Cas no 72692-06-9 (2,3,4-Tri-O-acetyl-α-D-glucuronic Acid Methyl Ester)

2,3,4-Tri-O-acetyl-α-D-glucuronic Acid Methyl Ester is a versatile derivative of α-D-glucuronic acid, known for its stability and hydrophilic properties. This compound finds application in pharmaceuticals, where it serves as a precursor for active pharmaceutical ingredients. Its acetylation enhances solubility and stability, making it suitable for drug delivery systems. The methyl ester group contributes to its chemical stability and ease of handling.
2,3,4-Tri-O-acetyl-α-D-glucuronic Acid Methyl Ester structure
72692-06-9 structure
Product Name:2,3,4-Tri-O-acetyl-α-D-glucuronic Acid Methyl Ester
CAS No:72692-06-9
MF:C13H18O10
MW:334.276025295258
CID:550029
PubChem ID:46783127
Update Time:2025-06-24

2,3,4-Tri-O-acetyl-α-D-glucuronic Acid Methyl Ester Chemical and Physical Properties

Names and Identifiers

    • 2,3,4-Tri-O-acetyl-α-D-glucuronic Acid Methyl Ester
    • 2,3,4-TRI-O-ACETYL-A-D-GLUCURONIC ACID METHYL ESTER
    • 2,3,4-Tri-O-acetyl-α
    • a-D-Glucopyranuronic acid, methylester, 2,3,4-triacetate
    • 2,3,4-TRI-O-ACETYL-D-GLUCURONIC ACID METHYL ESTER
    • methyl 2,3,4-tri-O-acetyl-D-glucopyranose uronate
    • methyl 2,3,4-tri-O-acetyl-D-glucopyranosyluronate
    • Methyl-(2,3,4-tri-O-acetyl-a-D-glucopyranosyl)uronate
    • methyl (3S,6R)-3,4,5-triacetyloxy-6-hydroxyoxane-2-carboxylate
    • BS-24490
    • 2,3,4-Tri-O-acetyl-
    • A-D-glucuronic Acid Methyl Ester
    • 2,3,4-Tri-O-acetyl-alpha-D-glucuronic Acid Methyl Ester
    • D96133
    • 72692-06-9
    • Inchi: 1S/C13H18O10/c1-5(14)20-8-9(21-6(2)15)11(22-7(3)16)13(18)23-10(8)12(17)19-4/h8-11,13,18H,1-4H3/t8-,9?,10?,11?,13+/m0/s1
    • InChI Key: CLHFNXQWJBTGBL-SHXYABRHSA-N
    • SMILES: O1[C@H](C(C([C@@H](C1C(=O)OC)OC(C)=O)OC(C)=O)OC(C)=O)O

Computed Properties

  • Exact Mass: 334.09000
  • Monoisotopic Mass: 334.08999677g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 1
  • Hydrogen Bond Acceptor Count: 10
  • Heavy Atom Count: 23
  • Rotatable Bond Count: 8
  • Complexity: 487
  • Covalently-Bonded Unit Count: 1
  • Defined Atom Stereocenter Count: 2
  • Undefined Atom Stereocenter Count : 3
  • Defined Bond Stereocenter Count: 0
  • Undefined Bond Stereocenter Count: 0
  • XLogP3: -0.8
  • Topological Polar Surface Area: 135?2

Experimental Properties

  • Melting Point: 103-105?C
  • Stability/Shelf Life: Acid Sensitive
  • PSA: 142.50000
  • LogP: -1.48570

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2,3,4-Tri-O-acetyl-α-D-glucuronic Acid Methyl Ester Related Literature

Additional information on 2,3,4-Tri-O-acetyl-α-D-glucuronic Acid Methyl Ester

72692-06-9: A Comprehensive Overview of 2,3,4-Tri-O-acetyl-α-D-glucuronic Acid Methyl Ester

72692-06-9, also known as 2,3,4-Tri-O-acetyl-α-D-glucuronic Acid Methyl Ester, is a highly specialized organic compound with significant applications in the fields of biochemistry, pharmacology, and materials science. This compound is a derivative of α-D-glucuronic acid, a key component in various biological processes, including cell wall synthesis and detoxification mechanisms in the liver. The acetylation and methylation modifications in this compound enhance its stability and bioavailability, making it a valuable tool in research and development.

The structure of 72692-06-9 consists of a glucuronic acid backbone with three acetyl groups attached to the hydroxyl groups at positions 2, 3, and 4. The methyl ester group further modifies the carboxylic acid group, contributing to its unique chemical properties. This modification not only improves solubility but also reduces potential side reactions during biochemical assays. Recent studies have highlighted the importance of such modifications in enhancing the compound's compatibility with various experimental conditions.

One of the most notable applications of 72692-06-9 is in the study of glycosaminoglycan metabolism. Glycosaminoglycans (GAGs) are long chains of repeating disaccharide units that play a critical role in maintaining extracellular matrix integrity. By incorporating 72692-06-9 into GAG synthesis models, researchers have gained deeper insights into the enzymatic mechanisms involved in GAG assembly. This has implications for understanding diseases such as mucopolysaccharidoses, where GAG metabolism is impaired.

Recent advancements in analytical techniques have enabled precise characterization of 72692-06-9 at the molecular level. High-resolution mass spectrometry (HRMS) and nuclear magnetic resonance (NMR) spectroscopy have been instrumental in confirming the compound's structure and purity. These studies have also revealed its thermal stability and reactivity under various conditions, which are crucial for its use in biochemical assays and drug delivery systems.

In addition to its role in fundamental research, 72692-06-9 has shown promise in the development of novel therapeutic agents. Its ability to act as a precursor for more complex glycosylated molecules makes it an attractive candidate for drug design. For instance, researchers are exploring its potential as a building block for creating glycoconjugates with enhanced pharmacokinetic properties.

The synthesis of 72692-06-9 involves multi-step chemical transformations that require meticulous control over reaction conditions. Key steps include the selective acetylation of hydroxyl groups and subsequent esterification to achieve the desired stereochemistry. Recent optimizations in these processes have significantly improved yield and purity, making large-scale production more feasible.

From an environmental perspective, understanding the biodegradation pathways of 72692-06-9 is essential for assessing its ecological impact. Studies indicate that under aerobic conditions, the compound undergoes microbial degradation through enzymatic cleavage of acetyl and methyl groups. This knowledge is critical for ensuring sustainable practices in its production and disposal.

In conclusion, 72692-06-9, or 2,3,4-Tri-O-acetyl-α-D-glucuronic Acid Methyl Ester, stands as a pivotal molecule in contemporary biochemical research. Its unique properties and versatile applications continue to drive innovation across multiple disciplines. As research progresses, it is anticipated that this compound will play an even greater role in advancing our understanding of glycan biology and developing novel therapeutic strategies.

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