Bromopyruvic acid

Bromopyruvic acid is the organic compound with the formula BrCH₂COCO₂H. This colorless solid is the brominated derivative of pyruvic acid. It bears structural similarity to lactic acid and pyruvic acid. It has been investigated as a metabolic poison and an anticancer agent.^[1] Like other α-bromoketones, it is a strong alkylating agent.

Bromopyruvic acid

Names
Preferred IUPAC name 3-Bromo-2-oxopropanoic acid
Other names Bromopyruvate 3-Bromopyruvic acid 3-Bromopyruvate 3-BrPA 3BP 3-Br-Pyr
Identifiers
CAS Number	1113-59-3 Y
3D model (JSmol)	Interactive image Interactive image
ChEBI	CHEBI:131461 N
ChEMBL	ChEMBL177837 Y
ChemSpider	63850 Y
ECHA InfoCard	100.012.915
EC Number	214-206-5
PubChem CID	70684
UNII	63JMV04GRK Y
CompTox Dashboard (EPA)	DTXSID7040940
InChI InChI=1S/C3H3BrO3/c4-1-2(5)3(6)7/h1H2,(H,6,7) Y Key: PRRZDZJYSJLDBS-UHFFFAOYSA-N Y InChI=1/C3H3BrO3/c4-1-2(5)3(6)7/h1H2,(H,6,7) Key: PRRZDZJYSJLDBS-UHFFFAOYAU
SMILES C(C(=O)C(=O)O)Br BrCC(=O)C(=O)O
Properties
Chemical formula	C3H3BrO3
Molar mass	166.958 g·mol−1
Appearance	white solid
Melting point	79 to 82 °C (174 to 180 °F; 352 to 355 K) (hydrate)
Hazards
GHS labelling:
Pictograms
Signal word	Danger
Hazard statements	H290, H314
Precautionary statements	P260, P264, P280, P301+P330+P331, P303+P361+P353, P304+P340, P305+P351+P338, P310, P321, P363, P405, P501
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

Research

Bromopyruvic acid attracts attention in the biomedical research capacity through its potential to inhibit tyrosine phosphatases. Activity of such phosphatases is required for the activation of platelets, especially in a process called venous thromboembolism, a major cause of mortality during gastrointestinal cancer. Bromopyruvic-mediated inhibition of tyrosine phosphatases can counteract such thromboembolism and is investigated as novel angel to combat cancer-associated mortality. ^[2] The pyruvate transporter system can be used to deliver bromopyruvate inside trypanosomal cells. Once intracellular, the primary target of 3BP is glyceraldehyde-3-phosphate dehydrogenase, which is highly sensitive to inhibition by bromopyruvate.^[3] The pyruvate transporter system, which is known to be overexpressed in cancer cells, was later identified to be a monocarboxylate transporter called monocarboxylate transporter 1.^[4]