HuagongsheHuagongshe Chemie-Druckbericht · Nur für Forschungszwecke
Indol-3-ylessigsure
IAA · INDOLEACETIC ACID · 2-(1H-INDOL-3-YL)ACETIC ACID · 3-INDOLEACETIC ACID · Gap · Indolylacetic acid · INDOL-3-YLACETIC ACID · HETEROAUXINE
Identifikatoren & physikalische Daten
| CAS No. | 87-51-4 |
|---|---|
| Summenformel | C10H9NO2 |
| Durchschnittliche Molmasse | 175,18 g/mol |
| Monoisotopische Masse | 175,06332853 g/mol |
| SMILES | O=C(O)Cc1c[nH]c2ccccc12 |
| InChIKey | SEOVTRFCIGRIMH-UHFFFAOYSA-N |
| PubChem CID | 802 |
| ChEMBL | CHEMBL82411 |
| ChEBI | CHEBI:16411 |
| EC No. | 201-748-2 |
| DTXSID | DTXSID5020738 |
| Lokaler Name | Indol-3-ylessigsure |
Chemische & physikalische Eigenschaften
| XLogP | 1,4 |
|---|---|
| Polarare Oberfläche (TPSA) | 53,1 |
| H-Brücken-Donoren | 2 |
| H-Brücken-Akzeptoren | 2 |
| Frei drehbare Bindungen | 2 |
| Schwere Atome | 13 |
| Formalladung | 0 |
| Komplexität | 205 |
| Arzneimittel | Pharmaceuticals -> Listed in ZINC15 |
| SpringerMaterials Properties | Angular frequency |
| Pestizide | Plant Growth RegulatorsActive substance -> EU Pesticides database: Not approvedPesticides -> Plant Growth Regulators |
| LogP (Verteilungskoeffizient) | 1.41 |
| Löslichkeit | 1.5 mg/mL>26.3 [ug/mL] (The mean of the results at pH 7.4)DMSO:30.0(Max Conc. mg/mL)171.25(Max Conc. mM)Soluble in ethanol (50 mg/ml), methanol, DMSO, and chloroform (sparingly). Insoluble in water. |
| Schmelzpunkt | 168.5 °C165-169 °C (lit.) |
| Dampfdruck | 0.00000526 [mmHg] |
| Physical Description | Solid[Merck Index] Light tan to light pink flaky powderOdorless[PhytoTechnology Laboratories MSDS] |
| Collision Cross Section | 136.2 Ų [M+H]+ [CCS Type: DTMethod: single field calibrated with Agilent tune mix (Agilent)]138.11 Ų [M+H]+ [CCS Type: DTMethod: stepped-field]143.5 Ų [M+Na]+ [CCS Type: DTMethod: single field calibrated with ESI Low Concentration Tuning Mix (Agilent)]143.6 Ų [M+Na]+ |
| Siedepunkt | 306.47°C (rough estimate) |
| Dichte | 1.1999 (rough estimate) |
| Brechungsindex | 1.5460 (estimate) |
| Flammpunkt | 171°C |
| Lagerbedingungen | -20°C |
| pKa (Säurekonstante) | 4.75(at 25℃) |
| Aggregatzustand | crystalline |
| Farbe | off-white to tan |
| Decomposition | 167 ºC |
| Merck | 14,4964 |
| BRN | 143358 |
| Stabilität | Stable. Incompatible with strong oxidizing agents. Light sensitive. |
| Hauptanwendungen | agricultureenvironmental |
| Kosmetik-Inhaltsstoffe Funktionen | SKIN CONDITIONING |
| InChI | 1S/C10H9NO2/c12-10(13)5-7-6-11-9-4-2-1-3-8(7)9/h1-4,6,11H,5H2,(H,12,13) |
| InChIKey | SEOVTRFCIGRIMH-UHFFFAOYSA-N |
| SMILES | OC(=O)Cc1c[nH]c2ccccc12 |
| LogP (Verteilungskoeffizient) | 1.410 |
| CAS Datenbank | 87-51-4(CAS DataBase Reference) |
| NIST chemische Informationen | Indole-3-acetic acid(87-51-4) |
| EPA chemische Informationen | Indole-3-acetic acid (87-51-4) |
Sicherheit & Vorschriften
| GHS-Einstufung | This chemical does not meet GHS hazard criteria for 8.9% (5 of 56) of reports.WarningH302 (58.9%): Harmful if swallowed [Warning Acute toxicity, oral]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)Aggregated GHS information provided per 56 reports by companies from 14 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies. |
|---|---|
| Regulatorische Informationen | Chemical: 1H-Indole-3-acetic acid2008/941Status: Active Update: 29-08-2022 https://echa.europa.eu/registration-dossier/-/registered-dossier/34003Indole-3-acetic acid: Does not have an individual approval but may be used under an appropriate group standard |
