Details
| Stereochemistry | ACHIRAL |
| Molecular Formula | C10H9NO2 |
| Molecular Weight | 175.184 |
| Optical Activity | NONE |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
OC(=O)CC1=CNC2=C1C=CC=C2
InChI
InChIKey=SEOVTRFCIGRIMH-UHFFFAOYSA-N
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)
| Molecular Formula | C10H9NO2 |
| Molecular Weight | 175.184 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Optical Activity | NONE |
Indoleacetic acid is the most abundant and basic plant hormone of auxin class. In plants, it plays a key role in both roots and shoots development. In mammals, indoleacetic acid is often produced by the action of gut bacteria. Elevated levels of indoleacetic acid have been found in the urine of patients with phenylketonuria. Indoleacetic acid was evaluated as a photosensitizer for acne treatment.
Approval Year
PubMed
| Title | Date | PubMed |
|---|---|---|
| Manipulation of chloride flux affects histamine-induced contraction in rabbit basilar artery. | 2002-04 |
|
| Crystal structures of a new class of allosteric effectors complexed to tryptophan synthase. | 2002-03-22 |
|
| Delayed abscission and shorter Internodes correlate with a reduction in the ethylene receptor LeETR1 transcript in transgenic tomato. | 2002-03 |
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| Oxic and anoxic enhancement of radiation-mediated toxicity by horseradish peroxidase/indole-3-acetic acid gene therapy. | 2002-03 |
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| Synthesis and bioactivity of C-2 and C-3 methyl ether derivatives of brassinolide. | 2002-03 |
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| Chemical defenses of crucifers: elicitation and metabolism of phytoalexins and indole-3-acetonitrile in brown mustard and turnip. | 2002-03 |
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| Analysis of plant hormones in tobacco flowers by micellar electrokinetic capillary chromatography coupled with on-line large volume sample stacking. | 2002-02-01 |
|
| Arabidopsis SHY2/IAA3 inhibits auxin-regulated gene expression. | 2002-02 |
|
| An emerging model of auxin transport regulation. | 2002-02 |
|
| Organogenesis and terpenoid synthesis in Mentha arvensis. | 2002-02 |
|
| Shoot-derived auxin is essential for early lateral root emergence in Arabidopsis seedlings. | 2002-02 |
|
| Gravity-stimulated changes in auxin and invertase gene expression in maize pulvinal cells. | 2002-02 |
|
| FQR1, a novel primary auxin-response gene, encodes a flavin mononucleotide-binding quinone reductase. | 2002-02 |
|
| A novel bifunctional molybdo-enzyme catalyzing both decarboxylation of indolepyruvate and oxidation of indoleacetaldehyde from a thermoacidophilic archaeon, Sulfolobus sp. strain 7. | 2002-01-16 |
|
| 5-Fluoroindole-3-acetic acid: a prodrug activated by a peroxidase with potential for use in targeted cancer therapy. | 2002-01-15 |
|
| Uraemic toxins induce proximal tubular injury via organic anion transporter 1-mediated uptake. | 2002-01 |
|
| Arabidopsis cytochrome P450 cyp83B1 mutations activate the tryptophan biosynthetic pathway. | 2002-01 |
|
| Optimisation of transgene action at the post-transcriptional level: high quality parthenocarpic fruits in industrial tomatoes. | 2002 |
|
| Oxidative stress, growth factor production and budding in potato tubers during cold storage. | 2001-12 |
|
| Quantitative analysis of indole-3-acetic acid metabolites in Arabidopsis. | 2001-12 |
|
| Bioactivity of 25-hydroxy-, 26-hydroxy, 25,26-dihydroxy- and 25,26-epoxybrassinolide. | 2001-12 |
|
| Auxin regulates SCF(TIR1)-dependent degradation of AUX/IAA proteins. | 2001-11-15 |
|
| Fungal auxin antagonist hypaphorine competitively inhibits indole-3-acetic acid-dependent superoxide generation by horseradish peroxidase. | 2001-11-02 |
|
| Auxin promotes gibberellin biosynthesis in decapitated tobacco plants. | 2001-11 |
|
| Sites and homeostatic control of auxin biosynthesis in Arabidopsis during vegetative growth. | 2001-11 |
|
| Maize VP1 complements Arabidopsis abi3 and confers a novel ABA/auxin interaction in roots. | 2001-11 |
|
| Determination of free and conjugated indole-3-acetic acid, tryptophan, and tryptophan metabolites in grape must and wine. | 2001-11 |
|
| The Arabidopsis pxa1 mutant is defective in an ATP-binding cassette transporter-like protein required for peroxisomal fatty acid beta-oxidation. | 2001-11 |
|
| Attenuation of phosphate starvation responses by phosphite in Arabidopsis. | 2001-11 |
|
