Itaconic acid

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Itaconic acid
Skeletal formula
Ball-and-stick model
Identifiers
CAS number 97-65-4 YesY
PubChem 811
ChemSpider 789 YesY
KEGG C00490 YesY
ChEBI CHEBI:30838 YesY
ChEMBL CHEMBL359159 YesY
Jmol-3D images Image 1
Properties
Molecular formula C5H6O4
Molar mass 130.10 g mol−1
Appearance White crystals
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]
Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
 YesY (verify) (what is: YesY/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[edit]

  1. ^ a b c d e Merck Index, 11th Edition, 5130
  2. ^ . doi:10.1073/pnas.1218599110.  Missing or empty |title= (help)