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Chemical Structure
Chemical Structure
Chemical Structure

Itaconic acid [97-65-4]

Research Use Only
AG-CN2-0426
AdipoGen Life Sciences
CAS Number97-65-4
Product group Chemicals
Estimated Purity>99%
Molecular Weight130.1
Price on request
Packing Size
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Overview

  • Supplier
    AdipoGen Life Sciences
  • Product Name
    Itaconic acid [97-65-4]
  • Delivery Days Customer
    10
  • CAS Number
    97-65-4
  • Certification
    Research Use Only
  • Estimated Purity
    >99%
  • Hazard Information
    Non-hazardous,Warning
  • Molecular Formula
    C5H6O4
  • Molecular Weight
    130.1
  • Scientific Description
    Chemical. CAS: 97-65-4. Formula: C5H6O4. MW: 130.1. Mammalian antibacterial metabolite. Inhibitor of isocitrate lyase, the key enzyme of the glyoxylate cycle, essential for bacterial growth. Antimicrobial. Antibacterial. Inhibits the growth of bacteria expressing isocitrate lyase. Phosphofructokinase (PFKII) inhibitor. Suppresses glycolysis by decreasing the level of fructose 2,6-bisphosphate, resulting in decreased visceral fat. Might be involved in the regulation of metabolism. One of the most highly induced metabolites in activated macrophages. Exerts anti-inflammatory effects in vitro and in vivo. Regulates succinate levels by inhibiting succinate dehydrogenase (SDH). Regulates mitochondrial respiration and cytokine production. Might induce inflammasome activation and consequently IL-1beta secretion by generating ROS. - Mammalian antibacterial metabolite. Inhibitor of isocitrate lyase, the key enzyme of the glyoxylate cycle, essential for bacterial growth [1, 4]. Antimicrobial. Antibacterial [1, 3, 4]. Inhibits the growth of bacteria expressing isocitrate lyase [1, 3, 4]. Phosphofructokinase (PFKII) inhibitor. Suppresses glycolysis by decreasing the level of fructose 2,6-bisphosphate, resulting in decreased visceral fat [2]. Might be involved in the regulation of metabolism [2]. One of the most highly induced metabolites in activated macrophages. Exerts anti-inflammatory effects in vitro and in vivo. Regulates succinate levels by inhibiting succinate dehydrogenase (SDH). Regulates mitochondrial respiration and cytokine production. Might induce inflammasome activation and consequently IL-1beta secretion by generating ROS.
  • SMILES
    OC(=O)CC(=C)C(O)=O
  • Storage Instruction
    2°C to 8°C
  • UNSPSC
    12352200

References

  • Itaconate, an isocitrate lyase-directed inhibitor in Pseudomonas indigofera: B.A. McFadden & S. Purohit; J. Bacteriol. 131, 136 (1977)
  • Itaconate reduces visceral fat by inhibiting fructose 2,6-bisphosphate synthesis in rat liver: A. Sakai, et al.; Nutrition 20, 997 (2004)
  • Itaconic acid is a mammalian metabolite induced during macrophage activation: C.L. Strelko, et al.; JACS 133, 16386 (2011)
  • Immune-responsive gene 1 protein links metabolism to immunity by catalyzing itaconic acid production: A. Michelucci, et al.; PNAS 110, 7820 (2013)
  • Itaconate links inhibition of succinate dehydrogenase with macrophage metabolic remodeling and regulation of inflammation: V. Lampropoulou, et al.; Cell Metab. 24, 158 (2016)
  • Food fight: Role of itaconate and other metabolites in antimicrobial defense: H.H. Luan & R. Medzhitov; Cell Metab. 24, 379 (2016)