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:
Molecular Weight:
203.19
UNSPSC Code:
12352100
NACRES:
NA.22
PubChem Substance ID:
EC Number:
206-874-1
Beilstein/REAXYS Number:
172966
MDL number:
Assay:
≥97%
Quality Level
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
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
signalword
Warning
hcodes
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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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)
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