Indole-3-carboxylic acid Chemical Properties

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

InChI

InChI=1S/C9H7NO2/c11-9(12)7-5-10-8-4-2-1-3-6(7)8/h1-5,10H,(H,11,12)

InChIKey

KMAKOBLIOCQGJP-UHFFFAOYSA-N

SMILES

N1C2=C(C=CC=C2)C(C(O)=O)=C1

CAS DataBase Reference

771-50-6(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xn,Xi

Risk Statements 

36/37/38-21/22

Safety Statements 

22-24/25-36/37/39-26

WGK Germany 

3

RTECS 

NK7882892

HazardClass 

IRRITANT

HS Code 

29339900

MSDS

• Language:English Provider:ACROS
• Language:English Provider:SigmaAldrich
• Language:English Provider:ALFA

Indole-3-carboxylic acid Usage And Synthesis

Description

Indole-3-carboxylic acid is a plant metabolite derived from tryptophan that has been found in Arabidopsis and has diverse biological activities.1,2,3,4 It induces resistance in Arabidopsis against the plant necrotrophic fungus P. cucumerina when applied as a soil-drenching solution at a concentration of 150 µM prior to infection.2 Indole-3-carboxylic acid is cytotoxic to A549 human lung and MCF-7 human breast cancer cells (EC50s = 4.6 and 12.9 µg/ml, respectively) and inhibits HIV replication in infected H9 lymphocytes (IC50 = 16.4 µg/ml).3 Indole-3-carboxylic acid has also been used as a precursor in the synthesis of substituted thiadiazoles with anticancer activity.4WARNING This product is not for human or veterinary use.

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.

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.

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%).

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.

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).

target

5-HT Receptor

Indole-3-carboxylic acid(771-50-6)Related Product Information

• Ethyl indole-3-carboxylate
• Indole-3-butyric acid
• Indometacin
• 3,5-Dihydroxybenzoic acid
• Ethyl 2-(Chlorosulfonyl)acetate
• Indole-3-acetic acid
• Indole
• Folic acid
• Glycine
• Methyl indole-3-carboxylate
• Indole-6-carboxylic acid
• 1H-Indole-7-carboxylic acid
• Indole-4-carboxylic acid
• Methyl indole-6-carboxylate
• Indole-2-carboxylic acid
• 5-Chloroindole
• Citric acid
• Indole-4-boronic acid