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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:
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

Signal Word

Warning

Hazard Statements

H302,H315,H319,H335

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

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Certificates of Analysis (COA)

Lot/Batch Number
BCCM8228
BCCL3637
BCCM1065
BCCM5835
BCCM0135

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  1. Which document(s) contains shelf-life or expiration date information for a given product?

    If available for a given product, the recommended re-test date or the expiration date can be found on the Certificate of Analysis.

  2. How do I get lot-specific information or a Certificate of Analysis?

    The lot specific COA document can be found by entering the lot number above under the "Documents" section.

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    Transportation information can be found in Section 14 of the product's (M)SDS.To access the shipping information for this material, use the link on the product detail page for the product. 

  5. Is Product 88460, Mercaptosuccinic acid, a racemic mixture?  

    Yes, Product 88460, Mercaptosuccinic acid is a racemic mixture.

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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)
Achala de Mel et al.
Regenerative medicine, 7(3), 335-347 (2012-05-19)
This study aimed to live monitor the degree of endothelial progenitor cell (EPC) integration onto tissue-engineering scaffolds by conjugating relevant antibodies to quantum dots (QDs). Biocompatible mercaptosuccinic acid-coated QDs were functionalized with two different antibodies to EPC (CD133 with QDs
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.
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
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