The world's first wiki where authorship really matters (Nature Genetics, 2008). Due credit and reputation for authors. Imagine a global collaborative knowledge base for original thoughts. Search thousands of articles and collaborate with scientists around the globe.

wikigene or wiki gene protein drug chemical gene disease author authorship tracking collaborative publishing evolutionary knowledge reputation system wiki2.0 global collaboration genes proteins drugs chemicals diseases compound
Hoffmann, R. A wiki for the life sciences where authorship matters. Nature Genetics (2008)
Chemical Compound Review

itaconate     2-methylidenebutanedioic acid

Synonyms: Itaconic acid, CHEMBL359159, NSC-3357, ACMC-1CFCS, I29204_ALDRICH, ...
Welcome! If you are familiar with the subject of this article, you can contribute to this open access knowledge base by deleting incorrect information, restructuring or completely rewriting any text. Read more.

Disease relevance of NSC3357


Psychiatry related information on NSC3357

  • The infrared spectra displayed a clear isolated absorption band at a wavenumber of 6186 cm(-1) (wavelength 1.617 microm) resulting from the =C-H bonds of itaconic acid, which was found to decrease in intensity with increasing reaction time [3].

High impact information on NSC3357


Biological context of NSC3357


Associations of NSC3357 with other chemical compounds

  • We report on a new class of P-O monophosphite ligands (designated 3a-k) with a double six-membered-ring backbone onto which are attached additional groups and on applications of their Rh complexes in the hydrogenation of enamides, alpha-dehydroamino acid esters, dimethyl itaconate, and beta-(acylamino)acrylates [12].
  • Rhodium complexes with chiral bisphospholanes are highly enantioselective catalysts for the asymmetric hydrogenation of various kinds of functionalized olefins such as dehydroamino acid derivatives, itaconic acid derivatives, and enamides [13].
  • The new ligands exhibit excellent enantioselectivities (over 99% ee) in the Rh-catalyzed asymmetric hydrogenation of enamides, dimethyl itaconate, and methyl (Z)-acetamidocinnamate even with high catalyst turnovers (S/C=10,000) [14].
  • The production of itaconic acid from glucose-based media by Aspergillus terreus NRRL 1960 was found to be controlled by stirring rate and pH [15].
  • Thermoprecipitation of lysozyme from egg white was demonstrated using copolymers of N-isopropylacrylamide with acrylic acid, methacrylic acid, 2-acryloylamido-2-methylpropane-sulfonic acid and itaconic acid, respectively [16].

Gene context of NSC3357

  • The effects of the isocitrate lyase-directed growth inhibitor itaconate on the growth of certain methylotrophic organisms was investigated [17].
  • It was shown that in cell extracts of R. rubrum itaconate inhibited propionyl-CoA carboxylase (PCC) activity [18].
  • We hypothesized that itaconate is incorporated into liver cells and suppresses fat synthesis by inhibiting liver glycolysis at the step of phosphofructokinase, which is activated by F26BP [1].

