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trans-3-Indoleacrylic acid

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trans-3-Indoleacrylic acid Basic information

Product Name:
trans-3-Indoleacrylic acid
Synonyms:
  • BETA-INDOLEACRYLIC ACID
  • INDOLE-3-ACRYLIC ACID
  • INDOLE ACRYLIC ACID
  • 3-BETA-INDOLEACRYLIC ACID
  • 3-(3-INDOLYL)ACRYLIC ACID
  • 2-BETA-INDOLEACRYLIC ACID
  • RARECHEM BK HD 0025
  • TIMTEC-BB SBB003692
CAS:
29953-71-7
MF:
C11H9NO2
MW:
187.19
EINECS:
621-733-8
Product Categories:
  • Indoles
  • Building Blocks
  • Indoles and derivatives
  • Heterocyclic Compounds
  • Heterocyclic Building Blocks
Mol File:
29953-71-7.mol
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trans-3-Indoleacrylic acid Chemical Properties

Melting point:
185 °C (dec.)(lit.)
Boiling point:
321.94°C (rough estimate)
Density 
1.1963 (rough estimate)
refractive index 
1.4900 (estimate)
storage temp. 
2-8°C
solubility 
DMSO (Slightly), Methanol (Slightly)
pka
4.59±0.10(Predicted)
form 
powder
color 
white to light yellow
Water Solubility 
freely soluble
BRN 
6317
Stability:
Stable under recommended storage conditions., Stable Under Recommended Storage C
InChI
InChI=1S/C11H9NO2/c13-11(14)6-5-8-7-12-10-4-2-1-3-9(8)10/h1-7,12H,(H,13,14)/b6-5+
InChIKey
PLVPPLCLBIEYEA-AATRIKPKSA-N
SMILES
C(O)(=O)/C=C/C1C2=C(NC=1)C=CC=C2
CAS DataBase Reference
29953-71-7(CAS DataBase Reference)
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Safety Information

Hazard Codes 
Xi
Risk Statements 
36/37/38
Safety Statements 
26-36-37/39
WGK Germany 
3
RTECS 
NL3680000
HS Code 
2933998090

MSDS

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trans-3-Indoleacrylic acid Usage And Synthesis

Chemical Properties

LIGHT BROWN CRYSTALLINE POWDER

Uses

trans-3-Indoleacrylic acid is an important raw material and intermediate used in organic synthesis, pharmaceuticals, agrochemicals.

Application

trans-3-Indoleacrylic acid is a metabolite of tryptophan.
Chromophoric L-Trp analog used to probe the allosteric properties of the internal aldimine of tryptophan synthase. Also shown to be a moderate inhibitor of tryptophan synthase, trypothan-2,3-dioxygenase (TDO), indoleamine-2,3-dioxygenase (IDO), L-dopachrome isomerase and xanthine oxidase.
Reagent used as a matrix for MALDI-TOF mass spectroscopy in order to characterize and analyze polyphenols and synthetic polymers.

Definition

ChEBI: trans-3-Indoleacrylic acid is an alpha,beta-unsaturated monocarboxylic acid that is acrylic acid in which one of the hydrogens at position 3 is replaced by an indol-3-yl group. It is an alpha,beta-unsaturated monocarboxylic acid and a member of indoles. It derives from an acrylic acid. It is a conjugate acid of an (E)-3-(indol-3-yl)acrylate(1-).

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