indole acetic acid
hexteroauxin
Identification
| Name | indole acetic acid |
| IUPAC | 2-(1H-indol-3-yl)acetic acid |
| CAS Number | 87-51-4 |
| EINECS | 201-748-2 |
| FDA UNII | 6U1S09C61L |
| Molecular Formula | C10 H9 N O2 |
| Molecular Weight | 175.18713000 |
| MDL Number | MFCD00005636 |
| Nikkaji Number | J5.156J |
| Beilstein | 0143358 |
| XlogP3 | 1.40 (est) |
Regulatory
Physical Properties
| Assay | 95.00 to 100.00 |
| Food Chemicals Codex Listed | No |
| Melting Point | 165.00 to 169.00 °C. @ 760.00 mm Hg |
| Boiling Point | 413.00 to 415.00 °C. @ 760.00 mm Hg |
| Vapor Pressure | 0.000005 mmHg @ 25.00 °C. (est) |
| Flash Point | 400.00 °F. TCC ( 204.44 °C. ) |
| logP (o/w) | 1.410 |
| Soluble in | alcohol |
Cosmetic Information
| CosIng | cosmetic data |
| Cosmetic Uses | skin conditioning |
No sensory data available
Safety Information
| Preferred SDS | View |
| European information | Most important hazard(s): |
| Oral/Parenteral Toxicity | oral-rat LD50 > 500 mg/kg |
| Dermal Toxicity | Not determined |
| Inhalation Toxicity | Not determined |
GHS Classification
['GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)', 'GHS Label elements, including precautionary statements']
Safety in Use
| Category | cosmetic ingredient for skin conditioning |
| Recommendation for indole acetic acid usage levels up to | not for fragrance use. |
| Recommendation for indole acetic acid flavor usage levels up to | not for flavor use. |
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Potential Uses
Natural Occurrence
Synonyms
auxin
hexteroauxin
(1H-
indol-3-yl)-acetic acid
2-(1H-
indol-3-yl)-acetic acid
indol-3-yl)acetic acid
(1H-
indol-3-yl)acetic acid
2-(1H-
indol-3-yl)acetic acid
2-(
indol-3-yl)ethanoic acid
1H-
indol-3-ylacetic acid
2-
indol-3-ylacetic acid
3-
indole acetic acid
indole-3-acetic acid
1H-
indole-3-acetic acid
1H-
indole-3-acetic acid (9CI)
indoleacetic acid
3-
indoleacetic acid
2-(3-
indolyl)acetic acid
3-
indolylacetic acid
3-
indolylmethylcarboxylic acid
rhizopin
rhizopon A
PubMed:
Functional analysis of a tomato salicylic acid methyl transferase and its role in synthesis of the flavor volatile methyl salicylate.
PubMed:
Characterization of three members of the Arabidopsis carotenoid cleavage dioxygenase family demonstrates the divergent roles of this multifunctional enzyme family.
PubMed:
"Untypical aging off-flavor" in wine: synthesis of potential degradation compounds of indole-3-acetic acid and kynurenine and their evaluation as precursors of 2-aminoacetophenone.
PubMed:
Determination of free and conjugated indole-3-acetic acid, tryptophan, and tryptophan metabolites in grape must and wine.
PubMed:
Cytochrome P450 CYP79B2 from Arabidopsis catalyzes the conversion of tryptophan to indole-3-acetaldoxime, a precursor of indole glucosinolates and indole-3-acetic acid.
PubMed:
Determination of tryptophan and tryptophan metabolites in grape must and wine.
PubMed:
Off-flavor compounds in wine and other food products formed by enzymatical, physical, and chemical degradation of tryptophan and its metabolites.
PubMed:
Induction of Oxidative Stress in Prototheca zopfii by Indole-3-Acetic Acid/HRP or 2,4-Pentanedione/HRP Systems and Their Oxidation Products.
PubMed:
Biosynthetic pathway of the phytohormone auxin in insects and screening of its inhibitors.
