143510

Sigma-Aldrich

5-Hydroxyindole-2-carboxylic acid

≥96.5%

Synonym(s):
NSC 117338
Empirical Formula (Hill Notation):
C9H7NO3
CAS Number:
Molecular Weight:
177.16
Beilstein/REAXYS Number:
153214
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.22

Quality Level

assay

≥96.5%

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

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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

Packaging

1, 5 g in glass bottle

Personal Protective Equipment

dust mask type N95 (US),Eyeshields,Gloves

RIDADR

NONH for all modes of transport

WGK Germany

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

E Pussard et al.
Clinical chemistry, 42(7), 1086-1091 (1996-07-01)
We describe an isocratic liquid-chromatographic method with amperometric detection for determination of serotonin by rapid sample preparation. Platelet-poor plasma and platelets were injected after a single deproteinization step with perchloric acid. Addition of sodium borohydride to whole blood avoids oxidation...
S Ito et al.
The Biochemical journal, 143(1), 207-217 (1974-10-01)
The reflecting material of the tapetum lucidum of the sea catfish (Arius felis) was chromatographed on Sephadex LH-20 in methanol-dimethyl sulphoxide-formic acid. Two components were present: one, showing an absorption maximum at 330nm, was tapetal pigment; the other, at 257nm...
Zebin Lin et al.
Biomedical chromatography : BMC, 33(10), e4626-e4626 (2019-06-22)
N-Ethylpentylone (NEP) is a popular synthetic cathinone abused worldwide. To obtain more information about its pharmacokinetics and pharmacodynamics, a rapid, simple and sensitive liquid chromatography-tandem mass spectrometry method was developed for the determination of NEP, two important neurotransmitters, dopamine and...
Yifeng Zeng et al.
Journal of chromatography. B, Analytical technologies in the biomedical and life sciences, 1110-1111, 133-143 (2019-02-27)
Gut microbiota-host co-metabolites play an essential role in maintaining homeostasis, and their concentration changes are closely related to a variety of diseases. Developing a targeted metabolomics analytical platform for these co-metabolites will help to elucidate the relationship between intestinal flora...

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