| Size | Price | Stock | Qty |
|---|---|---|---|
| 250mg |
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| 500mg |
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| Other Sizes |
| Targets |
trans-3-Indoleacrylic acid is an agonist of the aryl hydrocarbon receptor (AhR). It activates the AhR pathway, which reduces colonic inflammation and restores the expression of intestinal barrier proteins (e.g., tight junction proteins claudin and occludin). It also enhances IL-22 production.
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| ln Vitro |
In vitro, trans-3-Indoleacrylic acid (1-100 uM) activates the AhR pathway and has been shown to enhance intestinal epithelial barrier function by upregulating tight junction proteins. It protects against gut barrier dysfunction by reducing colonic inflammation and promoting goblet cell function.
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| ln Vivo |
In vivo, trans-3-Indoleacrylic acid has been shown to attenuate colitis in murine models (e.g., DSS-induced colitis). It reduces colonic inflammation and restores intestinal barrier function through AhR signaling activation. It is a key mediator of host-microbiota crosstalk in the gut.
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| Enzyme Assay |
A non-cell AhR activation assay uses a luciferase reporter gene system. HEK293 cells are transiently transfected with an AhR-responsive luciferase plasmid (e.g., pGud-Luc) and an AhR expression plasmid. The compound is added (0.1-100 uM), and after 6-24 hours, luciferase activity is measured. AhR activation is confirmed by measuring CYP1A1 expression by qPCR or Western blot.
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| Cell Assay |
Caco-2 cells, a model of the intestinal epithelium, are grown as a monolayer on Transwell inserts for 21 days to allow full differentiation. trans-3-Indoleacrylic acid (10-100 uM) is added to the apical compartment. Barrier integrity is assessed by measuring transepithelial electrical resistance (TEER) with an EVOM2 voltohmmeter and by measuring paracellular flux of FITC-dextran (4 kDa) across the monolayer.
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| Animal Protocol |
In animal studies, trans-3-Indoleacrylic acid is administered to mice by oral gavage (10-50 mg/kg) in colitis models (e.g., DSS-induced colitis). Mice are monitored daily for body weight loss, stool consistency, and blood in stool. After sacrifice, colon length is measured (shortened colon indicates inflammation). Colonic tissue is collected for histology (H&E staining), qPCR (IL-6, TNF-alpha, IL-22), and Western blot (tight junction proteins).
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| ADME/Pharmacokinetics |
The compound has low oral bioavailability due to rapid metabolism (phase II conjugation). It is stable in the gut lumen and likely acts locally on the intestinal epithelium. It is extensively glucuronidated and sulfated in the liver. Its half-life in circulation is short (minutes), but its effects on AhR signaling may be sustained.
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| Toxicity/Toxicokinetics |
The compound is considered non-toxic at physiological concentrations (1-50 uM). It is a natural metabolite produced by gut bacteria (e.g., Lactobacillus species) and is present in healthy individuals at low levels. High doses in animals (up to 100 mg/kg) have shown no significant adverse effects.
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| References | |
| Additional Infomation |
(E)-3-(indole-3-yl)acrylic acid is an α,β-unsaturated monocarboxylic acid, a derivative of acrylic acid in which a hydrogen atom at the 3-position is replaced by an indole-3-yl group. It is an α,β-unsaturated monocarboxylic acid belonging to the indole class of compounds. Its functional group is related to acrylic acid. It is the conjugate acid of (E)-3-(indole-3-yl)acrylate (1-). 3-Indoleacrylic acid has been reported to have been found in Chondria atropurpurea, and relevant data are available for reference.
trans-3-Indoleacrylic acid is used in microbiome research and metabolic phenotyping as a marker of tryptophan metabolism. It is being studied as a potential therapeutic agent for inflammatory bowel disease (IBD), ulcerative colitis, and Crohn's disease. It is also used to study AhR signaling and host-microbe interactions. |
| Molecular Formula |
C11H9NO2
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|---|---|
| Molecular Weight |
187.19
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| Exact Mass |
187.063
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| CAS # |
29953-71-7
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| PubChem CID |
5375048
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| Appearance |
White to off-white solid powder
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| Density |
1.4±0.1 g/cm3
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| Boiling Point |
432.8±20.0 °C at 760 mmHg
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| Melting Point |
180 - 186 °C
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| Flash Point |
215.6±21.8 °C
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| Vapour Pressure |
0.0±1.1 mmHg at 25°C
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| Index of Refraction |
1.750
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| LogP |
2.34
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| Hydrogen Bond Donor Count |
2
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| Hydrogen Bond Acceptor Count |
2
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| Rotatable Bond Count |
2
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| Heavy Atom Count |
14
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| Complexity |
250
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| Defined Atom Stereocenter Count |
0
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| SMILES |
C1=CC=C2C(=C1)C(=CN2)/C=C/C(=O)O
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| InChi Key |
PLVPPLCLBIEYEA-AATRIKPKSA-N
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| 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+
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| Chemical Name |
(E)-3-(1H-indol-3-yl)prop-2-enoic acid
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| HS Tariff Code |
2934.99.9001
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| Storage |
Powder -20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month |
| Shipping Condition |
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
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| Solubility (In Vitro) |
DMSO :~250 mg/mL (~1335.54 mM)
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|---|---|
| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 2.08 mg/mL (11.11 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 (11.11 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. View More
Solubility in Formulation 3: ≥ 2.08 mg/mL (11.11 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution. |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 5.3422 mL | 26.7108 mL | 53.4217 mL | |
| 5 mM | 1.0684 mL | 5.3422 mL | 10.6843 mL | |
| 10 mM | 0.5342 mL | 2.6711 mL | 5.3422 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.
Calculation results
Working concentration： mg/mL；
Method for preparing DMSO stock solution： mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.
Method for preparing in vivo formulation:：Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O，mix and clarify.
(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
(2) Be sure to add the solvent(s) in order.
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