Introduction：Basic information about Indole-3-carboxylic acid CAS 771-50-6, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.
Indole-3-carboxylic acid Basic information
| Product Name: | Indole-3-carboxylic acid |
| Synonyms: | Indole-3-carboxylic acid ,99%;INDOLE-3-CARBOXYLIC ACID(I3CA);INDOLE-3-CARBOXYLIC ACID pure;Indole-3-CarboxylicA;1H-Indole-3-carboxylic acid 98%;Indole-3-carboxylic;Indole-3-carboxylic acid (8CI);e-3-carboxyL |
| CAS: | 771-50-6 |
| MF: | C9H7NO2 |
| MW: | 161.16 |
| EINECS: | 212-231-6 |
| Product Categories: | Simple Indoles;Carboxylic Acids;Pyrroles & Indoles;Building Blocks;Heterocyclic Building Blocks;Indoles;Indoles and derivatives;IndoleDerivative;Carboxylic Acids;Pyrroles & Indoles;Indole;Organic acids;blocks;Carboxes;IndolesOxindoles;Indole/indoline/oxindole;indole derivative;Indole and Indoline;Alkaloids;Heterocycle-Indole series;zjh;bc0001;771-50-6 |
| Mol File: | 771-50-6.mol |
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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. |
| form | Powder |
| pka | 3.90±0.10(Predicted) |
| 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 |
| Storage Class | 11 - Combustible Solids |
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 Preparation Products And Raw materials
| Raw materials | 4-(Benzyloxy)pyridine N-oxide-->Methyl indole-3-carboxylate-->3-Bromoindole-->1-BENZYLINDOLE-3-CARBOXYLIC ACID-->3-(TRIFLUOROACETYL)INDOLE-->3-TRICHLOROACETYLINDOLE |
| Preparation Products | 1-Methyl-1H-indole-3-carboxylic acid-->Indole-2-carboxylic acid-->3-AMINOINDOLE HCL-->1-(PIVALOYLOXYMETHYL)-1H-INDOLE-3-CARBOXYLIC ACID-->1H-Indole-3-carboxaMide, N-(2-chlorophenyl)--->N-METHOXY-N-METHYL-1H-INDOLE-3-CARBOXAMIDE-->1-pentyl-1H-indole-3-carboxylic acid |