PubMed:
Agrobacterium tumefaciens responses to plant-derived signaling molecules.
PubMed:
Exploration of novel rhizospheric yeast isolate as fertilizing soil inoculant for improvement of maize cultivation.
PubMed:
Plant-available inorganic nutrient levels are increased in rice-derived distillery effluents inoculated with microbes.
PubMed:
Influence of phenolic acids on indole acetic acid production and on the type III secretion system gene transcription in food-associated Pseudomonas fluorescens KM05.
PubMed:
Metabolite of tryptophan promoting changes in EEG signal and the oxidative status of the brain.
PubMed:
Fruit load induces changes in global gene expression and in abscisic acid (ABA) and indole acetic acid (IAA) homeostasis in citrus buds.
PubMed:
Oral administration of melatonin counteracts several of the effects of chronic stress in rainbow trout.
PubMed:
Characterization and expression analysis of WOX5 genes from wheat and its relatives.
PubMed:
Efficient regeneration for enhanced steviol glycosides production in Stevia rebaudiana (Bertoni).
PubMed:
The importance of Arabidopsis glutathione peroxidase 8 for protecting Arabidopsis plant and E. coli cells against oxidative stress.
PubMed:
Effect of uremic serum and uremic toxins on drug metabolism in human microsomes.
PubMed:
Development of a rapid LC-DAD/FLD method for the simultaneous determination of auxins and abscisic acid in plant extracts.
PubMed:
Bacterial community compositions of tomato (Lycopersicum esculentum Mill.) seeds and plant growth promoting activity of ACC deaminase producing Bacillus subtilis (HYT-12-1) on tomato seedlings.
PubMed:
Integrated management strategies for tomato Fusarium wilt.
PubMed:
Development of indole-3-acetic acid-producing Escherichia coli by functional expression of IpdC, AspC, and Iad1.
PubMed:
Isolation and expression profiling of GhNAC transcription factor genes in cotton (Gossypium hirsutum L.) during leaf senescence and in response to stresses.
PubMed:
Contribution of proteomics in the identification of novel proteins associated with plant growth.
PubMed:
Phloem-specific expression of a melon Aux/IAA in tomato plants alters auxin sensitivity and plant development.
PubMed:
Potential for plant growth promotion of rhizobacteria associated with Salicornia growing in Tunisian hypersaline soils.
PubMed:
Effects of nitric oxide treatment on the cell wall softening related enzymes and several hormones of papaya fruit during storage.
PubMed:
Characterization of aryloxyalkanoate dioxygenase-12, a nonheme Fe(II)/α-ketoglutarate-dependent dioxygenase, expressed in transgenic soybean and Pseudomonas fluorescens.
PubMed:
Microcystin-LR-induced phytotoxicity in rice crown root is associated with the cross-talk between auxin and nitric oxide.
PubMed:
Determination of naphthalene-derived compounds in apples by ultra-high performance liquid chromatography-tandem mass spectrometry.
PubMed:
Black leaf streak disease affects starch metabolism in banana fruit.
PubMed:
Mapping QTL for grain yield and other agronomic traits in post-rainy sorghum [Sorghum bicolor (L.) Moench].
PubMed:
Low-temperature conditioning induces chilling tolerance in 'Hayward' kiwifruit by enhancing antioxidant enzyme activity and regulating en-dogenous hormones levels.
PubMed:
Differential expression of genes encoding acid invertases in multiple shoots of bamboo in response to various phytohormones and environmental factors.
PubMed:
Effect of growth hormones on some antioxidant parameters and gene expression in tomato.
PubMed:
Plant growth-promoting rhizobacteria strain Bacillus amyloliquefaciens NJN-6-enriched bio-organic fertilizer suppressed Fusarium wilt and promoted the growth of banana plants.
PubMed:
Auxin and Cytokinin Metabolism and Root Morphological Modifications in Arabidopsis thaliana Seedlings Infected with Cucumber mosaic virus (CMV) or Exposed to Cadmium.
