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Sigma-Aldrich

11-Mercaptoundecanoic acid

98%

Synonym(s):

MUA, MUDA

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About This Item

Linear Formula:
HS(CH2)10CO2H
CAS Number:
71310-21-9
Molecular Weight:
218.36
MDL number:
MFCD00022096
UNSPSC Code:
12352103
PubChem Substance ID:
329760593
NACRES:
NA.23

Assay

98%

form

solid

mp

46-50 °C (lit.)

storage temp.

2-8°C

SMILES string

OC(=O)CCCCCCCCCCS

InChI

1S/C11H22O2S/c12-11(13)9-7-5-3-1-2-4-6-8-10-14/h14H,1-10H2,(H,12,13)

InChI key

GWOLZNVIRIHJHB-UHFFFAOYSA-N

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General description

11-mercaptoundecanoic acid (MUA) has long alkane chains and carboxyl containing thiols that are highly packed and form a self-assembled monolayer (SAM). It modifies the surface of nanoparticles to facilitate their dispersion into water and solvent based mediums.

Application

MUA is used for the carboxylic acid functionalization of 1-dodecanethiol-protected gold nanoparticles (AuNPs) by Murray place-displacement reaction generally utilized in biomedical applications. It can also be used to modify the surface of platinum nanoparticles (PtNPs) by creating a ligand nano-assembly with a high surface coverage for use in surface-enhanced Raman spectroscopy (SERS). A single cell biochip platform can be developed utilizing a cell attachment technique with MUA forming a SAM that was attached to single cells. MUA may be used to prepare a tetrafluorophenyl-activated ester self-assembled monolayer to immobilize amine-modified oligonucleotides and DNA. It is also used to create 3D-assembled gold nanostructures for plasmonic biosensors.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H315,H319,H335

Hazard Classifications

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)

No data available

Flash Point(C)

No data available

Personal Protective Equipment

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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Development of single cell biochip platform based on silicon for multiple patch clamping technology.
2009 IEEE 3rd International Conference on Nano/Molecular Medicine and Engineering, 29(6), 138-141 (2009)
Thermogravimetry and evolved gas analysis for the investigation of ligand-exchange reaction in thiol-functionalized gold nanoparticles.
Locardi F, et al.
Journal of Analytical and Applied Pyrolysis, 132(5), 11-18 (2018)
Yonghai Song et al.
Microscopy research and technique, 68(2), 59-64 (2005-10-18)
Immobilized DNA on preformed 11-mercaptoundecanoic acids (MUDA) self-assembled monolayers (SAMs) on a gold (111) surface was bound by a divalent cation bridges was imaged by atomic force microscopy (AFM). The DNA immobilization was attributed to the formation of ionic bridges
Fabrication and characterisation of ligand-functionalised ultrapure monodispersed metal nanoparticle nanoassemblies employing advanced gas deposition technique.
Welearegay TG, et al.
Nanotechnology, 29(6), 065603-065603 (2018)
Matthew R Lockett et al.
Langmuir : the ACS journal of surfaces and colloids, 24(1), 69-75 (2007-12-01)
A tetrafluorophenyl (TFP) ester-terminated self-assembled monolayer (SAM) for the fabrication of DNA arrays on gold surfaces is described. Activated ester SAMs are desirable for biomolecule array fabrication because they readily react with amine-containing molecules to form a stable amide linkage.
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