Indole-3-carboxylic acid
Synonym(s):β-Indolylcarboxylic acid;3-Carboxyindole;3-Indole formic acid;3-Indolylcarboxylic acid;Indole-β-carboxylic acid
- CAS NO.:771-50-6
- Empirical Formula: C9H7NO2
- Molecular Weight: 161.16
- MDL number: MFCD00005624
- EINECS: 212-231-6
- SAFETY DATA SHEET (SDS)
- Update Date: 2024-08-13 17:19:14
What is Indole-3-carboxylic acid?
Chemical properties
light beige crystalline powder (recrystallized from acetate-petroleum ether). Soluble in ethanol, ether, acetate, insoluble in boiling water, benzene, insoluble in petroleum ether.
What are the applications of Application
Indole-3-carboxylic Acid is a specific and competitive inhibitor of the potentiation of glycine of NMDA-gated current. Chemical reagent in the synthesis of thiadiazole derivatives used for anticancer activity.
Definition
ChEBI: Indole-3-carboxylic acid is an indole-3-carboxylic acid carrying a carboxy group at position 3. It has a role as a human metabolite and a bacterial metabolite. It is a conjugate acid of an indole-3-carboxylate.
Preparation
indole-3-carboxylic acid can be synthesized by the hydrolysis reaction of 3-trichloroacetyl indole: add 235g 3-trichloroacetyl indole into 1000ml methanol, slowly drop an appropriate amount of 50% KOH solution, heat up and reflux for 18 hours, cool to room temperature, The methanol was recovered by concentration, and the residual liquid was left; 1500 ml of water was added to the residual liquid, hydrochloric acid was added dropwise to adjust pH=3~4, and then filtered, and the solid obtained by filtration was dried to obtain 144g of indole-3-carboxylic acid crude product; The crude product was slurried with 100g of ethyl acetate for 25 minutes,filtered and dried to obtain indole-3-carboxylic acid (137g, yield 91.8%).
General Description
The structures of the derivatives of indole-3-carboxylic acid were studied using gas chromatography with high resolution mass spectrometry (GC-HRMS), ultra-high performance liquid chromatography in combination with high resolution tandem mass spectrometry (UHPLC-HRMS), nuclear magnetic resonance spectroscopy (NMR) and Fourier transform infrared spectroscopy (FT-IR).
Properties of Indole-3-carboxylic acid
Melting point: | 232-234 °C (dec.)(lit.) |
Boiling point: | 287.44°C (rough estimate) |
Density | 1.2480 (rough estimate) |
refractive index | 1.5050 (estimate) |
storage temp. | 2-8°C |
solubility | Soluble in 95% Ethanol: 50 mg/ml, also soluble in methanol. |
pka | 3.90±0.10(Predicted) |
form | Powder |
color | Light beige |
BRN | 129435 |
CAS DataBase Reference | 771-50-6(CAS DataBase Reference) |
Safety information for Indole-3-carboxylic acid
Signal word | Warning |
Pictogram(s) |
Exclamation Mark Irritant GHS07 |
GHS Hazard Statements |
H315:Skin corrosion/irritation H319:Serious eye damage/eye irritation H335:Specific target organ toxicity, single exposure;Respiratory tract irritation |
Precautionary Statement Codes |
P261:Avoid breathing dust/fume/gas/mist/vapours/spray. P304+P340:IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing. P305+P351+P338:IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing. P405:Store locked up. |
Computed Descriptors for Indole-3-carboxylic acid
InChIKey | KMAKOBLIOCQGJP-UHFFFAOYSA-N |
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