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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

product line

ReagentPlus®

assay

≥99.0% (HPLC)

form

powder

mp

145-154 °C
155-157 °C (lit.)

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

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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)
Surface Chemistry of Thiomalic Acid Adsorption on Planar Gold and Gold Nanoparticles.
Azca?rate J, et al.
Langmuir, 30(7), 1820-1826 (2014)
Shiho Ishihara et al.
Acta biomaterialia, 6(3), 830-835 (2009-10-20)
Loading and releasing protein in a controllable way is extremely important for the protein vehicles used in bone tissue engineering. To obtain a suitable carrier material for basic proteins, such as BMP or bFGF, hydroxyapatite particles containing mercaptosuccinic acid (mercaptosuccinic
Jia Zhang et al.
The Analyst, 136(19), 3865-3868 (2011-08-11)
A colorimetric probe based on 2-mercaptosuccinic acid-functionalized gold nanoparticles has been developed to exhibit selectivity towards Ca(2+), Sr(2+), and Ba(2+) ions over other metallic cations under specified conditions and finds its practical application in detecting Ca(2+) levels in water.
Kochaporn Chullasat et al.
Biosensors & bioelectronics, 26(11), 4571-4578 (2011-06-15)
A multilayer electrode modified with a self-assembled thiourea monolayer (SATUM) followed by gold nanoparticles (AuNPs), mercaptosuccinic acid (MSA) and antibody was investigated for the detection of ultra trace amount of a small molecule (chloramphenicol) in an impedimetric system. The formation
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