Bromopyruvic acid (3-BP) - ≥96% , CAS No.1113-59-3

CAS: 1113-59-3 Cat. No.: B120321 Molecular Weight: 166.96 Beilstein Registry Number: 1746786 EC Number: 214-206-5

GRADE & PURITY ≥96%

Synonyms

AS-16146 | B1153 | 3-bromopyruvic acid | bromo-2-oxopropanoic acid | bromopyruvic acid | Bromopyruvic acid, >=97.0% (T) | J-650255 | 3-bromopyruvate | BPV | J-511892 | 3-bromo-2-oxopropanoic acid | AKOS015892643 | AM84337 | EINECS 214-206-5 | 3-BP | 3-BrP

Storage

Store at 2-8°C,Argon charged

Shipped In

Wet ice

Overview

3-Bromopyruvic acid is a brominated derivative of pyruvic acid , which inhibits HXK II (hexokinase II) in cancer cells. As a result of this inhibition the cells are unable to metabolize glucose into ATP directly. Studies conducted on MCF-7 breast cancer cells show that 3-Bromopyruvic acid hydrate reduces the expression of Bcl-2, c-Myc and mutant p53, which are involved in the cell death signal transduction pathway. Alternate studies indicate that 3-Bromopyruvic acid hydrate is a very selective antibiotic, inhibiting the growth of certain yeasts.
Affinity label for cysteine residues; Cross-linker between nucleic acids and proteins

Specifications

Synonyms

AS-16146 | B1153 | 3-bromopyruvic acid | bromo-2-oxopropanoic acid | bromopyruvic acid | Bromopyruvic acid, >=97.0% (T) | J-650255 | 3-bromopyruvate | BPV | J-511892 | 3-bromo-2-oxopropanoic acid | AKOS015892643 | AM84337 | EINECS 214-206-5 | 3-BP | 3-BrP

Specifications & Purity

≥96%

Biochemical and Physiological Mechanisms

Hexokinase II inhibitor. Antitumor agent. Inhibits glutathione S-transferase and SOD. Pyruvic acid derivative. Induces oxidative stress. Induces S and G2/M cell cycle arrest. Shows antiproliferative effects. Shows antitumor and antimicrobial

Storage

Store at 2-8°C, Argon charged

Shipped In

Wet ice

This product requires cold chain shipping. Ground and other economy services are not available.

Note

Wherever possible, you should prepare and use solutions on the same day. However, if you need to make up stock solutions in advance, we recommend that you store the solution as aliquots in tightly sealed vials at -20°C. Generally, these will be useable for up to one month. Before use, and prior to opening the vial we recommend that you allow your product to equilibrate to room temperature for at least 1 hour. Need more advice on solubility, usage and handling? Please visit our frequently asked questions (FAQ) page for more details.

Purity

≥96%

Names and Identifiers

• Pubchem Sid: 504754555
• Pubchem Sid Url: https://pubchem.ncbi.nlm.nih.gov/substance/504754555
• Canonical Smiles: C(C(=O)C(=O)O)Br
• IUPAC Name: 3-bromo-2-oxopropanoic acid
• InChIKey: PRRZDZJYSJLDBS-UHFFFAOYSA-N
• INCHI: 1S/C3H3BrO3/c4-1-2(5)3(6)7/h1H2,(H,6,7)
• Isomeric SMILES: C(C(=O)C(=O)O)Br
• WGK Germany: 3
• RTECS: UZ0840000
• Molecular Weight: 166.96
• Beilstein: 1746786
• Reaxy-Rn: 1746786
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=1746786&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Organic acids and derivatives
    • Class Keto acids and derivatives
      • Subclass Alpha-keto acids and derivatives