| A basic peroxidase from wheat kernel with antifungal activity. | 2001-11 |
|
| Design, synthesis, and bioactivity of the first nonsteroidal mimetics of brassinolide. | 2001-10-19 |
|
| Localization of the auxin permease AUX1 suggests two functionally distinct hormone transport pathways operate in the Arabidopsis root apex. | 2001-10-15 |
|
| Hormonal regulation of tissue-specific ectopic expression of an Arabidopsis endoplasmic reticulum-type omega-3 fatty acid desaturase (FAD3) gene. | 2001-10 |
|
| IAA and N(6)-benzyladenine inhibit ethylene-regulated expression of ACC oxidase and ACC synthase genes in mungbean hypocotyls. | 2001-10 |
|
| Auxin signalling: the beginning, the middle and the end. | 2001-10 |
|
| Auxin and the power of the proteasome in plants. | 2001-10 |
|
| Profiling of tryptophan-related plasma indoles in patients with carcinoid tumors by automated, on-line, solid-phase extraction and HPLC with fluorescence detection. | 2001-10 |
|
| [Aerobic methylobacteria are capable of synthesizing auxins]. | 2001-09-18 |
|
| Ab initio Hartree-Fock investigation of 1-H-pyrrolo[3,2-b]pyridine-3-yl acetic acid. | 2001-09-01 |
|
| Alterations in plant growth and in root hormone levels of lodgepole pines inoculated with rhizobacteria. | 2001-09 |
|
| Arabidopsis mutants with increased organ regeneration in tissue culture are more competent to respond to hormonal signals. | 2001-09 |
|
| The auxin signal for protoplast swelling is perceived by extracellular ABP1. | 2001-09 |
|
| Involvement of gacS and rpoS in enhancement of the plant growth-promoting capabilities of Enterobacter cloacae CAL2 and UW4. | 2001-08 |
|
| Characterization of two tomato aquaporins and expression during the incompatible interaction of tomato with the plant parasite Cuscuta reflexa. | 2001-08 |
|
| [Cloning and identification of an Agrobacterium radiobacter 5D-1 chromosome fragment involved in control of nitrogen metabolism, biosynthesis of indolylacetic acid and replication of ColE1 plasmids]. | 2001-07 |
|
| Selection and evaluation of Azospirillum brasilense strains growing at a sub-optimum temperature in rhizocoenosis with wheat. | 2001 |
|
| [Metabolism and transport of auxin in plants]. | 2001 |
|
| Suppression of maize root diseases caused by Macrophomina phaseolina, Fusarium moniliforme and Fusarium graminearum by plant growth promoting rhizobacteria. | 2001 |
|
| Gravitropism in cut flower stalks of snapdragon. | 2001 |
|
| Serotonin metabolism is pellagra. | 1975-10 |
Patents
Sample Use Guides
As a photosensitizer for the treatment of acne, 0.015% formulation of indoleacetic acid was applied topically.
Route of Administration:
Topical
To determine the level of indoleacetic acid in the urine, 4 ml of urine in a 40-ml glass-stoppered centrifuge tube wase acidified by the addition of 0.36 ml. of 12 N HCI. 10 ml. of CHCl3 were added and the tube was shaken for 5 minutes. After centrifugation 9 ml. of the CHCl3 were transferred to another 40 ml glass-stoppered centrifuge tube containing 0.6 ml. of 0.5 M phosphate buffer, pH 7.0. The tube was shaken for 5 minutes and the CHCl3 layer was aspirated and discarded. An aliquot of the buffer was then assayed calorimetrically by the use of a modification of the xanthydrol reaction of Dickman and Crockett (4) as follows: 0.4 ml. of the pH 7.0 buffer extract was transferred to a test tube containing 0.4 ml. of 12 N HCl; 1 ml. of the xanthydrol reagent was added, followed 5 minutes later by 0.5 ml. of the bisulfite reagent. The solution was mixed and the pink color measured within 5 to 10 minutes at 520 nm in a spectrophotometer.
| Substance Class |
Chemical
Created
by
admin
on
Edited
Mon Mar 31 17:45:12 GMT 2025
by
admin
on
Mon Mar 31 17:45:12 GMT 2025
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| Record UNII |
6U1S09C61L
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| Record Status |
Validated (UNII)
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| Record Version |
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EPA PESTICIDE CODE |
128915
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IAA
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Indoleacetic acid
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| Related Record | Type | Details | ||
|---|---|---|---|---|
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TRANSPORTER -> INHIBITOR |
| Related Record | Type | Details | ||
|---|---|---|---|---|
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PARENT -> METABOLITE INACTIVE |
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