I7017
Indole-3-pyruvic acid
≥97%
Synonym(s):
3-(3-Indolyl)-2-oxopropanoic acid, 3-Indolylpyruvic acid
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About This Item
Empirical Formula (Hill Notation):
C11H9NO3
CAS Number:
Molecular Weight:
203.19
UNSPSC Code:
12352100
NACRES:
NA.22
PubChem Substance ID:
EC Number:
206-874-1
Beilstein/REAXYS Number:
172966
MDL number:
Assay:
≥97%
InChI key
RSTKLPZEZYGQPY-UHFFFAOYSA-N
InChI
1S/C11H9NO3/c13-10(11(14)15)5-7-6-12-9-4-2-1-3-8(7)9/h1-4,6,12H,5H2,(H,14,15)
SMILES string
OC(=O)C(=O)Cc1c[nH]c2ccccc12
assay
≥97%
color
light yellow
mp
215 °C (dec.) (lit.)
storage temp.
−20°C
Quality Level
Application
Indole-3-pyruvic acid can be used:
- As a precursor for the synthesis of chromopyrrolic acid by a heme-containing enzyme.
- As a reactant in the Biginelli-like scaffold syntheses.
Other Notes
α-Keto analogue of tryptophan
signalword
Warning
hcodes
Hazard Classifications
Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3
target_organs
Respiratory system
Storage Class
11 - Combustible Solids
wgk
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
ppe
dust mask type N95 (US), Eyeshields, Gloves
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Cyclic ketones and substituted α-keto acids as alternative substrates for novel Biginelli-like scaffold syntheses
Abelman, Matthew M, et al.
Tetrahedron Letters, 44(24), 4559-4562 (2003)
Gavin Reineke et al.
Molecular plant pathology, 9(3), 339-355 (2008-08-19)
Infection of maize (Zea mays) plants with the smut fungus Ustilago maydis is characterized by excessive host tumour formation. U. maydis is able to produce indole-3-acetic acid (IAA) efficiently from tryptophan. To assess a possible connection to the induction of
Mark A Bittinger et al.
Molecular pharmacology, 64(3), 550-556 (2003-08-16)
The aryl hydrocarbon receptor (AHR) binds planar aromatic compounds and up-regulates the transcription of a battery of xenobiotic-metabolizing enzymes. To identify proteins involved in the biosynthesis of endogenous AHR ligands, we screened extracts of various mouse tissues for AHR signaling
Anna N Stepanova et al.
The Plant cell, 23(11), 3961-3973 (2011-11-24)
The effects of auxins on plant growth and development have been known for more than 100 years, yet our understanding of how plants synthesize this essential plant hormone is still fragmentary at best. Gene loss- and gain-of-function studies have conclusively
Elisabeth Stes et al.
The Plant journal : for cell and molecular biology, 70(3), 513-527 (2011-12-21)
The biotrophic phytopathogen Rhodococcus fascians has a profound impact on plant development, mainly through its principal virulence factors, a mix of synergistically acting cytokinins that induce shoot formation. Expression profiling of marker genes for several auxin biosynthesis routes and mutant
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