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| CAS No.: | 93-14-1 |
|---|---|
| Name: | Guaifenesin |
| Molecular Structure: | |
|
|
|
| Formula: | C10H14O4 |
| Molecular Weight: | 198.219 |
| Synonyms: | 1,2-Propanediol,3-(o-methoxyphenoxy)- (6CI,8CI);1,2-Dihydroxy-3-(2-methoxyphenoxy)propane;2-G;3-(2-Methoxyphenoxy)-1,2-propanediol;3-(o-Methoxyphenoxy)-1,2-propanediol;Actifed C;Aeronesin;Amonidren;Aresol;Calmipan;Colrex Expectorant;Creson;Dilyn;Equicol;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;Glycerylguaiacol;Glycodex;Glycotuss;Guaiacol glycerin ether;Guaiacolglycerol ether;Guaiacol glyceryl ether;Guaiacuran;Guaiacurane;Guaiacylglyceryl ether;Guaiamar;Guaianesin; |
| EINECS: | 202-222-5 |
| Density: | 1.195 g/cm3 |
| Melting Point: | 77-81 °C |
| Boiling Point: | 356.8 °C at 760 mmHg |
| Flash Point: | 169.6 °C |
| Solubility: | 5 g/100 mL (25 °C) in water |
| Appearance: | White Solid |
| Hazard Symbols: |
 Xn
|
| Risk Codes: | 22-36/37/38 |
| Safety: | 26-36 |
| PSA: | 58.92000 |
| LogP: | 0.42720 |
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oxiranyl-methanol
- 90-05-1
2-methoxy-phenol
A
- 14007-09-1
2-(2-methoxyphenoxy)-1,3-propanediol
B
- 93-14-1
guaifenesin
| Conditions | Yield |
|---|---|
| With calcined hydrotalcite In tetrahydrofuran at 120℃; for 4h; Kinetics; Reagent/catalyst; Temperature; Autoclave; | A 5% B 95% |
| Conditions | Yield |
|---|---|
| With potassium carbonate In acetonitrile at 65 - 70℃; for 12h; | 90% |
| With sodium hydroxide at 90 - 95℃; | 56% |
| With tetrabutylammomium bromide; potassium carbonate; palladium dichloride In water at 60℃; for 5h; | 55% |
| Stage #1: 2-methoxy-phenol With potassium hydroxide at 64.84℃; Inert atmosphere; Stage #2: oxiranyl-methanol With hydrogenchloride Inert atmosphere; |
| Conditions | Yield |
|---|---|
| With perchloric acid | 81% |
| With perchloric acid In water at 80℃; | 80% |
| With sulfuric acid; water at 70℃; for 2h; | 59.1% |
| Conditions | Yield |
|---|---|
| With sodium hydroxide In N,N-dimethyl-formamide at 210℃; for 0.25h; Microwave irradiation; | 75% |
| Stage #1: 2-methoxy-phenol With sodium hydroxide In ethanol; water for 0.5h; Heating; Stage #2: 3-monochloro-1,2-propanediol In ethanol; water for 8h; Heating; | 61% |
| With sodium hydroxide |
| Conditions | Yield |
|---|---|
| Stage #1: 2-methoxy-phenol With potassium chloride; sodium sulfite at 50℃; for 3h; Reflux; Stage #2: 3-Amino-1,2-propanediol at 90℃; for 5h; Temperature; Concentration; | 72% |
- 931-40-8
4-hydroxymethyl-1,3-dioxolan-2-one
- 90-05-1
2-methoxy-phenol
A
- 16929-60-5
1,3-bis(2-methoxyphenoxy)propan-2-ol
B
- 93-14-1
guaifenesin
| Conditions | Yield |
|---|---|
| With tetrabutyl ammonium fluoride In N,N-dimethyl-formamide at 160℃; for 9.5h; Inert atmosphere; Schlenk technique; | A 9% B 64% |
| Conditions | Yield |
|---|---|
| With ethanol |
| Conditions | Yield |
|---|---|
| With water at 70℃; Product distribution; Rate constant; further temperatures, pH 8.0-10.0; |
| Conditions | Yield |
|---|---|
| With potassium carbonate In acetone |
| Conditions | Yield |
|---|---|
| Multi-step reaction with 2 steps 1: 43 percent / NaOH / 16 h / 80 °C 2: 81 percent / perchloric acid View Scheme | |
| Multi-step reaction with 2 steps 1: 2.) 50percent aq. NaOH / 1.) 80 deg C, 2.) 4 h 2: 80 percent / 72percent HClO4 / H2O / 80 °C View Scheme |
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Chemistry
IUPAC Name: 3-(2-Methoxyphenoxy)propane-1,2-diol
Synonyms of Guaifenesin (CAS NO.93-14-1): (+-)-3-(o-Methoxyphenoxy)-1,2-propanediol ; 1,2,3-Propanetriol, ether with 2-methoxyphenol ;1,2-Propanediol, 3-(2-methoxyphenoxy)- ; 3-(2-Methoxyphenoxy)-1,2-propanediol ; Aether glycerinoguaiacolicus
