![]() | This article may be too technical for most readers to understand.(April 2024) |
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Names | |
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Preferred IUPAC name
Iodoacetic acid | |
Other names
2-Iodoacetic acid
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Identifiers | |
3D model (JSmol)
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ChEBI | |
ChEMBL | |
ChemSpider | |
ECHA InfoCard | 100.000.537 |
PubChem CID
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UNII | |
CompTox Dashboard (EPA)
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Properties | |
ICH2CO2H | |
Molar mass | 185.948 g·mol−1 |
Melting point | 81 °C (178 °F; 354 K) |
Boiling point | 208 °C (406 °F; 481 K) |
Acidity (pKa) | 3.12[1] |
Hazards | |
GHS labelling:[2] | |
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Danger | |
H301, H314 | |
P260, P280, P301+P310+P330, P303+P361+P353, P305+P351+P338, P310, P331 | |
Safety data sheet (SDS) | Oxford MSDS |
Related compounds | |
Related compounds
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Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Iodoacetic acid is an organic compound with the chemical formula ICH2CO2H. It is a derivative of acetic acid. It is a toxic compound, because, like many alkyl halides, it is an alkylating agent.
It reacts with cysteine residues in proteins. It is often used to modify −SH groups to prevent the re-formation of disulfide bonds after the reduction of cystine residues to cysteine during protein sequencing.
In 1929, Dr. Einar Lundsgaard (1899-1968) discovered that muscle poisoned in vitro with iodoacetic acid is unable to produce lactate as glycolysis from muscle glycogen is blocked, causing the muscle to result in an electrically silent contracture.[3][4][clarification needed] It was remembering this discovery, that lead Dr. Brian McArdle in 1951, to speculate that one of his patients that had electromyographically silent muscle contractures brought on by high-intensity aerobic activity and anaerobic activity must have a defective muscle glycogen mechanism.[5]
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