen, Hong-Wei Li, Yuqing Wu.  (2022)  Development of cytidine 5′-monophosphate-protected gold-nanoclusters to be a direct luminescent substrate via aggregation-induced emission enhancement for ratiometric determination of alkaline phosphatase and inhibitor evaluation.  COLLOIDS AND SURFACES A-PHYSICOCHEMICAL AND ENGINEERING ASPECTS,      [PMID:] [10.1016/j.colsurfa.2022.128423]

12. Liu Xiaoli, Xie Wancui, Yang Xihong, Zhan Xiaobei, Xia Wenshui.  (2019)  Antimicrobial Polymer with Enhanced Activity and Reduced Toxicity upon Grafting to Chitosan Oligosaccharide.  ARABIAN JOURNAL FOR SCIENCE AND ENGINEERING,  45  (1): (29-40).  [PMID:] [10.1007/s13369-019-04260-4]

13. Wen Li, Qi-Wen Chen, Jin-Xuan Fan, Zi-Yi Han, Wen-Fang Song, Xuan Zeng, Xian-Zheng Zhang.  (2024)  Bacterial Biohybrids for Invasion of Tumor Cells Promote Antigen Cross-Presentation Through Gap Junction.  ADVANCED MATERIALS,      [PMID:38563503] [10.1002/adma.202402532]

14. Shujie Cheng, Shimin Wu, Jianqiang Lan.  (2024)  Beta-carotene and astaxanthin inhibit the formation of polycyclic aromatic hydrocarbons and oxygenated polycyclic aromatic hydrocarbons in butter during heat treatment.  INTERNATIONAL JOURNAL OF DAIRY TECHNOLOGY,      [PMID:] [10.1111/1471-0307.13158]

15. Zhimin Deng, Hua Liu, Gantao Chen, Hongbing Deng, Xiangyang Dong, Linlin Wang, Fenghua Tao, Fangfang Dai, Yanxiang Cheng.  (2024)  Coaxial nanofibrous aerogel featuring porous network-structured channels for ovarian cancer treatment by sustained release of chitosan oligosaccharide.  INTERNATIONAL JOURNAL OF BIOLOGICAL MACROMOLECULES,      [PMID:39002906] [10.1016/j.ijbiomac.2024.133824]

16. Wenshang Guo, Ye Tao, Ruizhe Yang, Kaihao Mao, Hongwei Zhou, Minghui Xu, Tie Sun, Xiao Li, Changrui Shi, Zhenyou Ge, Rui Xue, Haizhou Zhou, Yukun Ren.  (2024)  Compact highly sensitive photothermal RT-LAMP chip for simultaneous multidisease detection.  Science Advances,  10  (46):   [PMID:39536102] [10.1126/sciadv.adq2899]

17. Nanqi Zhao, Chaofan Guo, Ziyao Liu, Lin Chen, Yayun Hu, Minyi Han, Feng Huang, Zhuangli Kang, Xianchao Feng.  (2024)  Effects of different hydrocolloids on the 3D printing and thermal stability of chicken paste.  INTERNATIONAL JOURNAL OF BIOLOGICAL MACROMOLECULES,      [PMID:39032898] [10.1016/j.ijbiomac.2024.134006]

18. Kangshuai Lou, Yuanrong Zheng, Hongmei Yu, Xiaohan Tan, Libin Wang, Changmin Tong, Siqiang Huang, Xintong Cai, Changyu Zhou, Jinxuan Cao, Daodong Pan, Zhen Wu, Hao Zhang, Qiang Xia.  (2024)  Influence of whey protein isolate-chitosan oligosaccharide micro gel pickering emulsion on reducing fat bioaccessibility and physicochemical features of cheddar cheese.  Food Bioscience,      [PMID:] [10.1016/j.fbio.2024.105771]

