3-(2-methoxyphenoxy)propane-1,2-diol

• ChemBase ID: 752
• Molecular Formular: C10H14O4
• Molecular Mass: 198.21576
• Monoisotopic Mass: 198.08920893
• SMILES: O(CC(O)CO)c1c(OC)cccc1
• Canonical SMILES: OCC(COc1ccccc1OC)O
• InChI: 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

NAMES AND DATABASE IDS

Names

• IUPAC name: 3-(2-methoxyphenoxy)propane-1,2-diol
• IUPAC Traditional name: guaifenesin; @guaifenesin
• Brand Name: Guaiacyl glyceryl ether; Guaiamar; Guaianesin; Guaicol glycerine ether; Guaicol glyceryl ether; Guaiphenesin; Guaiphenesine; Guaiphesin; Guajacol-glycerinaether; Guajacuran; Guajamar; Guanar; Guayanesin; Guiatuss; Gvaja; Halotussin; Humibid L.A; Humibid Sprinkle; Hustodil; Hustosil; Hytuss; Hytuss-2X; Mintosyl; Miocaina; Miocurin; Miorelax; Mucinex; Mucostop; Muskurelax; Myocain; Myocaine; Myorelax; Myoscain; Myoscaine; Naldecon Senior EX; Neuroton; Actifed-C; Aeronesin; Amonidren; Amonidrin; Anti-Tuss; Aresol; Balminil Expectorant; Benylin-E; Breonesin; Bronchol; Calmipan; Calmylin Expectorant; Colrex expectorant; Cortussin; Creson; Diabetic Tussin EX; Dilyn; Dorassin; Equicol; Fenesin; Flartussin; Gaiamar; Gee-Gee; Genatuss; Glycodex; Glycotuss; Glytuss; Gnaifenesin; Guaia-rom; Guaiacol glycerin ether; Guaiacol glycerol ether; Guaiacol glyceryl ether; Guaiacolglicerinetere; Guaiacuran; Guaiacurane; Neurotone; Oresol; Oreson; Organidin NR; Pneumomist; Propanosedyl; Reduton; Relaxil G; Relaxyl-G; Reorganin; Resil; Respenyl; Respil; Resyl; Ritussin; Robitussin; Scot-tussin Expectorant; Sinumist-SR; Sirotol; Tenntus; Tenntuss; Tolseron; Tolyn; Touro EX; Tulyl; Tulyn; Uni-tussin
• Synonyms: 3-(2-Methoxyphenoxy)-1,2-propanediol; Guaiacol glyceryl ether; 3-(O-METHOXYPHENOXY)-1,2-PROPANEDIOL; Guaiphenesin; 3-(2-Methoxyphenoxy)propane-1,2-diol 99+%; o-Methoxyphenyl glyceryl ether; Methoxypropanediol; Metfenossidiolo; Methphenoxydiol; Metossipropandiolo; Guiaphenesin; Glyceryl guiacolate; Glyceryl guaicolate; Glyceryl guaiacyl ether; Glyceryl guaiacolate ether; Glyceryl guaiacolate; Glyceryl guaiacol ether; Glyceryl guaiacol; Glycerol guaiacolate; Glycero-guaiacol ether; Glycerin monoguaiacol ether; Glycerin guaiacolate; Guaifenesin; 3-(o-Methoxyphenoxy)-1,2-propanediol; Guaiacol glyceryl ether; Guaifenesin; Guaifenesin; 3-[o-Methoxyphenoxy]-1,2-propanediol; GUAIACOL GLYCERYL ETHER; 3-(o-Methoxyphenoxy)-1,2-propanediol, Guaiacol Glyceryl Ether, Robitussin; rac Guaifenesin; 3-(2-甲氧基苯氧基)-1,2-丙烷二醇, 赤式+苏式; 3-(邻甲氧基苯氧基)-1,2-丙二醇; 愈甘醚; 甘油愈创木酯; 愈创甘油醚; 愈创甘油醚; 愈甘醚

