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Guaifenesin

Guaifenesin Structure
CAS No.
93-14-1
Chemical Name:
Guaifenesin
Synonyms
GLYCERYL GUAIACOLATE;GUAIPHENESIN;3-(2-methoxyphenoxy)propane-1,2-diol;gge;XL-90;Robitussin;RAC GUAIFENESIN;Glyceryl guaiacyl ether;GUAIACOL GLYCEROL ETHER;Glyceryl guaiacolate ether
CBNumber:
CB1743199
Molecular Formula:
C10H14O4
Molecular Weight:
198.22
MOL File:
93-14-1.mol
MSDS File:
SDS
Modify Date:
2024/7/24 17:31:20

Guaifenesin Properties

Melting point 77-81 °C
Boiling point 215 °C (19 mmHg)
Density 1.1825 (rough estimate)
refractive index 1.5550 (estimate)
Flash point 215°C/19mm
storage temp. 2-8°C
solubility 50g/l (experimental)
pka 13.53±0.20(Predicted)
form Solid
color White to Off-White
Water Solubility 5 g/100 mL (25 ºC)
Merck 14,4555
BRN 2049375
InChIKey HSRJKNPTNIJEKV-UHFFFAOYSA-N
LogP 1.390
CAS DataBase Reference 93-14-1(CAS DataBase Reference)
NIST Chemistry Reference 3-(O-methoxyphenoxy)-1,2-propanediol(93-14-1)
EPA Substance Registry System Guaifenesin (93-14-1)

SAFETY

Risk and Safety Statements

Symbol(GHS) 
GHS07
Signal word  Warning
Hazard statements  H302
Precautionary statements  P264-P270-P301+P312-P501
Hazard Codes  Xn
Risk Statements  22-36/37/38
Safety Statements  26-36
WGK Germany  1
RTECS  TY8400000
Hazard Note  Harmful
TSCA  Yes
HS Code  29093090
Toxicity LD50 oral in rabbit: 2553mg/kg
NFPA 704
1
2 0

Guaifenesin price More Price(8)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Sigma-Aldrich(India) G5627 Guaiacol glyceryl ether ≥98% (GC) 93-14-1 25G ₹2478.93 2022-06-14 Buy
Sigma-Aldrich(India) PHR1027 Guaifenesin certified reference material, pharmaceutical secondary standard 93-14-1 1G ₹8356.9 2022-06-14 Buy
Sigma-Aldrich(India) G5627 Guaiacol glyceryl ether ≥98% (GC) 93-14-1 500G ₹14440.55 2022-06-14 Buy
ALFA India ALF-A16827-30 3-(2-Methoxyphenoxy)-1,2-propanediol, 99+% 93-14-1 250g ₹5839 2022-05-26 Buy
TCI Chemicals (India) G0159 Guaiacol Glycerol Ether 93-14-1 25G ₹2000 2022-05-26 Buy
Product number Packaging Price Buy
G5627 25G ₹2478.93 Buy
PHR1027 1G ₹8356.9 Buy
G5627 500G ₹14440.55 Buy
ALF-A16827-30 250g ₹5839 Buy
G0159 25G ₹2000 Buy

Guaifenesin Chemical Properties,Uses,Production

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. Additionally, Guaifenesin is also a centrally-acting muscle relaxant and is used routinely in combination with analgesics and sedatives in large-animal veterinary surgery.

Chemical Properties

This substance is a white crystalline powder with a melting point of 78.5-79°C and a boiling point of 215°C (2.53kPa). It is soluble in 20ml of water and ethanol, chloroform, glycerin, and dimethylformamide. It is easily soluble in benzene but insoluble in petroleum ether. It has a slightly bitter taste and a slightly particular odor.

History

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

Guaifenesin is a muscle relaxant with expectorant properties often used as an expectorant to facilitate the removal of phlegm from the airways in acute respiratory tract infections. 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.