PubMed:
Correlation between hormonal homeostasis and morphogenic responses in Arabidopsis thaliana seedlings growing in a Cd/Cu/Zn multi-pollution context.
PubMed:
A family of indoles regulate virulence and Shiga toxin production in pathogenic E. coli.
PubMed:
Increased levels of IAA are required for system 2 ethylene synthesis causing fruit softening in peach (Prunus persica L. Batsch).
PubMed:
Major phenylpropanoid-derived metabolites in the human gut can arise from microbial fermentation of protein.
PubMed:
SEPALLATA1/2-suppressed mature apples have low ethylene, high auxin and reduced transcription of ripening-related genes.
PubMed:
Overexpression of the AtSHI gene in poinsettia, Euphorbia pulcherrima, results in compact plants.
PubMed:
Opening of Iris flowers is regulated by endogenous auxins.
PubMed:
Rapid capillary electrochromatographic profiling of phytohormones on a hydrophilic interaction/strong anion-exchange mixed-mode monolith.
PubMed:
In vitro cormlet production of saffron (Crocus sativus L. Kashmirianus) and their flowering response under greenhouse.
PubMed:
Effects of different combinations of benzyl adenine and indole acetic acid concentrations on in vitro plant regeneration in hexaploid wheat.
PubMed:
In vitro propagation of Dioscorea alata var. purpurae.
PubMed:
Analysis of plant hormones by microemulsion electrokinetic capillary chromatography coupled with on-line large volume sample stacking.
PubMed:
A protocol for transformation of Torenia.
PubMed:
Indole compounds in some culinary-medicinal higher basidiomycetes from Poland.
PubMed:
Phytohormone production and colonization of canola (Brassica napus L.) roots by Pseudomonas fluorescens 6-8 under gnotobiotic conditions.
PubMed:
A liquid chromatography tandem mass spectrometry method for simultaneous determination of acid/alkaline phytohormones in grapes.
PubMed:
Endophyte-assisted promotion of biomass production and metal-uptake of energy crop sweet sorghum by plant-growth-promoting endophyte Bacillus sp. SLS18.
PubMed:
Cryopreservation of scalps of Malaysian bananas using a pre-growth method.
PubMed:
Leaf volatiles and secretory cells of Alpinia zerumbet (Pers.) Burtt et Smith (Zingiberaceae).
PubMed:
Characterization of a single recessive yield trait mutant with elevated endogenous ABA concentration and deformed grains, spikelets and leaves.
PubMed:
Selective differentiation of indoleacetic acid and indolebutyric acid using colorimetric recognition after Ehrlich reaction.
PubMed:
Detection and quantification of some plant growth regulators in a seaweed-based foliar spray employing a mass spectrometric technique sans chromatographic separation.
PubMed:
Genome-wide analysis of ethylene-responsive element binding factor-associated amphiphilic repression motif-containing transcriptional regulators in Arabidopsis.
PubMed:
Hydrogen sulfide promotes root organogenesis in Ipomoea batatas, Salix matsudana and Glycine max.
PubMed:
Filmy channel microchip with amperometric detection.
PubMed:
Microbicidal action of indole-3-acetic acid combined with horseradish peroxidase on Prototheca zopfii from bovine mastitis.
PubMed:
Variations of water uptake, lipid consumption, and dynamics during the germination of Sesamum indicum seed: a nuclear magnetic resonance spectroscopic investigation.
PubMed:
Conversion of protocorm-like bodies of Dendrobium huoshanense to shoots: the role of polyamines in relation to the ratio of total cytokinins and indole-3-acetic acid.
PubMed:
Influence of growth regulators in biomass production and volatile profile of in vitro plantlets of Thymus vulgaris L.
PubMed:
Indole-3-acetic acid improves postharvest biological control of blue mold rot of apple by Cryptococcus laurentii.
PubMed:
Protective action of indole-3-acetic acid on induced hepatocarcinoma in mice.
