219878

Sigma-Aldrich

4-Hydroxyindole

99%

Synonym(s):
4-Indolol, 4-Hydroxyindole
Empirical Formula (Hill Notation):
C8H7NO
CAS Number:
Molecular Weight:
133.15
Beilstein/REAXYS Number:
114905
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.22

Quality Level

assay

99%

mp

97-99 °C (lit.)

SMILES string

Oc1cccc2[nH]ccc12

InChI

1S/C8H7NO/c10-8-3-1-2-7-6(8)4-5-9-7/h1-5,9-10H

InChI key

NLMQHXUGJIAKTH-UHFFFAOYSA-N

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General description

Glucouridination of 4-hydroxyindole by human uridine 5′-diphospho-glucuronosyltransferase has been repotrted.

Application

  • Reactant for preparation of N-β-D-xylosyl-indole derivatives as SGLT2 inhibitors for management of hyperglycemia in diabetes
  • Reactant for preparation of small molecules targeting interaction between HIV-1 integrase and LEDGF/p75 cofactor
  • Reactant for preparation of dopamine D2 receptor antagonists
  • Reactant for preparation of SCD inhibitor MF-438
  • Reactant for preparation of carbon-11-labeled 4-aryl-4H-chromenes as new PET agents for imaging of apoptosis in cancer
  • Reactant for preparation of indole/quinoline carbothioic acid amide derivatives as HCV inhibitors

Packaging

1 g in glass bottle

Pictograms

Exclamation mark

Signal Word

Warning

Hazard Statements

Precautionary Statements

Target Organs

Respiratory system

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

Stefan W Toennes et al.
Journal of pharmaceutical and biomedical analysis, 140, 215-222 (2017-04-04)
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Shalenie P den Braver-Sewradj et al.
Current drug metabolism, 19(4), 370-381 (2018-01-11)
Inter-individual variability in hepatic drug metabolizing enzyme (DME) activity is a major contributor to heterogeneity in drug clearance and safety. Accurate data on expression levels and activities of DMEs is an important prerequisite for in vitro-in vivo extrapolation and in...
Alexandra M Adams et al.
Metabolic engineering, 56, 111-119 (2019-09-25)
Psilocybin, the prodrug of the psychoactive molecule psilocin, has demonstrated promising results in clinical trials for the treatment of addiction, depression, and post-traumatic stress disorder. The development of a psilocybin production platform in a highly engineerable microbe could lead to...
Gavin Carr et al.
Journal of medicinal chemistry, 51(9), 2634-2637 (2008-04-09)
Synthetic analogues of the sponge natural product exiguamine A (3) have been prepared and evaluated for their ability to inhibit indoleamine 2,3-dioxygenase in vitro.

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