Guaifenesin (CHEM003516)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2014-08-30 21:03:55 UTC
Update Date2016-11-09 01:09:09 UTC
Accession NumberCHEM003516
Identification
Common NameGuaifenesin
ClassSmall Molecule
DescriptionAn expectorant that also has some muscle relaxing action. It is used in many cough preparations. [PubChem]
Contaminant Sources
  • FooDB Chemicals
  • HPV EPA Chemicals
  • STOFF IDENT Compounds
  • T3DB toxins
  • ToxCast & Tox21 Chemicals
Contaminant Type
  • Amine
  • Drug
  • Ether
  • Expectorant
  • Food Toxin
  • Organic Compound
  • Synthetic Compound
Chemical Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
HustosilKegg
RobitussinKegg
3-(2-Methoxyphenoxy)-1,2-propanediolHMDB
3-(O-Methoxyphenoxy)-1,2-propanediolHMDB
3-(O-Methoxyphenoxy)-propanediol-1,2HMDB
3-O-Methoxyphenoxypropane 1:2-diolHMDB
a-Glyceryl guaiacol etherHMDB
a-Glyceryl guaiacolate etherHMDB
Actifed CHMDB
AeronesinHMDB
alpha-Glyceryl guaiacol etherHMDB
alpha-Glyceryl guaiacolate etherHMDB
AmonidrenHMDB
AmonidrinHMDB
AresolHMDB
Benylin-eHMDB
BroncholHMDB
Glycerin etherHMDB
Glycerin guaiacolateHMDB
Glycero-guaiacol etherHMDB
Glycerol a-(2-methoxyphenyl) etherHMDB
Glycerol a-(O-methoxyphenyl)etherHMDB
Glycerol a-guaiacyl etherHMDB
Glycerol a-guiacyl etherHMDB
Glycerol a-monoguaiacol etherHMDB
Glycerol guaiacolateHMDB
Glycerol mono(2-methoxyphenyl) etherHMDB
Glycerol-a-guajakoletherHMDB
Glycerol-alpha-guajakoletherHMDB
Glyceryl guaiacolHMDB
Glyceryl guaiacol etherHMDB
Glyceryl guaiacolateHMDB
Glyceryl guaiacolate etherHMDB
Glyceryl guaiacyl etherHMDB
Glyceryl guaicolateHMDB
Glyceryl guiacolateHMDB
GlycerylguaiacolHMDB
Guaiacol glycerol etherHMDB
Guaiacol glyceryl etherHMDB
GuaiacolglicerinetereHMDB
GuaiacuranHMDB
GuaiacuraneHMDB
Guaiacyl glyceryl etherHMDB
GuaiamarHMDB
GuaianesinHMDB
Guaicol glycerine etherHMDB
Guaicol glyceryl etherHMDB
GuaifenesineHMDB
GuaiphenesinHMDB
GuaiphenesineHMDB
GuaiphesinHMDB
MethoxypropanediolHMDB
MethphenoxydiolHMDB
MetossipropandioloHMDB
O-Methoxyphenyl glyceryl etherHMDB
Organidin NRHMDB
p-Cresyl acetateHMDB
PneumomistHMDB
PropanosedylHMDB
RedutonHMDB
BreonesinHMDB
Ether, guaiacol glycerylHMDB
Glyceryl ether, guaiacolHMDB
HytussHMDB
GuaiphenezineHMDB
HumibidHMDB
Scott-tussinHMDB
Guaiacolate, glycerolHMDB
GuiatussHMDB
Scott tussinHMDB
ScottTussinHMDB
Chemical FormulaC10H14O4
Average Molecular Mass198.216 g/mol
Monoisotopic Mass198.089 g/mol
CAS Registry Number93-14-1
IUPAC Name3-(2-methoxyphenoxy)propane-1,2-diol
Traditional Nameguaifenesin
SMILESCOC1=CC=CC=C1OCC(O)CO
InChI IdentifierInChI=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
InChI KeyHSRJKNPTNIJEKV-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as anisoles. These are organic compounds containing a methoxybenzene or a derivative thereof.
