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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:
64-69-7
Molecular Weight:
185.95
Beilstein:
1739079
EC Number:
200-590-1
MDL number:
MFCD00002685
UNSPSC Code:
12352106
PubChem Substance ID:
24896056
NACRES:
NA.77

biological source

synthetic

Quality Level

200

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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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

Skull and crossbonesCorrosion
GHS06,GHS05

Signal Word

Danger

Hazard Statements

H301,H314

Hazard Classifications

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

WGK

WGK 1

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Information

危险化学品

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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Drinking water disinfection byproduct iodoacetic acid induces tumorigenic transformation of NIH3T3 cells
Wei X, et al.
Environmental Science & Technology, 47(11), 5913-5920 (2013)
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)
Antitumor activities of iodoacetate and dimethylsulphoxide against solid Ehrlich carcinoma growth in mice
Fahim FA, et al.
Biological Research, 36(2), 253-262 (2003)
Development of candidate biomarkers for pancreatic ductal adenocarcinoma using multiple reaction monitoring
Yu J, et al.
Biotechnology and Bioprocess Engineering: BBE, 18(5), 1038-1047 (2013)
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)
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