Cas no 117399-51-6 (Chitotetraose Tetradecaacetate)

Chitotetraose Tetradecaacetate is a fully acetylated derivative of chitotetraose, a tetrasaccharide composed of four β-(1→4)-linked N-acetyl-D-glucosamine units. This compound is characterized by its high degree of acetylation, which enhances its solubility in organic solvents and improves its stability for chemical modifications. It serves as a valuable intermediate in glycochemistry and biomedical research, particularly in the synthesis of chitosan oligosaccharides and their derivatives. The acetylated form facilitates controlled deprotection studies and enables precise structural modifications for applications in drug delivery, immunology, and material science. Its well-defined structure and reactivity make it a useful tool for investigating carbohydrate-protein interactions and developing bioactive polymers.
Chitotetraose Tetradecaacetate structure
117399-51-6 structure
Product Name:Chitotetraose Tetradecaacetate
CAS No:117399-51-6
MF:C52H74N4O31
MW:1251.15217828751
CID:132749
PubChem ID:14055046
Update Time:2025-06-08

Chitotetraose Tetradecaacetate Chemical and Physical Properties

Names and Identifiers

    • Chitotetraose Tetradecaacetate
    • Peracetylated Chitotetraose
    • b-D-Glucopyranose,O-3,4,6-tri-O-acetyl-2-(acetylamino)-2-deoxy-b-D-glucopyranosyl-(1&reg
    • 4)-2-(acetylamino)-2-deoxy-,1,3,6-triacetate
    • 4)-O-3,6-di-O-acetyl-2-(acetylamino)-2-deoxy-b-D-glucopyranosyl-(1&reg
    • O-(2-Acetamido-3,4,6-tri-O-acetyl-2-deoxy-b-D-glucopyranosyl)-(1-4)-O-(2-acetamido-3,6-di-O-acetyl-2-deoxy-b-D-glucopyranosyl)-(1-4)-O-(2-acetamido-3,
    • O-(2-Acetamido-3,4,6-tri-O-acetyl-2-deoxy--D-glucopyranosyl)-(1-4)-O-(2-acetamido-3,6-di-O-acetyl-2-deoxy--D-glucopyranosyl)-(1-4)-O-(2-acetamido-3,6-di-O-acetyl-2-deoxy--D-glucopyranosyl)-(1-4)-2-acetamido-1,3,6-tri-O-acetyl-2-deoxy--D-glucopyranose
    • tetra-N-acetylchitotetraose peracetate
    • (O-(2-Acetamido-3,4,6-tri-O-acetyl-2-deoxy- -D-glucopyranosyl)
    • O-(2-Acetamido-3,4,6-tri-O-acetyl-2-deoxy-b-D-glucopyranosyl)-(1-4)-O-(2-acetamido-3,6-di-O-acetyl-2-deoxy-b-D-glucopyranosyl)-(1-4)-O-(2-acetamido-3,6-di-O-acetyl-2-deoxy-b-D-glucopyranosyl)-(1-4)-2-acetamido-1,3,6-tri-O-acetyl-2-deoxy-b-D-glucopyranose
    • [(2R,3S,4R,5R,6S)-5-acetamido-6-[(2R,3S,4R,5R,6S)-5-acetamido-6-[(2R,3S,4R,5R,6S)-5-acetamido-4,6-diacetyloxy-2-(acetyloxymethyl)oxan-3-yl]oxy-4-acetyloxy-2-(acetyloxymethyl)oxan-3-yl]oxy-3-[(2S,3R,4R,5S,6R)-3-acetamido-4,5-diacetyloxy-6-(acetyloxymethyl)oxan-2-yl]oxy-4-acetyloxyoxan-2-yl]methyl acetate
    • O-(2-Acetamido-3,4,6-tri-O-acetyl-2-deoxy-beta-D-glucopyranosyl)-(1-4)-O-(2-acetamido-3,6-di-O-acetyl-2-deoxy-beta-D-glucopyranosyl)-(1-4)-O-(2-acetamido-3,6-di-O-acetyl-2-deoxy-beta-D-glucopyranosyl)-(1-4)-2-acetamido-1,3,6-tri-O-acetyl-2-deoxy-beta-D-glucopyra
    • W-200907
    • 117399-51-6
    • Inchi： 1S/C52H74N4O31/c1-19(57)53-37-46(77-29(11)67)42(34(16-72-24(6)62)81-49(37)80-32(14)70)85-51-39(55-21(3)59)48(79-31(13)69)44(36(83-51)18-74-26(8)64)87-52-40(56-22(4)60)47(78-30(12)68)43(35(84-52)17-73-25(7)63)86-50-38(54-20(2)58)45(76-28(10)66)41(75-27(9)65)33(82-50)15-71-23(5)61/h33-52H,15-18H2,1-14H3,(H,53,57)(H,54,58)(H,55,59)(H,56,60)/t33-,34-,35-,36-,37-,38-,39-,40-,41-,42-,43-,44-,45-,46-,47-,48-,49-,50+,51+,52+/m1/s1
    • InChI Key： OYGWXILTVZPHON-KEMNZMDTSA-N
    • SMILES： O([C@H]1[C@@H]([C@H]([C@@H]([C@@H](COC(C)=O)O1)O[C@H]1[C@@H]([C@H]([C@@H]([C@@H](COC(C)=O)O1)OC(C)=O)OC(C)=O)NC(C)=O)OC(C)=O)NC(C)=O)[C@@H]1[C@@H](COC(C)=O)O[C@H]([C@@H]([C@H]1OC(C)=O)NC(C)=O)O[C@@H]1[C@@H](COC(C)=O)O[C@H]([C@@H]([C@H]1OC(C)=O)NC(C)=O)OC(C)=O

