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143510 Sigma-Aldrich

5-Hydroxyindole-2-carboxylic acid

98%

Synonym: NSC 117338

  • CAS Number 21598-06-1

  • Empirical Formula (Hill Notation) C9H7NO3

  • Molecular Weight 177.16

  •  Beilstein/REAXYS Number 153214

  •  EC Number 244-468-6

  •  MDL number MFCD00005615

  •  PubChem Substance ID 24848591

  •  NACRES NA.22

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Properties

Related Categories Building Blocks, C7 to C9, Chemical Synthesis, Heterocyclic Building Blocks, Indoles More...
assay   98%
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

• 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

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

Packaging

1, 5 g in glass bottle

Safety & Documentation

Safety Information

Personal Protective Equipment 
RIDADR 
NONH for all modes of transport
WGK Germany 
WGK 3
Flash Point(F) 
Not applicable
Flash Point(C) 
Not applicable

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Protocols & Articles

Articles

Indoles

Sigma-Aldrich is proud to offer a new series of ChemFiles—called Privileged Structures, to our Drug Discovery and Organic Synthesis customers. Each piece will highlight a specific motif, selected app...
Chemfiles Volume 4 Article 8
Keywords: Building blocks, Cardiovascular, Diabetes, Diseases, Drug discovery, Medicinal chemistry, Organic synthesis, Respiratory

Peer-Reviewed Papers
15

References

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