5-Hydroxyindole
1H-INDOL-5-OL · 5-INDOLOL · 5-Hydroxyindoline · NSC 87503 · INDOL-5-OL · 5-hdroxyindole · 5-HYDROXYINDOLE · hydroxy-5indole
Identifiers & Physical Properties
| CAS No. | 1953-54-4 |
|---|---|
| Molecular formula | C8H7NO |
| Average molar mass | 133.15 g/mol |
| Monoisotopic mass | 133.05276384 g/mol |
| SMILES | Oc1ccc2[nH]ccc2c1 |
| InChIKey | LMIQERWZRIFWNZ-UHFFFAOYSA-N |
| PubChem CID | 16054 |
| ChEMBL | CHEMBL404923 |
| ChEBI | CHEBI:89649 |
| EC No. | 217-782-6 |
| DTXSID | DTXSID00173187 |
Chemical & Physical Properties
| XLogP | 2 |
|---|---|
| Topological polar surface area | 36 |
| Hydrogen bond donors | 2 |
| Hydrogen bond acceptors | 1 |
| Rotatable bonds | 0 |
| Heavy atoms | 10 |
| Formal charge | 0 |
| Complexity | 126 |
| Melting point | 106-108 °C(lit.) |
| Boiling point | 245.66°C (rough estimate) |
| Density | 1.1475 (rough estimate) |
| Refractive index | 1.5260 (estimate) |
| Storage conditions | Keep in dark place,Sealed in dry,Store in freezer, under -20°C |
| Solubility | 38g/l |
| Physical state | Crystalline Needles or Powder |
| pKa (acidity coefficient) | 9.98±0.40(Predicted) |
| Color | beige |
| Sensitivity | 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) |
| EWG's Food Scores | 1 |
| FDA UNII | 320UN7XZYN |
| NIST Chemistry Reference | Indol-5-ol(1953-54-4) |
| UNSPSC Code | 12352100 |
| NACRES | NA.22 |
| GHS pictogram | GHS07 |
| Signal word | Warning |
| GHS hazard statements | H315-H319-H335 |
| GHS precautionary statements | P261-P280a-P304+P340-P305+P351+P338-P405-P501a |
| Personal protective equipment (PPE) | dust mask type N95 (US), Eyeshields, Gloves |
| Hazard symbols | Xi |
| Risk statements (R) | 36/37/38 |
| Safety statements (S) | 26-36-37/39 |
| Water hazard class (WGK) | 3 |
| RTECS number | NM2430000 |
| Hazard class | IRRITANT, KEEP COLD |
| Customs code | 29339990 |
| Storage class | 11 - Combustible Solids |
Safety & Regulations
| GHS classification | WarningH315 (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 Classes and Categories | Skin Irrit. 2 (100%) |
| Personal protective equipment (PPE) | dust mask type N95 (US), Eyeshields, Gloves |
| Water hazard class (WGK) | 3 |
| RTECS number | NM2430000 |
| Customs code | 29339990 |
| Risk statements (R) | 36/37/38 |
| Signal word | Warning |
| GHS pictogram | GHS07 |
| Hazard symbols | Xi |
| Safety statements (S) | 26-36-37/39 |
| Hazard class | IRRITANT, KEEP COLD |
| Storage class | 11 - Combustible Solids |
| GHS hazard statements | H315-H319-H335 |
| GHS precautionary statements | P261-P280a-P304+P340-P305+P351+P338-P405-P501a |
Applications & Uses
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.