5-Hydroxyindole

HCID 16054CAS 1953-54-4
Substructure searchFind similar structures

Basic information

Standard SMILES
Oc1ccc2[nH]ccc2c1
InChIKey
LMIQERWZRIFWNZ-UHFFFAOYSA-N
Molecular formula
C8H7NO
Average molar mass
133.15 g/mol
Monoisotopic mass
133.05276384

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5-hydroxyindole is a member of the class of hydroxyindoles that is 1H-indole in which the hydrogen at position 5 has been replaced by a hydroxy group.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 indoleMFCD000056775-hydroxy indoleUNII-320UN7XZYN3fuhHydroxy-5 indole [French]

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

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

Safety & regulation

GHS classification

GHS Classification · 4 items

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

Chemistry & industry

Applications · 2 items

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

Suppliers50 total

国药集团化学试剂有限公司86-21-63210123 · [email protected]
梯希爱(上海)化成工业发展有限公司021-67121386 · [email protected]
衢州润东化工有限公司0570-8789886 18892685668 · [email protected]
上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]
T&W GROUP021-61551611 13296011611 · [email protected]

Additional notes

DefinitionChEBI: 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.

Related reactions

224 records
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Linked notes

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