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indole-3-pyruvic acid
indol-3-yl pyruvic acid

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Name:3-(1H-indol-3-yl)-2-oxopropanoic acid
CAS Number: 392-12-1Picture of molecule3D/inchi
ECHA EINECS - REACH Pre-Reg:206-874-1
FDA UNII: 4QM0LT13A8
Nikkaji Web:J39.033J
Beilstein Number:0172966
MDL:MFCD00005640
XlogP3:1.30 (est)
Molecular Weight:203.19733000
Formula:C11 H9 N O3
NMR Predictor:Predict (works with chrome, Edge or firefox)
Category:information only not used for fragrances or flavors
 
US / EU / FDA / JECFA / FEMA / FLAVIS / Scholar / Patent Information:
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Physical Properties:
Assay: 95.00 to 100.00
Food Chemicals Codex Listed: No
Soluble in:
 water, 3.716e+004 mg/L @ 25 °C (est)
 
Organoleptic Properties:
Odor and/or flavor descriptions from others (if found).
 
Cosmetic Information:
None found
 
Suppliers:
BOC Sciences
For experimental / research use only.
Indole pyruvic acid 95%
BST Tianjin Co.
Indole-3-pyruvic Acid
Santa Cruz Biotechnology
For experimental / research use only.
Indole-3-pyruvic Acid ≥98%
Sigma-Aldrich: Aldrich
For experimental / research use only.
Indole-3-pyruvic Acid
sds
 
Safety Information:
Preferred SDS: View
 
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:
Not determined
Dermal Toxicity:
Not determined
Inhalation Toxicity:
Not determined
 
Safety in Use Information:
Category:
information only not used for fragrances or flavors
Recommendation for indole-3-pyruvic acid usage levels up to:
 not for fragrance use.
 
Recommendation for indole-3-pyruvic acid flavor usage levels up to:
 not for flavor use.
 
Safety References:
EPI System: View
AIDS Citations:Search
Cancer Citations:Search
Toxicology Citations:Search
EPA ACToR:Toxicology Data
EPA Substance Registry Services (SRS):Registry
Laboratory Chemical Safety Summary :803
National Institute of Allergy and Infectious Diseases:Data
WGK Germany:3
3-(1H-indol-3-yl)-2-oxopropanoic acid
Chemidplus:0000392121
RTECS:NM1880000 for cas# 392-12-1
 
References:
 3-(1H-indol-3-yl)-2-oxopropanoic acid
NIST Chemistry WebBook:Search Inchi
Pubchem (cid):803
Pubchem (cas):392-12-1
 
Other Information:
(IUPAC):Atomic Weights of the Elements 2011 (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):C00331
HMDB (The Human Metabolome Database):Search
YMDB (Yeast Metabolome Database):YMDB00169
Export Tariff Code:2933.90.8000
ChemSpider:View
 
Potential Blenders and core components note
None Found
 
Potential Uses:
None Found
 
Occurrence (nature, food, other):note
 not found in nature
 
Synonyms:
 indol-3-yl pyruvic acid
3-(1H-indol-3-yl)-2-oxopropanoic acid
alpha-oxo-1H-indole-3-propanoic acid
1H-indole-3-propanoic acid, alpha-oxo-
 indole-3-pyruvic acid monohydrate
beta-indolepyruvic acid
 

Articles:

