Indole-3-Acetic Acid
Basic information
- CAS
87-51-4- Standard SMILES
O=C(O)Cc1c[nH]c2ccccc12- InChIKey
SEOVTRFCIGRIMH-UHFFFAOYSA-N- Molecular formula
- C10H9NO2
- Average molar mass
- 175.18 g/mol
- Monoisotopic mass
- 175.06332853
Overview
Indole-3-acetic acid is a monocarboxylic acid that is acetic acid in which one of the methyl hydrogens has been replaced by a 1H-indol-3-yl group.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.
Names & identifiers
- Preferred name
- Indole-3-Acetic Acid
- IUPAC
- 2-(1H-indol-3-yl)acetic acid
- English name
- Indole-3-acetic acid
- Molecular formula
- C10H9NO2
- Molecular weight
- 175.18
Names & synonyms
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
Show more names
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
Database identifiers
- CAS
87-51-4- PubChem CID
- 802
- DTXSID
DTXSID5020738- ChEMBL
CHEMBL82411- ChEBI
CHEBI:16411- UNII
- 6U1S09C61L
- EC Number
- 201-748-2
- Nikkaji
- J5.156J
Properties
Computed structural properties
- XLogP
- 1.4
- Topological polar surface area
- 53.1 Ų
- Hydrogen bond donors
- 2
- Hydrogen bond acceptors
- 2
- Rotatable bonds
- 2
- Heavy atoms
- 13
- Formal charge
- 0
- Complexity
- 205
Experimental & physicochemical properties
DrugsPharmaceuticals -> Listed in ZINC15
SpringerMaterials PropertiesAngular frequency
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)
Melting Point168.5 °C
Vapor Pressure0.00000526 [mmHg]
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)]
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
GHS classification
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.
Hazard information
Regulatory Information
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%)
Toxicology
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
Chemistry & industry
Pharmacology
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.
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
Uses & manufacturing
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).
General Manufacturing Information1H-Indole-3-acetic acid: ACTIVE
Applications
UsesIt is applied as plant growth hormone. is an inducer of plant cell elongation and division shown to cause uncontrolled growth.
UsesPlant growth regulator.
General Description3-Indoleacetic acid is a highly effective, growth promotor in lower plant life, formed by a variety of fungi, including yeast and has been isolated from Aspergillus niger and Rhizopus sp. It is commonly employed in horticulture and industry.
Related reactions
78 records
Compound notes
Loading…