R-(+)-Etomoxir

Base Information

• Chemical Name: R-(+)-Etomoxir
• CAS No.: 124083-20-1
• Molecular Formula: C17H23 Cl O4
• Molecular Weight: 326.82
• European Community (EC) Number: 602-976-9
• UNII: MSB3DD2XP6
• DSSTox Substance ID: DTXSID801025772
• Nikkaji Number: J425.307H
• Wikipedia: Etomoxir
• Wikidata: Q27077245
• NCI Thesaurus Code: C81111
• ChEMBL ID: CHEMBL2051959
• Mol file: 124083-20-1.mol

Synonyms:ethyl 2-(6-(4-chlorophenoxy)hexyl)oxirane-2-carboxylate;etomoxir

Chemical Property of R-(+)-Etomoxir

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 32-34°C
• Boiling Point: 405°Cat760mmHg
• Flash Point: 142.6°C
• PSA: 48.06000
• Density: 1.163g/cm³
• LogP: 4.00140
• Storage Temp.: Refrigerator
• Solubility.: ≥32.7 mg/mL in DMSO; ≥109.6 mg/mL in EtOH; ≥48.3 mg/mL in H2O with gentle warming
• XLogP3: 4.3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 11
• Exact Mass: 326.1284869
• Heavy Atom Count: 22
• Complexity: 342

Purity/Quality:

97% ^*data from raw suppliers

R-(+)-Etomoxir ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOC(=O)C1(CO1)CCCCCCOC2=CC=C(C=C2)Cl
• Isomeric SMILES: CCOC(=O)[C@]1(CO1)CCCCCCOC2=CC=C(C=C2)Cl
• Description: Etomoxir, or 2[6(4-chlorophenoxy)hexyl]oxirane-2-carboxylate, is an irreversible inhibitor of carnitine palmitoyltransferase-1 (CPT-1) on the outer face of the inner mitochondrial membrane.This prevents the formation of acyl carnitines, a step that is necessary for the transport of fatty acyl chains from the cytosol into the intermembrane space of the mitochondria. This step is essential to the production of ATP from fatty acid oxidation. Etomoxir has also been identified as a direct agonist of PPARα. An off-target effect has been demonstrated at high concentrations of etomoxir on Coenzyme-A (CoA) metabolism.
• Uses: An inhibitor of carnitine palmitoyltransferase A (CPT1), which is required for the oexidation of long-chain acyl CoA esters. A strong inhibitor of mitochondrial CPT1 and is a candidate as an anti-diabetic drug

Technology Process of R-(+)-Etomoxir

There total 22 articles about R-(+)-Etomoxir 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: 94.0%

4-chloro-phenol (106-48-9,82344-39-6) + (R)-2-(6-Hydroxy-hexyl)-oxirane-2-carboxylic acid ethyl ester (191412-56-3) → (R)-(+)-etomoxir (124083-20-1,828934-40-3)

Guidance literature:

With triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; for 2h; Ambient temperature;

DOI:10.1016/S0957-4166(97)00105-5

Reference yield:

ethyl 2-[6-(p-chlorophenoxy)hexyl]acrylate (82258-37-5) → (R)-(+)-etomoxir (124083-20-1,828934-40-3)

Guidance literature:

Multi-step reaction with 4 steps

1: 96 percent / NMO; water; OsO₄ / toluene; 2-methyl-propan-2-ol / 1 h / 20 °C

2: 44 percent / Amano AK / various solvent(s) / 2 h / 20 °C / Enzymatic reaction

3: triethylamine / tetrahydrofuran / 0.5 h / 0 °C

4: potassium carbonate / ethanol / 6 h / 20 °C

With osmium(VIII) oxide; N-methyl-2-indolinone; Amano AK; water; potassium carbonate; triethylamine; In tetrahydrofuran; ethanol; toluene; tert-butyl alcohol; 1: dihydroxylation / 2: kinetic resolution / 3: mesylation / 4: Cyclization;

DOI:10.1016/S0957-4166(00)00304-9

Reference yield:

8-(4-Chloro-phenoxy)-2-methylene-octanoyl chloride (124083-16-5) → (R)-(+)-etomoxir (124083-20-1,828934-40-3)

Guidance literature:

Multi-step reaction with 3 steps

1: 60 percent / NaBH₄-silica / diethyl ether / 18 h / Ambient temperature

2: 49 percent / t-butylhydroperoxide, titanium isopropoxide, diethyl L-(+)-tartrate / -20 deg C, 3 h. then room temp., 1 h.

3: 1.) NaIO₄; 2.) NaHCO₃ / 1.) RuCl₃ / 1.) CCl₄, CH₃CN, H₂O, room temp., 7 h.; 2.) DMF, room temp.

With titanium(IV) isopropylate; tert.-butylhydroperoxide; sodium tetrahydroborate; sodium periodate; diethyl (2R,3R)-tartrate; silica gel; sodium hydrogencarbonate; ruthenium trichloride; In diethyl ether;

DOI:10.1016/S0040-4039(01)80643-2

upstream raw materials:

diethyl sulfate

{(S)-2-[6-(4-Chloro-phenoxy)-hexyl]-oxiranyl}-methanol

4-chloro-phenol

(R)-2-(6-Hydroxy-hexyl)-oxirane-2-carboxylic acid ethyl ester

Downstream raw materials:

etomoxir