5-Hydroxyindol-3-ylessigsure

5-HIAA · HIAA · 2-(5-hydroxy-1H-indol-3-yl)acetic acid · 5-oxyindoleaceticacid · 5-HYDROXY-3-INDOLEACETIC ACID · 5&＃039 · 5-HO-IAA · NSC 90432

https://huagongshe.com/de/chemical/1826

Molekülstruktur von 5-Hydroxyindol-3-ylessigsure

Identifikatoren & physikalische Daten

CAS No.	54-16-0
Summenformel	C10H9NO3
Durchschnittliche Molmasse	191,18 g/mol
Monoisotopische Masse	191,05824315 g/mol
SMILES	O=C(O)Cc1c[nH]c2ccc(O)cc12
InChIKey	DUUGKQCEGZLZNO-UHFFFAOYSA-N
PubChem CID	1826
ChEMBL	CHEMBL395915
ChEBI	CHEBI:27823
EC No.	200-195-4
DTXSID	DTXSID50861582
Lokaler Name	5-Hydroxyindol-3-ylessigsure

Chemische & physikalische Eigenschaften

XLogP	1,1
Polarare Oberfläche (TPSA)	73,3
H-Brücken-Donoren	3
H-Brücken-Akzeptoren	3
Frei drehbare Bindungen	2
Schwere Atome	14
Formalladung	0
Komplexität	231
Löslichkeit	24 mg/mL>28.7 [ug/mL] (The mean of the results at pH 7.4)Soluble in ethanol (50 mg/ml).
Schmelzpunkt	161 - 163 °C161-164 °C (dec.) (lit.)
Physical Description	Light red crystalline solid[Sigma-Aldrich MSDS]
Collision Cross Section	148.4 Å² [M+Na]+ [CCS Type: DTMethod: single field calibrated with ESI Low Concentration Tuning Mix (Agilent)]137.1 Å² [M-H]- [CCS Type: DT140.9 Å² [M+H]+ [CCS Type: DTMethod: single field calibrated with Agilent tune mix (Agilent)]141.1 Å² [M+H]+148.6 Å² [M+Na]+137.3 Å² [M-H]-
Siedepunkt	326.92°C (rough estimate)
Dichte	1.2722 (rough estimate)
Brechungsindex	1.5310 (estimate)
Lagerbedingungen	-20°C
pKa (Säurekonstante)	4.54±0.30(Predicted)
Aggregatzustand	crystalline
Farbe	off-white to purple
BRN	168797
Stabilität	Air Sensitive, Light Sensitive
Hauptanwendungen	clinical testing
InChI	1S/C10H9NO3/c12-7-1-2-9-8(4-7)6(5-11-9)3-10(13)14/h1-2,4-5,11-12H,3H2,(H,13,14)
InChIKey	DUUGKQCEGZLZNO-UHFFFAOYSA-N
SMILES	OC(=O)Cc1c[nH]c2ccc(O)cc12
CAS Datenbank	54-16-0

Sicherheit & Vorschriften

GHS-Einstufung	WarningH302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]H319 (100%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]H335 (100%): May cause respiratory irritation [Warning Specific target organ toxicity, single exposureRespiratory tract irritation]P261, P264, P264+P265, P270, P271, P280, P301+P317, P302+P352, P304+P340, P305+P351+P338, P319, P321, P330, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)The GHS information provided by 1 company from 1 notification to the ECHA C&L Inventory.
Regulatorische Informationen	Chemical: 1H-Indole-3-acetic acid, 5-hydroxy-5-Hydroxyindol-3-ylacetic acid: Does not have an individual approval but may be used under an appropriate group standard
Weitere Sicherheitsinformationen	Evaluation - Chemicals not considered for in depth evaluation - Not commercially active in Australia
Gefahrenübersicht	Causes somnolence in intraperitoneal lethal-dose studies of mice (LD50 = 1,125 mg/kg)[RTECS] May cause irritation[Sigma-Aldrich MSDS] See Indole-3-butyric acid.
Hazard Classes and Categories	Acute Tox. 4 (100%)Skin Irrit. 2 (100%)Eye Irrit. 2A (100%)STOT SE 3 (100%)
F	8-10-23
Wassergefährdungsklasse (WGK)	3
Zollcode	29339980
RTECS-Nr.	NL3650000
Sicherheitshinweise (S)	22-24/25
Lagerklasse	11 - Combustible Solids

Anwendungen & Verwendung

Beschreibung

5-hydroxy Indole-3-acetic acid (5-HIAA) is the primary metabolite of serotonin (5-HT; ). It is formed when 5-HT is metabolized by monamine oxidase and aldehyde dehydrogenase in the liver. 5-HIAA is excreted in urine and has been used as a biomarker for detection of neuroendocrine tumors and an internal standard for the quantification of serotonin metabolism in rat brain using mass spectrometry. 5-HIAA has also been associated with autism, insomnia, and chronic migraine.

Verwenden

5-Hydroxyindole-3-acetic acid is an impurity of chlorpheniramine (C424300), an antihistaminic agent.