5-Hydroxyindole
Basic information
- CAS
1953-54-4- Standard SMILES
Oc1ccc2[nH]ccc2c1- InChIKey
LMIQERWZRIFWNZ-UHFFFAOYSA-N- Molecular formula
- C8H7NO
- Average molar mass
- 133.15 g/mol
- Monoisotopic mass
- 133.05276385
Overview
5-hydroxyindole is a member of the class of hydroxyindoles that is 1H-indole in which the hydrogen at position 5 has been replaced by a hydroxy group.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.
Names & identifiers
- Preferred name
- 5-Hydroxyindole
- IUPAC
- 1H-indol-5-ol
- English name
- 5-Hydroxyindole
- Molecular formula
- C8H7NO
- Molecular weight
- 133.15
Names & synonyms
5-Hydroxyindole1H-Indol-5-ol1953-54-4INDOL-5-OL5-Hydroxy-1H-indoleDTXSID00173187320UN7XZYNNSC-87503CHEBI:896491 H-indol-5-olRefChem:102888DTXCID5095678
Show more names
5-HydroxyindolineNSC 875035-hdroxyindolehydroxy-5indoleHydroxyindole,98%
217-782-65-IndololHydroxy-5 indole3fuhMFCD000056771h-indole-5-ol5-hydroxylindole5-hydroxy-indol
Database identifiers
- CAS
1953-54-4- PubChem CID
- 16054
- DTXSID
DTXSID00173187- ChEMBL
CHEMBL404923- ChEBI
CHEBI:89649- UNII
- 320UN7XZYN
- EC Number
- 217-782-6
- Nikkaji
- J41.080B
Properties
Computed structural properties
- XLogP
- 2
- Topological polar surface area
- 36 Ų
- Hydrogen bond donors
- 2
- Hydrogen bond acceptors
- 1
- Rotatable bonds
- 0
- Heavy atoms
- 10
- Formal charge
- 0
- Complexity
- 126
Experimental & physicochemical properties
LogP1.29
Physicochemical properties
- Melting point
- 106 · 106-108 °C(lit.)
- Boiling point
- 245.66 °C · 245.66°C (rough estimate)
- Density
- 1.1475 · 1.1475 (rough estimate)
- refractive index
- 1.526 · 1.5260 (estimate)
- storage temp.
- -20 °C · Keep in dark place,Sealed in dry,Store in freezer, under -20°C
- solubility
- 38 g/l · 38g/l
- form
- Crystalline Needles or Powder
- pka
- 9.98 · 9.98±0.40(Predicted)
- color
- beige
- Sensitive
- Light Sensitive
- BRN
- 112349 · 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
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
GHS classification
GHS Classification
Warning
H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]
P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 47 reports by companies from 7 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Hazard information
Hazard Classes and CategoriesSkin Irrit. 2 (100%)
Safety data
- PPE
- dust mask type N95 (US), Eyeshields, Gloves
- wgk
- 3
- rtecs
- NM2430000
- hs_code
- 29339990
- risk_code
- 36/37/38
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- hazard_code
- Xi
- safety_code
- 26-36-37/39
- hazard_class
- IRRITANT, KEEP COLD
- Storage Class
- 11 - Combustible Solids
- Hazard statements
- H315-H319-H335
- Precautionary statements
- P261-P280a-P304+P340-P305+P351+P338-P405-P501a
Chemistry & industry
Applications
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
Uses5-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.
Upstream & downstream products
Upstream raw materials
Related reactions
224 records
Compound notes
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