124083-20-1

Basic information

• Product Name: R-(+)-ETOMOXIR
• Synonyms: S-(+)-ETOMOXIR;(S)-2-[6-(4-CHLOROPHENOXY)HEXYL]OXIRANECARBOXYLIC ACID, ETHYL ESTER;R-(+)-ETOMOXIR;(R)-2-[6-(4-CHLOROPHENOXY)HEXYL]OXIRANECARBOXYLIC ACID, ETHYL ESTER;2-Oxiranecarboxylic acid, 2-[6-(4-chlorophenoxy)hexyl]-, ethyl ester, (2R)-(R)-(+)-Etomoxir;(R)-2-[6-(4-Chlorophenoxy)hexyl]oxirane-2-carboxylic acid ethyl ester;2-Oxiranecarboxylic acid, 2-[6-(4-chlorophenoxy)hexyl]-, ethyl ester, (2R)-;(2S)-2-[6-(4-chlorophenoxy)hexyl]oxirane-2-carboxylic acid ethyl ester
• CAS NO: 124083-20-1
• Molecular Formula: C₁₇H₂₃ClO₄
• Molecular Weight: 326.82
• EINECS: 200-258-5
• Product Categories: Chiral Reagents;Inhibitors
• Mol File: 124083-20-1.mol
• Article Data: 4

Chemical Properties

• Melting Point: 32-34°C
• Boiling Point: 405°Cat760mmHg
• Flash Point: 142.6°C
• Appearance: /
• Density: 1.163
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.52
• 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
• CAS DataBase Reference: R-(+)-ETOMOXIR(CAS DataBase Reference)
• NIST Chemistry Reference: R-(+)-ETOMOXIR(124083-20-1)
• EPA Substance Registry System: R-(+)-ETOMOXIR(124083-20-1)

Safety Data

• Hazardous Substances Data: 124083-20-1(Hazardous Substances Data)

Usage

Description

R-(+)-Etomoxir, also known as 2[6(4-chlorophenoxy)hexyl]oxirane-2-carboxylate, is a chiral compound and the active enantiomer of Etomoxir. It 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. R-(+)-Etomoxir has also been identified as a direct agonist of PPARα. It is a colorless oil with unique chemical properties and potential applications in various fields.

Uses

Used in Pharmaceutical Industry:
R-(+)-Etomoxir is used as an anti-diabetic drug candidate for its ability to inhibit fatty acid oxidation through CPT-1a. This inhibition can help regulate glucose and lipid metabolism, making it a promising candidate for the treatment of diabetes and related metabolic disorders.
Used in Research Applications:
R-(+)-Etomoxir is used as a research tool for studying the role of fatty acid oxidation in various cellular processes and diseases. Its ability to selectively inhibit CPT-1a makes it a valuable compound for investigating the mechanisms and consequences of altered fatty acid metabolism in health and disease.
Used in Drug Development:
R-(+)-Etomoxir is used in the development of new drugs targeting CPT-1a for the treatment of metabolic disorders, including diabetes, obesity, and related conditions. Its chiral nature and specific inhibitory activity make it a useful starting point for designing more potent and selective therapeutic agents.
Used in Metabolic Studies:
R-(+)-Etomoxir is used in metabolic studies to investigate the role of fatty acid oxidation in energy production, cellular respiration, and other physiological processes. Its ability to inhibit CPT-1a provides a means to modulate fatty acid metabolism and assess its impact on overall metabolic function.

Biological Activity

etomoxir is a cell-permeable, irreversible, and stereospecific compound. etomoxir is shown to inhibit carnitine palmitoyltransferase (cpt)-1 and dgat activity in the mitochondria of rat heart h9c2 myoblastic cells at a concentration of 1-80 μm and 40 μm, respectively.

InChI:InChI=1/C17H23ClO4/c1-2-20-16(19)17(13-22-17)11-5-3-4-6-12-21-15-9-7-14(18)8-10-15/h7-10H,2-6,11-13H2,1H3/t17-/m1/s1

Upstream product

• 106-48-9 4-chloro-phenol 
• 191412-56-3 (R)-2-(6-Hydroxy-hexyl)-oxirane-2-carboxylic acid ethyl ester 
• 82258-39-7 6-(4-chlorophenoxy)hexylmalonic acid diethyl ester 
• 124083-17-6 8-(4-Chloro-phenoxy)-2-methylene-octanoic acid 
• 124083-16-5 8-(4-Chloro-phenoxy)-2-methylene-octanoyl chloride 
• 124083-15-4 8-(4-Chloro-phenoxy)-2-methylene-octan-1-ol 
• 191412-50-7 (S)-1-(8-Benzyloxy-2-methylene-octanoyl)-pyrrolidine-2-carboxylic acid ethyl ester 
• 191412-52-9 (3S,8aS)-3-(6-Benzyloxy-hexyl)-3-bromomethyl-tetrahydro-pyrrolo[2,1-c][1,4]oxazine-1,4-dione 
• 191412-51-8 (S)-1-(8-Benzyloxy-2-methylene-octanoyl)-pyrrolidine-2-carboxylic acid 
• 191412-48-3 8-Benzyloxy-2-methylene-octanoic acid ethyl ester 
• 191412-49-4 2-(6-benzyloxy)hexyl-2-en-propionic acid 
• 191412-55-2 (S)-2-Bromomethyl-2,8-dihydroxy-octanoic acid methyl ester 
• 191412-53-0 (S)-2-Bromomethyl-2,8-dihydroxy-octanoic acid 
• 54247-27-7 1-bromo-6-benzyloxyhexane 

Downstream Products

• 124083-14-3 etomoxir 

Relevant articles and documents

A Unified and Desymmetric Approach to Chiral Tertiary Alkyl Halides

Enantioenriched tertiary alkyl halides are prevalent in bioactive molecules and can serve as versatile synthetic intermediates to construct complex structures. While conventional access to these motifs often hinges on stereoselective carbon-halogen or carbon-carbon bond formation reactions, desymmetric approaches using halogenated and prochiral tetrasubstituted carbons are largely elusive in comparison. Here, we report that a suite of dinuclear zinc catalysts with a prolinol- or pipecolinol-derived tetradentate ligand can reductively desymmetrize a large collection of easily available halomalonic esters to α-halo-β-hydroxyesters. These polyfunctionalized tertiary alkyl fluorides, chlorides, and bromides proved to be useful intermediates toward fluorinated drug analogs and polyhalogenated monoterpenes. The facile intramolecular epoxidation of the chiral chloride and bromide products has also enabled expeditious access to natural products containing tertiary alcohol motifs.

Asymmetric synthesis of (R)-(+)-etomoxir

An asymmetric synthesis of etomoxir 1, involving bromolactonization by using (S)-(-)-proline as a chiral auxiliary, is reported.