Computed Properties

  • Exact Mass: 1250.43000
  • Monoisotopic Mass: 1250.4337016g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 4
  • Hydrogen Bond Acceptor Count: 31
  • Heavy Atom Count: 87
  • Rotatable Bond Count: 34
  • Complexity: 2550
  • Covalently-Bonded Unit Count: 1
  • Defined Atom Stereocenter Count: 20
  • Undefined Atom Stereocenter Count : 0
  • Defined Bond Stereocenter Count: 0
  • Undefined Bond Stereocenter Count: 0
  • XLogP3: -3.8
  • Topological Polar Surface Area: 444?2

Experimental Properties

  • Refractive Index: 1.542
  • PSA: 444.01000
  • LogP: -1.90200

Chitotetraose Tetradecaacetate Pricemore >>

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Chitotetraose Tetradecaacetate Related Literature

Additional information on Chitotetraose Tetradecaacetate

Research Update on Chitotetraose Tetradecaacetate (CAS: 117399-51-6) in Chemical Biology and Pharmaceutical Applications

Chitotetraose Tetradecaacetate (CAS: 117399-51-6), a fully acetylated derivative of chitotetraose, has garnered significant attention in recent chemical biology and pharmaceutical research due to its unique structural properties and potential therapeutic applications. This research briefing synthesizes the latest findings on this compound, focusing on its synthesis, biological activities, and emerging applications in drug development and biomedicine.

Recent studies have highlighted the compound's role as a key intermediate in the synthesis of bioactive oligosaccharides. A 2023 publication in Carbohydrate Polymers demonstrated an optimized synthetic route for 117399-51-6 with improved yield (78%) using peracetylation of chitotetraose under mild conditions, addressing previous challenges in large-scale production. The acetylated structure enhances stability while maintaining the biological recognition properties of the native oligosaccharide.

In immunomodulation research, Chitotetraose Tetradecaacetate has shown promising activity as a Toll-like receptor (TLR) modulator. A Nature Communications study (2024) revealed its ability to selectively activate TLR4/MyD88 signaling pathways without inducing excessive cytokine storms, suggesting potential applications in vaccine adjuvants and immunotherapy. The acetyl groups appear to play a crucial role in this selective activation mechanism.

Pharmaceutical formulation studies have explored 117399-51-6 as a novel excipient for mucosal drug delivery. Its amphiphilic character, resulting from the acetylated sugar backbone, enables formation of stable nanoparticles capable of encapsulating both hydrophilic and hydrophobic drugs. Recent work in the Journal of Controlled Release demonstrated enhanced oral bioavailability of insulin when co-administered with Chitotetraose Tetradecaacetate-based carriers.

Emerging applications in regenerative medicine have been reported, particularly in cartilage tissue engineering. The compound's structural similarity to hyaluronic acid derivatives allows it to mimic extracellular matrix components while providing improved resistance to enzymatic degradation. A 2024 Biomaterials study showed that scaffolds incorporating 117399-51-6 promoted chondrocyte proliferation and collagen type II production at levels comparable to established materials.

Analytical characterization methods for Chitotetraose Tetradecaacetate have advanced significantly, with recent developments in LC-MS/MS protocols enabling precise quantification in complex biological matrices. This progress supports ongoing pharmacokinetic studies and quality control in potential pharmaceutical applications.

While promising, research gaps remain in understanding the complete structure-activity relationship of 117399-51-6 derivatives and their long-term biological effects. Current studies are exploring selective deacetylation patterns to optimize biological activity while minimizing potential toxicity. The compound continues to serve as a valuable tool in glycobiology research and a potential candidate for various therapeutic applications.

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