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Usage

Uses

Used in Pharmaceutical Industry:
(S)-Guaifenesin is used as an expectorant for the purpose of treating respiratory conditions. It is particularly effective in loosening and thinning mucus in the airways, which helps in the relief of symptoms associated with conditions such as bronchitis, pneumonia, and common cold-induced coughs.
The versatility of (S)-Guaifenesin is evident in its availability in various forms, including tablets, liquids, and dissolving powders. It is generally well-tolerated and has minimal side effects when used as directed, making it a popular choice for managing respiratory symptoms.

Upstream product

• 4125-43-3 O-allyl guaiacol 
• 92865-65-1 1,2-di-O-acetyl-3-(2-methoxyphenoxy)propane-1,2-diol 
• 333381-39-8 1-O-acetyl-3-(2-methoxyphenoxy)propane-1,2-diol 
• 556-52-5 oxiranyl-methanol 
• 90-05-1 2-methoxy-phenol 
• 2210-74-4 2-(2-methoxy-phenoxymethyl)-oxirane 
• 206259-32-7 (4R,5R)-2-chloro-N,N,N',N'-tetramethyl-1,3,2-dioxaphospholane-4,5-dicarboxamide 
• 93-14-1 guaifenesin 
• 60456-23-7 (S)-oxiranemethanol 
• 680185-89-1 3-(2-methoxyphenoxy)propanal 
• 136167-44-7 3-(2-methoxyphenoxy)propan-1-ol 
• 60827-45-4 (S)-3-chloropropan-1,2-diol 
• 150-76-5 4-methoxy-phenol 
• 108-24-7 acetic anhydride 

Downstream Products

• 719276-44-5 (R)-4-(2-Methoxy-phenoxymethyl)-[1,3,2]dioxathiolane 2-oxide 
• 77164-20-6 (2S)-1-(isopropylamino)-3-(2-methoxyphenoxy)propan-2-ol 
• 136166-42-2 (R)-(+)-Sulfamic acid 2-[(aminosulfonyl)oxy]-3-(2-methoxyphenoxy)-propyl ester 
• 1210796-90-9 (R)-1,2-dipalmitoyloxy-3-(2-methoxyphenoxy)propane 
• 108914-10-9 (R)-1-carbamoyloxy-2-hydroxy-3-(2-methoxyphenoxy)propane 
• 1334739-69-3 (S)-4-(2-methoxyphenoxy)methyl-3,6-dioxa-1,8-octanediol 
• 1334739-75-1 (S)-12-[(2-methoxyphenoxy)methyl]-2,3-naphtho-18-crown-6 
• 1334739-72-8 (S)-[(2-methoxyphenoxy)methyl]-15-crown-5 
• 61248-99-5 (S)-1,2-epoxy-3-(2-methoxyphenyloxy)-propane 
• 850427-92-8 (R)-4-(2-Methoxy-phenoxymethyl)-[1,3,2]dioxathiolane 2,2-dioxide 
• 128707-43-7 (R)-(+)-Methylsulfamic acid 3-(2-methoxyphenoxy)-2-[[(methylamino)sulfonyl]-oxy]propyl ester 

Relevant academic research and scientific papers

Resolution of Racemic Guaifenesin Applying a Coupled Preferential Crystallization-Selective Dissolution Process: Rational Process Development

Preferential crystallization is a cost efficient method to provide pure enantiomers from a racemic mixture of a conglomerate forming system. Exploiting small amounts of pure crystals of both enantiomers, several batch or continuous processes were develope

Chemoenzymatic Route for the Synthesis of (S)-Moprolol, a Potential β-Blocker

A biocatalytic route for the synthesis of a potential β-blocker, (S)-moprolol is reported here. Enantiopure synthesis of moprolol is mainly dependent on the chiral intermediate, 3-(2-methoxyphenoxy)-propane-1,2-diol. Various commercial lipases were screened for the enantioselective resolution of (RS)-3-(2-methoxyphenoxy)propane-1,2-diol to produce the desired enantiomer. Among them, Aspergillus Niger lipase (ANL) was selected on the basis of both stereo- and regioselectivity. The optimized values of various reaction parameters were determined such as enzyme (15 mg/mL), substrate concentration (10 mM), organic solvent (toluene), reaction temperature (30 °C), and time (18 h).The optimized conditions led to achieving >49% yield with high enantiomeric excess of (S)-3-(2-methoxyphenoxy)propane-1,2-diol. The lipase-mediated catalysis showed regioselective acylation with dual stereoselectivity. Further, the enantiopure intermediate was used for the synthesis of (S)-moprolol, which afforded the desired β-blocker. Chirality 28:313-318, 2016.

