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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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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

Related Categories

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

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

I7017-1G: + I7017-5G-PW: + I7017-BULK: + I7017-250MG: + I7017-500MG: + I7017-5G: + I7017-1G-PW: + I7017-VAR:

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Certificates of Analysis (COA)

Lot/Batch Number
099M4090V
13190133
088M4093V
088M4092V
13180320

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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)
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
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)
Thomas Rauhut et al.
Phytochemistry, 70(15-16), 1638-1644 (2009-06-16)
Structurally related secondary products are rather rarely shared by organisms from different kingdoms. Consequently, the evolution of biosynthetic pathways of defence metabolites between distantly related organisms has not been broadly investigated. Thiazolylindoles are found in Arabidopsis thaliana, as the phytoalexin
Anna N Stepanova et al.
Cell, 133(1), 177-191 (2008-04-09)
Plants have evolved a tremendous ability to respond to environmental changes by adapting their growth and development. The interaction between hormonal and developmental signals is a critical mechanism in the generation of this enormous plasticity. A good example is the
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