Basic information Safety Supplier Related

TRIPARANOL

Basic information Safety Supplier Related

TRIPARANOL Basic information

Product Name:
TRIPARANOL
Synonyms:
  • Benzeneethanol, 4-chloro-α-[4-[2-(diethylamino)ethoxy]phenyl]-α-(4-methylphenyl)-
  • 1-(p-(beta-diethylaminoethoxy)phenyl)-1-(p-tolyl)-2-(p-chlorophenyl)ethanol
  • 2-(p-chlorophenyl)-1-(p-(2-(diethylamino)ethoxy)phenyl)-1-p-tolyl-ethano
  • 2-(p-chlorophenyl)-1-(p-(beta-diethylaminoethoxy)phenyl)-1-(p-tolyl)ethanol
  • 2-p-chlorophenyl-1-(p-(2-diethylaminoethoxy)phenyl)-1-p-tolylethanol
  • alpha-(p-chlorobenzyl)-4-diethylaminoethoxy-4’-methylbenzhydrol
  • mer29
  • metasqualene
CAS:
78-41-1
MF:
C27H32ClNO2
MW:
438
EINECS:
201-115-0
Product Categories:
  • Inhibitors
  • Intermediates & Fine Chemicals
  • All Inhibitors
  • Pharmaceuticals
Mol File:
78-41-1.mol
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TRIPARANOL Chemical Properties

Melting point:
102.9-103.7 °C
Density 
1.0173 (rough estimate)
refractive index 
1.5830 (estimate)
storage temp. 
2-8°C
solubility 
DMSO: 15 mg/mL
Boiling point:
235-240 °C(Press: 0.08 Torr)
pka
13.44±0.29(Predicted)
form 
solid
color 
off-white
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Safety Information

Hazard Codes 
Xn
Risk Statements 
22-41
Safety Statements 
26-39
WGK Germany 
3
RTECS 
KK2400000
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TRIPARANOL Usage And Synthesis

Originator

Mer-29,Merrell National,US,1960

Uses

Desmosterol Delta 24 (D24) reductase inhibitor

Uses

Triparanol has been used to inhibit cholesterol biosynthesis in lipid rafts1. Triparanol has also been used as a 3β-hydroxysterol-Δ24-reductase inhibitor to study its effect on delayed-rectifier potassium current (Iks) channels2.

Definition

ChEBI: Triparanol is a stilbenoid. It has a role as an anticoronaviral agent.

Manufacturing Process

4-(β-diethylaminoethoxy)-4-methylbenzophenone was prepared as follows: a mixture of 200 g of 4-hydroxy-4-methylbenzophenone, 55 g of powdered sodium methoxide and 400 ml of ethanol was stirred for 30 minutes. A solution of 150 g of β-diethylaminoethyl chloride in 300 ml of toluene was added and the mixture was refluxed four hours. The solvent was removed, the residue was taken up in ether, extracted with 5% NaOH solution, twice with water, the ether was removed and the residue was distilled. The product was obtained as an oil boiling at 232°C at 0.6 mm.
1 liter of a 0.45 N ethereal solution of p-chlorobenzyl magnesium chloride was added in 30 minutes to a stirred solution of 104 g (0.35 mol) of 4-(β- diethylaminoethoxy)-4-methylbenzophenone in 400 ml of dry ether. After stirring an additional hour, the mixture was decomposed by pouring onto 1 liter of cold 10% ammonium chloride solution, the ether solution was washed with water, and the ether was replaced with hot isopropanol containing a trace of ammonia. 1-[p-(β-diethylaminoethoxy)phenyl]-1-phenyl-2-p-tolyl-2-p_x0002_chloroethanol separated as white crystals, melting at 104% to 106°C.

Therapeutic Function

Antihyperlipidemic

Biochem/physiol Actions

Triparanol is known to repress Hedgehog signaling in cancer cells and can also inhibit tumor growth3.

TRIPARANOLSupplier

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