Itaconic acid
Product Code: AG-CN2-0426
Product Group: Natural Products and Extracts
Supplier: AdipoGen Life Sciences
| Code | Size | Price |
|---|
| AG-CN2-0426-G001 | 1 g | £30.00 |
Quantity:
| AG-CN2-0426-G005 | 5 g | £65.00 |
Quantity:
Prices exclude any Taxes / VAT
Overview
Regulatory Status: RUO
Shipping:
Ambient
Storage:
+4°C
Documents
Further Information
Alternate Names/Synonyms:
Itaconate; Methylenesuccinic acid; 2-Propene-1,2-dicarboxylic acid
Appearance:
White powder.
CAS:
97-65-4
EClass:
32160000
Form (Short):
liquid
GHS Symbol:
GHS07
Handling Advice:
Keep cool and dry.
Hazards:
H315, H319, H335
InChi:
InChI=1S/C5H6O4/c1-3(5(8)9)2-4(6)7/h1-2H2,(H,6,7)(H,8,9)
InChiKey:
GDMMRLCQKPSXQG-USNJAYOWSA-N
Long 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.
MDL:
MFCD00004260
Molecular Formula:
C5H6O4
Molecular Weight:
130.1
Package Type:
Vial
Precautions:
P261, P271, P280, P312
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-1beta secretion by generating ROS.
Purity:
>99%
Signal word:
Warning
SMILES:
OC(=O)CC(=C)C(O)=O
Solubility Chemicals:
Soluble in water, ethanol or methanol.
Transportation:
Non-hazardous
UNSPSC Category:
Natural Products/Extracts
UNSPSC Number:
12352200
Use & Stability:
Stable for at least 2 years after receipt when stored at +4°C.
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)
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