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Guaifenesin(CAS No. 93-14-1)

Guaifenesin C10H14O4 (cas 93-14-1) Molecular Structure

93-14-1 Structure

Identification and Related Records

【CAS Registry number】
1,2-Propanediol,3-(o-methoxyphenoxy)- (6CI,8CI)
Actifed C
Colrex Expectorant
Glycerin guaiacolate
Glycerol guaiacolate
Glycerol a-(2-methoxyphenyl)ether
Glycerol a-(o-methoxyphenyl)ether
Glycerol a-guaiacyl ether
Glyceryl guaiacolether
Glyceryl guaiacolate
Glyceryl guaiacolate ether
Glyceryl guaiacylether
Guaiacol glycerin ether
Guaiacolglycerol ether
Guaiacol glyceryl ether
Guaiacylglyceryl ether
【Molecular Formula】
C10H14O4 (Products with the same molecular formula)
【Molecular Weight】
【MOL File】

Chemical and Physical Properties

White Solid
1.195 g/cm3
【Melting Point】
【Boiling Point】
215℃ (19 mmHg)
【Refractive Index】
【Flash Point】
169.6 °C
5 g/100 mL (25℃)
5 g/100 mL (25 °C) in water
Minute rhombic prisms from ether
【Storage temp】
【Spectral properties】
Intense mass spectral peaks: 109 m/z, 124 m/z, 198 m/z
IR: 10626 (Sadtler Research Laboratories IR Grating Collection)
UV: 5711 (Sadtler Research Laboratories Spectral Collection)
MASS: 107120 (NIST/EPA/MSDC Mass Spectral Database, 1990 Version)
【Computed Properties】
Molecular Weight:198.21576 [g/mol]
Molecular Formula:C10H14O4
H-Bond Donor:2
H-Bond Acceptor:4
Rotatable Bond Count:5
Exact Mass:198.089209
MonoIsotopic Mass:198.089209
Topological Polar Surface Area:58.9
Heavy Atom Count:14
Formal Charge:0
Isotope Atom Count:0
Defined Atom Stereocenter Count:0
Undefined Atom Stereocenter Count:1
Defined Bond Stereocenter Count:0
Undefined Bond Stereocenter Count:0
Covalently-Bonded Unit Count:1
Feature 3D Acceptor Count:4
Feature 3D Donor Count:2
Feature 3D Ring Count:1
Effective Rotor Count:5
Conformer Sampling RMSD:0.6
CID Conformer Count:228

Safety and Handling

【Hazard Codes】
【Risk Statements】
【Safety Statements 】
【Hazard Note】



Safety Information about?Guaifenesin (CAS NO.93-14-1):
Hazard Codes:?HarmfulXn
Risk Statements: 22-36/37/38
R22: Harmful if swallowed.?
R36/37/38: Irritating to eyes, respiratory system and skin.
Safety Statements: 26-36
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.?
S36: Wear suitable protective clothing.
WGK Germany: 1
RTECS: TY8400000
Hazard Note: Harmful
Guaifenesin has side effect if consumption in above-normal quantities.May be cause nausea, vomiting, and the formation of kidney stones of URIC ACID.

Oral /formulations/: Capsules 200 mg Hytuss-2X,(Hyrex); Capsules, extended-release 300 mg Humibid Pediatric, (Celltech); Solution 100 mg/5 mL Phanasin Diabetic Choice ( with parabens and propylene glycol), (Pharmakon); 200 mg/5 mL Naldecon Senior EX, (Bristol-Myers Squibb); Tablets 100 mg Hytuss (scored), (Hyrex); 200 mg guaifenesin Tablets, (United Research); Tablets, extended-release 600, 1200 mg Mucinex, (Adams).
Capsules: 100 & 200 mg; syrup NF: 100 mg/5 mL; tablets: 100 & 200 mg.
【Exposure Standards and Regulations】
The Approved Drug Products with Therapeutic Equivalence Evaluations List identifies currently marketed over-the-counter drug products, incl guaifenesin, approved on the basis of safety and effectiveness by FDA under sections 505 of the Federal Food, Drug, and Cosmetic Act.
Cold, cough, allergy, bronchodilator, and antiasthmatic drug products for over-the-counter human use. Expectorant active ingredient. The active ingredient of the product is guaifenesin when used within the dosage limits established in ?341.78(d).
Implantation or injectable dosage form new animal drugs. Guaifenesin sterile powder. ... It is indicated for intravenous use as a muscle relaxant in horses. ... Not to be used in horses intended for food. ... Federal law restricts this drug to use by or on the order of a licensed veterinarian.
Implantation or injectable dosage form new animal drugs. Guaifenesin injection. ... The drug is used intravenously in horses as a skeletal muscle relaxant. ... Not to be used in horses intended for food. ... Federal law restricts this drug to use by or on the order of a licensed veterinarian.

