5-hydroxy-1H-indole-2-carboxylic acid

• ChemBase ID: 103312
• Molecular Formular: C9H7NO3
• Molecular Mass: 177.15678
• Monoisotopic Mass: 177.04259309
• SMILES: OC(=O)c1cc2cc(O)ccc2[nH]1
• Canonical SMILES: Oc1ccc2c(c1)cc([nH]2)C(=O)O
• InChI: InChI=1S/C9H7NO3/c11-6-1-2-7-5(3-6)4-8(10-7)9(12)13/h1-4,10-11H,(H,12,13)
• InChIKey: BIMHWDJKNOMNLD-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 5-hydroxy-1H-indole-2-carboxylic acid
• IUPAC Traditional name: 5-hydroxy-1H-indole-2-carboxylic acid
• Synonyms: NSC 117338; 5-Hydroxyindole-2-carboxylic acid; 5-HYDROXYINDOLE-2-CARBOXYLIC ACID; 5-羟基吲哚-2-甲酸

Database IDs

• CAS Number: 21598-06-1
• EC Number: 244-468-6
• MDL Number: MFCD00005615
• Beilstein Number: 153214
• PubChem SID: 162090577; 24848591; 24879337
• PubChem CID: 88958

CALCULATED PROPERTIES

• Acid pKa: 3.602502
• H Acceptors: 3
• H Donor: 3
• LogD (pH = 5.5): -0.54695344
• LogD (pH = 7.4): -1.9990214
• Log P: 1.3460265
• Molar Refractivity: 46.2591 cm^3
• Polarizability: 18.468376 Å^3
• Polar Surface Area: 73.32 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 249 °C (dec.)(lit.); ca 245°C dec.

Safety Information

• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 26-36; 26-37
• TSCA Listed: 否
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338; P261-P305+P351+P338-P302+P352-P321-P405-P501A
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves

Product Information

• Purity: ≥97.0% (T); 97%; 98%
• Grade: purum
• Empirical Formula (Hill Notation): C9H7NO3

DETAILS

MP Biomedicals - 02151293

Crystalline

Sigma Aldrich - 143510

Packaging
1, 5 g in glass bottle
250 mg in glass bottle
Application

• Reactant for preparation of indole C5-O-substituted seco-cyclopropylindole analogs as potential anticancer agents
• Reactant for microwave combinatorial synthesis of indolic arylpiperazine derivatives as ligands for 5-HT1A, 5-HT2A, and 5-HT2C receptors1
• Reactant for preparation of melanins as novel nature-inspired radioprotectors2
• Reactant for preparation of 5-Hydroxyindole-2-carboxylic acid amides as histamine-3 receptor inverse agonists for the treatment of obesity3
• Reactant for preparation of conformationally constrained peptidomimetic inhibitors of signal transducer and activator of transcription 3 (Stat3)4
• Reactant for preparation of oxadiazole analogs as nonpeptidic SH2 inhibitors of tyrosine kinase ZAP-705

Sigma Aldrich - 55355

Application

• Reactant for preparation of indole C5-O-substituted seco-cyclopropylindole analogs as potential anticancer agents
• Reactant for microwave combinatorial synthesis of indolic arylpiperazine derivatives as ligands for 5-HT1A, 5-HT2A, and 5-HT2C receptors1
• Reactant for preparation of melanins as novel nature-inspired radioprotectors2
• Reactant for preparation of 5-Hydroxyindole-2-carboxylic acid amides as histamine-3 receptor inverse agonists for the treatment of obesity3
• Reactant for preparation of conformationally constrained peptidomimetic inhibitors of signal transducer and activator of transcription 3 (Stat3)4
• Reactant for preparation of oxadiazole analogs as nonpeptidic SH2 inhibitors of tyrosine kinase ZAP-705