• Kingdom: Organic compounds
• Superclass: Organic acids and derivatives
• Class: Keto acids and derivatives
• Subclass: Alpha-keto acids and derivatives
• Intermediate Tree Nodes: Not available
• Direct Parent: Alpha-keto acids and derivatives
• Alternative Parents: Alpha-hydroxy ketones Alpha-haloketones Monocarboxylic acids and derivatives Carboxylic acids Organobromides Organic oxides Hydrocarbon derivatives Alkyl bromides
• Molecular Framework: Aliphatic acyclic compounds
• Substituents: Alpha-keto acid - Alpha-haloketone - Alpha-hydroxy ketone - Ketone - Monocarboxylic acid or derivatives - Carboxylic acid - Carboxylic acid derivative - Organooxygen compound - Organobromide - Organohalogen compound - Carbonyl group - Organic oxide - Organic oxygen compound - Alkyl halide - Alkyl bromide - Hydrocarbon derivative - Aliphatic acyclic compound
• Description: This compound belongs to the class of organic compounds known as alpha-keto acids and derivatives. These are organic compounds containing an aldehyde substituted with a keto group on the adjacent carbon.
• External Descriptors: Not available

Data sources

1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.

DOI: 10.1186/s13321-016-0174-y

Associated Targets(non-human)

Hdac6 Histone deacetylase 6 (222 Activities)

Discover Target: Hdac6

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

dapA Dihydrodipicolinate synthase (65 Activities)

Discover Target: dapA

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Escherichia coli (133304 Activities)

Explore this target

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

rep Replicase polyprotein 1ab (378 Activities)

Discover Target: rep

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

icl1 Isocitrate lyase 1 (45 Activities)

Discover Target: icl1

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Mechanisms of Action

Chemical and Physical Properties

• Sensitivity: Air Sensitive,Hygroscopic,Heat Sensitive
• Melt Point(°C): 77°C
• Molecular Weight: 166.960 g/mol
• XLogP3: 0.500
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 165.927 Da
• Monoisotopic Mass: 165.927 Da
• Topological Polar Surface Area: 54.400 Ų
• Heavy Atom Count: 7
• Formal Charge: 0
• Complexity: 98.400
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 0
• Undefined Atom Stereocenter Count: 0
• Defined Bond Stereocenter Count: 0
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 0
• Covalently-Bonded Unit Count: 1

References

1. Xuan Meng, Lin Wang, Ning Zhao, Delong Zhao, Yongli Shen, Yuan Yao, Wenjie Jing, Shuli Man, Yujie Dai, Yanjun Zhao.  (2023)  Stimuli-responsive cancer nanomedicines inhibit glycolysis and impair redox homeostasis.  Acta Biomaterialia,      [PMID:37343908] [10.1016/j.actbio.2023.06.016]

2. Yongli Shen, Lin Wang, Binglong Ji, Xinlei Lu, Delong Zhao, Yujie Dai, Xuan Meng.  (2024)  Stimulus-responsive nanomedicine mediated by metabolic intervention mechanisms to amplify redox anticancer therapy.  CHEMICAL ENGINEERING JOURNAL,      [PMID:] [10.1016/j.cej.2024.150130]

3. Gongyuan Zhang, Tom Albrow-Owen, Wenjun Peng, Xin Liang, Xianming Zhang, Pan Wang, Dawei Di, Shurong Dong, Jikui Luo, Guo Wang, Hongfeng Mu, Qian Zhao, Xuhan Guo, Qi Jie Wang, Tawfique Hasan, Zongyin Yang.  (2025)  Stress-engineered ultra-broadband spectrometers.  Science Advances,  11  (20):   [PMID:40367181] [10.1126/sciadv.adu4225]

4. Chao Liu, Yanqiao Ren, Can Hong, Xuyu Li, Mengqing Guo, Le Zhao, Yan Liu, Chuansheng Zheng, Xiangliang Yang, Yanbing Zhao.  (2026)  Radiofrequency-responsive liposomal hydrogels loaded 3-bromopyruvate energizes artery embolization on liver cancer.  CHEMICAL ENGINEERING JOURNAL,      [PMID:] [10.1016/j.cej.2026.174632]

5. Tu Maopu, Deng Xiaoyu, Zhou Zhiyong, Li Xiaodong, Mao Shengxun, Lai Bin, Pang Lisong, Zhong Qilin, Cao Jiaqing, Liu Haipeng, Ouyang Xi.  (2026)  Multifunctional copper-based nanoparticles potentiate colorectal cancer immunotherapy via synergistic metabolic remodeling and cGAS-STING pathway activation.  JOURNAL OF NANOBIOTECHNOLOGY,      [PMID:] [10.1186/s12951-026-04267-8]