Itaconic acid

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Itaconic acid
Skeletal formula
Ball-and-stick model
Names
IUPAC name
2-Methylidenebutanedioic acid
Other names
Methylenesuccinic acid;[1] 1-Propene-2-3-dicarboxylic acid
Identifiers
97-65-4 YesY
ChEBI CHEBI:30838 YesY
ChEMBL ChEMBL359159 YesY
ChemSpider 789 YesY
Jmol-3D images Image
KEGG C00490 YesY
PubChem 811
Properties
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]
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)
 YesY verify (what isYesY/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)