Skip to Content
Merck
All Photos(1)

Key Documents

88460

Sigma-Aldrich

Mercaptosuccinic acid

ReagentPlus®, ≥99.0% (HPLC)

Synonym(s):

Thiomalic acid

Sign Into View Organizational & Contract Pricing


About This Item

Linear Formula:
HOOCCH(SH)CH2COOH
CAS Number:
Molecular Weight:
150.15
Beilstein:
1099858
EC Number:
MDL number:
UNSPSC Code:
12352100
PubChem Substance ID:
NACRES:
NA.22

Quality Level

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

Looking for similar products? Visit Product Comparison Guide

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

Signal Word

Warning

Hazard Statements

Hazard Classifications

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

Target Organs

Respiratory system

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Choose from one of the most recent versions:

Certificates of Analysis (COA)

Lot/Batch Number

Don't see the Right Version?

If you require a particular version, you can look up a specific certificate by the Lot or Batch number.

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

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)
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.
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

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service