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I4386

Sigma-Aldrich

Iodoacetic acid

≥98.0% (T)

Synonym(s):

2-Iodoacetic acid

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10 G
$59.40
25 G
$110.00
100 G
$300.60

About This Item

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

$59.40

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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,[1] serum proteins[2] and strawberry proteome samples extracted from different stages of ripened fruit.[3]
Reagent for the modification of cysteine residues in proteins.

Biochem/physiol Actions

Iodoacetic acid (IAA) blocks the thiol group of cysteine.[4] 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.[5] IAA is one of the iodinated disinfection byproducts in drinking water. It is cytotoxic to mammalian cells.[6]

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_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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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)
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)
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)
View All Related Papers

Questions

1–2 of 2 Questions  

  1. How can I determine the shelf life / expiration / retest date of this product?

    1 answer

    1. If this product has an expiration or retest date, it will be shown on the Certificate of Analysis (COA, CofA). If there is no retest or expiration date listed on the product's COA, we do not have suitable stability data to determine a shelf life. For these products, the only date on the COA will be the release date; a retest, expiration, or use-by-date will not be displayed.
      For all products, we recommend handling per defined conditions as printed in our product literature and website product descriptions. We recommend that products should be routinely inspected by customers to ensure they perform as expected.
      For products without retest or expiration dates, our standard warranty of 1 year from the date of shipment is applicable.
      For more information, please refer to the Product Dating Information document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/449/386/product-dating-information-mk.pdf

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  2. How is shipping temperature determined? And how is it related to the product storage temperature?

    1 answer

    1. Products may be shipped at a different temperature than the recommended long-term storage temperature. If the product quality is sensitive to short-term exposure to conditions other than the recommended long-term storage, it will be shipped on wet or dry-ice. If the product quality is NOT affected by short-term exposure to conditions other than the recommended long-term storage, it will be shipped at ambient temperature. As shipping routes are configured for minimum transit times, shipping at ambient temperature helps control shipping costs for our customers. For more information, please refer to the Storage and Transport Conditions document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/316/622/storage-transport-conditions-mk.pdf

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