PubMed:
Modulation of low-temperature-induced biochemical changes in bud and root band zones of sugar cane sets by potassium, zinc, and Ethrel for improving sprouting.
PubMed:
The role of aspterric acid in auxin-regulated reproductive growth of Arabidopsis thaliana.
PubMed:
Identification and quantitation of auxins in plants by liquid chromatography/electrospray ionization ion trap mass spectrometry.
PubMed:
A red algal cyclophilin has an effect on development and growth in Nicotiana tabacum.
PubMed:
Transport of glycerol by Pediococcus pentosaceus isolated from wine.
PubMed:
Nitrogen metabolism and flower symmetry of petunia corollas treated with glyphosate.
PubMed:
Dexamethasone reduces food intake, weight gain and the hypothalamic 5-HT concentration and increases plasma leptin in rats.
PubMed:
[Enhanced phytoextraction of heavy metal contaminated soil by chelating agents and auxin indole-3-acetic acid].
PubMed:
Endophytic colonization of Typha australis by a plant growth-promoting bacterium Klebsiella oxytoca strain GR-3.
PubMed:
Metabolic characterization of Brassica rapa leaves by NMR spectroscopy.
PubMed:
Indole-3-acetic acid enhances the biocontrol of Penicillium expansum and Botrytis cinerea on pear fruit by Cryptococcus laurentii.
PubMed:
Effect of indole-3-acetic acid administration by gavage and by subcutaneous injection on rat leukocytes.
PubMed:
Separation of plant hormones from biofertilizer by capillary electrophoresis using a capillary coated dynamically with polycationic polymers.
PubMed:
Glyphosate-induced anther indehiscence in cotton is partially temperature dependent and involves cytoskeleton and secondary wall modifications and auxin accumulation.
PubMed:
Selection, characterization, and CDR shuffling of naive llama single-domain antibodies selected against auxin and their cross-reactivity with auxinic herbicides from four chemical families.
PubMed:
Production of indolic compounds by rumen bacteria isolated from grazing ruminants.
PubMed:
Rice endophyte Pantoea agglomerans YS19 promotes host plant growth and affects allocations of host photosynthates.
PubMed:
Isolation and characterization of a novel banana rhizosphere bacterium as fungal antagonist and microbial adjuvant in micropropagation of banana.
PubMed:
Inoculation effects of Pseudomonas putida, Gluconacetobacter azotocaptans, and Azospirillum lipoferum on corn plant growth under greenhouse conditions.
PubMed:
Effects of 2 hrs. restraint stress on brain serotonin metabolism and memory in rats.
PubMed:
Grapes on steroids. Brassinosteroids are involved in grape berry ripening.
PubMed:
Influence of indole acetic acid on antioxidant levels and enzyme activities of glucose metabolism in rat liver.
PubMed:
Simultaneous determination of multiple phytohormones in plant extracts by liquid chromatography-electrospray tandem mass spectrometry.
PubMed:
Effect of indole acetic acid administration on the neutrophil functions and oxidative stress from neutrophil, mesenteric lymph node and liver.
PubMed:
Immunohistochemical localization of IAA and ABP1 in strawberry shoot apexes during floral induction.
PubMed:
Characterization of antifungal metabolite produced by a new strain Pseudomonas aeruginosa PUPa3 that exhibits broad-spectrum antifungal activity and biofertilizing traits.
PubMed:
Induction of phytohormones and differential gene expression in citrus flowers infected by the fungus Colletotrichum acutatum.
PubMed:
In vitro clonal propagation of bird eye chilli (Capsicum frutescens Mill.).
PubMed:
An auxin-responsive 1-aminocyclopropane-1-carboxylate synthase is responsible for differential ethylene production in gravistimulated Antirrhinum majus L. flower stems.
PubMed:
Production of 2-hydroxy-4-methoxybenzaldehyde in roots of tissue culture raised and acclimatized plants of Decalepis hamiltonii Wight & Arn., an endangered shrub endemic to Southern India and evaluation of its performance vis-a-vis plants from natural habitat.
