143510

5-Hydroxyindole-2-carboxylic acid

≥96.5%

• Synonym(s): NSC 117338
• Empirical Formula (Hill Notation): C₉H₇NO₃
• CAS Number: 21598-06-1
• Molecular Weight: 177.16
• Beilstein/REAXYS Number: 153214
• EC Number: 244-468-6
• MDL number: MFCD00005615
• UNSPSC Code: 12352100
• PubChem Substance ID: 24848591
• NACRES: NA.22

Properties

• assay: ≥96.5%
• form: powder
• mp: 249 °C (dec.) (lit.)
• solubility: chloroform/ethanol (1:1): soluble 50 mg/mL, clear to slightly hazy, yellow to brown
• SMILES string: Oc1ccc2[nH]c(cc2c1)C(O)=O
• 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)
• InChI key: BIMHWDJKNOMNLD-UHFFFAOYSA-N

Description

General description

5-Hydroxyindole-2-carboxylic acid on oxidation with KMnO₄ yields pyrrole-2,3,5-tricarboxylic acid.

Application

5-Hydroxyindole-2-carboxylic acid was used in HPLC-amperometric detection of serotonin in plasma, platelets and urine.

• 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 receptors
• Reactant for preparation of melanins as novel nature-inspired radioprotectors
• Reactant for preparation of 5-Hydroxyindole-2-carboxylic acid amides as histamine-3 receptor inverse agonists for the treatment of obesity
• Reactant for preparation of conformationally constrained peptidomimetic inhibitors of signal transducer and activator of transcription 3 (Stat3)
• Reactant for preparation of oxadiazole analogs as nonpeptidic SH2 inhibitors of tyrosine kinase ZAP-70

Safety Information

• Storage Class: 11 - Combustible Solids
• wgk_germany: WGK 3
• flash_point_f: Not applicable
• flash_point_c: Not applicable
• ppe: dust mask type N95 (US), Eyeshields, Gloves