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

Description

(S)-Guaifenesin is a medication that functions as an expectorant, designed to facilitate the loosening and thinning of mucus in the airways. This process makes it easier for individuals to cough up the mucus. The mechanism of action involves increasing the volume and reducing the viscosity of respiratory tract secretions, thus aiding in the removal of mucus from the lungs.

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 
• 108-24-7 acetic anhydride 
• 90-05-1 2-methoxy-phenol 
• 96-24-2 3-monochloro-1,2-propanediol 
• 556-52-5 oxiranyl-methanol 
• 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 
• 60827-45-4 (S)-3-chloropropan-1,2-diol 
• 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 

Downstream Products

• 128707-43-7 (R)-(+)-Methylsulfamic acid 3-(2-methoxyphenoxy)-2-[[(methylamino)sulfonyl]-oxy]propyl ester 
• 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 
• 850427-92-8 (R)-4-(2-Methoxy-phenoxymethyl)-[1,3,2]dioxathiolane 2,2-dioxide 
• 61248-99-5 (S)-1,2-epoxy-3-(2-methoxyphenyloxy)-propane 
• 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 
• 1334739-72-8 (S)-[(2-methoxyphenoxy)methyl]-15-crown-5 
• 1334739-75-1 (S)-12-[(2-methoxyphenoxy)methyl]-2,3-naphtho-18-crown-6 
• 1334739-69-3 (S)-4-(2-methoxyphenoxy)methyl-3,6-dioxa-1,8-octanediol 

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.