PubMed:
Indole-3-acetic acid increases glutamine utilization by high peroxidase activity-presenting leukocytes.
PubMed:
Determination of phytohormones of environmental impact by capillary zone electrophoresis.
PubMed:
The mechanism of indole acetic acid cytotoxicity.
PubMed:
Identification of the bacterial alarmone guanosine 5'-diphosphate 3'-diphosphate (ppGpp) in plants.
PubMed:
Indole derivatives produced by the fungus Colletotrichum acutatum causing lime anthracnose and postbloom fruit drop of citrus.
PubMed:
Pollination-, development-, and auxin-specific regulation of gibberellin 3beta-hydroxylase gene expression in pea fruit and seeds.
PubMed:
"Untypical aging off-flavor" in wine: synthesis of potential degradation compounds of indole-3-acetic acid and kynurenine and their evaluation as precursors of 2-aminoacetophenone.
PubMed:
Nutritional profile of food yeast Kluyveromyces fragilis biomass grown on whey.
PubMed:
Optimisation of transgene action at the post-transcriptional level: high quality parthenocarpic fruits in industrial tomatoes.
PubMed:
Determination of free and conjugated indole-3-acetic acid, tryptophan, and tryptophan metabolites in grape must and wine.
PubMed:
Effect of chronic protein restriction on motor co-ordination and brain neurotransmitters in albino rats.
PubMed:
Off-flavor compounds in wine and other food products formed by enzymatical, physical, and chemical degradation of tryptophan and its metabolites.
PubMed:
Effect of Wild-Type and Mutant Plant Growth-Promoting Rhizobacteria on the Rooting of Mung Bean Cuttings.
PubMed:
Chemical and Genetic Evaluation of Somaclonal Variants of Egyptian Garlic (Allium sativum L.).
PubMed:
Effects of the trichothecene mycotoxin T-2 toxin on neurotransmitters and metabolites in discrete areas of the rat brain.
PubMed:
The clinical pharmacokinetics of zolmitriptan.
PubMed:
Production of aflatoxin byAspergillus parasiticus and its control.
PubMed:
Influence of Auxin and Gibberellin on in Vivo Protein Synthesis during Early Pea Fruit Growth.
PubMed:
Regionally specific effects of diazepam on brain serotonin metabolism in rats: sustained effects following repeated administration.
PubMed:
Time course and auxin sensitivity of cortical microtubule reorientation in maize roots.
PubMed:
Changed central and peripheral catecholamines and indoleamines in one-way crossed-intestine rats: relationship to changes in feeding behavior and metabolism.
PubMed:
Effect of dietary T-2 toxin on biogenic monoamines in discrete areas of the rat brain.
PubMed:
Studies on the growth and indole-3-acetic acid and abscisic acid content of Zea mays seedlings grown in microgravity.
PubMed:
Glutamic acid-induced shoot differentiation in tobacco callus tissues and changes in nicotine content and in activities of aminotransferases, ornithine transcarbamylase, and arginase.
PubMed:
The clinical pharmacology, pharmacokinetics and metabolism of sumatriptan.
PubMed:
Effects of insulin on hypothalamic monoamine metabolism.
PubMed:
Non-steroidal anti-inflammatory analgesics other than salicylates.
PubMed:
Examination of North American bison saliva for potential plant growth regulators.
PubMed:
Plant Growth Substances Produced by Azospirillum brasilense and Their Effect on the Growth of Pearl Millet (Pennisetum americanum L.).
PubMed:
Initiation of Ripening in Bartlett Pear with an Antiauxin alpha(p-Chlorophenoxy)isobutyric Acid.
PubMed:
Effect of caffeic and p-coumaric acids on indole-3-acetic acid catabolism.
PubMed:
Conversion of Tryptophan to Indoleacetamide and Further Conversion to Indoleacetic Acid by Plant Preparations.