Grundinformationen
- Standard-SMILES
O=C(O)Cc1c[nH]c2ccccc12- InChIKey
SEOVTRFCIGRIMH-UHFFFAOYSA-N- Summenformel
- C10H9NO2
- Durchschnittliche Molmasse
- 175,18 g/mol
- Monoisotopische Masse
- 175,06332853
Überblick
Indole-3-acetic acid is a monocarboxylic acid that is acetic acid in which one of the methyl hydrogens has been replaced by a 1H-indol-3-yl group. It has a role as an auxin, a plant hormone, a mouse metabolite, a plant metabolite and a human metabolite. It is a member of indole-3-acetic acids and a monocarboxylic acid. It is a conjugate acid of an indole-3-acetate.
Namen und Bezeichner
- Bevorzugter Name
- Indole-3-Acetic Acid
- IUPAC
- 2-(1H-indol-3-yl)acetic acid
- Lokaler Name
- Indol-3-ylessigsure
- Englischer Name
- Indole-3-acetic acid
- Summenformel
- C10H9NO2
- Molmasse
- 175.18
Namen und Synonyme
Weitere Namen anzeigen
Datenbank-Bezeichner
- CAS
87-51-4- PubChem CID
- 802
- DTXSID
DTXSID5020738- ChEMBL
CHEMBL82411- ChEBI
CHEBI:16411- UNII
- 6U1S09C61L
- EC Number
- 201-748-2
- Nikkaji
- J5.156J
Eigenschaften
Berechnete Struktureigenschaften
- XLogP
- 1,4
- Polarare Oberfläche (TPSA)
- 53,1 Ų
- H-Brücken-Donoren
- 2
- H-Brücken-Akzeptoren
- 2
- Frei drehbare Bindungen
- 2
- Schwere Atome
- 13
- Formalladung
- 0
- Komplexität
- 205
Experimentelle und physikochemische Eigenschaften
Pesticides
Plant Growth Regulators
Active substance -> EU Pesticides database: Not approved
Pesticides -> Plant Growth Regulators
LogP
1.41
1.41
Solubility
1.5 mg/mL
>26.3 [ug/mL] (The mean of the results at pH 7.4)
Physical Description
Solid; [Merck Index] Light tan to light pink flaky powder; Odorless; [PhytoTechnology Laboratories MSDS]
Solid
Collision Cross Section
136.2 Ų [M+H]+ [CCS Type: DT; Method: single field calibrated with Agilent tune mix (Agilent)]
138.11 Ų [M+H]+ [CCS Type: DT; Method: stepped-field]
143.5 Ų [M+Na]+ [CCS Type: DT; Method: single field calibrated with ESI Low Concentration Tuning Mix (Agilent)]
143.6 Ų [M+Na]+
Physikochemische Eigenschaften
- Schmelzpunkt
- 165 · 165-169 °C (lit.)
- Siedepunkt
- 306.47 °C · 306.47°C (rough estimate)
- Dichte
- 1.1999 · 1.1999 (rough estimate)
- Brechungsindex
- 1.546 · 1.5460 (estimate)
- Flammpunkt
- 171 °C · 171°C
- storage temp.
- -20 °C · -20°C
- Löslichkeit
- 30 · DMSO:30.0(Max Conc. mg/mL);171.25(Max Conc. mM)
- pka
- 4.75 · 4.75(at 25℃)
- Aggregatzustand
- crystalline
- Farbe
- off-white to tan
- Wasserlöslichkeit
- Soluble in ethanol (50 mg/ml), methanol, DMSO, and chloroform (sparingly). Insoluble in water.
- Decomposition
- 167 · 167 ºC
- Merck
- 14 · 14,4964
- BRN
- 143358 · 143358
- Stabilität
- Stable. Incompatible with strong oxidizing agents. Light sensitive.
- Major Application
- 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
- 1.41 · 1.410
- CAS Datenbank
- 87 · 87-51-4(CAS DataBase Reference)
- NIST chemische Informationen
- -3 · Indole-3-acetic acid(87-51-4)
- EPA chemische Informationen
- -3 · Indole-3-acetic acid (87-51-4)
Sicherheit und Regulatorisches
GHS-Klassifizierung
GHS Classification
This chemical does not meet GHS hazard criteria for 8.9% (5 of 56) of reports.
Warning
H302 (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.
Gefahrenhinweise
Regulatory Information
Chemical: 1H-Indole-3-acetic acid
2008/941
Status: Active Update: 29-08-2022 https://echa.europa.eu/registration-dossier/-/registered-dossier/34003
Indole-3-acetic acid: Does not have an individual approval but may be used under an appropriate group standard
Toxikologische Informationen
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.
Health Effects
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.
Toxicity Summary
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.
Sicherheitsdaten
- F
- 8-10-23
- wgk
- 3
- tsca
- TSCA listed
- hs_code
- 29339990
- RTECS-Nr.
- NL3150000
- risk_code
- 36/37/38
- Toxizität
- LD50 intraperitoneal in mouse: 150mg/kg
- hazard_code
- Xi
- hazard_note
- Irritant
- safety_code
- 22-24/25
- Speicherklasse
- 11 - Combustible Solids
Chemie und Industrie
Pharmakologische Informationen
Metabolism/Metabolites
Indole-3-acetic-acid has known human metabolites that include Indole-3-acetic-acid-O-glucuronide.
Indoleacetic acid (IAA) is a breakdown product of tryptophan metabolism and is often produced by the action of bacteria in the mammalian gut. Some endogenous production of IAA in mammalian tissues also occurs. It may be produced by the decarboxylation of tryptamine or the oxidative deamination of tryptophan.
Verwendung und Herstellung
Uses
Used as a plant growth regulator; [Merck Index] Active product registrations in the US; [NPIRS]
Farming (Pesticides) [Category: Industry]
Naturally produced by the body (endogenous). Also a plant growth hormone (auxin).
Anwendungen
VerwendenPlant growth regulator.
Vor- und nachgelagerte Produkte
Vorgelagerte Rohstoffe
Nachgelagerte Produkte
Anbieter50 Anbieter
Ergänzende Hinweise
DefinitionChEBI: A monocarboxylic acid that is acetic acid in which one of the methyl hydrogens has been replaced by a 1H-indol-3-yl group.
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