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Hydroxy-PEG6-t-butyl ester

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Category Small-molecule Group Protected PEG
Catalog NO. BPG-2105
Product Name Hydroxy-PEG6-t-butyl ester
CAS 361189-64-2
Molecular Formula C19H38O9
Molecular Weight 410.50
Hydroxy-PEG6-t-butyl ester
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Product Information

Description Hydroxy-PEG6-t-butyl ester is a PEG linker containing a hydroxyl group and a t-butyl ester. The hydroxyl group enables further derivatization or replacement with other reactive functional groups. The t-butyl-protected carboxyl group can be deprotected under acidic conditions. The hydrophilic PEG spacer increases solubility in aqueous media.
Synonyms HO-PEG6-CH2CH2COOtBu; Hydroxy-PEG6-(CH2)2-Boc; OH-PEG6-TBA; OH-PEG6-CH2CH2COOtBu; HO-PEG6-t-butyl ester; tert-butyl 1-hydroxy-3,6,9,12,15,18-hexaoxahenicosan-21-oate; 2-Methyl-2-propanyl 1-hydroxy-3,6,9,12,15,18-hexaoxahenicosan-21-oate; 3,6,9,12,15,18-Hexaoxaheneicosan-21-oic acid, 1-hydroxy-, 1,1-dimethylethyl ester
IUPAC Name tert-butyl 3-[2-[2-[2-[2-[2-(2-hydroxyethoxy)ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]propanoate
Canonical SMILES CC(C)(C)OC(=O)CCOCCOCCOCCOCCOCCOCCO
InChI InChI=1S/C19H38O9/c1-19(2,3)28-18(21)4-6-22-8-10-24-12-14-26-16-17-27-15-13-25-11-9-23-7-5-20/h20H,4-17H2,1-3H3
InChIKey VGGDPFAYSOSIOK-UHFFFAOYSA-N
Boiling Point 481.8±40.0 °C at 760 mmHg
Purity ≥95%
Density 1.076±0.06 g/cm3 (Predicted)
Related CAS 1186025-29-5 (polymer) 892154-71-1 (polymer)
Appearance Pale Yellow or Colorless Oily Liquid
Storage Store at 2-8°C
Exact Mass 410.25158279
LogP 0.81010
Pictogram(s) Irritant
Signal Warning
Precautionary Statement Codes P264, P264+P265, P280, P302+P352, P305+P351+P338, P321, P332+P317, P337+P317, and P362+P364

Hydroxy-PEG6-t-butyl ester, due to its unique structural properties, finds extensive application in the synthesis of advanced drug delivery systems. Its functionality enables the attachment of therapeutics to the PEG chain, enhancing the solubility and stability of hydrophobic drugs. This improvement in solubility is particularly beneficial for poorly water-soluble drugs, as the PEG moiety facilitates their dispersion in aqueous environments. Moreover, the ester linkage allows for controlled release of the active drug, making it an ideal candidate for developing long-acting formulations and reducing dosing frequency. These attributes make Hydroxy-PEG6-t-butyl ester a critical component in optimizing drug administration and efficacy.

In the field of bioconjugation, Hydroxy-PEG6-t-butyl ester serves as a versatile linker. Its reactive hydroxy group can be exploited to attach various biomolecules such as antibodies, proteins, or peptides, creating conjugates that retain biological activity while benefiting from the stabilizing effects of PEGylation. This process improves the pharmacokinetics and pharmacodynamics of biologic drugs, extending their half-lives and reducing immunogenicity. By enhancing these properties, bioconjugates incorporating Hydroxy-PEG6-t-butyl ester can achieve more targeted therapeutic action, with fewer side effects compared to non-PEGylated counterparts.

Hydroxy-PEG6-t-butyl ester is also extensively used in material science, particularly for the modification of surfaces to resist protein adsorption and cell adhesion. Its hydrophilic PEG chain creates a steric barrier that reduces non-specific interactions, which is crucial for biomedical devices and implants where biocompatibility is paramount. By coating surfaces with this compound, medical devices such as stents, catheters, and biosensors gain improved performance and longevity as they are less prone to fouling and clot formation. This application underscores the importance of Hydroxy-PEG6-t-butyl ester in enhancing the functionality and safety of medical devices.

In the realm of diagnostics, Hydroxy-PEG6-t-butyl ester plays a significant role in the stabilization of nanoparticles, which are increasingly employed in imaging and diagnostic assays. The PEGylation of nanoparticles can prevent aggregation and improve their dispersion in biological fluids. This stability is critical for accurate and reliable diagnostic outcomes, as dispersed nanoparticles can more efficiently target and bind to specific biomarkers or cells. Consequently, Hydroxy-PEG6-t-butyl ester enhances the sensitivity and specificity of diagnostic tools.

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