KingdomOrganic compounds
Super ClassBenzenoids
ClassPhenol ethers
Sub ClassAnisoles
Direct ParentAnisoles
Alternative Parents
Substituents
  • Phenoxy compound
  • Methoxybenzene
  • Anisole
  • Alkyl aryl ether
  • Monocyclic benzene moiety
  • Secondary alcohol
  • 1,2-diol
  • Ether
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Primary alcohol
  • Organooxygen compound
  • Alcohol
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External DescriptorsNot Available
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • Cytoplasm
  • Extracellular
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateSolid
AppearanceWhite powder.
Experimental Properties
PropertyValue
Melting Point78.5-79°C
Boiling Point215 °C at 1.90E+01 mm Hg
Solubilityhighly water-soluble
Predicted Properties
PropertyValueSource
Water Solubility14.9 g/LALOGPS
logP0.76ALOGPS
logP0.34ChemAxon
logS-1.1ALOGPS
pKa (Strongest Acidic)13.62ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area58.92 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity51.24 m³·mol⁻¹ChemAxon
Polarizability20.59 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-02h9-9700000000-9c7025c23632b898d401Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-0fmi-9432000000-342d4da0e22ae9b9aeecSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_2) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_2_1) - 70eV, PositiveNot AvailableSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-qTof , Positivesplash10-0hb9-2900000000-261d308d57fa6814ad4eSpectrum
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-0hb9-2900000000-261d308d57fa6814ad4eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-1900000000-27c5135862d6c8167c73Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-005a-5900000000-9b8da4dd94b7fb1f4514Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-9600000000-73302276ee78da40b353Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-006t-0900000000-0f11215eb276a39fd06bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-05fr-1900000000-4b965972285b96b9e5dcSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-7900000000-4bcd84a8adc005d13314Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-1900000000-eb412f483f86ec8f705dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-9700000000-4723ff7a6d82ffc57f34Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0apj-9200000000-199acc3684b3ffda6264Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-1900000000-b243c8d4b91c35158893Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-9700000000-d4d9707e69287ac032f6Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9400000000-774a7e43dd3c0931c38fSpectrum
MSMass Spectrum (Electron Ionization)splash10-00di-3900000000-022756bf476e39b7c0beSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableSpectrum
Toxicity Profile
Route of ExposureRapidly absorbed from the GI tract
Mechanism of ToxicityGuaifenesin may act as an irritant to gastric vagal receptors, and recruit efferent parasympathetic reflexes that cause glandular exocytosis of a less viscous mucus mixture. Cough may be provoked. This combination may flush tenacious, congealed mucopurulent material from obstructed small airways and lead to a temporary improvement in dyspnea or the work of breathing.
MetabolismRapidly hydrolyzed (60% within seven hours) and then excreted in the urine, with beta-(2-methoxyphenoxy)-lactic acid as its major urinary metabolite. Half Life: 1 hour
Toxicity ValuesOral, Rat: LD50 1510 mg/kg
Lethal DoseNot Available
Carcinogenicity (IARC Classification)No indication of carcinogenicity to humans (not listed by IARC).
Uses/SourcesUsed to assist the expectoration of phlegm from the airways in acute respiratory tract infections.
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDDB00874
HMDB IDHMDB0247133
FooDB IDFDB023575
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN ID4057
PDB IDNot Available
Wikipedia LinkGuaifenesin
Chemspider ID3396
ChEBI ID200157
PubChem Compound ID3516
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis Reference

Wilfred P. Shum, Harry Mazurek, Jian Chen, “Process for producing enantiomerically enriched guaifenesin.” U.S. Patent US5495052, issued August, 1949.

MSDSNot Available
General References
1. Barupal DK, Fiehn O: Generating the Blood Exposome Database Using a Comprehensive Text Mining and Database Fusion Approach. Environ Health Perspect. 2019 Sep;127(9):97008. doi: 10.1289/EHP4713. Epub 2019 Sep 26.