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| 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 |
| Hazard Codes | Xn | | Risk Statements | 22-41 | | Safety Statements | 26-39 | | WGK Germany | 3 | | RTECS | KK2400000 |
| 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. | | 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. |
| TRIPARANOL Preparation Products And Raw materials |
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