General Description

Guaifenesin is an expectorant, widely used in the treatment of cough. Its mode of action involves the alleviating of cough discomfort by increasing sputum volume and decreasing its viscosity, thus resulting in effective cough.
Pharmaceutical secondary standards for application in quality control, provide pharma laboratories and manufacturers with a convenient and cost-effective alternative to the preparation of in-house working standards.

Mechanism of action

Guaiphenesin facilitates secretion from bronchial mucous membranes, thus relieving a cough in colds, bronchitis, and bronchial asthma.

Environmental Fate

Guaifenesin’s production and use as veterinary and human medicines may result in its release to the environment through various waste streams.
If released to air, an estimated vapor pressure of 1.5× 10–6 mm Hg at 25 ℃ indicates that guaifenesin will exist in both the vapor and particulate phase.
Based upon an estimated Henry’s law constant of 4.4 × 10-11 atm-m3 mol-1, volatilization from moist soil surfaces or from water surfaces are not expected to be important fate processes for guaifenesin.
Guaifenesin is expected to have high mobility in soil based upon an organic carbon–water partition coefficient (Koc) of 140, which indicates that it will have more solubility in water and is less likely to adsorb onto organic matter in soil and plants.

References

[1] Peter V. Dicpinigaitis and Yvonne E. Gayle, Effect of Guaifenesin on Cough Reflex Sensitivity, 2003, vol. 124, 2178-2181 DOI:10.1378/CHEST.124.6.2178
[2] Leonid Kagan, Eran Lavy and Ammon Hoffmann, Effect of mode of administration on guaifenesin pharmacokinetics and expectorant action in the rat model, Pulmonary Pharmacology & Therapeutics, 2009, vol. 22, 260-265 DOI:10.1016/j.pupt.2008.12.020
[3] Sittig's Pharmaceutical Manufacturing Encyclopedia
[4] Synthesis of Essential Drugs (2006, Elsevier)
[5] Plumb's Veterinary Drug Handbook
[6] https://pubchem.ncbi.nlm.nih.gov/compound/Guaifenesin

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1,2-Dihydroxy-3-(2-methoxyphenoxy)propane 1,2-Propanediol, 3-(2-methoxyphenoxy)- 1,2-Propanediol, 3-(o-methoxyphenoxy)- 2/G 2-G 3-(2-Methoxyphenosy)-1,2-propamediol 3-(2-methoxyphenoxy)-2-propanediol 3-(o-methoxyphenoxy)-2-propanediol 3-(o-Methoxyphenoxy)-propanediol-1,2 GUAIFENESIN /( )-3-(O-METHOXYPHENOXY)-1,2-PROPANEDIOL 3-(2-Methoxyphenoxy)-1,2-propanediol, erythro + threo, 99+% 3-o-Methoxyphenoxypropane 1:2-diol 3-o-methoxyphenoxypropane1:2-diol Aeronesin alpha-Glyceryl guaiacol ether alpha-Glyceryl guaiacolate ether alpha-glycerylguaiacolateether alpha-glycerylguaiacolether Aresol Breonesin Bronchol Calmipan component of Brondecon component of Colrex Expectorant component of Hycotuss component of Trind component of Trind-DM Cortussin Creson Dilyn Dorassin Flartussin G 87 g87 Gaiamar Glycerin guaiacolate Glycerin monoguaiacol ether glyceringuaiacolate glycerinmonoguaiacolether glycero-guaiacolether Glycerol alpha-(2-methoxyphenyl) ether Glycerol alpha-(o-methoxyphenyl)ether Glycerol alpha-guaiacyl ether Glycerol alpha-guiacyl ether Glycerol alpha-monoguaiacol ether Glycerol mono(2-methoxyphenyl) ether glycerolalpha-(2-methoxyphenyl)ether glycerolalpha-(o-methoxyphenyl)ether glycerolalpha-guaiacylether glycerol-alpha-guajakolether glycerol-alpha-monoguaiacolether glycerolmono(2-methoxyphenyl)ether Glyceryl guaiacol Glyceryl guaiacol ether Glyceryl guaicolate Glyceryl guiacolate glycerylguaiacol glycerylguaiacolateether