Guaifenesin CAS 93-14-1
Introduction：Basic information about Guaifenesin CAS 93-14-1, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.
Guaifenesin Basic information
| Product Name: | Guaifenesin |
| Synonyms: | 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 |
| CAS: | 93-14-1 |
| MF: | C10H14O4 |
| MW: | 198.22 |
| EINECS: | 202-222-5 |
| Product Categories: | Building Blocks;C10;Chemical Synthesis;Ethers;Organic Building Blocks;Oxygen Compounds;Methocarbamol;API's;Aromatics Compounds;API;MUCINEX;Aromatics;Intermediates & Fine Chemicals;Pharmaceuticals;Benzhydrols, Benzyl & Special Alcohols;93-14-1 |
| Mol File: | 93-14-1.mol |
Guaifenesin Chemical Properties
| Melting point | 77-81 °C |
| Boiling point | 215 °C (19 mmHg) |
| density | 1.1825 (rough estimate) |
| refractive index | 1.5550 (estimate) |
| Fp | 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 |
| InChI | 1S/C10H14O4/c1-13-9-4-2-3-5-10(9)14-7-8(12)6-11/h2-5,8,11-12H,6-7H2,1H3 |
| InChIKey | HSRJKNPTNIJEKV-UHFFFAOYSA-N |
| SMILES | COc1ccccc1OCC(O)CO |
| 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 Information
| Hazard Codes | Xn |
| Risk Statements | 22-36/37/38 |
| Safety Statements | 26-36 |
| WGK Germany | 1 |
| RTECS | TY8400000 |
| Hazard Note | Harmful |
| TSCA | TSCA listed |
| HS Code | 29093090 |
| Storage Class | 11 - Combustible Solids |
| Hazard Classifications | Acute Tox. 4 Oral |
| Hazardous Substances Data | 93-14-1(Hazardous Substances Data) |
| Toxicity | LD50 oral in rabbit: 2553mg/kg |
| 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. |
| Originator | GG Cen,Central,US,1975 |
| 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. |
| Definition | ChEBI: Guaifenesin is a member of methoxybenzenes. |
| Manufacturing Process | A mixture of o-methoxyphenol (57 g), glycidol (32 g) and pyridine (1 g) iswarmed to 95°C at which temperature a vigorous reaction takes place. Thereaction mixture is cooled to prevent the temperature rising above 110°C.When the exothermic reaction has subsided the reactants are heated at 95°Cfor one hour longer and then distilled under low pressure. The main fractionboils in the range 176°C to 180°C/0.5 mm. It crystallizes on cooling.Recrystallization from benzene gives the pure product, MP 78.5°C to 79.0°C. |
| Brand name | Mucinex (Adams). |
| 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 acough in colds, bronchitis, and bronchial asthma. |
| Synthesis | Guaiphenesin, 3-(o-methoxyphenoxy)-1,2-propandiol (23.2.3), is synthesizedby reacting guiacol with 3-chloropropan-1,2-diol or with glycidol. |
| Veterinary Drugs and Treatments | In veterinary medicine, guaifenesin is used to induce muscle relaxationand restraintas an adjunct to anesthesia for short procedures(30 – 60 minutes) in large and small animal species. There are combinationoral products containing guaifenesin for treating respiratoryconditions in horses. In human medicine, guaifenesin has long been touted as an oralexpectorant, but definitive proof of its efficacy is lacking. |
| Environmental Fate | Guaifenesin’s production and use as veterinary and humanmedicines may result in its release to the environment throughvarious waste streams. If released to air, an estimated vapor pressure of1.5× 10–6 mm Hg at 25 ℃ indicates that guaifenesin willexist in both the vapor and particulate phase. Based upon an estimated Henry’s law constant of4.4 × 10-11 atm-m3 mol-1, volatilization from moist soilsurfaces or from water surfaces are not expected to be importantfate processes for guaifenesin. Guaifenesin is expected to have high mobility in soil basedupon an organic carbon–water partition coefficient (Koc) of140, which indicates that it will have more solubility in waterand is less likely to adsorb onto organic matter in soil andplants. |
| Toxicity evaluation | Guaifenesin is an adrenergic antagonist in a class of medicationscalled expectorants. It stimulates afferent receptors in thegastric mucosa, reflexively increasing glandular secretion by therespiratory epithelium promoting lower respiratory tractdrainage by thinning bronchial secretions, lubricating irritatedrespiratory tract membranes through increased mucous flow,and facilitating removal of viscous mucus. The onset of actionappears to be within 15–30 min. Guaifenesin is believed toalleviate cough discomfort by improving sinus and bronchialdrainage, increasing sputum volume, and decreasing sputumviscosity, thereby promoting effective cough. In one study, theeffect of guaifenesin to increase mucociliary clearance from thelung was greater in patients with chronic bronchitis than inhealthy subjects. In another study, guaifenesin inhibited the cough reflexsensitivity in subjects with an upper respiratory tract infection(cough receptors are transiently hypersensitive), but not inhealthy volunteers. Possible mechanisms include a centralantitussive effect or a peripheral effect by increased sputumvolume serving as a physical barrier, shielding cough receptorswithin the respiratory epithelium. As a centrally acting muscle relaxant, guaifenesin is believedto depress or block nerve impulse transmission at the internuncialneuron level of the subcortical areas of the brain, brainstem, and spinal cord. It also has mild analgesic and sedativeactions. |
| Toxics Screening Level | The acute rat oral LD50 of 1.5 g/kg was used to determine the ITSL using R232(1 )(h) as follows. The initial threshold screening level (ITSL) for Guaifenesin is 5 μg/m3 annual average. |
| 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 |
Guaifenesin Preparation Products And Raw materials
| Raw materials | Ammonium hydroxide-->Diethyl carbonate-->Guaiacol-->3-Chloro-1,2-propanediol-->Glycidol-->3-Amino-1,2-propanediol |
| Preparation Products | Zinc oxide-->Lithopone-->Zinc nitrate hexahydrate-->Methocarbamol-->2-METHOXYPHENOXYACETIC ACID |
