Heptaethylene Glycol Monomethyl Ether Chemical Properties

Boiling point:

150 °C(Press: 0.005 Torr)

Density 

1.09

refractive index 

1.4540-1.4580

storage temp. 

-20°C

form 

clear liquid

pka

14.36±0.10(Predicted)

color 

Colorless to Light yellow to Light orange

InChI

InChI=1S/C15H32O8/c1-17-4-5-19-8-9-21-12-13-23-15-14-22-11-10-20-7-6-18-3-2-16/h16H,2-15H2,1H3

InChIKey

AGWKUHGLWHMYTG-UHFFFAOYSA-N

SMILES

C(O)COCCOCCOCCOCCOCCOCCOC

CAS DataBase Reference

4437-01-8(CAS DataBase Reference)

Safety Information

WGK Germany 

3

HS Code 

29094990

MSDS

• Language:English Provider:SigmaAldrich

Heptaethylene Glycol Monomethyl Ether Usage And Synthesis

Description

m-PEG7-alcohol is a PEG linker containing a hydroxyl group. The hydroxyl group enables further derivatization or replacement with other reactive functional groups. The hydrophilic PEG spacer increases solubility in aqueous media.

Uses

Applications may include: bioconjugation, drug delivery, PEG hydrogel, crosslinker, and surface functionalization

Definition

The presence of heptaethylene glycol monomethyl ether (HGME) as a process impurity and degradation impurity in the final purified form of Benzonatate is a determining factor in establishing the safety, identity, strength, purity, and quality of the drug substance. Owing to the cutaneous toxicity of HGME in the BNZ drug substance, a suitable and selective analysis method is required for its quantitation[1].

reaction suitability

reagent type: cross-linking reagent

Synthesis

A 60% NaH dispersion in mineral oil was added in batches to a stirred solution of triacetylene glycol (35.7 mmol) in anhydrous DMF (25.7 mL) under nitrogen protection, and the mixture was stirred for 1 hour at room temperature. Subsequently, a solution of 2-(2-(2-methoxyethoxy)ethoxy)ethyl methanesulfonate (23.36 mmol) in anhydrous DMF (4 mL) was added in a single addition to the resulting salt, and stirring was continued for 3.5 hours at room temperature. The progress of the reaction was monitored by thin layer chromatography (TLC with 12% unfolding agent ratio). Upon completion of the reaction, the reaction mixture was diluted with an equal volume of 1N HCl, extracted with ethyl acetate (2 x 20 mL) and the organic phase discarded. The aqueous phase was extracted and post-treated to give heptaglycol monomethyl ether in 82-84% yield.

IC 50

PEGs

References

[1] Lakshmi Narasimha Rao Katakam, Vishnu Murthy Marisetti, Santhosh Kumar Ettaboina. “Development and validation of LC–MS method for the determination of heptaethylene glycol monomethyl ether in benzonatate bulk drugs.” Biomedical Chromatography 35 7 (2021).

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