Itaconic acid is a precursor to synthetic polymers, chemicals and fuels that can be synthesized by fungi. Itaconic acid is also a macrophage-specific metabolite. Itaconic acid mediates cross-talk between macrophage metabolism and peritoneal tumors.

Physicochemical Properties

Molecular Formula	C5H6O4
Molecular Weight	130.10
Exact Mass	130.026
CAS #	97-65-4
Related CAS #	Itaconic acid-13C5;2095777-38-9
PubChem CID	811
Appearance	White to off-white solid powder
Density	1.4±0.1 g/cm3
Boiling Point	381.4±25.0 °C at 760 mmHg
Melting Point	165-168 °C(lit.)
Flash Point	198.7±19.7 °C
Vapour Pressure	0.0±1.9 mmHg at 25°C
Index of Refraction	1.498
LogP	0.38
Hydrogen Bond Donor Count	2
Hydrogen Bond Acceptor Count	4
Rotatable Bond Count	3
Heavy Atom Count	9
Complexity	158
Defined Atom Stereocenter Count	0
InChi Key	LVHBHZANLOWSRM-UHFFFAOYSA-N
InChi Code	InChI=1S/C5H6O4/c1-3(5(8)9)2-4(6)7/h1-2H2,(H,6,7)(H,8,9)
Chemical Name	2-methylidenebutanedioic acid
HS Tariff Code	2934.99.9001
Storage	Powder-20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month Note: Please store this product in a sealed and protected environment, avoid exposure to moisture.
Shipping Condition	Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)

Biological Activity

Targets	Human Endogenous Metabolite
References	[1]. Itaconic acid mediates crosstalk between macrophage metabolism and peritoneal tumors. J Clin Invest. 2018 Aug 31;128(9):3794-3805. [2]. Itaconic acid production in microorganisms. Biotechnol Lett. 2018 Mar;40(3):455-464. [3]. Itaconic acid induces ferroptosis by activating ferritinophagy. Biochem Biophys Res Commun. 2021 Oct 25;583:56-62. [4]. Itaconic acid exerts anti-inflammatory and antibacterial effects via promoting pentose phosphate pathway to produce ROS. Sci Rep. 2021 Sep 13;11(1):18173. [5]. Effects of itaconic acid on neuronal viability and brain mitochondrial functions. J Bioenerg Biomembr. 2021 Oct;53(5):499-511.
Additional Infomation	Itaconic acid is a dicarboxylic acid that is methacrylic acid in which one of the methyl hydrogens is substituted by a carboxylic acid group. It has a role as a fungal metabolite and a human metabolite. It is a dicarboxylic acid, an olefinic compound and a dicarboxylic fatty acid. It is functionally related to a succinic acid. It is a conjugate acid of an itaconate(2-). Itaconic acid is a metabolite found in or produced by Escherichia coli (strain K12, MG1655). Itaconic acid has been reported in Solanum tuberosum, Ustilago maydis, and other organisms with data available.

Solubility Data

Solubility (In Vitro)	H2O :~27.78 mg/mL (~213.53 mM)
Solubility (In Vivo)	Solubility in Formulation 1: 25 mg/mL (192.16 mM) in PBS (add these co-solvents sequentially from left to right, and one by one), clear solution; with sonication.  (Please use freshly prepared in vivo formulations for optimal results.)

Preparing Stock Solutions		1 mg	5 mg	10 mg
	1 mM	7.6864 mL	38.4320 mL	76.8640 mL
	5 mM	1.5373 mL	7.6864 mL	15.3728 mL
	10 mM	0.7686 mL	3.8432 mL	7.6864 mL

*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.