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Merck

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:
392-12-1
Molecular Weight:
203.19
UNSPSC Code:
12352100
NACRES:
NA.22
PubChem Substance ID:
57654306
EC Number:
206-874-1
Beilstein/REAXYS Number:
172966
MDL number:
MFCD00005640
Assay:
≥97%

Key Documents

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Product Name

Indole-3-pyruvic acid, ≥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

100

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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

pictograms

Exclamation mark
GHS07

signalword

Warning

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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Certificates of Analysis (COA)

Lot/Batch Number
0000458771
0000458771
0000453909
0000453909
0000359859

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Direct formation of chromopyrrolic acid from indole-3-pyruvic acid by StaD, a novel hemoprotein in indolocarbazole biosynthesis
Asamizu, S, et al.
Tetrahedron Letters, 47(4), 473-475 (2006)
L Bacciottini et al.
Pharmacological research communications, 19(11), 803-817 (1987-11-01)
The effects of acute or repeated administration of indole-pyruvic acid (IPA), a keto-analogue of tryptophan (TRP), were studied in various brain areas of rats by measuring the changes of 5-hydroxytryptamine (5-HT) and of norepinephrine (NE) content and metabolism. The analgesic
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)
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
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
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