PubMed:The activation of OsEIL1 on YUC8 transcription and auxin biosynthesis is required for ethylene-inhibited root elongation in rice early seedling development.
PubMed:Preference of Arabidopsis thaliana GH3.5 acyl amido synthetase for growth versus defense hormone acyl substrates is dictated by concentration of amino acid substrate aspartate.
PubMed:Novel tryptophan metabolic pathways in auxin biosynthesis in silkworm.
PubMed:Auxin signaling through SCF(TIR1/AFBs) mediates feedback regulation of IAA biosynthesis.
PubMed:Biochemical and Chemical Biology Study of Rice OsTAR1 Revealed that Tryptophan Aminotransferase is Involved in Auxin Biosynthesis: Identification of a Potent OsTAR1 Inhibitor, Pyruvamine2031.
PubMed:Functional roles of Arabidopsis CKRC2/YUCCA8 gene and the involvement of PIF4 in the regulation of auxin biosynthesis by cytokinin.
PubMed:The auxins, IAA and PAA, are synthesized by similar steps catalyzed by different enzymes.
PubMed:Identification of Genes Involved in Indole-3-Acetic Acid Biosynthesis by Gluconacetobacter diazotrophicus PAL5 Strain Using Transposon Mutagenesis.
PubMed:Indole-3-acetic acid in Fusarium graminearum: Identification of biosynthetic pathways and characterization of physiological effects.
PubMed:Preparation and Characterization of Four Stereoisomers of Monatin.
PubMed:Dynamic Precision Phenotyping Reveals Mechanism of Crop Tolerance to Root Herbivory.
PubMed:Local auxin metabolism regulates environment-induced hypocotyl elongation.
PubMed:The Thiol Reductase Activity of YUCCA6 Mediates Delayed Leaf Senescence by Regulating Genes Involved in Auxin Redistribution.
PubMed:Auxin Biosynthesis: Are the Indole-3-Acetic Acid and Phenylacetic Acid Biosynthesis Pathways Mirror Images?
PubMed:Indole-3-acetic acid biosynthetic pathways in the basidiomycetous yeast Rhodosporidium paludigenum.
PubMed:Analysis and cloning of the synthetic pathway of the phytohormone indole-3-acetic acid in the plant-beneficial Bacillus amyloliquefaciens SQR9.
PubMed:Auxin and Tryptophan Homeostasis Are Facilitated by the ISS1/VAS1 Aromatic Aminotransferase in Arabidopsis.
PubMed:Auxin Produced by the Indole-3-Pyruvic Acid Pathway Regulates Development and Gemmae Dormancy in the Liverwort Marchantia polymorpha.
PubMed:Transcriptional feedback regulation of YUCCA genes in response to auxin levels in Arabidopsis.
PubMed:The ipdC, hisC1 and hisC2 genes involved in indole-3-acetic production used as alternative phylogenetic markers in Azospirillum brasilense.
PubMed:Evidence for catalytic intermediates involved in generating the chromopyrrolic acid scaffold of rebeccamycin by RebO and RebD.
PubMed:Enhancement of stability of L-tryptophan dehydrogenase from Nostoc punctiforme ATCC29133 and its application to L-tryptophan assay.
PubMed:Analysis of a putative auxin biosynthesis inhibitor, indole-3-oxoethylphosphonic acid, in Arabidopsis.
PubMed:The rice FISH BONE gene encodes a tryptophan aminotransferase, which affects pleiotropic auxin-related processes.
PubMed:Indole-3-acetic acid in plant-microbe interactions.
PubMed:Yucasin is a potent inhibitor of YUCCA, a key enzyme in auxin biosynthesis.
PubMed:Development of indole-3-acetic acid-producing Escherichia coli by functional expression of IpdC, AspC, and Iad1.
PubMed:YUCCA8 and YUCCA9 overexpression reveals a link between auxin signaling and lignification through the induction of ethylene biosynthesis.
PubMed:Genetic aspects of auxin biosynthesis and its regulation.
PubMed:Disturbed local auxin homeostasis enhances cellular anisotropy and reveals alternative wiring of auxin-ethylene crosstalk in Brachypodium distachyon seminal roots.
PubMed:Roles of YUCCAs in auxin biosynthesis and drought stress responses in plants.
PubMed:Indole-3-acetic acid biosynthetic pathway and aromatic amino acid aminotransferase activities in Pantoea dispersa strain GPK.
PubMed:Coordination of auxin and ethylene biosynthesis by the aminotransferase VAS1.
PubMed:Indole-3-acetic acid biosynthesis in Fusarium delphinoides strain GPK, a causal agent of Wilt in Chickpea.
PubMed:Metabolic analysis of the cutaneous fungi Malassezia globosa and M. restricta for insights on scalp condition and dandruff.
PubMed:A mutation affecting the synthesis of 4-chloroindole-3-acetic acid.
PubMed:Overexpression of Arabidopsis YUCCA6 in potato results in high-auxin developmental phenotypes and enhanced resistance to water deficit.
PubMed:Indole derivative production by the root endophyte Piriformospora indica is not required for growth promotion but for biotrophic colonization of barley roots.
