EU/US Properties Organoleptics Cosmetics Suppliers Safety Safety in use Safety references References Other Blenders Uses Occurrence Synonyms Articles Notes
 

indole acetic acid
hexteroauxin

Supplier Sponsors

Name:2-(1H-indol-3-yl)acetic acid
CAS Number: 87-51-4Picture of molecule3D/inchi
ECHA EINECS - REACH Pre-Reg:201-748-2
FDA UNII:6U1S09C61L
Nikkaji Web:J5.156J
Beilstein Number:0143358
MDL:MFCD00005636
XlogP3:1.40 (est)
Molecular Weight:175.18713000
Formula:C10 H9 N O2
NMR Predictor:Predict (works with chrome or firefox)
Category:cosmetic ingredient for skin conditioning
 
US / EU / FDA / JECFA / FEMA / FLAVIS / Scholar / Patent Information:
Google Scholar:Search
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Google Scholar: with word "flavor"Search
Google Scholar: with word "odor"Search
Google Patents:Search
US Patents:Search
EU Patents:Search
Pubchem Patents:Search
PubMed:Search
NCBI:Search
 
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 mm/Hg @ 25.00 °C. (est)
Flash Point: 400.00 °F. TCC ( 204.44 °C. )
logP (o/w): 1.410
Soluble in:
 alcohol
 water, 1500 mg/L @ 20 °C (exp)
 
Organoleptic Properties:
Odor Description:odorless mild sour
Odor and/or flavor descriptions from others (if found).
 
Cosmetic Information:
CosIng:cosmetic data
Cosmetic Uses: skin conditioning
 
Suppliers:
BOC Sciences
For experimental / research use only.
3-Indoleacetic acid >98.0%(T)
BST Tianjin Co.
Indole-3-acetic acid
Santa Cruz Biotechnology
For experimental / research use only.
3-Indoleacetic Acid ≥99%
Sigma-Aldrich: Aldrich
For experimental / research use only.
3-Indoleacetic acid 98%
TCI AMERICA
For experimental / research use only.
3-Indoleacetic Acid >98.0%(T)
 
Safety Information:
Preferred SDS: View
European information :
Most important hazard(s):
None - None found.
S 02 - Keep out of the reach of children.
S 22 - Do not breath dust.
S 24/25 - Avoid contact with skin and eyes.
 
Hazards identification
 
Classification of the substance or mixture
GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)
None found.
GHS Label elements, including precautionary statements
 
Pictogram
 
Hazard statement(s)
None found.
Precautionary statement(s)
None found.
Oral/Parenteral Toxicity:
oral-rat LD50 > 500 mg/kg
National Academy of Sciences, National Research Council, Chemical-Biological Coordination Center, Review.Vol.5,Pg.7,1953

intraperitoneal-mouse LD50 150 mg/kg
National Technical Information Service. Vol. AD691-490

oral-rat LD > 500 mg/kg
National Academy of Sciences, National Research Council, Chemical-Biological Coordination Center, Review. Vol. 5, Pg. 7, 1953.

Dermal Toxicity:
Not determined
Inhalation Toxicity:
Not determined
 
Safety in Use Information:
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.
 
Safety References:
European Food Safety Authority (EFSA) reference(s):

Reasoned opinion on the review of the existing maximum residue levels (MRLs) for indolylacetic acid according to Article 12 of Regulation (EC) No 396/2005
View page or View pdf

EPI System: View
Chemical Carcinogenesis Research Information System:Search
Cancer Citations:Search
Toxicology Citations:Search
Carcinogenic Potency Database:Search
Env. Mutagen Info. Center:Search
NLM Developmental and Reproductive Toxicity:Search
EPA Substance Registry Services (TSCA):87-51-4
EPA ACToR:Toxicology Data
EPA Substance Registry Services (SRS):Registry
Laboratory Chemical Safety Summary :802
National Institute of Allergy and Infectious Diseases:Data
WGK Germany:3
2-(1H-indol-3-yl)acetic acid
Chemidplus:0000087514
RTECS:NL3150000 for cas# 87-51-4
 
References:
 2-(1H-indol-3-yl)acetic acid
NIST Chemistry WebBook:Search Inchi
Canada Domestic Sub. List:87-51-4
Pubchem (cid):802
Pubchem (sid):134971702
 
Other Information:
(IUPAC):Atomic Weights of the Elements 2009
(IUPAC):Atomic Weights of the Elements 2009 (pdf)
Videos:The Periodic Table of Videos
tgsc:Atomic Weights use for this web site
(IUPAC):Periodic Table of the Elements
CHEBI:View
CHEMBL:View
Golm Metabolome Database:Search
Metabolomics Database:Search
KEGG (GenomeNet):C00954
HMDB (The Human Metabolome Database):HMDB00197
FooDB:FDB003573
YMDB (Yeast Metabolome Database):YMDB00576
Export Tariff Code:2933.99.9700
VCF-Online:VCF Volatile Compounds in Food
Wikipedia:View
RSC Learn Chemistry:View
 
Potential Blenders and core components note
None Found
 
Potential Uses:
 skin conditioning
 
Occurrence (nature, food, other):note
 apple leaf
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 apple paradise apple
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 apple plant
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 apple stem bark
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 banana fruit
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 bean field bean
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 bean hyacinth bean
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 black gram
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 brassica oleracea
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 carrot tissue culture
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 cherry sour cherry
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 chestnut japanese chestnut
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 corn cotyledon
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 corn juice
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 corn root
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 currant black currant seed
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 currant red currant seed
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 garlic bulb
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 gooseberry seed
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 grape
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 hazelnut
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 marango fruit
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 oregano plant
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 pea plant
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 persimmon
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 plum
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 radish
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 radish root
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 soybean nodule
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 soybean shoot
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 soybean tissue culture
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 spinach sprout
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 tomato root
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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
 

Articles:

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.
 
Notes:
Widely distributed in higher plants Indole-3-acetic acid, also known as IAA, is a heterocyclic compound that is a phytohormone called auxin. This colourless solid is probably the most important plant auxin. The molecule is derived from indole, containing a carboxymethyl group (acetic acid). (Wikipedia) Auxins are a class of plant growth substances and morphogens (often called phytohormone or plant hormone). Auxins have an essential role in coordination of many growth and behavioral processes in the plant's life cycle. IAA (indole-3-acetic acid) is the most abundant and the basic native auxin in plants. (Wikipedia)
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