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Indol-3-ylessigsure

Indole-3-Acetic Acid

HCID 802
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Grundinformationen

CAS
87-51-4
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Indole-3-acetic acid is a monocarboxylic acid that is acetic acid in which one of the methyl hydrogens has been replaced by a 1H-indol-3-yl group.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

indole-3-acetic acid87-51-43-Indoleacetic acidindoleacetic acidHeteroauxin1H-Indole-3-acetic acid2-(1H-Indol-3-yl)acetic acidRhizopin1H-indol-3-ylacetic acidRhizopon A3-Indolylacetic acid3-Iaa
Weitere Namen anzeigen
IAAGapIndolylacetic acidINDOL-3-YLACETIC ACIDHETEROAUXINEIndoleacetateindole-3-acetic
3-(Carboxymethyl)indolebeta-Indoleacetic acidbeta-Indolylacetic acidIndolyl-3-acetic acidKyselina 3-indolyloctovaDTXSID50207382-(indol-3-yl)ethanoic acid(indol-3-yl)acetic acid

Datenbank-Bezeichner

CAS
87-51-4
PubChem CID
802
DTXSID
DTXSID5020738
ChEMBL
CHEMBL82411
ChEBI
CHEBI:16411

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

DrugsPharmaceuticals -> Listed in ZINC15
SpringerMaterials PropertiesAngular frequency
Pesticides · 3 Einträge

Plant Growth Regulators

Active substance -> EU Pesticides database: Not approved

Pesticides -> Plant Growth Regulators

LogP · 2 Einträge

1.41

1.41

Solubility · 2 Einträge

1.5 mg/mL

>26.3 [ug/mL] (The mean of the results at pH 7.4)

Melting Point168.5 °C
Vapor Pressure0.00000526 [mmHg]
Physical Description · 2 Einträge

Solid; [Merck Index] Light tan to light pink flaky powder; Odorless; [PhytoTechnology Laboratories MSDS]

Solid

Collision Cross Section · 4 Einträge

Sicherheit und Regulatorisches

Sicherheitsangaben dienen nur zur Orientierung und ersetzen weder das Sicherheitsdatenblatt (SDB) des Lieferanten noch geltende Vorschriften oder eine fachliche Bewertung.

GHS-Klassifizierung

GHS Classification · 5 Einträge

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 · 4 Einträge

Chemical: 1H-Indole-3-acetic acid

2008/941

REACH registered substance: Indol-3-ylacetic acid (EC: 201-748-2)

Indole-3-acetic acid: Does not have an individual approval but may be used under an appropriate group standard

Hazards SummaryAn irritant; [PhytoTechnology Laboratories MSDS] See Indole. See Indole-3-butyric acid.
Hazard Classes and CategoriesAcute Tox. 4 (58.9%)

Toxikologische Informationen

Treatment · 1 Eintrag

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

Chemie und Industrie

Pharmakologische Informationen

Metabolism/Metabolites · 2 Einträge

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.

MeSH Pharmacological ClassificationAny of the hormones produced naturally in plants and active in controlling growth and other functions. There are three primary classes: auxins, cytokinins, and gibberellins.
Tissue LocationsBrain
Cellular LocationsCytoplasm
Metabolite PathwaysTryptophan metabolism

Verwendung und Herstellung

Uses · 3 Einträge

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).

General Manufacturing Information1H-Indole-3-acetic acid: ACTIVE

Anwendungen

VerwendenPlant growth regulator.

Vor- und nachgelagerte Produkte

Vorgelagerte Rohstoffe

Indol

Zugehörige Reaktionen

78
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HRID 37065als Eduktuspto-grants-1995_05
Reaktionsgleichung von HRID 55397
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Reaktionsgleichung von HRID 55400
HRID 55400als Eduktuspto-grants-1997_04
Reaktionsgleichung von HRID 55410
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Reaktionsgleichung von HRID 55413
HRID 55413als Eduktuspto-grants-1997_04
Reaktionsgleichung von HRID 55435
HRID 55435als Eduktuspto-grants-1997_04
Reaktionsgleichung von HRID 55437
HRID 55437als Eduktuspto-grants-1997_04
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UNII
6U1S09C61L
EC Number
201-748-2
Nikkaji
J5.156J

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]

135.9 Ų [M+H]+ [CCS Type: DT; Method: single field calibrated with ESI Low Concentration Tuning Mix (Agilent)]

136.4 Ų [M+H]+

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)
· 1 Eintrag

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.

Exposure RoutesEndogenous, Ingestion, Dermal (contact)
Toxicity Summary · 1 Eintrag

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 · 1 Eintrag

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 ClassificationNo indication of carcinogenicity to humans (not listed by IARC).

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
Kaliumacetat
Glykolsaeure

Nachgelagerte Produkte

1-Methyl-3-indoleacetic acid3-(2-Chlorethyl)-1H-indolβ-Indol-3-ylethanolChinolin-4-carbaldehyd1H-Indole-3-acetic acid, α-methyl-, methyl ester1-(1H-Benzotriazol-1-yl)-2-(1H-indol-3-yl)ethanoneEthyl N-Boc-(indol-3-yl)acetate/tert-butyl 3-(2-ethoxy-2-oxoethyl)-1H-indole-1-carboxylateN-2-(indol-3-yl)ethyl-indole-3-acetamide

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.