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767751

Sigma-Aldrich

2-{2-[2-(2-Mercaptoethoxy)ethoxy]ethoxy}ethanol

97%

Synonym(s):

MEEE, 1-Mercapto-11-hydroxy-3,6,9-trioxaundecane

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About This Item

Empirical Formula (Hill Notation):
C8H18O4S
Molecular Weight:
210.29
MDL number:
MFCD22574773
UNSPSC Code:
12352200
PubChem Substance ID:
329767336
NACRES:
NA.22

Assay

97%

form

liquid

reaction suitability

reagent type: cross-linking reagent

refractive index

n20/D 1.481

density

1.098 g/mL at 25 °C

SMILES string

OCCOCCOCCOCCS

InChI

1S/C8H18O4S/c9-1-2-10-3-4-11-5-6-12-7-8-13/h9,13H,1-8H2

InChI key

GKKYNULPAQDGHI-UHFFFAOYSA-N

Related Categories

Application

2-{2-[2-(2-Mercaptoethoxy)ethoxy]ethoxy}ethanol may be used in the synthesis of 2-(2-(2-((7-nitrobenzo[c][1,2,5]oxadiazol-4-yl)thio)ethoxy)ethoxy)ethanol, an nitrobenzoxadiazole (NBD) analog of the anticancer agent 6-((7-nitrobenzo[c][1,2,5]oxadiazol-4-yl)thio)hexan-1-ol (NBDHEX). This analog is a potent glutathione S-transferase (GST) and a potential therapeutic antimelanoma agent with enhanced water solubility and antitumor efficacy when compared to NBDHEX in a study.
  • Oligo-ehtylene glycol of peptides and small molecules (PEGylation)
  • PEG-disulfide formation
  • ultra-thin protein-resistant monolayers
  • Densely packed monolayer and a flexible-hydrophilic oligo ethylene glycol arm for avoiding non-specific adsorption

Pictograms

Skull and crossbonesCorrosion
GHS06,GHS05

Signal Word

Danger

Hazard Statements

H301,H314

Hazard Classifications

Acute Tox. 3 Oral - Skin Corr. 1B

Storage Class Code

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

WGK

WGK 3

Certificates of Analysis (COA)

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Oligosaccharide and glycoprotein microarrays as tools in HIV glycobiology: glycan-dependent gp120/protein interactions.
Adams EW, et al.
Chemistry & Biology, 11(6), 875-881 (2004)
Thiol functionalized oligo-ethylene glycol, for modification of peptides/small molecules containing thiols or maleimide functional groups
Journal of Materials Chemistry, 9, 1121-1121 (1999)
Carbohydrates as the next frontier in pharmaceutical research.
Werz DB & Seeberger PH
Chemistry?A European Journal , 11(11), 3194-3206 (2005)
Click and chemically triggered declick reactions through reversible amine and thiol coupling via a conjugate acceptor
Diehl KL, et al.
Nature Chemistry, 8(10) (2016)
Influence of surface functionalization and particle size on the aggregation kinetics of engineered nanoparticles.
Liu J, et al.
Chemosphere, 87(8), 918-924 (2012)
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