Iodoacetic acid

Iodoacetic acid
	; Carbon, C Hydrogen Oxygen, O Iodine, I
Names
	Preferred IUPAC name Iodoacetic acid
	Other names 2-Iodoacetic acid
Identifiers
CAS Number	64-69-7 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:74571 ;
ChEMBL	ChEMBL376280 ;
ChemSpider	5050 ;
ECHA InfoCard	100.000.537
PubChem CID	5240;
UNII	WF5188V710 ;
CompTox Dashboard (EPA)	DTXSID5025445 ;
	InChI InChI=1S/C2H3IO2/c3-1-2(4)5/h1H2,(H,4,5) Key: JDNTWHVOXJZDSN-UHFFFAOYSA-N ; InChI=1/C2H3IO2/c3-1-2(4)5/h1H2,(H,4,5) Key: JDNTWHVOXJZDSN-UHFFFAOYAA;
	SMILES C(C(=O)O)I;
Properties
Chemical formula	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
Hazards
	GHS labelling:
Pictograms
Signal word	Danger
Hazard statements	H301, H314
Precautionary statements	P260, P280, P301+P310+P330, P303+P361+P353, P305+P351+P338, P310, P331
Safety data sheet (SDS)	Oxford MSDS
Related compounds
Related compounds	Acetic acid; Fluoroacetic acid; Chloroacetic acid; Bromoacetic acid; Tribromoacetic acidIodoacetamide; Ethyl bromoacetate;
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). verify (what is ?) Infobox references

Iodoacetic acid is an organic compound with the chemical formula I C H₂CO₂H. 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]

^ 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.
^ GHS: GESTIS 510268
^ 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.
^ Lundsgaard, E., Biochem. Z., 217,162 (1930).
^ 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.

[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.

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Names

Carbon, C Hydrogen Oxygen, O Iodine, I
Preferred IUPAC name Iodoacetic acid
Other names 2-Iodoacetic acid
Identifiers
CAS Number	64-69-7^Y
3D model (JSmol)	Interactive image
ChEBI	CHEBI:74571^N
ChEMBL	ChEMBL376280^Y
ChemSpider	5050^Y
ECHA InfoCard	100.000.537
PubChem CID	5240
UNII	WF5188V710^Y
CompTox Dashboard (EPA)	DTXSID5025445
InChI 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
SMILES C(C(=O)O)I
Properties
Chemical formula	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 (pK_a)	3.12^[1]
Hazards
GHS labelling:^[2]
Pictograms
Signal word	Danger
Hazard statements	H301, H314
Precautionary statements	P260, P280, P301+P310+P330, P303+P361+P353, P305+P351+P338, P310, P331
Safety data sheet (SDS)	Oxford MSDS
Related compounds
Related compounds	Acetic acid Fluoroacetic acid Chloroacetic acid Bromoacetic acid Tribromoacetic acid Iodoacetamide Ethyl bromoacetate
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