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I4386

Sigma-Aldrich

Iodoacetic acid

≥98.0% (T)

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Synonym(s):
2-Iodoacetic acid
Linear Formula:
ICH2CO2H
CAS Number:
Molecular Weight:
185.95
Beilstein/REAXYS Number:
1739079
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.77

biological source

synthetic

Quality Level

assay

≥98.0% (T)

form

powder or flakes

color

white to yellow

mp

77-79 °C (lit.)

solubility

H2O: soluble, clear to hazy

storage temp.

−20°C

SMILES string

OC(=O)CI

InChI

1S/C2H3IO2/c3-1-2(4)5/h1H2,(H,4,5)

InChI key

JDNTWHVOXJZDSN-UHFFFAOYSA-N

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1 of 4

This Item
I2512I914857858
vibrant-m

I4386

Iodoacetic acid

-
vibrant-m

I2512

Sodium iodoacetate

-
vibrant-m

I9148

Sodium iodoacetate

-
vibrant-m

57858

Sodium iodoacetate

Premium Grade
assay

≥98.0% (T)

assay

≥98%

assay

≥98%

assay

≥99.5% (NT)

biological source

synthetic

biological source

synthetic (organic)

biological source

synthetic (organic)

biological source

-

color

white to yellow

color

-

color

-

color

-

form

powder or flakes

form

powder

form

powder

form

-

mp

77-79 °C (lit.)

mp

208 °C (dec.) (lit.)

mp

208 °C (dec.) (lit.)

mp

208 °C (dec.) (lit.)

Application

Iodoacetic acid has been used as an alkylating agent for antibody AR37, serum proteins and strawberry proteome samples extracted from different stages of ripened fruit.
Reagent for the modification of cysteine residues in proteins.

Biochem/physiol Actions

Iodoacetic acid (IAA) blocks the thiol group of cysteine. IAA inhibits glyceraldehyde-3-phosphate dehydrogenase (G3PDH) by interacting with sulfhydryl group of the active site cysteine. IAA inhibits the progression of solid Ehrlich carcinoma. IAA is one of the iodinated disinfection byproducts in drinking water. It is cytotoxic to mammalian cells.

pictograms

CorrosionSkull and crossbones

signalword

Danger

Hazard Classifications

Acute Tox. 3 Oral - Eye Dam. 1 - Skin Corr. 1A

Storage Class

6.1A - Combustible, acute toxic Cat. 1 and 2 / very toxic hazardous materials

wgk_germany

WGK 1

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Faceshields, Gloves, type P3 (EN 143) respirator cartridges


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Database-independent Protein Sequencing (DiPS) Enables Full-length de Novo Protein and Antibody Sequence Determination
Savidor A, et al.
Molecular and Cellular Proteomics, 16(6), 1151-1161 (2017)
Drinking water disinfection byproduct iodoacetic acid induces tumorigenic transformation of NIH3T3 cells
Wei X, et al.
Environmental Science & Technology, 47(11), 5913-5920 (2013)
Antitumor activities of iodoacetate and dimethylsulphoxide against solid Ehrlich carcinoma growth in mice
Fahim FA, et al.
Biological Research, 36(2), 253-262 (2003)
Quantitative proteomic investigation employing stable isotope labeling by peptide dimethylation on proteins of strawberry fruit at different ripening stages
Li L, et al.
Journal of Proteomics, 94(5), 219-239 (2013)
Carboxymethylation of cysteine using iodoacetamide/iodoacetic acid
The Protein Protocols Handbook, 455-456 (2002)

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