Guaifenesin

Base Information

• Chemical Name: Guaifenesin
• CAS No.: 93-14-1
• Deprecated CAS: 12041-73-5,128707-44-8,1336-67-0,128707-44-8
• Molecular Formula: C10H14O4
• Molecular Weight: 198.219
• Hs Code.: 29093090
• European Community (EC) Number: 202-222-5
• NSC Number: 757052,62112
• UNII: 495W7451VQ
• DSSTox Substance ID: DTXSID5023114
• Nikkaji Number: J3.936E
• Wikipedia: Guaifenesin
• Wikidata: Q420682
• NCI Thesaurus Code: C29081
• RXCUI: 5032
• Metabolomics Workbench ID: 38691
• ChEMBL ID: CHEMBL980
• Mol file: 93-14-1.mol

Synonyms:Breonesin;Ether, Guaiacol Glyceryl;Glycerol Guaiacolate;Glyceryl Ether, Guaiacol;Guaiacol Glyceryl Ether;Guaiacolate, Glycerol;Guaifenesin;Guaiphenesin;Guaiphenezine;Guiatuss;Humibid;Hytuss;My 301;My-301;My301;Scott Tussin;Scott-Tussin;ScottTussin

Chemical Property of Guaifenesin

Chemical Property:

• Appearance/Colour: White Solid
• Vapor Pressure: 1.04E-05mmHg at 25°C
• Melting Point: 77-81 °C
• Refractive Index: 1.538
• Boiling Point: 356.8 °C at 760 mmHg
• PKA: 13.53±0.20(Predicted)
• Flash Point: 169.6 °C
• PSA: 58.92000
• Density: 1.195 g/cm³
• LogP: 0.42720
• Storage Temp.: Refrigerator
• Solubility.: 50g/l (experimental)
• Water Solubility.: 5 g/100 mL (25 ºC)
• XLogP3: 1.4
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 5
• Exact Mass: 198.08920892
• Heavy Atom Count: 14
• Complexity: 151

Purity/Quality:

≥99.0% ^*data from raw suppliers

rac Guaifenesin ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 22-36/37/38
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: COC1=CC=CC=C1OCC(CO)O
• Recent ClinicalTrials: Preventing Frequent Sinus Infections in HIV-Infected Patients
• Description: Guaifenesin is an oral expectorant drug. The expectorant action of guaifenesin is mediated by stimulation of the gastrointestinal tract. It is a common ingredient in prescription and over-the-counter medications used to treat cough due to colds and minor upper respiratory infections. Guaifenesin was originally derived from the guaiac tree and used by Native Americans for health purposes. Synthesis of guaifenesin was first reported in 1912. Guaifenesin has been used in the treatment of respiratory diseases since the nineteenth century. The United States’ Food and Drug Administration (FDA) approved guaifenesin for use in overthe- counter medications in 1989. Guaifenesin is widely consumed alone and combined with antihistamines, cough suppressants, and decongestants. Guaifenesin is also a centrally acting muscle relaxant and is used routinely in combination with analgesics and sedatives in large-animal veterinary surgery.
• Uses: Centrally acting muscle relaxant with expectorant properties Used to assist the expectoration of phlegm from the airways in acute respiratory tract infections. Guaifenesin is commonly used as an expectorant. Guaifenesin comes in tablet and capsule form, as syrup, as dissolving granules, and recently as an extended-release (longacting) tablet. The tablets, capsules, dissolving granules, and syrup are usually taken with or without food every 4 h as needed. The extended-release tablet is usually taken with or without food every 12 h. In veterinary medicine, guaifenesin is given intravenously to induce muscle relaxation when administering anesthesia. It relaxes both laryngeal and pharyngeal muscles, allowing easier intubation. Guaifenesin is also used in the treatment of horses with exertional rhabdomyolysis and in dogs with strychnine intoxication.

Technology Process of Guaifenesin

There total 22 articles about Guaifenesin which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 98.0%

4-iodoanisol (529-28-2) + glycerol (56-81-5,25618-55-7,64333-26-2,8013-25-0) → guaifenesin (93-14-1)

Guidance literature:

With copper(l) iodide; potassium carbonate; at 80 ℃; for 6h;

DOI:10.1002/cssc.202102211

Reference yield: 95.0%

oxiranyl-methanol (556-52-5) + 2-methoxy-phenol (90-05-1) → 2-(2-methoxyphenoxy)-1,3-propanediol (14007-09-1) + guaifenesin (93-14-1)

Guidance literature:

With calcined hydrotalcite; In tetrahydrofuran; at 120 ℃; for 4h; Reagent/catalyst; Temperature; Kinetics; Autoclave;

DOI:10.1016/j.cattod.2016.12.008

Reference yield: 90.0%

oxiranyl-methanol (556-52-5) + 2-methoxy-phenol (90-05-1) → guaifenesin (93-14-1)

Guidance literature:

With potassium carbonate; In acetonitrile; at 65 - 70 ℃; for 12h;

DOI:10.1002/chir.22574

upstream raw materials:

2-methoxy-phenol

3-monochloro-1,2-propanediol

sodium 2-methoxyphenolate

methocarbamol

Downstream raw materials:

1,2-di-O-acetyl-3-(2-methoxyphenoxy)propane-1,2-diol

Acetic acid (R)-2-hydroxy-3-(2-methoxy-phenoxy)-propyl ester

Acetic acid (S)-2-hydroxy-3-(2-methoxy-phenoxy)-propyl ester

(R)-3-(2-methoxyphenoxy)propane-1,2-diyl diacetate

Refernces

• 1、 Thawabteh, Amin,Lelario, Filomena,Scrano, Laura,Bufo, Sabino A.,Nowak, Stefanie,Behrens, Maik,Di Pizio, Antonella,Niv, Masha Y.,Karaman, Rafik. "Bitterless guaifenesin prodrugs—design, synthesis, characterization, in vitro kinetics, and bitterness studies". . p. 262 - 271. Retrieved 2019.
• 2、 Kao, Shih-Chieh,Lin, Yi-Ching,Ryu, Ilhyong,Wu, Yen-Ku. "Revisiting Hydroxyalkylation of Phenols with Cyclic Carbonates". supporting information. p. 3639 - 3644. Retrieved 2019/07/10.