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Itaconic acid

AG-CN2-0426-G001 1 g INQ
AG-CN2-0426-G005 5 g INQ
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Additional Information

Product Data
Synonyms Methylenesuccinic acid; 2-Propene-1,2-dicarboxylic acid; Itaconate
Properties
Formula C5H6O4
MW 130.1
CAS 97-65-4
Purity ≥99%
Appearance White powder.
Solubility Soluble in water, ethanol or methanol.
InChi Key GDMMRLCQKPSXQG-USNJAYOWSA-N
Product Type Chemical
Shipping and Handling
Shipping AMBIENT
Short Term Storage +4°C
Long Term Storage +4°C
Handling Advice Keep cool and dry.
Use/Stability Stable for at least 2 years after receipt when stored at +4°C.
Documents
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Product Description

  • 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-1β secretion by generating ROS.

Product References

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