| Gefahrenübersicht | An irritant[PhytoTechnology Laboratories MSDS] See Indole. See Indole-3-butyric acid. |
| Hazard Classes and Categories | Acute Tox. 4 (58.9%) |
| Treatment | Chronic Exposure: Kidney dialysis is usually needed to relieve the symptoms of uremic syndrome until normal kidney function can be restored. Acute Exposure: EYES: irrigate opened eyes for several minutes under running water. INGESTION: do not induce vomiting. Rinse mouth with water (never give anything by mouth to an unconscious person). Seek immediate medical advice. |
| Gesundheitliche Auswirkungen | Indoleacetic acid is listed in its MSDS as potentially mutagenic to mammalian somatic cells. It is also identified as a potential skin, eye, and respiratory irritant, and users are warned not to ingest it. Acute exposure to Indoleacetic acid can lead to some mild skin and eye irritation. Chronic exposure to uremic toxins can lead to a number of conditions including renal damage, chronic kidney disease and cardiovascular disease. Chronically high levels of Indoleacetic acid are associated with the inborn error of metabolism known as Hartnup disease. |
| Expositionspfade | Endogenous, Ingestion, Dermal (contact) |
| Toxizitätsübersicht | Uremic toxins such as indole-3-acetic acid are actively transported into the kidneys via organic ion transporters (especially OAT3). Increased levels of uremic toxins can stimulate the production of reactive oxygen species. This seems to be mediated by the direct binding or inhibition by uremic toxins of the enzyme NADPH oxidase (especially NOX4 which is abundant in the kidneys and heart) (A7868). Reactive oxygen species can induce several different DNA methyltransferases (DNMTs) which are involved in the silencing of a protein known as KLOTHO. KLOTHO has been identified as having important roles in anti-aging, mineral metabolism, and vitamin D metabolism. A number of studies have indicated that KLOTHO mRNA and protein levels are reduced during acute or chronic kidney diseases in response to high local levels of reactive oxygen species (A7869) |
| Signs and Symptoms | As a uremic toxin, this compound can cause uremic syndrome. Uremic syndrome may affect any part of the body and can cause nausea, vomiting, loss of appetite, and weight loss. It can also cause changes in mental status, such as confusion, reduced awareness, agitation, psychosis, seizures, and coma. Abnormal bleeding, such as bleeding spontaneously or profusely from a very minor injury can also occur. Heart problems, such as an irregular heartbeat, inflammation in the sac that surrounds the heart (pericarditis), and increased pressure on the heart can be seen in patients with uremic syndrome. Shortness of breath from fluid buildup in the space between the lungs and the chest wall (pleural effusion) can also be present. |
| Carcinogen Classification | No indication of carcinogenicity to humans (not listed by IARC). |
| F | 8-10-23 |
| Wassergefährdungsklasse (WGK) | 3 |
| TSCA-Inventar-Status | TSCA listed |
| Zollcode | 29339990 |
| RTECS-Nr. | NL3150000 |
| R-Sätze (R) | 36/37/38 |
| Toxizität | LD50 intraperitoneal in mouse: 150mg/kg |
| Gefahrensymbole | Xi |
| hazard_note | Irritant |
| Sicherheitshinweise (S) | 22-24/25 |
| Lagerklasse | 11 - Combustible Solids |
Anwendungen & Verwendung
Verwenden
Plant growth regulator.