PubMed:Protocol: High-throughput and quantitative assays of auxin and auxin precursors from minute tissue samples.
PubMed:Development and Validation of a Reversed-Phase Liquid Chromatography Method for the Simultaneous Determination of Indole-3-Acetic Acid, Indole-3-Pyruvic Acid, and Abscisic Acid in Barley (Hordeum vulgare L.).
PubMed:The pathway of auxin biosynthesis in plants.
PubMed:Plant-derived auxin plays an accessory role in symptom development upon Rhodococcus fascians infection.
PubMed:The Arabidopsis YUCCA1 flavin monooxygenase functions in the indole-3-pyruvic acid branch of auxin biosynthesis.
PubMed:A small-molecule screen identifies L-kynurenine as a competitive inhibitor of TAA1/TAR activity in ethylene-directed auxin biosynthesis and root growth in Arabidopsis.
PubMed:The main auxin biosynthesis pathway in Arabidopsis.
PubMed:vanishing tassel2 encodes a grass-specific tryptophan aminotransferase required for vegetative and reproductive development in maize.
PubMed:Functional characterization of the CKRC1/TAA1 gene and dissection of hormonal actions in the Arabidopsis root.
PubMed:Cold-adapted and rhizosphere-competent strain of Rahnella sp. with broad-spectrum plant growth-promotion potential.
PubMed:Sugar-hormone cross-talk in seed development: two redundant pathways of IAA biosynthesis are regulated differentially in the invertase-deficient miniature1 (mn1) seed mutant in maize.
PubMed:Auxin biosynthesis inhibitors, identified by a genomics-based approach, provide insights into auxin biosynthesis.
PubMed:L-Tryptophan catabolism by Rubrivivax benzoatilyticus JA2 occurs through indole 3-pyruvic acid pathway.
PubMed:D-amino acid oxidase generates agonists of the aryl hydrocarbon receptor from D-tryptophan.
PubMed:Structural identification of Diindole agonists of the aryl hydrocarbon receptor derived from degradation of indole-3-pyruvic acid.
PubMed:High rates and substrate selectivities in water by polyvinylimidazoles as transaminase enzyme mimics with hydrophobically bound pyridoxamine derivatives as coenzyme mimics.
PubMed:Biochemical characterization and substrate specificity of the gene cluster for biosyntheses of K-252a and its analogs by in vitro heterologous expression system of Escherichia coli.
PubMed:The TRANSPORT INHIBITOR RESPONSE2 gene is required for auxin synthesis and diverse aspects of plant development.
PubMed:Evolution of camalexin and structurally related indolic compounds.
PubMed:Investigating the initial steps in the biosynthesis of cyanobacterial sunscreen scytonemin.
PubMed:Indole-3-acetic acid (IAA) biosynthesis in the smut fungus Ustilago maydis and its relevance for increased IAA levels in infected tissue and host tumour formation.
PubMed:Functional identification and expression of indole-3-pyruvate decarboxylase from Paenibacillus polymyxa E681.
PubMed:TAA1-mediated auxin biosynthesis is essential for hormone crosstalk and plant development.
PubMed:Rapid synthesis of auxin via a new tryptophan-dependent pathway is required for shade avoidance in plants.
PubMed:A new gene for auxin synthesis.
PubMed:Organization of the ipdC region regulates IAA levels in different Azospirillum brasilense strains: molecular and functional analysis of ipdC in strain SM.
PubMed:Crystal structure of VioE, a key player in the construction of the molecular skeleton of violacein.
PubMed:An ipdC gene knock-out of Azospirillum brasilense strain SM and its implications on indole-3-acetic acid biosynthesis and plant growth promotion.
PubMed:Enzymatic generation of the chromopyrrolic acid scaffold of rebeccamycin by the tandem action of RebO and RebD.
PubMed:Aldehyde oxidase (AO) in the root nodules of Lupinus albus and Medicago truncatula: identification of AO in meristematic and infection zones.
PubMed:Biosynthesis of auxin by the gram-positive phytopathogen Rhodococcus fascians is controlled by compounds specific to infected plant tissues.
PubMed:Separation and determination of L-tryptophan and its metabolites by capillary micellar electrokinetic chromatography with amperometric detection.
PubMed:The enol tautomer of indole-3-pyruvic acid as a biological switch in stress responses.
PubMed:Studies on structure-function relationships of indolepyruvate decarboxylase from Enterobacter cloacae, a key enzyme of the indole acetic acid pathway.
PubMed:[Research of indole-3-acetic acid biosynthetic pathway of Klebsiella oxytoca SG-11 by HPLC and GC-MS].
PubMed:Tryptophan biosynthesis and production of other related compounds from indolepyruvic acid by mixed ruminal bacteria, protozoa, and their mixture in vitro.
