53942-45-3

Basic information

• Product Name: O-3,4,6-Tri-O-acetyl-2-(acetylamino)-2-deoxy-b-D-glucopyranosyl-(1-4)-O-3,6-di-O-acetyl-2-(acetylamino)-2-deoxy-b-D-glucopyranosyl-(1-4)-2-(acetylamino)-2-deoxy-1,3,6-triacetate-a-D-glucopyranose
• Synonyms: O-3,4,6-Tri-O-acetyl-2-(acetylamino)-2-deoxy-b-D-glucopyranosyl-(1-4)-O-3,6-di-O-acetyl-2-(acetylamino)-2-deoxy-b-D-glucopyranosyl-(1-4)-2-(acetylamino)-2-deoxy-1,3,6-triacetate-a-D-glucopyranose;Tri-N-acetyl Chitotriose Octaacetate;O-3,4,6-Tri-O-acetyl-2-(acetylamino)-2-deoxy--D-glucopyranosyl-(1-4)-O-3,6-di-O-acetyl-2-(acetylamino)-2-deoxy--D-glucopyranosyl-(1-4)-2-(acetylamino)-2-deoxy-1,3,6-triacetate-a-D-glucopyranose;O-3,4,6-Tri-O-acetyl-2-(acetylaMino)-2-deoxy-β-D-glucopyranosyl-(1-4)-O-3,6-di-O-acetyl-2-(acetylaMino)-2-deoxy-β-D-glucopyranosyl-(1-4)-2-(acetylaMino)-2-deoxy-1,3,6-triacetate-α-D-glucopyranose;Tri-N-acetyl Chitotriose Octaac
• CAS NO: 53942-45-3
• Molecular Formula: C₄₀H₅₇N₃O₂₄
• Molecular Weight: 963.887
• Product Categories: Fluorescent Labels & Indicators;Oligosaccharides
• Mol File: 53942-45-3.mol

Chemical Properties

• Melting Point: 315 °C
• Boiling Point: 1018.947°C at 760 mmHg
• Flash Point: 570.038°C
• Appearance: /
• Density: 1.387g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.533
• PKA: 13.46±0.70(Predicted)
• CAS DataBase Reference: O-3,4,6-Tri-O-acetyl-2-(acetylamino)-2-deoxy-b-D-glucopyranosyl-(1-4)-O-3,6-di-O-acetyl-2-(acetylamino)-2-deoxy-b-D-glucopyranosyl-(1-4)-2-(acetylamino)-2-deoxy-1,3,6-triacetate-a-D-glucopyranose(CAS DataBase Reference)
• NIST Chemistry Reference: O-3,4,6-Tri-O-acetyl-2-(acetylamino)-2-deoxy-b-D-glucopyranosyl-(1-4)-O-3,6-di-O-acetyl-2-(acetylamino)-2-deoxy-b-D-glucopyranosyl-(1-4)-2-(acetylamino)-2-deoxy-1,3,6-triacetate-a-D-glucopyranose(53942-45-3)
• EPA Substance Registry System: O-3,4,6-Tri-O-acetyl-2-(acetylamino)-2-deoxy-b-D-glucopyranosyl-(1-4)-O-3,6-di-O-acetyl-2-(acetylamino)-2-deoxy-b-D-glucopyranosyl-(1-4)-2-(acetylamino)-2-deoxy-1,3,6-triacetate-a-D-glucopyranose(53942-45-3)

Safety Data

• Hazardous Substances Data: 53942-45-3(Hazardous Substances Data)

Usage

Uses

1. Used in Pharmaceutical Industry:
O-3,4,6-Tri-O-acetyl-2-(acetylamino)-2-deoxy-b-D-glucopyranosyl-(1-4)-O-3,6-di-O-acetyl-2-(acetylamino)-2-deoxy-b-D-glucopyranosyl-(1-4)-2-(acetylamino)-2-deoxy-1,3,6-triacetate-a-D-glucopyranose is used as an intermediate for the synthesis of various pharmaceutical compounds. Its unique structure allows for the development of new drugs with potential applications in treating various diseases.
2. Used in Chemical Research:
O-3,4,6-Tri-O-acetyl-2-(acetylamino)-2-deoxy-b-D-glucopyranosyl-(1-4)-O-3,6-di-O-acetyl-2-(acetylamino)-2-deoxy-b-D-glucopyranosyl-(1-4)-2-(acetylamino)-2-deoxy-1,3,6-triacetate-a-D-glucopyranose serves as a valuable research tool in the field of organic chemistry. It can be used to study the properties and reactivity of complex carbohydrates and their derivatives, contributing to the advancement of knowledge in this area.
3. Used in Synthesis of Chitosan Derivatives:
O-3,4,6-Tri-O-acetyl-2-(acetylamino)-2-deoxy-b-D-glucopyranosyl-(1-4)-O-3,6-di-O-acetyl-2-(acetylamino)-2-deoxy-b-D-glucopyranosyl-(1-4)-2-(acetylamino)-2-deoxy-1,3,6-triacetate-a-D-glucopyranose is used as an intermediate in the synthesis of chitosan derivatives, such as 4-Methylumbelliferyl β-D-N,N',N"-Triacetylchitotrioside. These derivatives have potential applications in various fields, including pharmaceuticals, agriculture, and environmental science.
4. Used in Diagnostic Applications:
As an intermediate in the synthesis of 4-Methylumbelliferyl β-D-N,N',N"-Triacetylchitotrioside, O-3,4,6-Tri-O-acetyl-2-(acetylamino)-2-deoxy-b-D-glucopyranosyl-(1-4)-O-3,6-di-O-acetyl-2-(acetylamino)-2-deoxy-b-D-glucopyranosyl-(1-4)-2-(acetylamino)-2-deoxy-1,3,6-triacetate-a-D-glucopyranose can be utilized in the development of diagnostic tools for detecting specific enzymes, such as chitinases, which are important in various biological processes and disease states.

