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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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Thiol-functionalized undecagold clusters by ligand exchange: Synthesis, mechanism, and properties.
Woehrle GH & Hutchison JE
Inorganic Chemistry, 44(18), 6149-6158 (2005)
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)
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)
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)
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