PubMed:Formation of kynurenic and xanthurenic acids from kynurenine and 3-hydroxykynurenine in the dinoflagellate Lingulodinium polyedrum: role of a novel, oxidative pathway.
PubMed:Evidence for production of the phytohormone indole-3-acetic acid by cyanobacteria.
PubMed:[Aerobic methylobacteria are capable of synthesizing auxins].
PubMed:Evidence for the presence of DNA-binding proteins involved in regulation of the gene expression of indole-3-pyruvic acid decarboxylase, a key enzyme in indole-3-acetic acid biosynthesis in Azospirillum lipoferum FS.
PubMed:Involvement of naphthalene dioxygenase in indole-3-acetic acid biosynthesis by Pseudomonas putida.
PubMed:Azospirillum, a free-living nitrogen-fixing bacterium closely associated with grasses: genetic, biochemical and ecological aspects.
PubMed:Isolation and characterization of low-indole-3-acetic acid-producing mutants from Bradyrhizobium elkanii.
PubMed:Off-flavor compounds in wine and other food products formed by enzymatical, physical, and chemical degradation of tryptophan and its metabolites.
PubMed:Radical scavenging properties of tryptophan metabolites. Estimation of their radical reactivity.
PubMed:Clinical experiences with the use of indole-3-pyruvic acid.
PubMed:Biosynthesis of indole-3-acetic acid in Azospirillum brasilense. Insights from quantum chemistry.
PubMed:Indole-3-acetic acid biosynthesis in colletotrichum gloeosporioides f. sp. aeschynomene
PubMed:Increased excretion of aromatic amino acid catabolites in animals infected with Trypanosoma brucei evansi.
PubMed:Determination of indole-3-pyruvic acid levels in Arabidopsis thaliana by gas chromatography-selected ion monitoring-mass spectrometry.
PubMed:Two potential indole-3-acetaldehyde dehydrogenases in the phytopathogenic fungus Ustilago maydis.
PubMed:The excessive production of indole-3-acetic acid and its significance in studies of the biosynthesis of this regulator of plant growth and development.
PubMed:Cloning and characterization of a locus encoding an indolepyruvate decarboxylase involved in indole-3-acetic acid synthesis in Erwinia herbicola.
PubMed:Purification and properties of aromatic amino acid aminotransferases from Azospirillum brasilense UAP 14 strain.
PubMed:Characterization of two new matrices for matrix-assisted laser desorption/ionization mass spectrometry.
PubMed:Antioxidant properties of indole-3-pyruvic acid.
PubMed:Catabolism of tryptophan by Trypanosoma evansi.
PubMed:Synthesis of phytohormones by plant-associated bacteria.
PubMed:Involvement of L-tryptophan aminotransferase in indole-3-acetic acid biosynthesis in Enterobacter cloacae.
PubMed:Molecular cloning and sequence analysis of an Azospirillum brasilense indole-3-pyruvate decarboxylase gene.
PubMed:Anxiolytic effect of indole-3-pyruvic acid (IPA) in mice.
PubMed:Purification and characterization of indolepyruvate decarboxylase. A novel enzyme for indole-3-acetic acid biosynthesis in Enterobacter cloacae.
PubMed:Indole-3-pyruvic acid as a possible hypnotic agent in insomniac subjects.
PubMed:Metabolic fates of L-tryptophan in Saccharomyces uvarum (Saccharomyces carlsbergensis).
PubMed:Molecular cloning of the gene for indolepyruvate decarboxylase from Enterobacter cloacae.
PubMed:Indole-3-pyruvic acid as a direct precursor of kynurenic acid.
PubMed:The role of transaminations in the pharmacological effects of indole-3-pyruvic acid.
PubMed:The regulation of brain kynurenic acid content: focus on indole-3-pyruvic acid.
PubMed:Antihypertensive activity of indolepyruvic acid: a keto analogue of tryptophan.
PubMed:Stereochemistry and mechanism of a new single-turnover, half-transamination reaction catalyzed by the tryptophan synthase alpha 2 beta 2 complex.
PubMed:Increased urinary excretion of aromatic amino acid catabolites by Microtus montanus chronically infected with Trypanosoma brucei gambiense.
PubMed:Improved Procedure for the Estimation of Nanogram Quantities of Indole-3-acetic Acid in Plant Extracts using the Indolo-alpha-pyrone Fluorescence Method.
PubMed:Indole-3-pyruvic acid as a potential luciferin.
PubMed:Tryptophol formation by Zygosaccharomyces priorianus.
PubMed:Studies on the hormonal relationships of algae in pure culture : III. Tryptamine is an intermediate in the conversion of tryptophan to indole-3-acetic acid by the blue-green alga Chlorogloea fritschii.
PubMed:[Occurrence and metabolism of auxin in multicellular algae of the baltic sea : II. On the formation of Indoleacetic acid from tryptophan, with regard to the influence of the marine bacteria].
PubMed:Microbiological method for the determination of L-tryptophan.
 
Notes:
None found
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