Determine the necessary mass, volume, or concentration for preparing a solution.
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≥98% for sensitive chromatographic and analytical workflows requiring minimal baseline interference.
Store at 2-8°C Ships Wet ice Check lot-specific COA for exact specifications.
SDS, COA, datasheet, and spec sheet available for download. Lot-specific COA accessible via lot number lookup.
Cited in 14 peer-reviewed publications across chromatography, organic synthesis, and cross-coupling reactions.
| Canonical Smiles | CC(=O)NC1C(C(C(OC1O)CO)O)O |
|---|---|
| IUPAC Name | N-[(3R,4R,5R,6R)-2,4,5-trihydroxy-6-(hydroxymethyl)oxan-3-yl]acetamide |
| InChIKey | OVRNDRQMDRJTHS-KEWYIRBNSA-N |
| INCHI | 1S/C8H15NO6/c1-3(11)9-5-7(13)6(12)4(2-10)15-8(5)14/h4-8,10,12-14H,2H2,1H3,(H,9,11)/t4-,5-,6+,7-,8?/m1/s1 |
| Isomeric SMILES | CC(=O)N[C@@H]1[C@H]([C@H]([C@H](OC1O)CO)O)O |
| Molecular Weight | 221.21 |
| Beilstein | 4(4)2039 |
| Reaxy-Rn | 1913591 |
| Reaxys-RN_link_address | https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=1913591&ln= |
Comprehensive hazard, handling, storage, and regulatory compliance document.
Download SDS →Lot-specific quality data. Enter your lot number to retrieve the exact COA.
Look up COA →Full quality attributes and acceptance criteria for this grade.
View spec sheet →Taxonomy Tree
| Kingdom | Organic compounds |
|---|---|
| Superclass | Organic oxygen compounds |
| Class | Organooxygen compounds |
| Subclass | Carbohydrates and carbohydrate conjugates |
| Intermediate Tree Nodes | Aminosaccharides - Amino sugars |
| Direct Parent | Acylaminosugars |
| Alternative Parents | N-acyl-alpha-hexosamines Hexoses Oxanes Acetamides Secondary carboxylic acid amides Secondary alcohols Hemiacetals Polyols Oxacyclic compounds Primary alcohols Organopnictogen compounds Organonitrogen compounds Organic oxides Hydrocarbon derivatives Carbonyl compounds |
| Molecular Framework | Aliphatic heteromonocyclic compounds |
| Substituents | Acylaminosugar - N-acyl-alpha-hexosamine - Hexose monosaccharide - Monosaccharide - Oxane - Acetamide - Carboxamide group - Hemiacetal - Secondary carboxylic acid amide - Secondary alcohol - Carboxylic acid derivative - Oxacycle - Organoheterocyclic compound - Polyol - Alcohol - Hydrocarbon derivative - Organic oxide - Organic nitrogen compound - Organopnictogen compound - Organonitrogen compound - Primary alcohol - Carbonyl group - Aliphatic heteromonocyclic compound |
| Description | This compound belongs to the class of organic compounds known as acylaminosugars. These are organic compounds containing a sugar linked to a chain through N-acyl group. |
| External Descriptors | Amino sugars |
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| Specific Rotation[α] | 85 ° (C=1, H2O) |
|---|---|
| Melt Point(°C) | 158-162°C |
| Molecular Weight | 221.210 g/mol |
| XLogP3 | -1.700 |
| Hydrogen Bond Donor Count | 5 |
| Hydrogen Bond Acceptor Count | 6 |
| Rotatable Bond Count | 2 |
| Exact Mass | 221.09 Da |
| Monoisotopic Mass | 221.09 Da |
| Topological Polar Surface Area | 119.000 Ų |
| Heavy Atom Count | 15 |
| Formal Charge | 0 |
| Complexity | 235.000 |
| Isotope Atom Count | 0 |
| Defined Atom Stereocenter Count | 4 |
| Undefined Atom Stereocenter Count | 1 |
| Defined Bond Stereocenter Count | 0 |
| Undefined Bond Stereocenter Count | 0 |
| The total count of all stereochemical bonds | 0 |
| Covalently-Bonded Unit Count | 1 |
| 1. Yanan Wang, Huichao Wei, Keyang Li, Liru Liu, Yingfei Zhu, Xinyuan Wang, Jiahui Yan, Liangmin Yu, Xuefeng Yan, Zhiyu He. (2023) Ros-responsive dextran-phenylboronic acid-silibinin nanoparticles for targeting delivery of BAPTA-AM to effectively eliminate calcium overload-mediated inflammatory cascades and mitochondrial apoptosis: Alleviating acute liver injury. CHEMICAL ENGINEERING JOURNAL, [PMID:] [10.1016/j.cej.2023.148283] |