General Information: As in any fire, wear a self-contained breathing apparatus in pressure-demand, MSHA/NIOSH (approved or equivalent), and full protective gear.
Extinguishing Media: Use water spray, dry chemical, carbon dioxide, or chemical foam .
Handling: Avoid breathing dust, vapor, mist, or gas. Avoid contact with skin and eyes. Use only in a chemical fume hood.
Storage: Store in a cool, dry place. Store in a tightly closed container.

【Octanol/Water Partition Coefficient】
log Kow = 1.39
【Disposal Methods】
SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices.

Use and Manufacturing

【Use and Manufacturing】
Methods of Manufacturing

Reaction of guaiacol and 3-chloro-1,2-propanediol by warming a mixture of the reactants with a base
Prepn: Marle, J. Chem Soc 101, 305(1912); Yale et al, J Am Chem Soc, 72, 3710 (1950); Roviralta, Astoul, ES 212920 (1954), CA 49, 8332b (1955). Prepn from 2-methoxyphenol and glycidol; W Merck et al, DE 3106995; eidem US 4390732 (1982, 1983 to Degussa AG).
Production: guaiacol and chlorohydrin (epoxidation)
... Made by the reaction of guaiacol with oxiranylmethanol or with 3-chloro-1,2-propanediol in the presence of sodium hydroxide.
Guaifenesin may be prepared by the coupling of sodium guaiacolate and glyceryl monochlorohydrin.
U.S. Exports

(1972) ND
(1975) ND
U.S. Imports

(1975) 4.14X10+7 GRAMS
U.S. Production

(1972) 6.0X10+8 G (GUAIACOL & DERIVS)
(1975) GREATER THAN 9.08X10+5 GRAMS
Production volumes for non-confidential chemicals reported under the Inventory Update Rule. Year Production Range (pounds) 1986 10 thousand - 500 thousand 1990 No Reports 1994 No Reports 1998 No Reports 2002 No Reports
Consumption Patterns

Essentally 100% in human and veterinary medicine (1976)

