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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:
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

Signal Word

Warning

Hazard Statements

H315,H319,H335

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
0000368466
0000359859
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
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)
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
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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