Itaconic acid

Itaconic acid
IUPAC name 2-Methylidenebutanedioic acid
Other names Methylenesuccinic acid
Identifiers
CAS number	97-65-4 Y
PubChem	811
ChemSpider	789 Y
KEGG	C00490 Y
ChEBI	CHEBI:30838 Y
ChEMBL	CHEMBL359159 Y
Jmol-3D images	Image 1
SMILES O=C(O)C(=C)CC(=O)O
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
Properties
Molecular formula	C5H6O4
Molar mass	130.1 g mol−1
Appearance	White crystals
Density	1.63 g/cm3
Melting point	162-164 °C, 435-437 K, 324-327 °F (decomp.)
Solubility in water	1 g/12 mL
Solubility in ethanol	1 g/5 mL
Y (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
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 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 styrene-butadiene-acrylonitrile and acrylate latexes with applications in the paper and architectural coating industry.

Since Cargill, the last of the U.S. companies to manufacture itaconic acid, exited the business, itaconic acid has mainly been procured by importing the product directly from China where it is still made by several different companies.