Indole-3-pyruvic acid, a ketone analog of tryptophan, is an orally bioactive AHR agonist. Indole-3-pyruvic acid has antioxidant properties and may be utilized to treat inflammation and anxiety.

Physicochemical Properties

Molecular Formula	C11H9NO3
Molecular Weight	203.19406
Exact Mass	203.058
CAS #	392-12-1
PubChem CID	803
Appearance	Light yellow to brown solid powder
Density	1.4±0.1 g/cm3
Boiling Point	445.2±28.0 °C at 760 mmHg
Melting Point	215 °C (dec.)(lit.)
Flash Point	223.0±24.0 °C
Vapour Pressure	0.0±1.1 mmHg at 25°C
Index of Refraction	1.685
LogP	0.46
Hydrogen Bond Donor Count	2
Hydrogen Bond Acceptor Count	3
Rotatable Bond Count	3
Heavy Atom Count	15
Complexity	277
Defined Atom Stereocenter Count	0
InChi Key	RSTKLPZEZYGQPY-UHFFFAOYSA-N
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)
Chemical Name	3-(1H-indol-3-yl)-2-oxopropanoic acid
HS Tariff Code	2934.99.9001
Storage	Powder-20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month Note: Please store this product in a sealed and protected environment (e.g. under nitrogen), avoid exposure to moisture and light.
Shipping Condition	Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)

Biological Activity

ln Vitro	In HepG2 cells, indole-3-pyruvic acid (50 and 250 μM, 24 h) activates AHR[1]. Triole-3-pyruvic acid (50 μM, 4 days) stimulates Tr1 cells but does not prevent Th1 cell elimination [1]. Indole-3-pyruvic acid (1 mM, 24 h) lessens the cytotoxicity of UVB-induced HaCaT [1]. In HaCaT cells, indole-3-pyruvic acid (25 mM, 6 hours) lowers COX-2 levels [2].
ln Vivo	Mice BALB/c are given indole-3-pyruvic acid (face, 0.1% chow; 5 d) to activate their AHR [1]. Indole-3-pyruvic acid (100 μM, dose at skin) protects HR-1 hairless shell from UVB-induced skin damage. Indole-3-pyruvic acid (face, fed MF food (0.1%) for 5 weeks) eliminates T cells [ 2]. mediated long-term inflammation in vaginitis models [1]. -In the elevated plus maze, mice can open their arms for a longer period of time when given pyruvate (ip, 100–200 mg/kg) [3].
Cell Assay	RT-PCR[2] Cell Types: HaCaT cells Tested Concentrations: 5-25mM Incubation Duration: 6 hrs (hours) Experimental Results: Inhibition of UVB-stimulated mRNA expression of IL-1β, IL-6 and cyclooxygenase 2 (Cox-2).
Animal Protocol	Animal/Disease Models: balb/c (Bagg ALBino) mouse [1] Doses: Fed with MF feed. 0.1% for 5 days. Route of Administration: Oral. Experimental Results: Up-regulated the expression of Cyp1a1 (a biomarker of AHR activation) in the colon. Animal/Disease Models: SCID mouse T cell-mediated colitis model [1] Doses: fed with 0.1% MF feed for 5 consecutive weeks. Route of Administration: oral. Experimental Results: inhibited diarrhea and improved colon inflammation. Downregulates the expression of Th1 and pro-inflammatory cytokines and upregulates the expression of IL-10 in the colon. Animal/Disease Models: HR-1 hairless mice [2] Doses: 100 μM Route of Administration: Skin Dose Experimental Results: Increased epidermal thickness. Attenuation of UVB-induced necrosis was observed in the upper dermis.
References	[1]. Indole-3-Pyruvic Acid, an Aryl Hydrocarbon Receptor Activator, Suppresses Experimental Colitis in Mice. J Immunol. 2018 Dec 15;201(12):3683-3693. [2]. Protective effect of indole-3-pyruvate against ultraviolet b-induced damage to cultured HaCaT keratinocytes and the skin of hairless mice. PLoS One. 2014 May 8;9(5):e96804. [3]. Anxiolytic effect of indole-3-pyruvic acid (IPA) in mice. Pharmacol Res. 1993 Sep;28(2):129-34.

Solubility Data

Solubility (In Vitro)

DMSO : ~166.67 mg/mL (~820.27 mM) H2O : ~20 mg/mL (~98.43 mM)

Solubility (In Vivo)

Solubility in Formulation 1: ≥ 2.08 mg/mL (10.24 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 20.8 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL. Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution. Solubility in Formulation 2: ≥ 2.08 mg/mL (10.24 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 20.8 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly. Preparation of 20% SBE-β-CD in Saline (4°C，1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution.  (Please use freshly prepared in vivo formulations for optimal results.)

Preparing Stock Solutions		1 mg	5 mg	10 mg
	1 mM	4.9215 mL	24.6075 mL	49.2150 mL
	5 mM	0.9843 mL	4.9215 mL	9.8430 mL
	10 mM	0.4922 mL	2.4608 mL	4.9215 mL

*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.