5-Hydroxyindole Chemical Properties

Melting point:

106-108 °C(lit.)

Boiling point:

245.66°C (rough estimate)

Density 

1.1475 (rough estimate)

refractive index 

1.5260 (estimate)

storage temp. 

Keep in dark place,Sealed in dry,Store in freezer, under -20°C

solubility 

38g/l

form 

Crystalline Needles or Powder

pka

9.98±0.40(Predicted)

color 

beige

Sensitive 

Light Sensitive

BRN 

112349

InChI

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

InChIKey

LMIQERWZRIFWNZ-UHFFFAOYSA-N

SMILES

N1C2=C(C=C(O)C=C2)C=C1

CAS DataBase Reference

1953-54-4(CAS DataBase Reference)

NIST Chemistry Reference

Indol-5-ol(1953-54-4)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36-37/39

WGK Germany 

3

RTECS 

NM2430000

HazardClass 

IRRITANT, KEEP COLD

HS Code 

29339990

MSDS

• Language:English Provider:5-Hydroxyindole
• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS
• Language:English Provider:ALFA

5-Hydroxyindole Usage And Synthesis

Chemical Properties

beige to brown crystalline needles or powder

Uses

• ;Reactant for preparation of (oxoimidazolidinyl/oxopyrimidinyl)benzenesulfonates as antitumor agents and tubulin inhibitors1• ;Reactant for preparation of anthranilic acids2• ;Reactant for preparation of indole compounds as dopamine D2 receptor antagonists3• ;Reactant for preparation of naphthalimide- or carbazole-containing human β-adrenoceptor ligands4• ;Reactant for preparation of melanins as nature-inspired radioprotectors5• ;Reactant for preparation of 5-vinyl-3-pyridinecarbonitriles as PKCθ inhibitors6

Uses

5-Hydroxyindole is a hydroxylated indole used as a building block in the preparation of various pharmaceutical compounds such as indole based neurochemicals. 5-Hydroxyindole is a metabolite of Tryptophan (T894800). 5-Hydroxyindole displayed weak inhibitory activity on human melanoma tyrosinase. 5-Hydroxyindole also showed inhibition of serotonin transport by blood platelets.

Definition

ChEBI: 5-hydroxyindole is a member of the class of hydroxyindoles that is 1H-indole in which the hydrogen at position 5 has been replaced by a hydroxy group. It has a role as a human metabolite.

Synthesis Reference(s)

Journal of the American Chemical Society, 76, p. 5579, 1954 DOI: 10.1021/ja01651a001
The Journal of Organic Chemistry, 49, p. 4833, 1984 DOI: 10.1021/jo00199a017

5-Hydroxyindole(1953-54-4)Related Product Information

• Indole-3-acetic acid
• Indole-3-butyric acid
• Chrysin
• Indometacin
• 5-HYDROXYOXINDOLE
• 2,3-DIHYDROINDOL-5-OL
• 5-Methoxyindole-3-carboxaldehyde
• 5,6-Dimethoxyindole
• 5-Methoxyindole
• 5-METHOXY-2-METHYLINDOLE
• 5-BENZYLOXYGRAMINE
• Melatonine
• DL-5-HYDROXYTRYPTOPHAN
• 5-Benzyloxyindole
• 5-Methoxytryptamine
• 7-HYDROXYINDOLE
• 5-METHOXY-DL-TRYPTOPHAN
• 4-HYDROXYINDOLE