61248-76-8

Basic information

• Product Name: (S)-Guaifenesin
• Synonyms: (S)-3-(2-Methoxyphenoxy)-1,2-propanediol;(S)-Guaifenesin;1,2-Propanediol, 3-(2-methoxyphenoxy)-, (2S)-;1,2-Propanediol, 3-(2-methoxyphenoxy)-, (S)-
• CAS NO: 61248-76-8
• Molecular Formula: C₁₀H₁₄O₄
• Molecular Weight: 198.22
• Mol File: 61248-76-8.mol
• Article Data: 22

Chemical Properties

• Appearance: /
• CAS DataBase Reference: (S)-Guaifenesin(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-Guaifenesin(61248-76-8)
• EPA Substance Registry System: (S)-Guaifenesin(61248-76-8)

Safety Data

• Hazardous Substances Data: 61248-76-8(Hazardous Substances Data)

Usage

General Description

(S)-Guaifenesin is a medication commonly used as an expectorant to help loosen and thin mucus in the airways, making it easier to cough up. It works by increasing the volume and reducing the viscosity of respiratory tract secretions, thereby promoting the removal of mucus from the lungs. Guaifenesin is often used to relieve symptoms of respiratory conditions such as bronchitis, pneumonia, and other coughs associated with the common cold. It is available in various forms, including tablets, liquids, and dissolving powders, and is generally well-tolerated with minimal side effects when taken as directed.

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 
• 60456-23-7 (S)-oxiranemethanol 
• 2210-74-4 2-(2-methoxy-phenoxymethyl)-oxirane 
• 136167-44-7 3-(2-methoxyphenoxy)propan-1-ol 
• 680185-89-1 3-(2-methoxyphenoxy)propanal 
• 93-14-1 guaifenesin 
• 60827-45-4 (S)-3-chloropropan-1,2-diol 
• 206259-32-7 (4R,5R)-2-chloro-N,N,N',N'-tetramethyl-1,3,2-dioxaphospholane-4,5-dicarboxamide 
• 556-52-5 oxiranyl-methanol 
• 108-24-7 acetic anhydride 
• 96-24-2 3-monochloro-1,2-propanediol 
• 333381-39-8 1-O-acetyl-3-(2-methoxyphenoxy)propane-1,2-diol 

Downstream Products

• 128707-43-7 (R)-(+)-Methylsulfamic acid 3-(2-methoxyphenoxy)-2-[[(methylamino)sulfonyl]-oxy]propyl ester 
• 77164-20-6 (2S)-1-(isopropylamino)-3-(2-methoxyphenoxy)propan-2-ol 
• 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 
• 136166-42-2 (R)-(+)-Sulfamic acid 2-[(aminosulfonyl)oxy]-3-(2-methoxyphenoxy)-propyl ester 
• 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 
• 719276-44-5 (R)-4-(2-Methoxy-phenoxymethyl)-[1,3,2]dioxathiolane 2-oxide 

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

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.