Database IDs

• CAS Number: 93-14-1
• EC Number: 202-222-5
• MDL Number: MFCD00016873
• Beilstein Number: 2049375
• Merck Index: 144555
• PubChem SID: 24895219; 46508004; 160964215
• PubChem CID: 3516

CALCULATED PROPERTIES

JChem

• Acid pKa: 13.624145
• H Acceptors: 4
• H Donor: 2
• LogD (pH = 5.5): 0.33746633
• LogD (pH = 7.4): 0.33746606
• Log P: 0.33746633
• Molar Refractivity: 51.2392 cm^3
• Polarizability: 20.314726 Å^3
• Polar Surface Area: 58.92 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 0.76
• LOG S: -1.12
• Solubility (Water): 1.49e+01 g/l

PROPERTIES

Physical Property

• Solubility: 50 mg/mL; Chloroform; Methanol
• Apperance: White Solid
• Melting Point: 77-79°C; 78-79°C; 78-82°C; 80-82°C
• Boiling Point: 215°C/15mm; 215°C/19mm
• Hydrophobicity(logP): 0.2

Safety Information

• Storage Condition: -20°C; Refrigerator; Room Temperature (15-30°C)
• Storage Warning: Harmful/Irritant
• RTECS: TY8400000
• European Hazard Symbols: X; Harmful (Xn)
• German water hazard class: 1
• Risk Statements: 22; 22-36/37/38; R:22
• Safety Statements: 26-36; 36; S:36/37/39
• TSCA Listed: 是
• GHS Pictograms: GHS06; GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H301; H302-H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338; P264-P270-P301+P310-P321-P405-P501A
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves

Product Information

• Purity: ≥98% (GC); 99+%
• Salt Data: Free Base
• Pharmacopeia Traceability: traceable to PhEur G0700000; traceable to USP 1301007
• Empirical Formula (Hill Notation): C10H14O4

DETAILS

MP Biomedicals - 05208844

MP Biomedicals Rare Chemical collection

MP Biomedicals - 02157278

Crystalline

DrugBank - DB00874

• Drug Groups: approved
• Description: An expectorant that also has some muscle relaxing action. It is used in many cough preparations. [PubChem]
• Indication: Used to assist the expectoration of phlegm from the airways in acute respiratory tract infections.
• Pharmacology: Guaifenesin is an expectorant which increases the output of phlegm (sputum) and bronchial secretions by reducing adhesiveness and surface tension. The increased flow of less viscous secretions promotes ciliary action and changes a dry, unproductive cough to one that is more productive and less frequent. By reducing the viscosity and adhesiveness of secretions, guaifenesin increases the efficacy of the mucociliary mechanism in removing accumulated secretions from the upper and lower airway.
• Toxicity: LD₅₀ 1510 mg/kg (rat, oral)
• Affected Organisms: Humans and other mammals
• Biotransformation: Rapidly hydrolyzed (60% within seven hours) and then excreted in the urine, with beta-(2-methoxyphenoxy)-lactic acid as its major urinary metabolite.
• Absorption: Rapidly absorbed from the GI tract
• Half Life: 1 hour
• External Links: Wikipedia; RxList; PDRhealth; Drugs.com

Selleck Chemicals - S1740

Research Area: Respiratory Diseases
Biological Activity:
Guaifenesin(Guaiphenesin) is thought to act as an expectorant by increasing the volume and reducing the viscosity of secretions in the trachea and bronchi. Thus, it may increase the efficiency of the cough reflex and facilitate removal of the secretions; however, objective evidence for this is limited and conflicting. [1]

Sigma Aldrich - G5627

包装
25, 500 g in poly bottle

Toronto Research Chemicals - G810500

Centrally acting muscle relaxant with expectorant properties.

REFERENCES

• http://en.wikipedia.org/wiki/Guaifenesin
• Clinical use in chronic respiratory disease: D.G. Workmann et. al. Curr. Ther. Res. 41 1751 (1980).