Analytical, diagnostic and therapeutic context of NSC3357


  1. Itaconate reduces visceral fat by inhibiting fructose 2,6-bisphosphate synthesis in rat liver. Sakai, A., Kusumoto, A., Kiso, Y., Furuya, E. Nutrition (Burbank, Los Angeles County, Calif.) (2004) [Pubmed]
  2. Efficient conversion of itaconic acid to (S)-(+)-citramalic acid by Alcaligenes xylosoxydans IL142. He, B.F., Ozawa, T., Nakajima-Kambe, T., Nakahara, T. J. Biosci. Bioeng. (2000) [Pubmed]
  3. Monitoring of itaconic acid hydrogenation in a trickle bed reactor using fiber-optic coupled near-infrared spectroscopy. Wood, J., Turner, P.H. Applied spectroscopy. (2003) [Pubmed]
  4. Identification of the gene and characterization of the activity of the trans-aconitate methyltransferase from Saccharomyces cerevisiae. Cai, H., Dumlao, D., Katz, J.E., Clarke, S. Biochemistry (2001) [Pubmed]
  5. Design and synthesis of new transition-state analogue inhibitors of aspartate transcarbamylase. Farrington, G.K., Kumar, A., Wedler, F.C. J. Med. Chem. (1985) [Pubmed]
  6. Synthesis and application of phosphinoferrocenylaminophosphine ligands for asymmetric catalysis. Boaz, N.W., Mackenzie, E.B., Debenham, S.D., Large, S.E., Ponasik, J.A. J. Org. Chem. (2005) [Pubmed]
  7. Itaconate biosynthesis in Aspergillus terreus. Bonnarme, P., Gillet, B., Sepulchre, A.M., Role, C., Beloeil, J.C., Ducrocq, C. J. Bacteriol. (1995) [Pubmed]
  8. Asymmetric hydrogenation of itaconic acid and enol acetate derivatives with the Rh-TangPhos catalyst. Tang, W., Liu, D., Zhang, X. Org. Lett. (2003) [Pubmed]
  9. In vitro swelling studies and preliminary biocompatibility evaluation of acrylamide-based hydrogels. Karadağ, E., Saraydin, D., Cetinkaya, S., Güven, O. Biomaterials (1996) [Pubmed]
  10. Factors affecting broadband acoustic emission measurements of a heterogeneous reaction. Nordon, A., Carella, Y., Gachagan, A., Littlejohn, D., Hayward, G. The Analyst. (2006) [Pubmed]
  11. Novel method for cell immobilization and its application for production of organic acid. Iqbal, M., Saeed, A. Lett. Appl. Microbiol. (2005) [Pubmed]
  12. A novel class of P-O monophosphite ligands derived from D-mannitol: broad applications in highly enantioselective Rh-catalyzed hydrogenations. Huang, H., Zheng, Z., Luo, H., Bai, C., Hu, X., Chen, H. J. Org. Chem. (2004) [Pubmed]
  13. Synthesis of chiral hydroxyl phospholanes from D-mannitol and their use in asymmetric catalytic reactions. Li, W., Zhang, Z., Xiao, D., Zhang, X. J. Org. Chem. (2000) [Pubmed]
  14. Unsymmetrical hybrid ferrocene-based phosphine-phosphoramidites: a new class of practical ligands for Rh-catalyzed asymmetric hydrogenation. Hu, X.P., Zheng, Z. Org. Lett. (2004) [Pubmed]
  15. Effect of pH and stirring rate on itaconate production by Aspergillus terreus. Riscaldati, E., Moresi, M., Federici, F., Petruccioli, M. J. Biotechnol. (2000) [Pubmed]
  16. Thermoprecipitation of lysozyme from egg white using copolymers of N-isopropylacrylamide and acidic monomers. Vaidya, A.A., Lele, B.S., Kulkarni, M.G., Mashelkar, R.A. J. Biotechnol. (2001) [Pubmed]
  17. Inhibition by itaconate of growth of methylotrophic bacteria. Bellion, E., Kelley, R.L. J. Bacteriol. (1979) [Pubmed]
  18. Inhibition of acetate and propionate assimilation by itaconate via propionyl-CoA carboxylase in isocitrate lyase-negative purple bacterium Rhodospirillum rubrum. Berg, I.A., Filatova, L.V., Ivanovsky, R.N. FEMS Microbiol. Lett. (2002) [Pubmed]
  19. Itaconic acid carrier ampholytes for isoelectric focusing. Brenna, O. J. Chromatogr. (1977) [Pubmed]
  20. Monitoring of a heterogeneous reaction by acoustic emission. Nordon, A., Waddell, R.J., Bellamy, L.J., Gachagan, A., McNab, D., Littlejohn, D., Hayward, G. The Analyst. (2004) [Pubmed]
  21. Identification of a novel series of alkylitaconic acids in wood cultures of Ceriporiopsis subvermispora by gas chromatography/mass spectrometry. del Río, J.C., Gutiérrez, A., Martínez, M.J., Martínez AT, A.T. Rapid Commun. Mass Spectrom. (2002) [Pubmed]
  22. A new NMR airlift bioreactor used in 31P-NMR studies of itaconic acid producing Aspergillus terreus. Lyngstad, M., Grasdalen, H. J. Biochem. Biophys. Methods (1993) [Pubmed]
WikiGenes - Universities