All Photos(1)

18805

Sigma-Aldrich

6-Hydroxyindole

≥99.0% (GC)

Synonym(s):
6-Indolol
Empirical Formula (Hill Notation):
C8H7NO
CAS Number:
Molecular Weight:
133.15
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.22

Quality Level

assay

≥99.0% (GC)

mp

126-132 °C

SMILES string

Oc1ccc2cc[nH]c2c1

InChI

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

InChI key

XAWPKHNOFIWWNZ-UHFFFAOYSA-N

Application

  • Reactant for preparation of tryptophan dioxygenase inhibitors pyridyl-ethenyl-indoles as potential anticancer immunomodulators
  • Reactant for asymmetrical synthesis of notoamide J as a potential biosynthetic precursor of prenylated indole alkaloids
  • Reactant for preparation of (quinolinyloxymethyl)isoxazolecarboxylate esters antituberculosis agents
  • Reactant for preparation of indolyl(propanolamine) derivatives as HIV inhibitors
  • Reactant for preparation of indoleoxyacetic acid derivatives as peroxisome proliferator-activated receptor agonists
  • Reactant for preparation of 1-aroylindole 3-aroylindoles combretastatin A-4 analogs as antitumor agents and tubulin polymerization inhibitors

Packaging

1 g in glass bottle

Signal Word

Danger

Hazard Statements

Precautionary Statements

Hazard Classifications

Acute Tox. 4 Oral - Aquatic Chronic 2 - Eye Dam. 1 - Skin Sens. 1

Storage Class Code

13 - Non 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

Certificate of Analysis

Certificate of Origin

Damon Borg et al.
Journal of analytical toxicology, 41(1), 6-16 (2016-09-30)
Synthetic cannabinoids are a group of psychoactive compounds that mimic the effects of Δ9-tetrahydrocannabinol, the primary psychoactive constituent of marijuana (Cannabis sativa L). The Drug Enforcement Administration has classified many of the most common cannabinoids as Schedule 1 controlled substances....
Jintae Lee et al.
Applied and environmental microbiology, 73(13), 4100-4109 (2007-05-08)
Since indole is present at up to 500 microM in the stationary phase and is an interspecies biofilm signal (J. Lee, A. Jayaraman, and T. K. Wood, BMC Microbiol. 7:42, 2007), we investigated hydroxyindoles as biofilm signals and found them...
Stefan W Toennes et al.
Drug testing and analysis, 10(4), 644-650 (2017-10-03)
Each year, synthetic cannabinoids occur in high numbers on the illicit drug market, but data on their detectability are rarely available. A pilot study was performed to assess adverse effects of JWH-018, which is one of the oldest and best...
Martin Švidrnoch et al.
Talanta, 150, 568-576 (2016-02-04)
Perfluoroheptanoic acid was employed as a volatile micellar phase in background electrolyte for micellar electrokinetic chromatography-tandem mass spectrometry separation and determination of 15 selected naphthoyl- and phenylacetylindole- synthetic cannabinoids and main metabolites derived from JWH-018, JWH-019, JWH-073, JWH-200 and JWH-250....
Yoshimitsu Yamazaki et al.
Zeitschrift fur Naturforschung. C, Journal of biosciences, 65(1-2), 49-54 (2010-04-02)
A recent study showed that N-acylserotonin derivatives have strong inhibitory activity against tyrosinase. To clarify the role of the 5-hydroxy group in the indole ring, 2-, 4-, 5-, 6-, and 7-hydroxyindole and 11 related compounds such as 5-hydroxyindan and 6-hydroxyquinoline...

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