5-Hydroxyindoleacetic Acid (HCID 1826)

Namen und Bezeichner

Bevorzugter Name: 5-Hydroxyindoleacetic Acid
IUPAC: 2-(5-hydroxy-1H-indol-3-yl)acetic acid
Lokaler Name: 5-Hydroxyindol-3-ylessigsure
Englischer Name: 5-HYDROXYINDOLE-3-ACETIC ACID
Summenformel: C10H9NO3
Molmasse: 191.18

Namen und Synonyme

5-Hydroxyindole-3-acetic acid54-16-02-(5-hydroxy-1H-indol-3-yl)acetic acid5-HIAA5-Hydroxyindoleacetic acidHydroxyindoleacetic acid5-Hydroxyindol-3-ylacetic acidYHC763JY1PCHEBI:27823NSC-90432NSC90432Acid, Hydroxyindoleacetic

Weitere Namen anzeigen

HIAA5-oxyindoleaceticacid5-HYDROXY-3-INDOLEACETIC ACID5&＃0395-HO-IAANSC 90432Nature ProductTIMTEC-BB SBB003639

5 Hydroxy 3 Indoleacetic Acid5 Hydroxyindolamine Acetic Acid5-Hydroxyindolamine Acetic AcidAcid, 5-Hydroxy-3-IndoleaceticAcetic Acid, 5-HydroxyindolamineAcid, 5-Hydroxyindolamine AceticRefChem:789490200-195-4

Datenbank-Bezeichner

CAS: 54-16-0
PubChem CID: 1826
DTXSID: DTXSID50861582
ChEMBL: CHEMBL395915
ChEBI: CHEBI:27823
UNII: YHC763JY1P
EC Number: 200-195-4
Nikkaji: J11.030B

Eigenschaften

Berechnete Struktureigenschaften

XLogP: 1,1
Polarare Oberfläche (TPSA): 73,3 Å²
H-Brücken-Donoren: 3
H-Brücken-Akzeptoren: 3
Frei drehbare Bindungen: 2
Schwere Atome: 14
Formalladung: 0
Komplexität: 231

Experimentelle und physikochemische Eigenschaften

Solubility · 2 Einträge

24 mg/mL

>28.7 [ug/mL] (The mean of the results at pH 7.4)

Melting Point161 - 163 °C

Physical Description · 2 Einträge

Light red crystalline solid; [Sigma-Aldrich MSDS]

Solid

Collision Cross Section · 3 Einträge

148.4 Å² [M+Na]+ [CCS Type: DT; Method: single field calibrated with ESI Low Concentration Tuning Mix (Agilent)]；137.1 Å² [M-H]- [CCS Type: DT; Method: single field calibrated with ESI Low Concentration Tuning Mix (Agilent)]；140.9 Å² [M+H]+ [CCS Type: DT; Method: single field calibrated with ESI Low Concentration Tuning Mix (Agilent)]

140.9 Å² [M+H]+ [CCS Type: DT; Method: single field calibrated with Agilent tune mix (Agilent)]

141.1 Å² [M+H]+；148.6 Å² [M+Na]+；137.3 Å² [M-H]-

Physikochemische Eigenschaften

Schmelzpunkt: 161 · 161-164 °C (dec.) (lit.)
Siedepunkt: 326.92 °C · 326.92°C (rough estimate)
Dichte: 1.2722 · 1.2722 (rough estimate)
Brechungsindex: 1.531 · 1.5310 (estimate)
storage temp.: -20 °C · -20°C
Löslichkeit: Soluble in ethanol (50 mg/ml).
pka: 4.54 · 4.54±0.30(Predicted)
Aggregatzustand: crystalline
Farbe: off-white to purple
BRN: 168797 · 168797
Stabilität: Air Sensitive, Light Sensitive
Major Application: 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 · 54-16-0

Sicherheit und Regulatorisches

GHS-Klassifizierung

GHS Classification · 5 Einträge

Warning

H302 (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 exposure; Respiratory 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.

Gefahrenhinweise

Regulatory Information · 2 Einträge

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

Other Safety InformationEvaluation - Chemicals not considered for in depth evaluation - Not commercially active in Australia

Hazards SummaryCauses 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 CategoriesAcute Tox. 4 (100%)；Skin Irrit. 2 (100%)；Eye Irrit. 2A (100%)；STOT SE 3 (100%)

Regulatorische Informationen

Regulatory Information · 2 Einträge

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

Sicherheitsdaten

F: 8-10-23
wgk: 3
hs_code: 29339980
RTECS-Nr.: NL3650000
safety_code: 22-24/25
Speicherklasse: 11 - Combustible Solids

Chemie und Industrie

Pharmakologische Informationen

Tissue LocationsBrain；Liver；Neuron；Platelet；Prostate；Spleen；Testis

Cellular LocationsCytoplasm；Mitochondria

Metabolite PathwaysTryptophan metabolism

Verwendung und Herstellung

UsesIndole-3-acetic acid is a naturally occurring plant-growth hormone; [EPA]

Anwendungen · 2 Einträge

Beschreibung5-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.

Verwenden5-Hydroxyindole-3-acetic acid is an impurity of chlorpheniramine (C424300), an antihistaminic agent.