N-Acetylglucosamine

Base Information

• Chemical Name: N-Acetylglucosamine
• CAS No.: 7512-17-6
• Deprecated CAS: 134-61-2,173382-53-1,7132-76-5,98632-70-3,948887-87-4,7132-76-5,948887-87-4,98632-70-3
• Molecular Formula: C8H15NO6
• Molecular Weight: 221.21
• Hs Code.: 2932.99
• UNII: V956696549
• DSSTox Substance ID: DTXSID3045855
• Nikkaji Number: J81.413J
• Wikidata: Q32030210
• NCI Thesaurus Code: C83975
• Metabolomics Workbench ID: 144888
• ChEMBL ID: CHEMBL4303483
• Mol file: 7512-17-6.mol

Synonyms:2 Acetamido 2 Deoxy D Glucose;2 Acetamido 2 Deoxyglucose;2-Acetamido-2-Deoxy-D-Glucose;2-Acetamido-2-Deoxyglucose;Acetylglucosamine;N Acetyl D Glucosamine;N-Acetyl-D-Glucosamine

Chemical Property of N-Acetylglucosamine

Chemical Property:

• Appearance/Colour: white crystalline powder
• Vapor Pressure: 7.12E-19mmHg at 25°C
• Melting Point: 211 °C (dec.)(lit.)
• Refractive Index: 40.5 ° (C=1, H2O)
• Boiling Point: 636.4 °C at 760 mmHg
• PKA: 13.04±0.20(Predicted)
• Flash Point: 338.7 °C
• PSA: 127.09000
• Density: 1.423 g/cm³
• LogP: -2.84410
• Storage Temp.: 2-8°C
• Sensitive.: Hygroscopic
• Solubility.: H2O: 50 mg/mL colorless to faint yellow solution, clear to
• Water Solubility.: Soluble in concentrated hydrochloric acid, sulfuric acid, phosphoric acid and formic acid. Insoluble in water, dilute acids, dil
• XLogP3: -3.4
• Hydrogen Bond Donor Count: 5
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 6
• Exact Mass: 221.08993720
• Heavy Atom Count: 15
• Complexity: 221

Purity/Quality:

98% ^*data from raw suppliers

N-Acetyl-D-glucosamine 97% ^*data from reagent suppliers

Safty Information:

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

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=O)NC(C=O)C(C(C(CO)O)O)O
• Isomeric SMILES: CC(=O)N[C@@H](C=O)[C@H]([C@@H]([C@@H](CO)O)O)O
• Sources: N-Acetylglucosamine (GlcNAc) is derived from chitin, the most abundant nitrogen-containing biopolymer on Earth. Chitin can be found in the exoskeletons of crustaceans and insects, as well as in fungal cell walls.^[1]
• Chemical Composition and Structure: GlcNAc is a deacetylated derivative of glucosamine and is a major structural component of cell walls in bacteria and the extracellular matrix in animal cells. Its chemical structure consists of a glucose molecule with an N-acetyl group attached to the amine group.^[2]
• Uses: N-Acetylglucosamine (GlcNAc) is studied for its potential therapeutic effects in arthritis, cartilage protection, and as a signaling molecule in microbial pathogenesis.; GlcNAc is used as a precursor for the synthesis of various nitrogen-containing compounds and as a raw material for the production of pharmaceuticals and biopharmaceuticals.^[3]
• Production Methods: Microbial fermentation, particularly using engineered strains of Corynebacterium glutamicum, has emerged as a promising method for GlcNAc production.^[3]
• References: [1] N-Acetylglucosamine as a platform chemical produced from renewable resources: opportunity, challenge, and future prospects; DOI 10.1039/D1GC03725K; [2] Candida albicans exploits N-acetylglucosamine as a gut signal to establish the balance between commensalism and pathogenesis; DOI 10.1038/s41467-023-39284-w; [3] Engineering Corynebacterium glutamicum for the efficient production of N-acetylglucosamine; DOI 10.1016/j.biortech.2023.129865

