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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-Propene-2-3-dicarboxylic acid
Identifiers
CAS Number
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.002.364 Edit this at Wikidata
KEGG
PubChem CID
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C5H6O4/c1-3(5(8)9)2-4(6)7/h1-2H2,(H,6,7)(H,8,9)Key: LVHBHZANLOWSRM-UHFFFAOYSA-N
  • 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 130.099 g·mol
Appearance White crystals
Density 1.63 g/cm
Melting point 162 to 164 °C (324 to 327 °F; 435 to 437 K) (decomposes)
Solubility in water 1 g/12 mL
Solubility in ethanol 1 g/5 mL
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). checkY verify (what is  ?) Infobox references
Chemical compound

Itaconic acid, or methylenesuccinic acid, is an organic compound. The name itaconic was devised as an anagram of aconitic. Historically, itaconic acid was obtained by the distillation of citric acid.

Properties:

The dicarbonic acid is a white crystalline, scentless powder. Itaconic acid is a naturally occurring compound, non-toxic, and readily biodegradable. It is soluable in water, ethanol, and aceton. The molecular weight is 130.10 g·mol with a density of 1,63 g·cm.

Production:

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

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.

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

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.

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

Application:

Itaconic acid 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.

References

  1. ^ Merck Index, 11th Edition, 5130
  2. "Rocket NXT". gestis.itrust.de. Retrieved 2016-08-30.
  3. Steiger, Matthias Georg; Blumhoff, Marzena Lidia; Mattanovich, Diethard; Sauer, Michael (2013-01-01). "Biochemistry of microbial itaconic acid production". Microbial Physiology and Metabolism. 4: 23. doi:10.3389/fmicb.2013.00023. PMC 3572532. PMID 23420787.{{cite journal}}: CS1 maint: unflagged free DOI (link)
  4. Geiser, Elena; Przybilla, Sandra K; Friedrich, Alexandra; Buckel, Wolfgang; Wierckx, Nick; Blank, Lars M; Bölker, Michael (2016-01-01). "Ustilago maydis produces itaconic acid via the unusual intermediate trans-aconitate". Microbial Biotechnology. 9 (1): 116–126. doi:10.1111/1751-7915.12329. ISSN 1751-7915. PMC 4720413. PMID 26639528.
  5. Geiser, Elena; Przybilla, Sandra K; Friedrich, Alexandra; Buckel, Wolfgang; Wierckx, Nick; Blank, Lars M; Bölker, Michael (2016-01-01). "Ustilago maydis produces itaconic acid via the unusual intermediate trans-aconitate". Microbial Biotechnology. 9 (1): 116–126. doi:10.1111/1751-7915.12329. ISSN 1751-7915. PMC 4720413. PMID 26639528.
  6. Michelucci, A.; Cordes, T.; Ghelfi, J.; Pailot, A.; Reiling, N.; Goldmann, O.; Binz, T.; Wegner, A.; Tallam, A.; Rausell, A.; Buttini, M.; Linster, C. L.; Medina, E.; Balling, R.; Hiller, K. (2013). "Immune-responsive gene 1 protein links metabolism to immunity by catalyzing itaconic acid production". Proceedings of the National Academy of Sciences. 110 (19): 7820–5. Bibcode:2013PNAS..110.7820M. doi:10.1073/pnas.1218599110. PMC 3651434. PMID 23610393.
  7. Nemeth, B.; Doczi, J.; Csete, D.; Kacso, G.; Ravasz, D.; Adams, D.; Kiss, G.; Nagy, A. M.; Horvath, G.; Tretter, L.; Mocsai, A.; Csepanyi-Komi, R.; Iordanov, I.; Adam-Vizi, V.; Chinopoulos, C. (2015). "Abolition of mitochondrial substrate-level phosphorylation by itaconic acid produced by LPS-induced Irg1 expression in cells of murine macrophage lineage". The FASEB Journal. doi:10.1096/fj.15-279398. PMID 26358042.{{cite journal}}: CS1 maint: unflagged free DOI (link)
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