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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
Goutam Chowdhury et al.
Chemical research in toxicology, 22(12), 1905-1912 (2009-10-29)
Aerobic incubation of the tryptophan transamination/oxidation product indole-3-pyruvic acid (I3P) at pH 7.4 and 37 degrees C yielded products with activity as Ah receptor (AHR) agonists. The extracts were fractionated using HPLC and screened for AHR agonist activity. Two compounds
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