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143510

Sigma-Aldrich

5-Hydroxyindole-2-carboxylic acid

≥96.5%

Synonym(s):

NSC 117338

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About This Item

Empirical Formula (Hill Notation):
C9H7NO3
CAS Number:
Molecular Weight:
177.16
Beilstein:
153214
EC Number:
MDL number:
UNSPSC Code:
12352100
PubChem Substance ID:
NACRES:
NA.22

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

functional group

carboxylic acid

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

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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

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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