Itaconic acid

Itaconic acid

Names
IUPAC name 2-Methylidenebutanedioic acid
Other names Methylenesuccinic acid;[1] 1-Propene-2-3-dicarboxylic acid
Identifiers
CAS Registry Number	97-65-4 Y
ChEBI	CHEBI:30838 Y
ChEMBL	ChEMBL359159 Y
ChemSpider	789 Y
InChI InChI=1S/C5H6O4/c1-3(5(8)9)2-4(6)7/h1-2H2,(H,6,7)(H,8,9) Y Key: LVHBHZANLOWSRM-UHFFFAOYSA-N Y InChI=1/C5H6O4/c1-3(5(8)9)2-4(6)7/h1-2H2,(H,6,7)(H,8,9) Key: LVHBHZANLOWSRM-UHFFFAOYAS
Jmol-3D images	Image
KEGG	C00490 Y
PubChem	811
SMILES O=C(O)C(=C)CC(=O)O
Properties
Molecular formula	C5H6O4
Molar mass	130.10 g·mol−1
Appearance	White crystals
Density	1.63 g/cm3[1]
Melting point	162 °C (324 °F; 435 K) (decomposes)[1]
Solubility in water	1 g/12 mL[1]
Solubility in ethanol	1 g/5 mL[1]
Except where noted otherwise, data is given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
Y verify (what is: Y/N?)
Infobox references

Itaconic acid, or methylenesuccinic acid, is an organic compound. Itaconic acid is a white crystalline powder. Itaconic acid is a naturally occurring compound, non-toxic, and readily biodegradable. The name itaconic was devised as an anagram of aconitic.

Historically, itaconic acid was obtained by the distillation of citric acid. Since the 1960s, it is produced industrially by the fermentation of carbohydrates such as glucose using Aspergillus terreus. As such, it is a fully sustainable industrial building block. It is primarily used as a co-monomer in the production of acrylonitrile-butadiene-styrene and acrylate latexes with applications in the paper and architectural coating industry.

Itaconic acid has in vitro activity against bacteria expressing the enzyme isocitrate lyase such as Salmonella enterica and Mycobacterium tuberculosis.^[2]

References