2,5,8,11,14-Pentaoxaheptadec-16-yne
Molecular Formula: C12H22O5
CAS#: 1101668-39-6
SMILES: COCCOCCOCCOCCOCC#C
MDL#: MFCD28155212
Catalog#: AMTGC345-PY17
Molecular weight: 246.30 g/mol
Appearance: Pale orange liquid
Purity: 97.9%
Storage: Long-term storage in a fridge at 2-8 °C
Solubility: Dichloromethane, Chloroform, Methanol
Other names:
- mPEG4-Alkyne
- mPEG4-Propargyl
- mPEG5-Propargyl
- Methoxy PEG alkyne
- mPEG4-Propyne
Fields of Interest
Click chemistry, PEGylation, bioconjugation, chemical biology, medicinal chemistry, drug delivery, PROTAC research, polymer chemistry, surface functionalization, materials science, specialty chemical synthesis
Background
2,5,8,11,14-Pentaoxaheptadec-16-yne (CAS 1101668-39-6) is a monofunctional, alkyne-terminated PEG derivative commonly known as mPEG4-Alkyne. The molecule combines a terminal propargyl/alkyne group with a methoxy-capped oligoethylene glycol chain, providing a compact, flexible, and hydrophilic spacer.
The terminal alkyne provides a reactive handle for copper-catalyzed azide–alkyne cycloaddition (CuAAC) with azide-functionalized molecules, forming a stable triazole linkage. In contrast, the methoxy-terminated end of the molecule is nonreactive under typical conjugation conditions. This combination makes mPEG4-Alkyne useful when a single click-reactive site is desired while the PEG chain provides additional molecular spacing and hydrophilic character.
Applications
mPEG4-Alkyne is useful in click chemistry, bioconjugation, chemical biology, drug discovery, polymer modification, surface functionalization, and specialty chemical synthesis. Its terminal alkyne can be conjugated with azide-functionalized small molecules, peptides, polymers, surfaces, and other appropriately modified substrates through CuAAC.
The methoxy-capped PEG chain can introduce a flexible, hydrophilic segment without adding a second reactive terminus, making the compound useful for PEGylation, molecular modification, probe development, and preparation of functional materials. It can also serve as a building block for more complex linker architectures where an alkyne is required for subsequent click chemistry. Commercial sources additionally classify this compound as a PEG-based linker applicable to PROTAC synthesis.
Literature:
- Bioorganic and Medicinal Chemistry, 2008, vol. 16, # 24, p. 10295 – 10300
- Chemistry – A European Journal, 2009, vol. 15, # 2, p. 388 – 404
- Carbohydrate Polymers, 2025, vol. 359, art. no. 123587