19. Xiaokang Na, Bowen Zou, Xiaohan Zheng, Xueer Yu, Ling Zhang, Xianbing Xu, Ming Du, Chao Wu.  (2024)  One-step spraying of protein-anchored chitosan oligosaccharide antimicrobial coating for food preservation.  INTERNATIONAL JOURNAL OF BIOLOGICAL MACROMOLECULES,      [PMID:38908638] [10.1016/j.ijbiomac.2024.133330]

20. Hongmei Yu, Yuanrong Zheng, Kangshuai Lou, Changyu Zhou, Jinxuan Cao, Lihui Du, Yangying Sun, Jun He, Daodong Pan, Zhendong Cai, Qiang Xia.  (2024)  Proposing moderate unfolding of interfacial proteins to enhance the techno-functional features of complex microgel particles formed by whey protein-chitooligosaccharide conjugation.  FOOD HYDROCOLLOIDS,      [PMID:] [10.1016/j.foodhyd.2024.110329]

21. Zhaoxin Xia, Yulong Liao, Ge Gao, Shiyong Zhang.  (2024)  Rifampicin-Loaded Polyelectrolyte Complex Eliminates Intracellular Bacteria through Thiol-Mediated Cellular Uptake and Oxidative Stress Enhancement.  ACS Applied Bio Materials,      [PMID:38507285] [10.1021/acsabm.4c00143]

22. Jia Wan, Meifang Yin, Feng Wang, Guangtao Huang, Ilaria Dal Pra, Yongzhi Liang, Jun Wu.  (2025)  Natural gelatin / chitosan oligosaccharides / emodin eutectogels with multiple antibacterial effects for accelerated infected wound healing.  INTERNATIONAL JOURNAL OF BIOLOGICAL MACROMOLECULES,      [PMID:40628324] [10.1016/j.ijbiomac.2025.145771]

23. Yuting Sun, Junnan He, Yongyan Sun, Lidong Wang, Haidu Li, Yaqi Miao, Ping Shi, Jin Zhang, Kaixuan Luo, Yan Zhao.  (2025)  Smart-responsive dual cross-linked chitooligosaccharide nanoparticles with high stability and ROS-triggered self-accelerating drug release for enhanced breast cancer therapy.  CARBOHYDRATE RESEARCH,      [PMID:40967161] [10.1016/j.carres.2025.109671]

24. Zilin Wang, Ye Zhao, Min Yang, Yuanli Wang, Yue Wang, Chongying Shi, Tianyi Dai, Yifan Wang, Liang Tao, Yang Tian.  (2024)  Glycated Walnut Meal Peptide–Calcium Chelates: Preparation, Characterization, and Stability.  Foods,  13  (7): (1109).  [PMID:38611413] [10.3390/foods13071109]

25. Tian Xiuzhi, Xiao Jiale, Bai Haozhe, Aissa Fatima Ait, Li Wei, Zhao Dou, Jiang Xue.  (2025)  Nanocomposites of chito-oligosaccharide grafted boron nitride nanosheets/carboxymethyl cellulose for thermal management of flexible electronic devices.  CELLULOSE,      [PMID:] [10.1007/s10570-025-06790-7]

26. Yunfeng Tang, Xiangtian Deng, Min Yi, Dong Wang, Cheng Zheng, Shichang Zhao, Renliang Zhao.  (2025)  An Injectable Hydrogel Co-Delivering Propranolol and Imiquimod to Synergistically Enhance Immunogenic Cell Death after Melanoma Resection.  Advanced Healthcare Materials,      [PMID:41126715] [10.1002/adhm.202503019]

27. Wei Wan, Rui Zhang, Lingyi Gao, Aijun Jian, Xianbing Xu, Xiaokang Na, Ming Du, Jianyu Zhu, Beiwei Zhu, Chao Wu.  (2025)  Mechanisms of heat-activated soy protein isolate-chitosan oligosaccharide complexation: Synergistic interactions for enhanced gelation.  CARBOHYDRATE POLYMERS,      [PMID:41371847] [10.1016/j.carbpol.2025.124703]