Itaconic acid

More Information
Product Details
Synonyms	Itaconate; Methylenesuccinic acid; 2-Propene-1,2-dicarboxylic acid
Product Type	Chemical
Properties
Formula	C₅H₆O₄
MW	130.1
CAS	97-65-4
Purity Chemicals	≥99%
Appearance	White powder.
Solubility	Soluble in water, ethanol or methanol.
InChi Key	GDMMRLCQKPSXQG-USNJAYOWSA-N
Smiles	OC(=O)CC(=C)C(O)=O
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
MSDS	Download PDF
Product Specification Sheet
Datasheet	Download PDF

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

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)
Itaconate is an anti-inflammatory metabolite that activates Nrf2 via alkylation of KEAP1: E.L. Mills, et al.; Nature 556, 113 (2018)
Itaconate Suppresses the Activation of Mitochondrial NLRP3 Inflammasome and Oxidative Stress in Allergic Airway Inflammation: Q-M. Xie, et al.; Antioxidants 12, 489 (2023)

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