61248-75-7

Basic information

• Product Name: (R)-Guaifenesin
• Synonyms: (R)-Guaifenesin;1,2-Propanediol, 3-(2-methoxyphenoxy)-, (2R)-;1,2-Propanediol, 3-(2-methoxyphenoxy)-, (R)-
• CAS NO: 61248-75-7
• Molecular Formula: C₁₀H₁₄O₄
• Molecular Weight: 198.22
• Mol File: 61248-75-7.mol
• Article Data: 17

Chemical Properties

• Appearance: /
• CAS DataBase Reference: (R)-Guaifenesin(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-Guaifenesin(61248-75-7)
• EPA Substance Registry System: (R)-Guaifenesin(61248-75-7)

Safety Data

• Hazardous Substances Data: 61248-75-7(Hazardous Substances Data)

Usage

Uses

(R)-Guaifenesin is an isomer of Guaifenesin (G810500); a centrally acting muscle relaxant with expectorant properties.

Upstream product

• 4125-43-3 O-allyl guaiacol 
• 92865-65-1 1,2-di-O-acetyl-3-(2-methoxyphenoxy)propane-1,2-diol 
• 90-05-1 2-methoxy-phenol 
• 57044-25-4 (R)-oxiranemethanol 
• 57090-45-6 (2R)-3-chloro-1,2-propanediol 
• 93-14-1 guaifenesin 
• 92865-65-1 (R)-3-(2-methoxyphenoxy)propane-1,2-diyl diacetate 
• 2210-74-4 2-(2-methoxy-phenoxymethyl)-oxirane 
• 333381-39-8 1-O-acetyl-3-(2-methoxyphenoxy)propane-1,2-diol 
• 61267-51-4 (S)-4-(2-methoxy-phenoxymethyl)-2,2-dimethyl-[1,3]dioxolane 

Downstream Products

• 1334739-76-2 (R)-12-[(2-methoxyphenoxy)methyl]-2,3-naphtho-18-crown-6 
• 1334739-71-7 (R)-[(2-methoxyphenoxy)methyl]-12-crown-4 
• 1334739-70-6 (R)-4-(2-methoxyphenoxy)methyl-3,6-dioxa-1,8-octanediol 
• 1334739-74-0 (R)-12-[(2-methoxyphenoxy)methyl]-2,3-benzo-18-crown-6 
• 1334739-73-9 (R)-[(2-methoxyphenoxy)methyl]-15-crown-5 
• 128707-42-6 (S)-(-)-Methylsulfamic acid 3-(2-methoxyphenoxy)-2-[[(methylamino)sulfonyl]-oxy]propyl ester 
• 136199-48-9 (S)-(-)-Sulfamic acid 2-[(aminosulfonyl)oxy]-3-(2-methoxyphenoxy)-propyl ester 

Relevant articles and documents

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.

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.