| Identification | More | [Name]
3-Indoleformic acid | [CAS]
771-50-6 | [Synonyms]
1H-INDOLE-3-CARBOXYLIC ACID
3-CARBOXYINDOLE
3-INDOLECARBOXYLIC ACID
3-Indoleformic acid
3-INDOLYLCARBOXYLIC ACID
INDOLE-3-CARBOXYLIC ACID
RARECHEM AL BO 0353
TIMTEC-BB SBB003952
Indole-3-carboxylie acid
IndolecarboxylicAcid
INDOLECARBOXYLIC ACID 98%
3-Indoleformic
INDOLE-3-CARBOXYLIC ACID pure
Indole-3-carboxylic acid ,99% | [EINECS(EC#)]
212-231-6 | [Molecular Formula]
C9H7NO2 | [MDL Number]
MFCD00005624 | [Molecular Weight]
161.16 | [MOL File]
771-50-6.mol |
| Chemical Properties | Back Directory | [Appearance]
light beige powder | [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 Data | Back Directory | [Hazard Codes ]
Xn,Xi | [Risk Statements ]
R36/37/38:Irritating to eyes, respiratory system and skin .
R21/22:Harmful in contact with skin and if swallowed . | [Safety Statements ]
S22:Do not breathe dust .
S24/25:Avoid contact with skin and eyes .
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection .
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice . | [WGK Germany ]
3
| [RTECS ]
NK7882892 | [Hazard Note ]
Irritant | [HazardClass ]
IRRITANT | [HS Code ]
29339900 |
| Hazard Information | Back Directory | [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. | [Uses]
Indole-3-carboxylic acid is used as a raw material in synthesis. It is useful for the synthesis of anticancer agents, serotonin receptor antagonists, primary acylureas, and amino acid derivatives.Indole-3-carboxylic acid is a normal urinary indolic tryptophan metabolite and has been found elevated in patients with liver diseases. | [Uses]
Reactant for preparation of:
Anticancer agents
Derivatives of amino acids and peptides
Serotonin 5-HT4 receptor antagonists
Primary acylureas
Inhibitors of Gli1-mediated transcription in the Hedgehog pathway
Serotonin 5-HT6 antagonists
Very Late Antigen-4 (VLA-4) sntagonists
EphB3 receptor tyrosine kinase inhibitors
Potential Therapeutic Agent for Alzheimer′s Disease
Vinyl ester pseudotripeptide proteasome inhibitors | [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). | [target]
5-HT Receptor |
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