CAS NO: 93-14-1
Molecular Formula: C10H14O4
Molecular Weight: 198.22
Molecular Structure: 
EINECS: 202-222-5
H bond acceptors: 4
H bond donors: 2
Freely Rotating Bonds: 7
Polar Surface Area: 36.92 Å2
Index of Refraction: 1.538
Molar Refractivity: 51.9 cm3
Molar Volume: 165.8 cm3
Surface Tension: 45.6 dyne/cm
Density: 1.195 g/cm3
Flash Point: 169.6 °C
Enthalpy of Vaporization: 63.53 kJ/mol
Boiling Point: 356.8 °C at 760 mmHg
Vapour Pressure: 1.04E-05 mmHg at 25°C
Melting Point: 77-81 °C
Water Solubility: 5 g/100 mL (25 °C)
Appearance: White Solid
Product Categories og Guaifenesin (CAS NO.93-14-1): Benzhydrols, Benzyl & Special Alcohols;Aromatics Compounds;Aromatics;Intermediates & Fine Chemicals;Pharmaceuticals;API's
History
There are similar medicines derived from the guaiac tree were in use as a generic remedy by Native Americans when explorers reached North America in the 1500s. Guaifenesin was first approved by the Food and Drug Administration in 1952.Guaifenesin is sold as pills or syrups under many brand names. It is also included in many other over-the-counter cough and cold remedy combinations
Uses
Guaifenesin (CAS NO.93-14-1) is mainly used in the treatment of coughing, but the drug has numerous other uses, including medical, veterinary, and personal.
Toxicity Data With Reference
| Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
|---|---|---|---|---|---|
| dog | LD50 | intravenous | 335mg/kg (335mg/kg) | Nippon Yakurigaku Zasshi. Japanese Journal of Pharmacology. Vol. 54, Pg. 688, 1958. | |
| mouse | LD50 | intramuscular | 2210mg/kg (2210mg/kg) | Oyo Yakuri. Pharmacometrics. Vol. 8, Pg. 429, 1974. | |
| mouse | LD50 | intraperitoneal | 495mg/kg (495mg/kg) | "Psychotropic Drugs and Related Compounds," 2nd ed., Usdin, E., and D.H. Efron, Washington, DC, 1972Vol. -, Pg. 398, 1972. | |
| mouse | LD50 | intravenous | 400mg/kg (400mg/kg) | Oyo Yakuri. Pharmacometrics. Vol. 8, Pg. 429, 1974. | |
| mouse | LD50 | oral | 690mg/kg (690mg/kg) | "Psychotropic Drugs and Related Compounds," 2nd ed., Usdin, E., and D.H. Efron, Washington, DC, 1972Vol. -, Pg. 398, 1972. | |
| mouse | LD50 | subcutaneous | 800mg/kg (800mg/kg) | AUTONOMIC NERVOUS SYSTEM: "SMOOTH MUSCLE RELAXANT (MECHANISM UNDEFINED, SPASMOLYTIC)" | Arzneimittel-Forschung. Drug Research. Vol. 15, Pg. 1355, 1965. |
| rabbit | LD50 | oral | 2553mg/kg (2553mg/kg) | Applied Therapeutics. Vol. 9, Pg. 55, 1967. | |
| rat | LD50 | intramuscular | 4gm/kg (4000mg/kg) | BEHAVIORAL: ALTERED SLEEP TIME (INCLUDING CHANGE IN RIGHTING REFLEX) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES | Oyo Yakuri. Pharmacometrics. Vol. 8, Pg. 429, 1974. |
| rat | LD50 | intraperitoneal | 1gm/kg (1000mg/kg) | BEHAVIORAL: ALTERED SLEEP TIME (INCLUDING CHANGE IN RIGHTING REFLEX) | Archives Internationales de Pharmacodynamie et de Therapie. Vol. 191, Pg. 147, 1971. |
| rat | LD50 | intravenous | 360mg/kg (360mg/kg) | BEHAVIORAL: ATAXIA KIDNEY, URETER, AND BLADDER: HEMATURIA LUNGS, THORAX, OR RESPIRATION: DYSPNEA | Proceedings of the Society for Experimental Biology and Medicine. Vol. 85, Pg. 323, 1954. |
| rat | LD50 | oral | 1510mg/kg (1510mg/kg) | BEHAVIORAL: ALTERED SLEEP TIME (INCLUDING CHANGE IN RIGHTING REFLEX) LUNGS, THORAX, OR RESPIRATION: CHRONIC PULMONARY EDEMA LUNGS, THORAX, OR RESPIRATION: RESPIRATORY DEPRESSION | Pharmacological Research Communications. Vol. 1, Pg. 413, 1969. |
| rat | LD50 | subcutaneous | 2550mg/kg (2550mg/kg) | Drugs in Japan Vol. 6, Pg. 210, 1982. |
Safety Profile
Safety Information about Guaifenesin (CAS NO.93-14-1):
Hazard Codes: 
Xn
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.
Specification
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.