7149-82-8

Usage

InChI:InChI=1/C11H16O3/c1-2-9-5-3-4-6-11(9)14-8-10(13)7-12/h3-6,10,12-13H,2,7-8H2,1H3

Upstream product

• 90-00-6 o-Hydroxyethylbenzene 
• 96-24-2 3-monochloro-1,2-propanediol 

Downstream Products

• 174689-39-5 SR 59483A 
• 174689-39-5 3-(2-ethylphenoxy)-1[(1R)-1,2,3,4-tetrahydronaphth-1-ylamino]-(2S)-2-propanol hydrogen oxalate 
• 174689-39-5 (S)-1-(2-Ethyl-phenoxy)-3-[(S)-(1,2,3,4-tetrahydro-naphthalen-1-yl)amino]-propan-2-ol; compound with oxalic acid 
• 174689-39-5 SR 59231A 
• 1616790-43-2 1-(2′-ethylphenoxy)-2,3-epoxy-propane 
• 15620-78-7 (R,S)-1-(2′-ethylphenoxy)-2,3-epoxy-propane 
• 1430052-95-1 1-(2′-ethylphenoxy)-2,3-epoxy-propane 
• 1092799-94-4 (R)-3-(2'-ethylphenoxy)-propane-1,2-diol 
• 1092799-92-2 (S)-3-(2'-ethylphenoxy)-propane-1,2-diol 

Relevant academic research and scientific papers

Synthesis of all of the stereoisomers of β3-adrenoceptor antagonist SR 59230 based on the spontaneous resolution of 3-(2-ethylphenoxy)propane-1,2-diol

Racemic 3-(2-ethylphenoxy)propane-1,2-diol 2 has been effectively resolved into (S)- and (R)-enantiomers by a preferential crystallization procedure. Non-racemic diols 2, obtained via a Mitsunobu reaction, have been converted into the non-racemic 1,2-epox

Three different types of chirality-driven crystallization within the series of uniformly substituted phenyl glycerol ethers

Seven chiral arylglycerol ethers 2-R-C6H4-O-CH2CH(OH)CH2OH (R 5 H, Me, Et, Allyl, n-Pr, i-Pr, tert-Bu) were synthesized in racemic and scalemic form. The IR spectra, melting points, and enthalpies of fusion for racemic and scalemic samples of every species were measured, the entropies of enantiomers mixing in the liquid state and Gibbs free energies of a racemic compound formation were derived and binary phase diagrams were reconstructed for the whole family. Solid racemic compounds stabilities were ranked for the four substances. Spontaneous resolution was established for the registered chiral drug mephenesin and its ethyl analogue. Metastable anomalous conglomerate, forming crystals having three independent R and one independent S molecules in the unit cell, is formed during solution crystallization of tert-butyl derivative; metastable phase transforms slowly into traditional racemic conglomerate. Chirality 20:1092-1103, 2008.

Guaifenesin derivatives promote neurite outgrowth and protect diabetic mice from neuropathy

In diabetic patients, an early index of peripheral neuropathy is the slowing of conduction velocity in large myelinated neurons and a lack of understanding of the basic pathogenic mechanisms hindered therapeutics development. Racemic (R/S)-guaifenesin (1) was identified as a potent enhancer of neurite outgrowth using an in vitro screen. Its R-enantiomer (R)-1 carried the most biological activity, whereas the S-enantiomer (S)-1 was inactive. Focused structural variations to (R/S)-1 was conducted to identify potentially essential groups for the neurite outgrowth activity. In vivo therapeutic studies indicated that both (R/S)-1 and (R)-1 partially prevented motor nerve conduction velocity slowing in a mouse model of type 1 diabetes. In vitro microsomal assays suggested that compounds (R)-1 and (S)-1 are not metabolized rapidly, and PAMPA assay indicated moderate permeability through the membrane. Findings revealed here could lead to the development of novel drugs for diabetic neuropathy.