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88460

Sigma-Aldrich

Mercaptosuccinic acid

ReagentPlus®, ≥99.0% (HPLC)

Synonym(s):

Thiomalic acid

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About This Item

Linear Formula:
HOOCCH(SH)CH2COOH
CAS Number:
70-49-5
Molecular Weight:
150.15
Beilstein/REAXYS Number:
1099858
EC Number:
200-736-4
MDL number:
MFCD00004860
UNSPSC Code:
12352100
PubChem Substance ID:
57653308
NACRES:
NA.22

Quality Level

200

product line

ReagentPlus®

assay

≥99.0% (HPLC)

form

powder

mp

145-154 °C
155-157 °C (lit.)

functional group

carboxylic acid
thiol

SMILES string

OC(=O)CC(S)C(O)=O

InChI

1S/C4H6O4S/c5-3(6)1-2(9)4(7)8/h2,9H,1H2,(H,5,6)(H,7,8)

InChI key

NJRXVEJTAYWCQJ-UHFFFAOYSA-N

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General description

Mercaptosuccinic acid is a hydrophilic thiol that can form thiomalate self-assembled monolayers when adsorbed on Au(III) surface.

Application

Mercaptosuccinic acid has been used as a dopant for the synthesis of carbon nanodots from citric acid. It can be used as a capping and reducing agent to synthesize monolayer-capped gold nanoparticles.

Legal Information

ReagentPlus is a registered trademark of Merck KGaA, Darmstadt, Germany

pictograms

Exclamation mark
GHS07

signalword

Warning

Hazard Classifications

Acute Tox. 4 Oral - Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

target_organs

Respiratory system

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
BCCL3637
BCCM1065
BCCM5835
BCCM0135
BCCK2515

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Surface Chemistry of Thiomalic Acid Adsorption on Planar Gold and Gold Nanoparticles.
Azca?rate J, et al.
Langmuir, 30(7), 1820-1826 (2014)
A switchable peroxidase mimic derived from the reversible co-assembly of cytochrome c and carbon dots.
Essner J, et al.
Journal of Materials Chemistry, 4(12), 2163-2170 (2016)
M S Bootharaju et al.
Langmuir : the ACS journal of surfaces and colloids, 27(13), 8134-8143 (2011-06-15)
We report the chemical interactions of unsupported and alumina-supported Ag(7) and Ag(8) clusters protected with MSA (mercaptosuccinic acid) with heavy metal ions Hg(II), Cd(II), and Pb(II) in water at different concentrations. The investigation was carried out to determine the feasibility
Siqiu Ye et al.
The Analyst, 137(14), 3365-3371 (2012-06-05)
A colorimetric sensor for Cu(II) ions has been developed based on mixed self-assembled monolayers (SAMs) modified gold nanoparticles (AuNPs). The AuNPs were modified with mixed SAMs consisting of mercaptosuccinic acid and the product of electrochemically triggered Michael addition reaction of
Ming Yan et al.
Toxicology, 282(3), 94-103 (2011-02-05)
Quantum dots (QDs), as novel bioimaging and drug delivery agents, are generally introduced into vascular system by injection, and thus directly exposed to vascular endothelial cells (ECs). However, the adverse effects of QDs on ECs are poorly understood. In this
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