Technology Process of N-Acetylglucosamine

There total 157 articles about N-Acetylglucosamine 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: 46.3%

chitosan (deacetylation degree, 93%) + sodium acetate (127-09-3) → chitosan oligosaccharides + 2-amino-2-deoxyglucose (3416-24-8) + 2-acetamido-2-deoxy-D-glucose (7512-17-6,282727-46-2,478518-83-1,127959-06-2,78393-48-3) + Low molecular weight chitosan

Guidance literature:

With chitosanase; In water; at 40 ℃; for 20h; pH=4.5; Further Variations:; Reagents; pH-values; Product distribution; Enzymatic reaction;

DOI:10.1016/j.carres.2007.08.023

Reference yield:

3-O-{α-D-xylopyranosyl-(1→3)-α-L-arabinopyranosyl-(1→6)-[β-D-glucopyranosyl-(1→3)]-2-(acetamido)-2-deoxy-β-D-glucopyranosyl}echinocystic acid 28-O-{β-D-apiofuranosyl-(1→3)-β-D-xylopyranosyl-(1→2)-[2-O-cinnamoyl-α-L-arabinopyranosyl-(1→4)]-6-O-acetyl-β-D-glucopyranosyl} ester → D-xylose (58-86-6) + D-apiose (639-97-4,6477-44-7,42927-70-8) + L-arabinose (5328-37-0) + D-glucose (50-99-7) + 2-acetamido-2-deoxy-D-glucose (7512-17-6,282727-46-2,478518-83-1,127959-06-2,78393-48-3) + echinocystic acid (510-30-5)

Guidance literature:

With hydrogenchloride; water; at 85 ℃; for 2h;

DOI:10.1016/j.phytol.2017.09.008

Reference yield:

3-O-{α-D-xylopyranosyl-(1→3)-α-L-arabinopyranosyl-(1→6)-[β-D-glucopyranosyl-(1→3)]-2-(acetamido)-2-deoxy-β-D-glucopyranosyl}echinocystic acid 28-O-(β-D-apiofuranosyl-(1→3)-β-D-xylopyranosyl-(1→2)-{2-O-[(6S,2E)-2,6-dimethyl-6-hydroxy-2,7-octadienoyl]-α-L-arabinopyranosyl-(1→4)}-6-O-acetyl-β-D-glucopyranosyl) ester → D-xylose (58-86-6) + D-apiose (639-97-4,6477-44-7,42927-70-8) + L-arabinose (5328-37-0) + D-glucose (50-99-7) + 2-acetamido-2-deoxy-D-glucose (7512-17-6,282727-46-2,478518-83-1,127959-06-2,78393-48-3) + echinocystic acid (510-30-5)

Guidance literature:

With hydrogenchloride; water; at 85 ℃; for 2h;

DOI:10.1016/j.phytol.2017.09.008

upstream raw materials:

acetic anhydride

pyridine

N-acetyl-D-mannosamine

nickel diacetate

Downstream raw materials:

methyl N-acetyl-β-D-glucosaminide

N-acetyl-D-mannosamine

N-(furan-3-yl)acetamide

2-acetylamino-D-erythro-2,3-dideoxy-hex-2c-enose

Refernces

• 1、 Cao, L.,Cao, Zh.,Chen, Ch.,Jiang, K.,Liu, Sh.,Liu, W.,Lu, X.,Shao, Zh.,Shi, D.,Su, Z.,Wang, L.,Wang, Y.,Wu, Y.. "Synthesis and Anti-Cholinesterase Activity of Novel Glycosyl Benzofuranylthiazole Derivatives". . p. 1513 - 1518. Retrieved 2021/10/26.
• 2、 Cao, Zhi-Ling,Liu, Shu-Hao,Liu, Wei-Wei,Ren, Shu-Ting,Shi, Da-Hua,Wang, Lei,Wang, You-Xian,Wu, Yu-Ran. "Synthesis and anticholinesterase activities of novel glycosyl benzoxazole derivatives". . p. 363 - 366. Retrieved 2020/02/05.