4,7,10,13-Tetraoxahexadeca-1,15-diyne

 CAS No.: 126422-58-0  Cat No.: BP-500623  Purity: >95% 4.5  

4,7,10,13-Tetraoxahexadeca-1,15-diyne is a polyethylene glycol–like ether linker architecture featuring two terminal alkyne groups separated by an extended, oxygen-rich chain. The alternating ether units provide conformational flexibility and improved solvation, while the diyne termini enable orthogonal chemical handles for coupling strategies commonly used in PROTAC synthesis. In targeted protein degradation constructs, such linkers are employed to tune the spatial relationship between a ligand-binding warhead and an E3-recruiting moiety, thereby optimizing productive ternary complex formation and degradation efficiency. The long, oxygenated backbone can reduce steric strain and help maintain favorable linker geometry, which is critical because linker length and rigidity strongly influence ubiquitination kinetics and cellular potency. This compound is therefore valuable for researchers seeking modular, alkyne-functionalized linkers to build and systematically optimize PROTACs and related bifunctional degraders, including workflows that use alkyne-compatible conjugation chemistry for rapid analog generation.

4,7,10,13-Tetraoxahexadeca-1,15-diyne

Structure of 126422-58-0

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Category
PROTAC Linker
Molecular Formula
C12H18O4
Molecular Weight
226.27
Appearance
Pale Yellow Oily Liquid

* For research and manufacturing use only. Not for human or clinical use.

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Purity
>95%
Solubility
Soluble in DMSO
Appearance
Pale Yellow Oily Liquid
Storage
Store at 2-8°C for short term (days to weeks) or -20°C for long term (months to years)
Shipping
Room temperature in continental US; may vary elsewhere.
IUPACName
3-[2-[2-(2-prop-2-ynoxyethoxy)ethoxy]ethoxy]prop-1-yne
Synonyms
Bis-propargyl-PEG4; Alkyne-PEG4-Alkyne; Propargyl-PEG4-Propargyl; Bis-propargyl-PEG3; 4,7,10,13-Tetraoxa-1,15-hexadecadiyne; α,ω-bis(O-propargyl)triethylene glycol
Boiling Point
292.2±30.0 °C at 760 mmHg
Density
1.0±0.1 g/cm3
InChI Key
PHRQSGRBGBTBAD-UHFFFAOYSA-N
InChI
InChI=1S/C12H18O4/c1-3-5-13-7-9-15-11-12-16-10-8-14-6-4-2/h1-2H,5-12H2
SMILES
C#CCOCCOCCOCCOCC#C
1. Two [7.3.1]azabicyclo-z-3-ene-1,5-diyne analogues of dynemicin A
V M Lynch, R A Fairhurst, T N Iliadis, P Magnus, B E Davis Acta Crystallogr C. 1995 Apr 15;51 ( Pt 4):782-6.doi: 10.1107/s0108270194010231.
The crystal structures of methyl 6-methoxy-17-oxo-2-azatricyclo[7.7.1.0(3,8)]heptadeca-3(8),4 ,6,13-tetraene- 11,15-diyne-2-carboxylate ethyl acetate solvate, (1), 2C19H15NO4.0.5C4H8O2, and tricyclo[3.3.1.1(3,7)]decyl 6-methoxy-17-oxo-2-azatricyclo[7.7.1.0(3,8)]heptadeca-3(8),4 ,6,13-tetraene- 11,15-diyne-2-carboxylate ethyl acetate solvate, (2), C28H27NO4.0.5C4H8O2, are reported. For compound (1), two crystallographically independent molecules are observed. Interestingly, for both compounds (1) and (2), a molecule of ethyl acetate is found in the crystal lattice disordered about an inversion center. The azabicyclo[7.3.1]enediyne core appears to be fairly rigid. Only minor differences are observed in the ring conformation between the two independent molecules in (1) and between compounds (1) and (2) themselves. The conformation is also similar to that found in deoxydynemicin A [Shiomi, Iinuma, Naganawa, Hamada, Hattori, Nakamura, Takeuchi & Iitaka (1990). J. Antibiot. 43, 1000-1005] and triacetyldynemicin A [Konishi, Ohkuma, Tsuno, Oki, Van Duyne & Clardy (1990). J. Am. Chem. Soc. 112, 3715-3716]. The transannular diyne distance (C3...C8) averages 3.428 (2) A for compound (1) and is 3.403 (3) A for compound (2).
ConcentrationVolumeMass1 mg5 mg10 mg
1 mM4.4195 mL22.0975 mL44.1950 mL
5 mM0.8839 mL4.4195 mL8.8390 mL
10 mM0.4419 mL2.2097 mL4.4195 mL

4,7,10,13-Tetraoxahexadeca-1,15-diyne, is designed to provide a rigid, well-defined spacer between targeting and E3-ligase-binding modules. Its oxygen-rich scaffold supports favorable conformational behavior and solubility tuning, while the terminal alkyne handles enable modular assembly. Such linkers are widely used in targeted protein degradation workflows to optimize linker length, geometry, and attachment chemistry, improving the reliability of conjugate synthesis.

Structure: The linker contains an internal polyether framework with multiple ether oxygen atoms and two terminal alkyne functionalities. It features carbon–carbon triple bonds at the termini and ether linkages along the backbone, yielding a polar, conformationally informative spacer with chemical stability suited to iterative PROTAC synthesis.

Reactivity: The terminal alkynes are compatible with common PROTAC conjugation strategies that rely on alkyne functional group reactivity, including copper-catalyzed azide–alkyne cycloaddition and related click-type coupling approaches. Typical conditions use copper catalysts, appropriate ligands, and polar organic solvents under inert or controlled atmospheres to minimize side reactions and preserve sensitive functional groups on the binding partners.

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It is commonly abbreviated as: C1V1 = C2V2

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Tip: Chemical formula is case sensitive. C22H30N4O c22h30n40
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