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Indole-3-pyruvic Acid (Synonyms: Indole-3-pyruvate, IPA, IPyr, NSC 88874)

Catalog No.GC47456

Indole-3-pyruvic Acid, a keto analogue of tryptophan, is an orally active AHR agonist.

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Indole-3-pyruvic Acid Chemical Structure

Cas No.: 392-12-1

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Sample solution is provided at 25 µL, 10mM.

Description of Indole-3-pyruvic Acid

Indole-3-pyruvic acid is an endogenous metabolite of tryptophan and intermediate in the biosynthesis of the major auxin hormone, indole-3-acetic acid , 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 Il1bIfngTnfa, 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 and 3-hydroxy kynurenine, but not pentylenetetrazole or phenylethylamine, in the elevated plus maze in mice.

Reference:
[1].Aoki, R., Aoki-Yoshida, A., Suzuki, C., et al.Indole-3-pyruvic acid, an aryl hydrocarbon receptor activator, suppresses experimental colitis in miceJ. Immunol.201(12)3683-3693(2018)
[2].Lapin, I.P., and Politi, V.Anxiolytic effect of indole-3-pyruvic acid (IPA) in micePharmacol. Res.28(2)129-134(1993)
[3].Mashiguchi, K., Tanaka, K., Sakai, T., et al.The main auxin biosynthesis pathway in ArabidopsisProc. Natl. Acad. Sci. USA108(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 micePLoS One9(5)e96804(2014)

Chemical Properties of Indole-3-pyruvic Acid

Cas No. 392-12-1 SDF
Synonyms Indole-3-pyruvate, IPA, IPyr, NSC 88874
Canonical SMILES O=C(C(O)=O)CC1=CNC2=CC=CC=C21
Formula C11H9NO3 M.Wt 203.2
Solubility DMF: 30 mg/ml,DMSO: 30 mg/ml,DMSO:PBS (pH 7.2) (1:6): 0.14 mg/ml Storage Store at -20°C
General tips Please select the appropriate solvent to prepare the stock solution according to the solubility of the product in different solvents; once the solution is prepared, please store it in separate packages to avoid product failure caused by repeated freezing and thawing.Storage method and period of the stock solution: When stored at -80°C, please use it within 6 months; when stored at -20°C, please use it within 1 month.
To increase solubility, heat the tube to 37°C and then oscillate in an ultrasonic bath for some time.
Shipping Condition Evaluation sample solution: shipped with blue ice. All other sizes available: with RT, or with Blue Ice upon request.

Complete Stock Solution Preparation Table of Indole-3-pyruvic Acid

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1 mg 5 mg 10 mg
1 mM 4.9213 mL 24.6063 mL 49.2126 mL
5 mM 0.9843 mL 4.9213 mL 9.8425 mL
10 mM 0.4921 mL 2.4606 mL 4.9213 mL
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