Centrally acting muscle relaxant with expectorant properties

Biomedical Effects and Toxicity

【Therapeutic Uses】
Guaifenesin is indicated as an expectorant in the temporary symptomatic management of cough due to minor upper respiratory infections and related conditions, such as sinusitis, pharyngitis, and bronchitis, when these conditions are complicated by viscous mucus and congestion. However, because supporting data are very limited, there is some controversy about its effectiveness. /Included in US product label/
VET: Guaifenesin (glyceryl guaiacolate) is a centrally acting muscle relaxant that is believed to depress or block nerve impulse transmission at the internuncial neuron level of the subcortical areas of the brain, brain stem, and spinal cord. It also has mild analgesic and sedative actions. Guaifenesin is given IV to induce muscle relaxation as an adjunct to anesthesia for short procedures. It relaxes both laryngeal and pharyngeal muscles, allowing easier intubation, but has little effect on diaphragm and respiratory function. It may cause transient increases in cardiac rate and decreases in blood pressure. It is also used in treatment of horses with exertional rhabdomyolysis and in dogs with strychnine intoxication.
VET: The drug is used intravenously as a skeletal muscle relaxant in horses. /Gecolate, Glycodex Injection/
【Biomedical Effects and Toxicity】
Readily absorbed from the gastrointestinal tract.
It is not known whether guaifenesin is distributed into breast milk.
Elimination /is/ renal, as inactive metabolites.
Five donkeys and three horses were given guaifenesin, intravenously, by gravity administration, until recumbency was produced. The time and dose required to produce recumbency, recovery time to sternal and standing were recorded. Blood samples were collected for guaifenesin assay at 10, 20, 30, 40, 50, 60 min, and 2, 3, 4 and 6 hr after guaifenesin administration. Serum was analysed for guaifenesin using HPLC and pharmacokinetic values were calculated using a computer software package. In donkeys, heart and respiratory rates and blood pressures were recorded before and at 5-min intervals during recumbency. Arterial blood samples were collected before and at 5 and 15 min intervals during recumbency for analysis of pH, CO2, and O2. ANOVA was used to evaluate dynamic data, while t-tests were used for kinetic values. Respiratory rate was decreased significantly during recumbency, but no other significant changes from baseline occurred. The mean (+/- SD) recumbency dose of guaifenesin was 131 mg/kg (27) for donkeys and 211 mg/kg (8) for horses. Recovery time to sternal (min) was 15 (SD, 11) for donkeys and 34 (SD, 1.4) for horses. Time to standing was 32 min for donkeys and 36 min for horses. Calculation of AUC (area under the concentration-time curve) microgram/mL) (dose-dependent variable) was 231 (SD, 33) for donkeys and 688 (SD, 110) for horses. The clearance (CL) (mL/ was 546 (SD, 73) for donkeys, which was significantly different from 313 (SD, 62) for horses. Mean residence time (MRT) (hr) was 1.2 (SD, 0.1) for donkeys and 2.6 (SD, 0.5) for horses. Volume of distribution Vd(area) (mL/kg) was 678 (SD, 92) for donkeys and 794 (SD, 25) for horses. At the rate of administration used in this study, donkeys required less guaifenesin than horses to produce recumbency, but cleared it more rapidly. [Matthews N, Peck K et al; J Vet Pharmacol Ther 20 (6): 442-6 (1997)] PubMed Abstract

Environmental Fate and Exposure Potential

【Environmental Fate/Exposure Summary】
TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 140(SRC), determined from a log Kow of 1.39(2) and a regression-derived equation(3), indicates that guaifenesin is expected to have high mobility in soil(SRC). Volatilization of guaifenesin from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 4.4X10-11 atm-cu m/mole(SRC), using a fragment constant estimation method(4). Guaifenesin is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 1.52X10-6 mm Hg(SRC), determined from a fragment constant method(5). Biodegradation data were not available(SRC, 2007).
AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 140(SRC), determined from a log Kow of 1.39(2) and a regression-derived equation(3), indicates that guaifenesin is not expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is not expected(3) based upon an estimated Henry's Law constant of 4.4X10-11 atm-cu m/mole(SRC), developed using a fragment constant estimation method(4). According to a classification scheme(5), an estimated BCF of 7.0(SRC), from its log Kow(2) and a regression-derived equation(6), suggests the potential for bioconcentration in aquatic organisms is low(SRC). Biodegradation data were not available(SRC, 2007).
ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), guaifenesin, which has an estimated vapor pressure of 1.5X10-6 mm Hg at 25 deg C(SRC), determined from a fragment constant method(2), will exist in both the vapor and particulate phases in the ambient atmosphere. Vapor-phase guaifenesin is degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals(SRC); the half-life for this reaction in air is estimated to be 9.4 hours(SRC), calculated from its rate constant of 4.1X10-11 cu cm/molecule-sec at 25 deg C(SRC) that was derived using a structure estimation method(3). Particulate-phase guaifenesin may be removed from the air by wet or dry deposition(SRC). Guaifenesin does not contain chromophores that absorb at wavelengths >290 nm(4) and therefore is not expected to be susceptible to direct photolysis by sunlight(SRC).

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