Iodoacetic acid

Iodoacetic acid
Skeletal formula
Space-filling model
  Carbon, C
  Hydrogen
  Oxygen, O
  Iodine, I
Names
Preferred IUPAC name
Iodoacetic acid
Other names
2-Iodoacetic acid
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.000.537 Edit this at Wikidata
UNII
  • InChI=1S/C2H3IO2/c3-1-2(4)5/h1H2,(H,4,5) checkY
    Key: JDNTWHVOXJZDSN-UHFFFAOYSA-N checkY
  • InChI=1/C2H3IO2/c3-1-2(4)5/h1H2,(H,4,5)
    Key: JDNTWHVOXJZDSN-UHFFFAOYAA
  • C(C(=O)O)I
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]
GHS06: ToxicGHS05: Corrosive
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
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)

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]

  1. ^ Dippy, J. F. J.; Hughes, S. R. C.; Rozanski, A. (1959). "The dissociation constants of some symmetrically disubstituted succinic acids". Journal of the Chemical Society: 2492–2498. doi:10.1039/jr9590002492.
  2. ^ GHS: GESTIS 510268
  3. ^ Shorr, E.; Barker, S. B.; Malam, M. (1938-02-18). "The Influence of Iodoacetic Acid on the Respiratory Metabolism of Mammalian Tissues". Science. 87 (2251): 168–169. Bibcode:1938Sci....87..168S. doi:10.1126/science.87.2251.168. ISSN 0036-8075. PMID 17740354.
  4. ^ Lundsgaard, E., Biochem. Z., 217,162 (1930).
  5. ^ Layzer, Robert B. (1985-02-07). "McArdle's Disease in the 1980s". New England Journal of Medicine. 312 (6): 370–371. doi:10.1056/NEJM198502073120609. ISSN 0028-4793. PMID 3855500.