Iodoacetic acid

Iodoacetic acid is a derivative of acetic acid. It is a toxic compound, because, like many alkyl halides, it is an alkylating agent.

Iodoacetic acid
Names
Preferred IUPAC name
Iodoacetic acid
Other names
2-Iodoacetic acid
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.000.537
UNII
  • InChI=1S/C2H3IO2/c3-1-2(4)5/h1H2,(H,4,5) Y
    Key: JDNTWHVOXJZDSN-UHFFFAOYSA-N Y
  • InChI=1/C2H3IO2/c3-1-2(4)5/h1H2,(H,4,5)
    Key: JDNTWHVOXJZDSN-UHFFFAOYAA
  • C(C(=O)O)I
Properties
C2H3IO2
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
Hazards
GHS labelling:
Danger
H301, H314
P260, P280, P301+P310+P330, P303+P361+P353, P305+P351+P338, P310, P331
Safety data sheet (SDS) Oxford MSDS
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N verify (what is YN ?)
Infobox references

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. 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.

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