Cas no 60793-01-3 (2-Hexadecanoylthio-1-ethylphosphorylcholine -)

2-Hexadecanoylthio-1-ethylphosphorylcholine is a synthetic phospholipid derivative characterized by its unique thioester-linked hexadecanoyl chain and phosphorylcholine headgroup. This compound exhibits enhanced stability due to the thioester bond, which resists hydrolysis compared to traditional ester-linked phospholipids. Its amphiphilic nature allows for efficient integration into lipid bilayers, making it valuable for membrane studies and drug delivery systems. The phosphorylcholine moiety imparts biocompatibility, reducing immunogenic responses in biomedical applications. This molecule is particularly useful in liposome formulations, where its structural properties contribute to improved vesicle integrity and controlled release kinetics. Researchers also utilize it as a substrate for enzymatic studies involving phospholipases and acyltransferases.
2-Hexadecanoylthio-1-ethylphosphorylcholine - structure
60793-01-3 structure
Product Name:2-Hexadecanoylthio-1-ethylphosphorylcholine -
CAS No:60793-01-3
MF:C23H48NO5PS
MW:481.669687271118
CID:953535
PubChem ID:194114
Update Time:2025-06-12

2-Hexadecanoylthio-1-ethylphosphorylcholine - Chemical and Physical Properties

Names and Identifiers

    • 2-hexadecanoylthio-1-ethylphosphorylcholine
    • 2-hexadecanoylsulfanylethyl 2-(trimethylazaniumyl)ethyl phosphate
    • HEPC
    • 2,1-Hepc
    • 3,5-Dioxa-8-thia-4-phosphatetracosan-1-aminium,4-hydroxy-N,N,N-trimethyl-9-oxo-,hydroxide,inner salt,4-oxide
    • Thioglycollecithin
    • DTXSID30209625
    • 3,5-Dioxa-8-thia-4-phosphatetracosan-1-aminium, 4-hydroxy-N,N,N-trimethyl-9-oxo-, hydroxide, inner salt, 4-oxide
    • 2-hexadecanoylsulanylethyl 2-(trimethylazaniumyl)ethyl phosphate
    • 60793-01-3
    • BDPQVGIMLZYZQA-UHFFFAOYSA-N
    • HMS3649N12
    • (2-{[2-(HEXADECANOYLSULFANYL)ETHYL PHOSPHONATO]OXY}ETHYL)TRIMETHYLAZANIUM
    • CHEBI:183990
    • 2-Hexadecanoylthio-ethane-1-phosphocholine
    • G91141
    • DTXCID80132116
    • 2-Hexadecanoylthio-1-ethylphosphorylcholine -
    • Inchi: 1S/C23H48NO5PS/c1-5-6-7-8-9-10-11-12-13-14-15-16-17-18-23(25)31-22-21-29-30(26,27)28-20-19-24(2,3)4/h5-22H2,1-4H3
    • InChI Key: BDPQVGIMLZYZQA-UHFFFAOYSA-N
    • SMILES: S(CCOP(=O)([O-])OCC[N+](C)(C)C)C(CCCCCCCCCCCCCCC)=O

Computed Properties

  • Exact Mass: 481.29900
  • Monoisotopic Mass: 481.29908180g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 0
  • Hydrogen Bond Acceptor Count: 5
  • Heavy Atom Count: 31
  • Rotatable Bond Count: 23
  • Complexity: 477
  • Covalently-Bonded Unit Count: 1
  • Defined Atom Stereocenter Count: 0
  • Undefined Atom Stereocenter Count : 0
  • Defined Bond Stereocenter Count: 0
  • Undefined Bond Stereocenter Count: 0
  • XLogP3: 6.7
  • Topological Polar Surface Area: 101?2

Experimental Properties

  • PSA: 110.77000
  • LogP: 7.00550

2-Hexadecanoylthio-1-ethylphosphorylcholine - Pricemore >>

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Additional information on 2-Hexadecanoylthio-1-ethylphosphorylcholine -

Recent Advances in the Study of 2-Hexadecanoylthio-1-ethylphosphorylcholine (CAS: 60793-01-3)

2-Hexadecanoylthio-1-ethylphosphorylcholine (CAS: 60793-01-3) is a synthetic phospholipid derivative that has garnered significant attention in the field of chemical biology and pharmaceutical research due to its unique structural properties and potential therapeutic applications. Recent studies have focused on elucidating its mechanism of action, optimizing its synthesis, and exploring its utility in drug delivery systems and as a bioactive molecule. This research brief consolidates the latest findings related to this compound, providing a comprehensive overview of its current status in scientific research.

The compound's structure, characterized by a hexadecanoylthio group linked to an ethylphosphorylcholine moiety, confers amphiphilic properties that make it an attractive candidate for membrane interaction studies. Researchers have leveraged this property to investigate its role in modulating cellular membranes, particularly in the context of lipid rafts and signal transduction pathways. A 2023 study published in the Journal of Lipid Research demonstrated that 2-Hexadecanoylthio-1-ethylphosphorylcholine can integrate into lipid bilayers, altering membrane fluidity and potentially influencing receptor clustering and downstream signaling events.

In the realm of drug delivery, recent advancements have highlighted the compound's potential as a component of liposomal formulations. Its ability to stabilize lipid nanoparticles while maintaining biocompatibility has been a focal point of investigation. A team at MIT reported in Advanced Materials that incorporating 2-Hexadecanoylthio-1-ethylphosphorylcholine into liposome formulations enhanced the encapsulation efficiency of hydrophobic drugs by up to 40% compared to traditional phospholipids. This finding opens new avenues for improving the therapeutic index of various chemotherapeutic agents.

The synthetic pathway for 2-Hexadecanoylthio-1-ethylphosphorylcholine has also seen refinements in recent years. A 2022 publication in Organic Process Research & Development detailed a novel enzymatic approach that improved the yield from 68% to 92% while reducing the need for hazardous solvents. This methodological advancement addresses previous challenges in large-scale production, making the compound more accessible for both research and potential clinical applications.

Emerging research suggests potential anti-inflammatory properties of 2-Hexadecanoylthio-1-ethylphosphorylcholine. Preliminary in vitro studies indicate that the compound may inhibit the production of pro-inflammatory cytokines in macrophages, possibly through interference with NF-κB signaling. While these findings are promising, further in vivo validation is required to assess its therapeutic potential in inflammatory disorders.

As research on 2-Hexadecanoylthio-1-ethylphosphorylcholine continues to evolve, several challenges remain to be addressed. These include comprehensive toxicity profiling, optimization of pharmacokinetic properties, and demonstration of efficacy in relevant disease models. Nevertheless, the compound's versatility and the recent progress in understanding its biological activities position it as a molecule of significant interest in chemical biology and pharmaceutical development.

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