A smart library of epoxide hydrolase variants and the top hits for synthesis of (S)-β-blocker precursors

Microtuning of the enzyme active pocket has led to a smart library of epoxide hydrolase variants with an expanded substrate spectrum covering a series of typical β-blocker precursors. Improved activities of 6- to 430-fold were achieved by redesigning the active site at two predicted hot spots. This study represents a breakthrough in protein engineering of epoxide hydrolases and resulted in enhanced activity toward bulky substrates. Hot pockets: Microtuning of the enzyme active pocket gives a smart library of epoxide hydrolase variants with an expanded substrate spectrum covering a series of typical β-blocker precursors. Improved activities of 6- to 430-fold were achieved by redesigning the active site at two predicted hot spots, and enhanced activity toward bulky substrates was found.

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.

Crystallographic evidence of side-arm lariat effect in the series of chiral ortho- and para-methoxyphenoxymethyl-15-crown-5 complexes with sodium perchlorate

The single crystals of the NaClO4 complexes with two potential lariat 15-crowns-5 having ortho- or para-methoxyphenoxymethyl side arms were investigated by X-ray analysis in racemic and enantiopure form. Only ortho-derivative demonstrates laria

Synthesis and extraction properties of some lariat ethers derived from the spontaneously resolved guaifenesin, 3-(2-methoxyphenoxy)propane-1,2-diol

Capable of spontaneous resolution rac-3-(2-methoxyphenoxy)propane-1,2-diol, guaifenesin 1 has been proposed as a cheap and readily available enantiopure precursor for the synthesis of nonracemic crown ethers having ligating OAr and OMe arms (lariat ethers). The crowns studied failed to form stable host/guest complexes with amine hydrochloride salts; the effective complexation was achieved using hexafluorophosphate salts. Moderate enantiomeric recognition of R*NH2·HPF6 was achieved with the lariat ethers 11c. As a whole, the enantioselectivity of the extraction is inversely related to the extractive power of the lariat ether. ARKAT-USA, Inc.

Exploration of l-proline-catalyzed α-aminoxylation of aldehyde to (s)-guaifenesin-related drug molecules

An efficient enantioselective synthesis of (S)-guaifenesin with >99% ee using L-proline-catalyzed α-aminoxylation of aldehyde as key step is described and explored for asymmetric syntheses of (S)-moprolol and (R)-methocarbamol.

Bacillus alcalophilus MTCC10234 catalyzed enantioselective kinetic resolution of aryl glycidyl ethers

The phenyl glycidyl ether derivatives have been kinetically resolved with the growing cells of Bacillus alcalophilus MTCC10234 yielding (S)-epoxides with up to >99% ee and (R)-diols with up to 89% ee. The enantiomeric ratio (E) of up to 67 has been obtained for biohydrolysis process. The effect of different substituents of phenyl glycidyl ether on the biocatalytic efficiency of B. alcalophilus MTCC10234 showed preference for methyl- and chloro-substituted aryl glycidyl ether derivatives whereas nitro-derivatives were transformed at a slower rate. 2,6-Dimethylphenyl glycidyl ether which contains a bulky aryl group having methyl group on both the ortho positions was resolved with an E=39.

4(2)-Methoxyphenyl glycerol ethers in the synthesis of nonracemic di-O,O-acylglycerols

Effective methods for the synthesis of nonracemic 4-and 2-methoxyphenyl glycerol ethers from nonracemic 3-chloropropanediols and by direct resolution of the racemate, respectively, were developed. Some existing discrepancies related to the to chiroptical properties of their derivatives were eliminated. Both ethers were used to synthesize nonracemic 3-O-aryloxy-1,2-di-O',O'-palmitoyl glycerols.

Spontaneous resolution among chiral glycerol derivatives: crystallization features of ortho-alkoxysubstituted phenyl glycerol ethers

Five chiral arylglycerol ethers 2-R-C6H4-O-CH2CH(OH)CH2OH (R = OMe, OEt, OPrn, OPri, OBut) have been prepared in racemic and enantiopure form. The melting points and enthalpies of fusion of every species were measured by differential scanning calorimetry. Binary phase diagrams were reconstructed for the whole family, the entropies of the mixing of the enantiomers in the liquid state, and Gibbs free energy of formation of the racemic compound, as well as Pettersson i-values were derived from the thermal data. The differences in the phase behavior of the investigated compounds were associated with the conformations of the alkoxy fragments.