TRIPARANOL
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
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
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.
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