TRIPARANOL Property

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

Safety

Hazard Codes 

Xn

Risk Statements 

22-41

Safety Statements 

26-39

WGK Germany 

3

RTECS 

KK2400000

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Danger

Hazard statements

H302Harmful if swallowed

H318Causes serious eye damage

Precautionary statements

P280Wear protective gloves/protective clothing/eye protection/face protection.

TRIPARANOL Chemical Properties,Usage,Production

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 (I_ks) 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.