3-Bromopyruvic acid

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Names

[ Name ]:
3-Bromopyruvic acid

[Synonym ]:
Propanoic acid, 3-bromo-2-oxo-
3-Bromo-2-oxopropanoic acid
3-BROMOPYRUVIC ACID HYDRATE
EINECS 214-206-5
3-Bromo-2-oxopropionic Acid
3-BROMOPYRUVICACID(3-BROMOPYRUVATE)
3-BROMO-2-OXOPROPANOICACID
3-BromopYHuvic acid
3-Bromopyruvicacid
BROMOPYRUVIC ACID/3-BROMO-2-OXOPROPIONIC ACID
BROMOPYRUVICACID
MFCD00002587
PROPANOIC ACID,3-BROMO-2-OXO-
3-Bromopyruvic acid
3-BROMO-2-OXO-PROPIONIC ACID

Chemical & Physical Properties

[ Density]:
2.0±0.1 g/cm3

[ Boiling Point ]:
223.4±23.0 °C at 760 mmHg

[ Melting Point ]:
77-82 °C

[ Molecular Formula ]:
C₃H₃BrO₃

[ Molecular Weight ]:
166.958

[ Flash Point ]:
88.9±22.6 °C

[ Exact Mass ]:
165.926544

[ PSA ]:
54.37000

[ LogP ]:
-0.54

[ Vapour Pressure ]:
0.0±0.9 mmHg at 25°C

[ Index of Refraction ]:
1.521

MSDS

Click to get detail MSDS

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: UZ0840000

CHEMICAL NAME :: Pyruvic acid, bromo-

CAS REGISTRY NUMBER :: 1113-59-3

BEILSTEIN REFERENCE NO. :: 1746786

LAST UPDATED :: 199701

DATA ITEMS CITED :: 2

MOLECULAR FORMULA :: C3-H3-Br-O3

MOLECULAR WEIGHT :: 166.97

WISWESSER LINE NOTATION :: QVV1E

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 72 mg/kg

TOXIC EFFECTS :: Sense Organs and Special Senses (Eye) - lacrimation Lungs, Thorax, or Respiration - respiratory stimulation Gastrointestinal - changes in structure or function of salivary glands

REFERENCE :: JPETAB Journal of Pharmacology and Experimental Therapeutics. (Williams & Wilkins Co., 428 E. Preston St., Baltimore, MD 21202) V.1- 1909/10- Volume(issue)/page/year: 123,48,1958

Safety Information

[ Symbol ]:

GHS05

[ Signal Word ]:
Danger

[ Hazard Statements ]:
H314

[ Precautionary Statements ]:
P280-P305 + P351 + P338-P310

[ Personal Protective Equipment ]:
Eyeshields;Faceshields;full-face particle respirator type N100 (US);Gloves;respirator cartridge type N100 (US);type P1 (EN143) respirator filter;type P3 (EN 143) respirator cartridges

[ Hazard Codes ]:
C:Corrosive;

[ Risk Phrases ]:
R20/21/22;R34

[ Safety Phrases ]:
S26-S36/37/39-S45-S27

[ RIDADR ]:
UN 3261 8/PG 2

[ WGK Germany ]:
3

[ RTECS ]:
UZ0840000

[ Packaging Group ]:
II

[ Hazard Class ]:
8

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Hydroxypyruvic acid
5-methoxycarbonylimidazo[1,2-a]pyridine-2-carboxylic acid
meso-2,3-Dibromosuccinic acid
Succinic acid
Bromoacetic acid
2,3-Butanedione,1,4-dibromo-
BETA-HYDROXYPYRUVIC ACID LITHIUM SALT HYDRATE
2-(Ethoxycarbonyl)-1,3-thiazole-4-carboxylic acid
Pyruvic acid
2(1H)-Quinoxalinone,3-(bromomethyl)-

Articles

3-Bromopyruvate: A novel antifungal agent against the human pathogen Cryptococcus neoformans

Biochem. Biophys. Res. Commun. 434(2) , 322-7, (2013)

Highlights • We examined the antifungal activity of 3-bromopyruvic acid (3-BP). • 3-BP could be a novel antifungal agent against Cryptococcus neoformans. • 3-BP acts on C. neoformans through fast depl...

Inhibition of glucose turnover by 3-bromopyruvate counteracts pancreatic cancer stem cell features and sensitizes cells to gemcitabine.

Oncotarget 5(13) , 5177-89, (2014)

According to the cancer stem cell (CSC) hypothesis, the aggressive growth and early metastasis of pancreatic ductal adenocarcinoma (PDA) is due to the activity of CSCs, which are not targeted by curre...

Insights into the carboxyltransferase reaction of pyruvate carboxylase from the structures of bound product and intermediate analogs.

Biochem. Biophys. Res. Commun. 441(2) , 377-82, (2013)

Pyruvate carboxylase (PC) is a biotin-dependent enzyme that catalyzes the MgATP- and bicarbonate-dependent carboxylation of pyruvate to oxaloacetate, an important anaplerotic reaction in central metab...