InChI:InChI=1/C40H57N3O24/c1-15(44)41-29-36(60-23(9)52)33(27(13-56-19(5)48)63-38(29)62-25(11)54)66-40-31(43-17(3)46)37(61-24(10)53)34(28(65-40)14-57-20(6)49)67-39-30(42-16(2)45)35(59-22(8)51)32(58-21(7)50)26(64-39)12-55-18(4)47/h26-40H,12-14H2,1-11H3,(H,41,44)(H,42,45)(H,43,46)/t26?,27?,28?,29-,30-,31-,32+,33+,34+,35+,36+,37+,38+,39-,40-/m0/s1

Upstream product

• 108-24-7 acetic anhydride 
• 9012-76-4 chitosan 

Downstream Products

• 53643-13-3 4-methylumbelliferyl β-D-N,N′,N′′-triacetylchitotrioside 

Relevant articles and documents

Acetylated chitosan oligosaccharides act as antagonists against glutamate-induced PC12 cell death via Bcl-2/Bax signal pathway

Chitosan oligosaccharides (COSs), depolymerized products of chitosan composed of β-(1→4) D-glucosamine units, have broad range of biological activities such as antitumour, antifungal, and antioxidant activities. In this study, peracetylated chitosan oligosaccharides (PACOs) and N-acetylated chitosan oligosaccharides (NACOs) were prepared from the COSs by chemcal modification. The structures of these monomers were identified using NMR and ESI-MS spectra. Their antagonist effects against glutamate-induced PC12 cell death were investigated. The results showed that pretreatment of PC12 cells with the PACOs markedly inhibited glutamate-induced cell death in a concentration-dependent manner. The PACOs were better glutamate antagonists compared to the COSs and the NACOs, suggesting the peracetylation is essential for the neuroprotective effects of chitosan oligosaccharides. In addition, the PACOs pretreatment significantly reduced lactate dehydrogenase release and reactive oxygen species production. It also attenuated the loss of mitochondrial membrane potential. Further studies indicated that the PACOs inhibited glutamate-induced cell death by preventing apoptosis through depressing the elevation of Bax/Bcl-2 ratio and caspase-3 activation. These results suggest that PACOs might be promising antagonists against glutamate-induced neural cell death.

Synthesis of 4-Methylcoumarin-7-yloxy Tetra-N-acetyl-β-chitotetraoside, a Novel Synthetic Substrate for the Fluorometric Assay of Lysozyme

4-Methylcoumarin-7-yloxy tetra-N-acetyl-β-chitotetraoside (10) was synthesized from chitin in pure form by a novel procedure.After acetolysis of chitin, chitotetraose tetradecaacetate (4) was isolated by Sephadex LH-20 column chromatography.Compound 4 was chlorinated with dry hydrogen chloride to produce tridecaacetyl chitotetraosyl chloride (6). 7-Hydroxy-4-methylcoumarin sodium salt was condensed with 6 under Koenigs-Knorr reaction conditions, and the final product (10) was obtained by de-O-acetylation of condensation product (8) with sodium methoxide. 4-Methylcoumarin-7-yloxy tri-N-acetyl-β-chitotrioside (9) was also synthesized through chitotriose undecaacetate (3) isolated together with 4 in the same chromatography.Compound 10 was used in a fluorometric assay of lysozyme in comparison with 9.The high sensitivity of fluorometric determination of 7-hydroxy-4-methylcoumarin (12) made it possible to determine lysozyme concentration in the microgram range by using this substrate (10).Unlike the assay using Micrococcus lysodeikticus cell powder, lysozyme assay with this synthetic substrate (10) could be performed directly in biological materials.Keywords - synthesis; lysozyme; enzyme assay; fluorometry; substrate; Sephadex LH-20; 7-hydroxy-4-methylcoumarin; 4-methylcoumarin-7-yloxy tetra-N-acetyl-β-chitotetraoside; 4-methylcoumarin-7-yloxy tri-N-acetyl-β-chitotrioside