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Sigma-Aldrich

8-Mercaptooctanoic acid

95%

Synonym(s):

8-Thiooctanoic acid, MOA

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About This Item

Empirical Formula (Hill Notation):
C8H16O2S
CAS Number:
Molecular Weight:
176.28
MDL number:
UNSPSC Code:
12352103
PubChem Substance ID:
NACRES:
NA.23

assay

95%

refractive index

n20/D 1.4808

density

1.0326 g/mL at 25 °C

storage temp.

−20°C

SMILES string

OC(=O)CCCCCCCS

InChI

1S/C8H16O2S/c9-8(10)6-4-2-1-3-5-7-11/h11H,1-7H2,(H,9,10)

InChI key

FYEMIKRWWMYBFG-UHFFFAOYSA-N

General description

8-Mercaptooctanoic acid (MOA) is an carboxylic acid terminated alkanethiol that forms self-assembled monolayers (SAMs) that facilitate subsequent surface immobilization of other molecular species.
8-mercaptooctanoic acid (MOA) forms a self-assembled monolayer (SAM) on the surface of nanoparticles. MOA consists of thiol and carboxylic groups which helps in the surface treatment of different nanoparticles.

Application

MOA is a used as a SAM for surface modification of gold electrodes for quartz crystal microbalance (QCMB) measurement. It may be used as a monolayer that facilitates ferritin absorption on gold electrodes for uptake of excess iron in the cell. It may also be used for preparation of nitric oxide based gold nanoparticles (NO-AuNPs) for macrophage photo-thermal therapy under NIR irradiation.
MOA may form SAM that can be used in the surface modification of gold electrodes which are useful for the study of surface characteristics of ferritin. It may also be used to form SAM with hydrophilic end groups to be used as a protective coating on the electrodes for efficient electron transport in semiconductor devices.
This compound is used to produce hydrophilic SAMs. The resulting monolayers which are terminated with carboxylic acids can be further functionalized to introduce more complex end groups. Can also be used to form a protective barrier monolayer to allow deposition of a passivating oxide layer.

Other Notes

This product should be stored in the freezer, 0 to -20 °C

pictograms

Exclamation mark

signalword

Warning

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

target_organs

Respiratory system

Storage Class

10 - Combustible liquids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type ABEK (EN14387) respirator filter


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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Preiner, M. J.; Melosh, N. A.
Applied Physics Letters, 92, 213301-213301 (2008)
Chapman, R. G.; et al.
Journal of the American Chemical Society, 122, 8308-8308 (2000)
George Haddad et al.
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The microvascular endothelium of the kidney glomerulus is injured in Shiga-like toxigenic bacterial infection, genetic or acquired loss of complement regulatory protein function, and allo-immune responses of solid-organ or bone marrow transplantation. Existing models of diseases with glomerular endothelial cell
Surface-electrochemistry of ferritin adsorbed on 8-mercaptooctanoic acid-modified gold electrodes.
Ritzert NL, et al.
Electrochemical Communications, 11(4), 827-830 (2009)
Hongbo Guo et al.
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Articles

Recent research highlights tunable properties of inorganic nanoparticles, driving interest in optoelectronics.

Self-assembled monolayers (SAMs) have diverse applications; article compares benefits of alkylthiolates on gold SAM systems.

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

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