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I7017

Sigma-Aldrich

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
Beilstein/REAXYS Number:
172966
EC Number:
206-874-1
MDL number:
MFCD00005640
UNSPSC Code:
12352100
PubChem Substance ID:
57654306
NACRES:
NA.22

Quality Level

100

assay

≥97%

color

light yellow

mp

215 °C (dec.) (lit.)

storage temp.

−20°C

SMILES string

OC(=O)C(=O)Cc1c[nH]c2ccccc12

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)

InChI key

RSTKLPZEZYGQPY-UHFFFAOYSA-N

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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.

Linkage

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_germany

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
0000359859
0000368466
0000359860
0000351534
0000351534

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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
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
Nathan D Tivendale et al.
Plant physiology, 159(3), 1055-1063 (2012-05-11)
Seeds of several agriculturally important legumes are rich sources of the only halogenated plant hormone, 4-chloroindole-3-acetic acid. However, the biosynthesis of this auxin is poorly understood. Here, we show that in pea (Pisum sativum) seeds, 4-chloroindole-3-acetic acid is synthesized via
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)
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