CAS 21598-06-1 5-Hydroxyindole-2-carboxylic acid (HCID 88958)

Overview

5-Hydroxyindole-2-carboxylic acid is an indolyl carboxylic acid.

Names & identifiers

Preferred name: 5-Hydroxyindole-2-carboxylic acid
IUPAC: 5-hydroxy-1H-indole-2-carboxylic acid
English name: 5-Hydroxyindole-2-carboxylic acid
Molecular formula: C9H7NO3
Molecular weight: 177.16

Names & synonyms

21598-06-15-Hydroxyindole-2-carboxylic acid5-Hydroxy-1H-indole-2-carboxylic acid5-Hydroxy-2-indolecarboxylic acid5XP5R85YFDNSC 1173381H-Indole-2-carboxylic acid, 5-hydroxy-NSC-117338DTXSID50175959EINECS 244-468-6RefChem:102889DTXCID7098450

Show more names

5-HO-ICA5-Hydroxyindole-2-carboxylicacid,97%5-Hydroxy-2-indolecarboxylic acid 98%5-Hydroxyindole-2-carboxylic acid 98%5-Hydroxy-2-indolecarboxylic acid,98%

244-468-6BIMHWDJKNOMNLD-UHFFFAOYSA-NMFCD000056155-Hydroxyindole-2-carboxylicacidNSC117338Oprea1_4122525-Hydroxyindole-2-carboxylic acid, 98%SY039818

Database identifiers

CAS: 21598-06-1
PubChem CID: 88958
DTXSID: DTXSID50175959
ChEMBL: CHEMBL1368373
ChEBI: CHEBI:167509
UNII: 5XP5R85YFD
EC Number: 244-468-6
Nikkaji: J226.235E

Properties

Computed structural properties

XLogP: 2
Topological polar surface area: 73.3 Å²
Hydrogen bond donors: 3
Hydrogen bond acceptors: 3
Rotatable bonds: 1
Heavy atoms: 13
Formal charge: 0
Complexity: 219

Physicochemical properties

Melting point: 249 °C · 249 °C (dec.) (lit.)
Boiling point: 309.06 °C · 309.06°C (rough estimate)
Density: 1.3312 · 1.3312 (rough estimate)
refractive index: 1.52 · 1.5200 (estimate)
storage temp.: 2 · Sealed in dry,2-8°C
solubility: chloroform/ethanol (1:1): soluble50mg/mL, clear to slightly hazy, yellow to brown
form: Fuming Liquid
pka: 4.38 · 4.38±0.30(Predicted)
color: Clear colorless to slightly yellow
BRN: 153214 · 153214
CAS DataBase Reference: 21598 · 21598-06-1(CAS DataBase Reference)
FDA UNII: 5 XP5R85YFD · 5XP5R85YFD
UNSPSC Code: 12352100 · 12352100
NACRES: 22 · NA.22
Symbol(GHS): 7 · GHS07
Signal word: Warning
Hazard statements: 315 · H315-H319-H335
Precautionary statements: 261 · P261-P280a-P304+P340-P305+P351+P338-P405-P501a
Hazard Codes: Xi,Xn
Risk Statements: 36 · 36/37/38-21/22
Safety Statements: 26 · 26-36-36/37/39
WGK Germany: 3 · 3
HS Code: 29339900 · 29339900

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 45 reports by companies from 4 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

wgk: 3
hs_code: 29339900
risk_code: 36/37/38-21/22
Signal word: Warning
Symbol(GHS): GHS07
hazard_code: Xi,Xn
safety_code: 26-36-36/37/39
Hazard statements: H315-H319-H335
Precautionary statements: P261-P280a-P304+P340-P305+P351+P338-P405-P501a

Chemistry & industry

Applications · 4 items

Uses• ;Reactant for preparation of indole C5-O-substituted seco-cyclopropylindole analogs as potential anticancer agents• ;Reactant for microwave combinatorial synthesis of indolic arylpiperazine derivatives as ligands for 5-HT1A, 5-HT2A, and 5-HT2C receptors1• ;Reactant for preparation of melanins as novel nature-inspired radioprotectors2• ;Reactant for preparation of 5-Hydroxyindole-2-carboxylic acid amides as histamine-3 receptor inverse agonists for the treatment of obesity3• ;Reactant for preparation of conformationally constrained peptidomimetic inhibitors of signal

Uses5-Hydroxyindole-2-carboxylic acid was used in HPLC-amperometric detection of serotonin in plasma, platelets and urine.

UsesA competitive antagonist of potentiation by glycine at the N-methyl-D-aspartate receptors that have been linked to neuronal death, assiciated to such afflictions as stroke and epilepsy.

General Description5-Hydroxyindole-2-carboxylic acid on oxidation with KMnO4 yields pyrrole-2,3,5-tricarboxylic acid.