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675075

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

Quality Level

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

Signal Word

Warning

Hazard Statements

Hazard Classifications

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

Target Organs

Respiratory system

Storage Class Code

10 - Combustible liquids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

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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Chapman, R. G.; et al.
Journal of the American Chemical Society, 122, 8308-8308 (2000)
Preiner, M. J.; Melosh, N. A.
Applied Physics Letters, 92, 213301-213301 (2008)
George Haddad et al.
PloS one, 8(10), e78244-e78244 (2013-10-22)
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
Active carboxylic acid-terminated alkanethiol self-assembled monolayers on gold bead electrodes for immobilization of cytochromes c.
Tanimura R, et al.
Electrochemical and Solid-State Letters, 5(12), E67-E70 (2002)
Anna Paula V Moura et al.
ACS central science, 3(9), 1026-1031 (2017-10-06)
Secreted and surface-displayed carbohydrates are essential for virulence and viability of many parasites, including for immune system evasion. We have identified the α-Gal trisaccharide epitope on the surface of the protozoan parasites

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