57128-28-6

Basic information

• Product Name: propanoic acid, 2-(1-naphthalenyloxy)-, (2S)-
• Synonyms: (2S)-2-(1-Naphthyloxy)propanoic acid
• CAS NO: 57128-28-6
• Molecular Formula: C₁₃H₁₂O₃
• Molecular Weight: 216.2326
• Mol File: 57128-28-6.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 389.659°C at 760 mmHg
• Flash Point: 152.087°C
• Density: 1.232g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.619
• CAS DataBase Reference: propanoic acid, 2-(1-naphthalenyloxy)-, (2S)-(CAS DataBase Reference)
• NIST Chemistry Reference: propanoic acid, 2-(1-naphthalenyloxy)-, (2S)-(57128-28-6)
• EPA Substance Registry System: propanoic acid, 2-(1-naphthalenyloxy)-, (2S)-(57128-28-6)

Safety Data

• Hazardous Substances Data: 57128-28-6(Hazardous Substances Data)

Upstream product

• 57057-81-5 (S)-(+)-ethyl 2-(naphthalen-1-yloxy)propionate 
• 13949-67-2 2-Methyl-2-α-naphthylacetic acid 
• 90-15-3 α-naphthol 
• 33798-78-6 2-(naphthalene-1-yloxy)propionic acid ethyl ester 
• 2007-13-8 (RS)-2-(1-naphthyloxy)propionyl chloride 
• 62784-66-1 bis(1-naphthyl)methanol 

Downstream Products

• 120680-74-2 2-[(S)-2-(Naphthalen-1-yloxy)-propionylamino]-3-phenyl-propionic acid 

Relevant articles and documents

HPLC separation of 2-aryloxycarboxylic acid enantiomers on chiral stationary phases

The possibility for separating enantiomers of a number of practically significant 2-aryloxycarboxylic acids was studied by normal- and reversed-phase HPLC on popular chiral stationary phases. The best separation parameters were achieved on the chiral phases with the polysaccharide base Chiralcel OD-H and Chiralpack AD under the normal-phase HPLC conditions. The (S)- and (R)-enantiomers of 2-(1-naphthyloxy)- and 2-(2-iodophenoxy)propionic acids with enantiomeric excess ee >99% were isolated using preparative chiral HPLC.

Synthesis of Naphthyl-, Quinolin- and Anthracenyl Analogues of Clofibric Acid as PPARα Agonists

PPARα is a ligand activated transcription factor belonging to the nuclear receptor subfamily, involved in fatty acid metabolism in tissues with high oxidative rates such as muscle, heart and liver. PPARα activation is important in steatosis, inflammation and fibrosis in preclinical models of non-alcoholic fatty liver disease identifying a new potential therapeutic area. In this work, three series of clofibric acid analogues conjugated with naphthyl, quinolin, chloroquinolin and anthracenyl scaffolds were synthesized. In an effort to obtain new compounds active as PPARα agonists, these molecules were evaluated for PPARα transactivation activity. Naphthyl and quinolin derivatives showed a good activation of PPARα; noteworthy, optically active naphthyl derivatives activated PPARα better than corresponding parent compound.

Substitution of 2-(Sulfonyloxy)carboxylates with Oxygene and Sulfur Nucleophiles without Racemization

The ethyl 2-(sulfonyloxy)propionates (S)-1a-c react with phenolates formed from 2 and with carboxylates 8 to give the respective 2-(aryloxy)- (R)-3 and 2-(acyloxy)propionates (R)-9 with inversion of configuration.Due to the high leaving tendency of the triflate group, (S)-1a generally give higher yields of substitution products under milder conditions than the corresponding mesylate (S)-1b and tosylate (S)-1c.In the case of the reaction of malic and succinic acid derivatives only the triflate (S)-10a is converted to the acyloxy compounds (R)-12 with carboxylates 8 atlow temperature (-45 deg C); with the mesylates 10b and the bromide 10d only elimination is observed.Mercaptides and thiophenolates formed from 17 react with (S)-1a-c analogously.With potassium thiocyanate 1a,b react almost exclusively to give the thiocyanate 19; only traces of the corresponding isothiocyanate 20 are obtained.