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Merck
CN

I4386

Iodoacetic acid

≥98.0% (T)

Synonym(s):

2-Iodoacetic acid

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About This Item

Linear Formula:
ICH2CO2H
CAS Number:
64-69-7
Molecular Weight:
185.95
UNSPSC Code:
12352106
NACRES:
NA.77
PubChem Substance ID:
24896056
EC Number:
200-590-1
Beilstein/REAXYS Number:
1739079
MDL number:
MFCD00002685

Key Documents

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Product Name

Iodoacetic acid, ≥98.0% (T)

Quality Level

200

InChI key

JDNTWHVOXJZDSN-UHFFFAOYSA-N

InChI

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

SMILES string

OC(=O)CI

biological source

synthetic

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

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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

signalword

Danger

hcodes

H301,H314

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

WGK 1

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

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

Regulatory Information

危险化学品
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Certificates of Analysis (COA)

Lot/Batch Number
BCCM4203
BCCM4536
BCCH8786
BCCJ1462
BCCG9968

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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)
Carboxymethylation of cysteine using iodoacetamide/iodoacetic acid
The Protein Protocols Handbook, 455-456 (2002)
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)
Antitumor activities of iodoacetate and dimethylsulphoxide against solid Ehrlich carcinoma growth in mice
Fahim FA, et al.
Biological Research, 36(2), 253-262 (2003)
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