TRIPARANOL

Base Information

• Chemical Name: TRIPARANOL
• CAS No.: 78-41-1
• Molecular Formula: C27H32 Cl N O2
• Molecular Weight: 438.01
• European Community (EC) Number: 201-115-0
• NSC Number: 65345
• UNII: 63S8C3RXGS
• DSSTox Substance ID: DTXSID6046507
• Nikkaji Number: J5.241H
• Wikipedia: Triparanol
• Wikidata: Q5988254
• NCI Thesaurus Code: C152752
• Pharos Ligand ID: SQ8XXJPVXCX3
• Metabolomics Workbench ID: 71484
• ChEMBL ID: CHEMBL187709
• Mol file: 78-41-1.mol

Synonyms:Ethanol,2-(p-chlorophenyl)-1-[p-[2-(diethylamino)ethoxy]phenyl]-1-p-tolyl- (6CI,8CI);1-[4-[2-(Diethylamino)ethoxy]phenyl]-1-(p-tolyl)-2-(p-chlorophenyl)ethanol;1-[p-(b-Diethylaminoethoxy)phenyl]-1-(p-tolyl)-2-(p-chlorophenyl)ethanol;2-(p-Chlorophenyl)-1-[p-(b-diethylaminoethoxy)phenyl]-1-(p-tolyl)ethanol; 2-p-Chlorophenyl-1-[p-(2-diethylaminoethoxy)phenyl]-1-p-tolylethanol;Acosterina; Clotrox; Diticyl; Drenaren; Hipocolestina; MER 29; MER 2p;Metasclene; Metasqualene; NSC 65345; Sclane; TR; Trianel; Trikosterol;Triparanol; Triparin; Tropalin; Valip; Verdiana

Chemical Property of TRIPARANOL

Chemical Property:

• Vapor Pressure: 8.57E-13mmHg at 25°C
• Melting Point: 102.9-103.7 °C
• Refractive Index: 1.5830 (estimate)
• Boiling Point: 546.9°C at 760 mmHg
• PKA: 13.44±0.29(Predicted)
• Flash Point: 284.5°C
• PSA: 32.70000
• Density: 1.133g/cm³
• LogP: 5.84760
• Storage Temp.: 2-8°C
• Solubility.: DMSO: 15 mg/mL
• XLogP3: 6.2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 10
• Exact Mass: 437.2121570
• Heavy Atom Count: 31
• Complexity: 490

Purity/Quality:

98%,99%, ^*data from raw suppliers

Triparanol ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 22-41
• Safety Statements: 26-39

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CCN(CC)CCOC1=CC=C(C=C1)C(CC2=CC=C(C=C2)Cl)(C3=CC=C(C=C3)C)O
• Uses: Desmosterol Delta 24 (D24) reductase inhibitor 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.
• Therapeutic Function: Antihyperlipidemic

Technology Process of TRIPARANOL

There total 3 articles about TRIPARANOL which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 87.0%

4'-<2-Diaethylamino-aethoxy>-4-methyl-benzophenon (90-95-9) + 4-chlorobenzylmagnesium chloride (874-72-6) → triparanol (78-41-1)

Guidance literature:

In tetrahydrofuran; at 25 ℃; for 1h; Inert atmosphere; Schlenk technique;

DOI:10.1002/anie.201712618

Reference yield:

(4-(dimethylamino)phenyl)(p-tolyl)methanone (68587-15-5) → triparanol (78-41-1)

Guidance literature:

Multi-step reaction with 3 steps

1.1: dichloromethane / 25 °C / Inert atmosphere; Schlenk technique

2.1: potassium tert-butylate / N,N-dimethyl-formamide / 0.17 h / 25 °C / Schlenk technique; Inert atmosphere

2.2: 3 h / 25 °C / Inert atmosphere; Schlenk technique

3.1: tetrahydrofuran / 1 h / 25 °C / Inert atmosphere; Schlenk technique

With potassium tert-butylate; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1002/anie.201712618

Reference yield:

→ triparanol (78-41-1)

Guidance literature:

p-Diaethylaminoaethoxy-p'-methylbenzophenon 1.Na/ NH3(fl.) 2.p-Chlorbenzylchlorid/ Et2O;

upstream raw materials:

(4-(dimethylamino)phenyl)(p-tolyl)methanone

4'-<2-Diaethylamino-aethoxy>-4-methyl-benzophenon

4-chlorobenzylmagnesium chloride

Refernces