| Identification | Back Directory | [Name]
TRIPARANOL | [CAS]
78-41-1 | [Synonyms]
mer29
MER 2p
Clotrox
Diticyl
Drenaren
nsc65345
Metasqua
Acosterina
Metasclene
metasqualene
Hipocolestina
alpha-(p-chlorobenzyl)-4-diethylaminoethoxy-4’-methylbenzhydrol
2-p-chlorophenyl-1-(p-(2-diethylaminoethoxy)phenyl)-1-p-tolylethanol
2-(p-chlorophenyl)-1-(p-(2-(diethylamino)ethoxy)phenyl)-1-p-tolyl-ethano
1-(4-(2-(diethylamino)ethoxy)phenyl)-1-(p-tolyl)-2-(p-chlorophenyl)ethanol
2-(p-chlorophenyl)-1-(p-(beta-diethylaminoethoxy)phenyl)-1-(p-tolyl)ethanol
1-(p-(beta-diethylaminoethoxy)phenyl)-1-(p-tolyl)-2-(p-chlorophenyl)ethanol
4-Chloro-α-[4-[2-(diethylamino)ethoxy]phenyl]-α-(4-methylphenyl)benzeneethanol
4-Chloro-a-[4-[2-(diethylamino)ethoxy]phenyl]-a-(4-methylphenyl)benzeneethanol
2-(4-chlorophenyl)-1-[4-(2-diethylaminoethyloxy)phenyl]-1-(4-methylphenyl)ethanol
Benzeneethanol, 4-chloro-α-[4-[2-(diethylamino)ethoxy]phenyl]-α-(4-methylphenyl)- | [EINECS(EC#)]
201-115-0 | [Molecular Formula]
C27H32ClNO2 | [MDL Number]
MFCD00865748 | [MOL File]
78-41-1.mol | [Molecular Weight]
438 |
| Chemical Properties | Back Directory | [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) | [form ]
solid
| [pka]
13.44±0.29(Predicted) | [color ]
off-white
|
| Hazard Information | Back Directory | [Originator]
Mer-29,Merrell National,US,1960 | [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. | [Uses]
Desmosterol Delta 24 (D24) reductase inhibitor | [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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