A metabolite of L-tryptophan
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trans-Indole-3-acrylic Acid

Item No. 40655

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
3-(1H-indol-3-yl)-2E-propenoic acid
CAS Number
29953-71-7
Synonyms
  • IA
  • trans-3-Indoleacrylic acid
Molecular Formula
C11H9NO2
Formula Weight
187.2
Purity
≥98%
Formulation (Request formulation change)
A solid
Solubility(Learn about Variance in Solubility)
DMSO: Soluble: ≥10 mg/mlEthanol: Soluble: ≥10 mg/ml
SMILES
O=C(O)/C=C/C1=CNC2=CC=CC=C21
InChi Code
InChI=1S/C11H9NO2/c13-11(14)6-5-8-7-12-10-4-2-1-3-9(8)10/h1-7,12H,(H,13,14)/b6-5+
InChi Key
PLVPPLCLBIEYEA-AATRIKPKSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    1 g

    $29

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    10 g

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    25 g

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    Product Description

    trans-Indole-3-acrylic acid is a metabolite of the essential amino acid L-tryptophan (Item No. 29600).1 It is formed from tryptophan by gut microbiota. trans-Indole-3-acrylic acid (100 µM) increases the levels of mRNA encoding mucin 2 and Il-10, as well as decreases mRNA encoding Tnf-α, in primary mouse large intestinal spheroids co-cultured with LPS-stimulated primary mouse bone marrow-derived macrophages (BMDMs). It has been used as a precursor in the synthesis of anticancer agents and tubulin polymerization inhibitors, as well as used as a reactive chromophore probe to assess the α and β subunit conformational changes of S. typhimurium tryptophan synthase in tryptophan biosynthesis.2,3

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Wlodarska, M., Luo, C., Kolde, R., et al. Indoleacrylic acid produced by commensal peptostreptococcus species suppresses inflammation. Cell Host Microbe 22(1), 25-37 (2017).

    2. Baytas, S.N., Inceler, N., Yilmaz, A., et al. Synthesis, biological evaluation and molecular docking studies of trans-indole-3-acrylamide derivatives, a new class of tubulin polymerization inhibitors. Bioorg. Med. Chem. 22(12), 3096-3104 (2014).

    3. Casino, P., Niks, D., Ngo, H., et al. Allosteric regulation of tryptophan synthase channeling: The internal aldimine probed by trans-3-indole-3'-acrylate binding. Biochemistry 46(26), 7728-7739 (2007).