trans-Indole-3-acrylic acid

CHF 40.00
In stock
AG-CR1-3677-M250250 mgCHF 40.00
AG-CR1-3677-G0011 gCHF 75.00
 
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Product Details
Synonyms IAcrA; trans-3-Indoleacrylic acid; trans-β-Indoleacrylic Acid; (E)-3-(1H-Indol-3-yl)acrylic acid; NSC29428; NSC137806; BRN0006317
Product Type Chemical
Properties
Formula C11H9NO2
MW 187.2
CAS 29953-71-7
Purity Chemicals ≥98%
Appearance Off-white solid.
Solubility Soluble in DMSO or ethanol. Slightly soluble in water.
Other Product Data Note: Warming and sonication may be required when dissolving the compound in the solvent of choice.
InChi Key PLVPPLCLBIEYEA-AATRIKPKSA-N
Shipping and Handling
Shipping AMBIENT
Short Term Storage +20°C
Long Term Storage +4°C
Handling Advice Protect from moisture.
Use/Stability Stable for at least 2 years after receipt when stored at +4°C.
Documents
MSDS Download PDF
Product Specification Sheet
Datasheet Download PDF
  • Inflammation suppressor. Tryptophan metabolite produced by human microbiota (intestinal commensale Peptostreptococcus sp.). Involved in keeping the intestinal barrier intact and works as anti-inflammatory molecule. Patients with Inflammatory Bowel Disease (IBD) have an altered microbiota, with less Peptostreptococcus sp., and therefore reduced production of trans-indole-3-acrylic acid.
  • Chromophoric L-Trp analog used to probe the allosteric properties of the internal aldimine of tryptophan synthase. Also shown to be a moderate inhibitor of tryptophan synthase, trypothan-2,3-dioxygenase (TDO), indoleamine-2,3-dioxygenase (IDO), L-dopachrome isomerase and xanthine oxidase.
  • Reagent used as a matrix for MALDI-TOF mass spectroscopy in order to characterize and analyze polyphenols and synthetic polymers.
  • Used as heterocyclic building block or intermediate for the synthesis of indolyl acrylamide-derived inhibitors, pharmaceuticals or agrochemicals.
Product References
  1. Inhibition of tryptophan synthetase by indoleacrylic acid: W.H. Matchett; J. Bacteriol. 110, 146 (1972)
  2. Stereospecificity of hepatic L-tryptophan 2,3-dioxygenase: Y. Watanabe, et al.; Biochem. J. 189, 393 (1980)
  3. Inhibition of indoleamine 2,3-dioxygenase and tryptophan 2,3-dioxygenase by beta-carboline and indole derivatives: N. Eguchi; Arch. Biochem. Biophys. 232, 602 (1984)
  4. The structural basis for the interaction between L-tryptophan and the Escherichia coli trp aporepressor: R.Q. Marmorstein, et al.; J. Biol. Chem. 262, 4922 (1987)
  5. Interaction of Indoleacrylic Acid with Trp aporepressor from Escherichia coli: D. Hu & M.R. Eftink; Arch. Biochem. Biophys. 305, 588 (1993)
  6. Photosensizied inactivation of infectious DNA by urocanic acid, indoleacrylic acid and rhodiuk complexes: T. Mohammad, et al.; Photochem. Photobiol. 59, 189 (1994)
  7. Desorption behavior and distributions of fluorinated polymers in MALDI and electrospray ionization mass spectrometry: L. Latourte, et al.; Anal. Chem. 69, 2742 (1997)
  8. Substrate specificity for isomerase activity of macrophage migration inhibitory factor and its inhibition by indole derivatives: M. Suzuki, et al.; J. Biochem. 122, 1040 (1997)
  9. Where does indolylacrylic acid come from?: E. Marklova; Amino Acids 17, 401 (1999)
  10. Novel allosteric effectors of the tryptophan synthase K2L2 complex identifed by computer-assisted molecular modelling: A. Marabotti, et al.; Biochim. Biophys. Acta 1476, 287 (2000)
  11. MALDI-TOF mass spectrometry of oligomeric food polyphenols: J.D. Reed, et al.; Phytochemistry 66, 2248 (2005)
  12. Allosteric regulation of tryptophan synthase channeling: the internal aldimine probed by trans-3-indole-3'-acrylate binding: P. Casino, et al.; Biochemistry 46, 7728 (2007)
  13. Structural insight into the inhibition of human kynurenine aminotransferase I/glutamine transaminase KII: Q. Han, et al.; J. Med. Chem. 52, 2786 (2009)
  14. Tryptophan 2,3-dioxygenase (TDO) inhibitors. 3-(2-(pyridyl)ethenyl)indoles as potential anticancer immunomodulators: E. Dolusic, et al.; J. Med. Chem. 54, 5320 (2011)
  15. Discovery of indolyl acrylamide derivatives as human diacylglycerol acyltransferase-2 selective inhibitors: K. Lee, et al.; Org. Biomol. Chem. 11, 849 (2013)
  16. Synthesis, biological evaluation and molecular docking studies of trans-indole-3-acrylamide derivatives, a new class of tubulin polymerization inhibitors: S.N. Baytas, et al.; Bioorg. Med. Chem. 22, 3096 (2014)
  17. Indoleacrylic acid produced by commensal Peptostreptococcus species suppresses inflammation: M. Wlodarska, et al.; Cell Host & Microbe 22, 25 (2017)
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