| 2. Shiwei Liu, Shuang Han, Yuzhuo Song, Ruonan Sun, Le Zhao, Chen Yan. (2023) Disulfide-Bridged Dendritic Organosilicas-Based Biodegradable Molecularly Imprinted Polymers for Multiple Targeting and pH/Redox-Responsive Drug Release toward Chemical/Photodynamic Synergistic Tumor Therapy. Advanced Healthcare Materials, 12 (20): (2300184). [PMID:36943098] [10.1002/adhm.202300184] |
| 3. Liu Jing, Xu Mingze, Zhang Tingsong, Chu Xueying, Shi Kaixi, Li Jinhua. (2022) Al/TiO2 composite as a photocatalyst for the degradation of organic pollutants. ENVIRONMENTAL SCIENCE AND POLLUTION RESEARCH, 30 (4): (9738-9748). [PMID:36063271] [10.1007/s11356-022-22861-9] |
| 4. Chunyan Yang, Zixuan Guan, Xincheng Pang, Zengqi Tan, Xiaomin Yang, Xiang Li, Feng Guan. (2022) Desialylated Mesenchymal Stem Cells-Derived Extracellular Vesicles Loaded with Doxorubicin for Targeted Inhibition of Hepatocellular Carcinoma. Cells, 11 (17): (2642). [PMID:36078050] [10.3390/cells11172642] |
| 5. Han Xu, Ninghua Fu, Jie Zheng, Muhammad Sohail, Xing Zhang. (2022) Mn-doped bimetallic synergistic catalysis boosts for enzymatic phosphorylation of N-Acetylglucosamine/ N-Acetylgalactosamine and their derivatives. BIOORGANIC CHEMISTRY, [PMID:35907378] [10.1016/j.bioorg.2022.106041] |
| 6. Yan Ma, Na Gao, Zhichuang Zuo, Shanni Li, Wenqi Zheng, Xiang Shi, Qipei Liu, Ting Ma, Ronghua Yin, Xian Li, Jinhua Zhao. (2021) Five distinct fucan sulfates from sea cucumber Pattalus mollis: Purification, structural characterization and anticoagulant activities. INTERNATIONAL JOURNAL OF BIOLOGICAL MACROMOLECULES, [PMID:34246676] [10.1016/j.ijbiomac.2021.07.049] |
| 7. Xiang Shi, Ruowei Guan, Lutan Zhou, Zhichuang Zuo, Xuelin Tao, Pin Wang, Yanrong Zhou, Ronghua Yin, Longyan Zhao, Na Gao, Jinhua Zhao. (2021) Structural Characterization and Heparanase Inhibitory Activity of Fucosylated Glycosaminoglycan from Holothuria floridana. Marine Drugs, 19 (3): (162). [PMID:33803892] [10.3390/md19030162] |
| 8. Lizhen Chen, Jie Wu, Feng Yan, Huangxian Ju. (2020) A facile strategy for quantitative sensing of glycans on cell surface using organic electrochemical transistors. BIOSENSORS & BIOELECTRONICS, [PMID:33298337] [10.1016/j.bios.2020.112878] |
| 9. Zhenjun Zhu, Xiuping Dong, Chunhong Yan, Chunqing Ai, Dayong Zhou, Jingfeng Yang, Hui Zhang, Xiaoling Liu, Shuang Song, Hang Xiao, Beiwei Zhu. (2019) Structural Features and Digestive Behavior of Fucosylated Chondroitin Sulfate from Sea Cucumbers Stichopus japonicus. JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY, [PMID:31464434] [10.1021/acs.jafc.9b04996] |
| 10. Lijing Nan, Jiao Li, Wanjun Jin, Ming Wei, Mengjun Tang, Chengjian Wang, Guiping Gong, Linjuan Huang, Ying Zhang, Zhongfu Wang. (2019) Comprehensive quali-quantitative profiling of neutral and sialylated O-glycome by mass spectrometry based on oligosaccharide metabolic engineering and isotopic labeling. RSC Advances, 9 (28): (15694-15702). [PMID:35521403] [10.1039/C9RA01114E] |
| 11. Ruowei Guan, Yuan Peng, Lutan Zhou, Wenqi Zheng, Xixi Liu, Pin Wang, Qingxia Yuan, Na Gao, Longyan Zhao, Jinhua Zhao. (2019) Precise Structure and Anticoagulant Activity of Fucosylated Glycosaminoglycan from Apostichopus japonicus: Analysis of Its Depolymerized Fragments. Marine Drugs, 17 (4): (195). [PMID:30934713] [10.3390/md17040195] |
| 12. Longyan Zhao, Yujing Qin, Ruowei Guan, Wenqi Zheng, Jikai Liu, Jinhua Zhao. (2018) Digestibility of fucosylated glycosaminoglycan from sea cucumber and its effects on digestive enzymes under simulated salivary and gastrointestinal conditions. CARBOHYDRATE POLYMERS, [PMID:29455981] [10.1016/j.carbpol.2018.01.029] |
| 13. Dong Yang, Xinchuan Zheng, Ning Wang, Shijun Fan, Yongjun Yang, Yongling Lu, Qian Chen, Xin Liu, Jiang Zheng. (2016) Kukoamine B promotes TLR4-independent lipopolysaccharide uptake in murine hepatocytes. Oncotarget, [PMID:27542278] [10.18632/oncotarget.11292] |
| 14. Yao Wang, Lijing Ye, Ruikun Yan, Haibo Zhou, Guojun Zhao. (2025) Ilex asprella polysaccharides alleviate liver injury via antioxidative, anti-inflammatory, and gut microbiota modulating effect. INTERNATIONAL JOURNAL OF BIOLOGICAL MACROMOLECULES, [PMID:40081689] [10.1016/j.ijbiomac.2025.142024] |