An endogenous metabolite of tryptophan
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Indole-3-pyruvic Acid

Item No. 29876

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
α-oxo-1H-indole-3-propanoic acid
CAS Number
392-12-1
Synonyms
  • Indole-3-pyruvate
  • IPA
  • IPyr
  • NSC 88874
Molecular Formula
C11H9NO3
Formula Weight
203.2
Purity
≥98%
Formulation (Request formulation change)
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 30 mg/mlDMSO: 30 mg/mlDMSO:PBS (pH 7.2) (1:6): 0.1 mg/ml
λmax
233, 326 nm
SMILES
O=C(C(O)=O)CC1=CNC2=CC=CC=C21
InChi Code
InChI=1S/C11H9NO3/c13-10(11(14)15)5-7-6-12-9-4-2-1-3-8(7)9/h1-4,6,12H,5H2,(H,14,15)
InChi Key
RSTKLPZEZYGQPY-UHFFFAOYSA-N
Origin
Synthetic
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    250 mg

    $70

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    500 mg

    $124

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    1 g

    $179

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    Product Description

    Indole-3-pyruvic acid is an endogenous metabolite of tryptophan and intermediate in the biosynthesis of the major auxin hormone, indole-3-acetic acid (IAA; Item No. 16954), in plants.1,2,3 Indole-3-pyruvic acid (50 and 250 µM) activates the aryl hydrocarbon receptor (AhR) in a reporter assay.1 It reduces UVB-induced cytotoxicity and the levels of COX-2 in HaCaT keratinocytes.4 Topical administration of indole-3-pyruvic acid (100 µmol) reduces the severity of UVB-induced damage in mouse skin. Dietary administration of indole-3-pyruvic acid (0.1%) reduces diarrhea, colonic inflammation, and the colonic expression of Il1b, Ifng, Tnfa, and Il12b in a mouse model of T cell-mediated colitis.1 It increases the time spent in the open arms of the elevated plus maze in mice when administered at a dose of 100 mg/kg.2 It also reverses the anxiogenic effect of caffeine (Item No. 14118) and 3-hydroxy kynurenine, but not pentylenetetrazole (Item No. 18682) or phenylethylamine, in the elevated plus maze in mice.

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Aoki, R., Aoki-Yoshida, A., Suzuki, C., et al. Indole-3-pyruvic acid, an aryl hydrocarbon receptor activator, suppresses experimental colitis in mice. J. Immunol. 201(12), 3683-3693 (2018).

    2. Lapin, I.P., and Politi, V. Anxiolytic effect of indole-3-pyruvic acid (IPA) in mice. Pharmacol. Res. 28(2), 129-134 (1993).

    3. Mashiguchi, K., Tanaka, K., Sakai, T., et al. The main auxin biosynthesis pathway in Arabidopsis. Proc. Natl. Acad. Sci. USA 108(45), 18512-18517 (2011).

    4. Aoki, R., Aoki-Yoshida, A., Suzuki, C., et al. Protective effect of indole-3-pyruvate against ultraviolet b-induced damage to cultured HaCaT keratinocytes and the skin of hairless mice. PLoS One 9(5), e96804 (2014).