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TRYPTANTHRIN

Product Name
TRYPTANTHRIN
CAS No.
13220-57-0
Chemical Name
TRYPTANTHRIN
Synonyms
Couroupitine A;INDOLO[2,1-B]QUINAZOLINE-6,12-DIONE;NSC 349447;TRYPTANTHRIN;Trypanthrine;tryptanthrine;TRYPTANTHRIN-D4;Tryptanthrine-RM;Color amine ketone;6,12-Dihydroindolo[2,1-b]quinazoline-6,12-dione
CBNumber
CB4477493
Molecular Formula
C15H8N2O2
Formula Weight
248.24
MOL File
13220-57-0.mol
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TRYPTANTHRIN Property

Melting point:
258 °C(Solv: ethanol (64-17-5))
Boiling point:
469.3±28.0 °C(Predicted)
Density 
1.45±0.1 g/cm3(Predicted)
storage temp. 
2-8°C
solubility 
DMSO: soluble2mg/mL (warmed)
pka
-3.06±0.20(Predicted)
form 
powder
color 
faint yellow to dark yellow
Stability:
Stable for 1 year from date of purchase as supplied. Solutions in DMSO may be stored at -20°C for up to 3 months.
InChIKey
VQQVWGVXDIPORV-UHFFFAOYSA-N
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Safety

WGK Germany 
3
HS Code 
29339900
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Warning
Hazard statements

H302Harmful if swallowed

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
SML0310
Product name
Tryptanthrin
Purity
≥98% (HPLC)
Packaging
5mg
Price
$78.1
Updated
2024/03/01
Sigma-Aldrich
Product number
SML0310
Product name
Tryptanthrin
Purity
≥98% (HPLC)
Packaging
25mg
Price
$252
Updated
2024/03/01
Cayman Chemical
Product number
17913
Product name
Tryptanthrin
Purity
≥95%
Packaging
1mg
Price
$32
Updated
2024/03/01
Cayman Chemical
Product number
17913
Product name
Tryptanthrin
Purity
≥95%
Packaging
5mg
Price
$63
Updated
2024/03/01
Sigma-Aldrich
Product number
PHL83458
Product name
Tryptanthrine
Purity
phyproof Reference Substance
Packaging
10mg
Price
$430
Updated
2024/03/01
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TRYPTANTHRIN Chemical Properties,Usage,Production

Description

The matured fruit of Couroupita guianensis yields two highly unsaturated alkaloids. Couroupitine A is obtained in the form of yellow needles when crystallized from MeOH-CHCI3. It gives an ultraivolet spectrum with absorption maxima at 225 and 251 nm and an inflexion at 315 nm in EtOH.

Uses

Tryptanthrin is natural alkaloid, and a potent inhibitor of cyclooxygenase COX-2 and 5-lipoxygenase acting as an anti-inflammatory agent.

Definition

ChEBI: Tryptanthrine is an organonitrogen heterocyclic compound, an organic heterotetracyclic compound and an alkaloid antibiotic.

General Description

This substance is a primary reference substance with assigned absolute purity (considering chromatographic purity, water, residual solvents, inorganic impurities). The exact value can be found on the certificate. Produced by PhytoLab GmbH & Co. KG

Biochem/physiol Actions

Tryptanthrin is a plant alkaloid with anti-inflammatory and anti cancer activities. Tryptanthrin blocks leukotriene production in neutrophils and in whole blood assays, and in an in vivo rat pleurisy model. The compound also inhibits P-glycoprotein, and sensitizes resistant cancer cell lines to killing by cytotoxic agents.

in vitro

in human hepatocyte-derived hepg2 cells, tryptanthrin inhibited the reactive oxygen species formation, mitochondrial dysfunction, and cell death triggered by tert-butyl hydroperoxide (tbhp). furthermore, tryptanthrin reversed the reduction of glutathione (gsh) induced by tbhp. specifically, nuclear translocation, transactivation of nuclear factor erythroid 2-related factor 2 (nrf2), and phosphorylation of extracellular signal-regulated kinase (erk) were evoked by the treatment of tryptanthrin. additionally, the expression of the heme oxygenase 1 and glutamate was upregulated by tryptanthrin [1].

in vivo

balb/c (h-2d) mice, intraperitoneally (i.p.) inoculated with leukemia wehi-3b jcs cells, were injected i.p with tryptanthrin at doses of 0.04 mg/kg, 0.08 mg/kg and 0.16 mg/kg body weight for 5 consecutive days. tryptanthrin inhibited the growth of wehi-3b jcs cells in balb/c mice, and at the dosages of 0.08 mg/kg and 0.16 mg/kg, significant inhibition was seen. moreover, tryptanthrin, in a dose-dependent fashion, triggered cell cycle arrest of the wehi-3b jcs cells at g0/g1 phase [2].

References

Sen, Mahato, Dutta, Tetrahedron Lett., 609 (1974)

TRYPTANTHRIN Preparation Products And Raw materials

Raw materials

Preparation Products

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13220-57-0, TRYPTANTHRINRelated Search:


  • TRYPTANTHRIN
  • INDOLO[2,1-B]QUINAZOLINE-6,12-DIONE
  • tryptanthrine
  • 6,12-Dihydroindolo[2,1-b]quinazoline-6,12-dione
  • Couroupitine A
  • Trypanthrine
  • NSC 349447
  • CouroupitineAIndolo(2,1-b)quinazoline-6,12-dioneTryptanthrine
  • TRYPTANTHRIN-D4
  • Color amine ketone
  • Tryptanthrine-RM
  • 13220-57-0
  • C15H8N2O2
  • Indoles and derivatives