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901199

Sigma-Aldrich

6-Acetylthiohexyl methacrylate

≥98.0%, contains 100 ppm MEHQ as inhibitor

Synonym(s):

ATA

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About This Item

Empirical Formula (Hill Notation):
C12H20O3S
CAS Number:
Molecular Weight:
244.35
UNSPSC Code:
12162002

assay

≥98.0%

form

liquid

contains

100 ppm MEHQ as inhibitor

color

colorless to pale yellow

storage temp.

−20°C

General description

6-Acetylthiohexyl acrylate (ATA) is a methacrylate-based monomer most commonly used in the synthesis of thiol-functionalized polymers and copolymers. Thiols are commonly used in drug delivery systems to form disulfide bonds as reversible cross linkers due to their stability and capability to be reductively cleaved once internalized into cells. However, it is difficult to polymerize monomers with free thiols. ATA features an acetate-protected thiol that can be easily deprotected post-polymerization to yield a comb-like polymer with thiol-terminated, pendant aliphatic chains.

pictograms

Exclamation mark

signalword

Warning

hcodes

Hazard Classifications

Eye Irrit. 2

Storage Class

10 - Combustible liquids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable


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Qian Zhang et al.
Chemical communications (Cambridge, England), 48(61), 7542-7552 (2012-06-28)
(Bio)degradation in response to external stimuli (stimuli-responsive degradation, SRD) is a desired property in constructing novel nanostructured materials. For polymer-based multifunctional drug delivery applications, the degradation enables fast and controlled release of encapsulated therapeutic drugs from delivery vehicles in targeted
Amphiphilic block copolymers with pendant thiol groups in side chains by RAFT polymerization.
Hrsic E, et al.
Polymer, 54(2), 495-504 (2013)
Temperature-responsive mixed core nanoparticle properties determined by the composition of statistical and block copolymers in the core.
Kotsuchibashi Y, et al.
Polym. Chem., 6, 1693-1697 (2015)
Kanjiro Miyata et al.
Journal of the American Chemical Society, 126(8), 2355-2361 (2004-02-26)
A block catiomer polyplex, showing a high stability in the extracellular medium and an efficient release of plasmid DNA (pDNA) in the intracellular compartment, was developed by controlling both the cationic charge and disulfide cross-linking densities of the backbone polycations.

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