Itaconic acid

Itaconic acid

Names
Preferred IUPAC name 2-Methylidenebutanedioic acid
Other names 2-Methylenesuccinic acid Methylenesuccinic acid[1] 1-Propene-2-3-dicarboxylic acid
Identifiers
CAS Number	97-65-4 Y
3D model (JSmol)	Interactive image
ChEBI	CHEBI:30838 Y
ChemSpider	789 Y
ECHA InfoCard	100.002.364
KEGG	C00490 Y
PubChem CID	811
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
SMILES O=C(O)C(=C)CC(=O)O
Properties
Chemical formula	C5H6O4
Molar mass	130.10 g·mol−1
Appearance	White solid
Density	1.63 g/cm3[1]
Melting point	162 to 164 °C (324 to 327 °F; 435 to 437 K) (decomposes)[1]
Solubility in water	1 g/12 mL[1]
Solubility in ethanol	1 g/5 mL[1]
Magnetic susceptibility (χ)	-57.57·10−6 cm3/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Y verify (what is YN ?)
Infobox references

Itaconic acid, or methylenesuccinic acid, is an organic compound. This dicarboxylic acid is a white solid that is soluble in water, ethanol, and acetone. The name itaconic was devised as an anagram of aconitic. Historically, itaconic acid was obtained by the distillation of citric acid, but currently it is produced by fermentation.

Laboratory synthesis and reactions

Dry distillation of citric acid affords itaconic anhydride, which readily undergoes hydrolysis to itaconic acid.^[2] Upon heating, itaconic anhydride isomerizes to citraconic acid anhydride, which can be hydrolyzed to citraconic acid (2-methylmaleic acid).^[3]

Production

Since the 1960s, it is produced industrially by the fermentation of carbohydrates such as glucose or molasses using fungi such as Aspergillus itaconicus or Aspergillus terreus.^[4]

For A. terreus the itaconate pathway is mostly elucidated. The generally accepted route for itaconate is via glycolysis, tricarboxylic acid cycle, and a decarboxylation of cis-aconitate to itaconate via cis-aconitate-decarboxylase.^[5]

The smut fungus Ustilago maydis uses an alternative route. Cis-aconitate is converted to the thermodynamically favoured trans-aconitate via aconitate-Δ-isomerase (Adi1).^[6] trans-Aconitate is further decarboxylated to itaconate by trans-aconitate-decarboxylase (Tad1).^[6]

Itaconic acid is also produced in cells of macrophage lineage and as such it has in vitro activity against bacteria expressing the enzyme isocitrate lyase such as Salmonella enterica and Mycobacterium tuberculosis.^[7]

However, cells of macrophage lineage have to "pay the price" for making itaconate, and they lose the ability to perform mitochondrial substrate-level phosphorylation,^[8]

Application

Itaconic acid 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.

References