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Record Information
Version3.6
Creation Date2006-10-16 11:31:22 UTC
Update Date2016-02-11 01:07:01 UTC
HMDB IDHMDB04998
Secondary Accession NumbersNone
Metabolite Identification
Common NameGuaifenesin
DescriptionGuaifenesin (International Noproprietary Name) or guaiphenesin (former British Approved Name) is an expectorant drug usually taken orally to assist the expectoration ('bringing up') of phlegm from the airways in acute respiratory tract infections. It is a common ingredient in many over-the-counter cough/cold medications. Guaifenesin is also used in the experimental guaifenesin protocol in the treatment of fibromyalgia. It was first approved by the Food and Drug Administration (FDA) in 1952. Guaifenesin works by drawing water into the bronchi. The water both thins mucus and lubricates the airway, facilitating the removal of mucus by coughing.
Structure
Thumb
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
Chemical FormulaC10H14O4
Average Molecular Weight198.2158
Monoisotopic Molecular Weight198.089208936
IUPAC Name3-(2-methoxyphenoxy)propane-1,2-diol
Traditional Nameguaifenesin
CAS Registry Number93-14-1
SMILES
COC1=CC=CC=C1OCC(O)CO
InChI Identifier
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
InChI KeyInChIKey=HSRJKNPTNIJEKV-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound 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
ClassBenzene and substituted derivatives
Sub ClassPhenol ethers
Direct ParentAnisoles
Alternative Parents
Substituents
  • Methoxybenzene
  • Anisole
  • Alkyl aryl ether
  • Secondary alcohol
  • 1,2-diol
  • Ether
  • Hydrocarbon derivative
  • Primary alcohol
  • Organooxygen compound
  • Alcohol
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External DescriptorsNot Available
Ontology
StatusExpected but not Quantified
Origin
  • Drug
BiofunctionNot Available
ApplicationNot Available
Cellular locationsNot Available
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point78.5 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogP1.39SMITH,JT & VINJAMOORI,DT (1995)
Predicted Properties
PropertyValueSource
Water Solubility14.9 mg/mLALOGPS
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 Å2ChemAxon
Rotatable Bond Count5ChemAxon
Refractivity51.24 m3·mol-1ChemAxon
Polarizability20.59 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
MSMass Spectrum (Electron Ionization)splash10-00di-3900000000-022756bf476e39b7c0beView in MoNA
1D NMR1H NMR SpectrumNot Available
1D NMR1H NMR SpectrumNot Available
1D NMR13C NMR SpectrumNot Available
2D NMR[1H,13C] 2D NMR SpectrumNot Available
Biological Properties
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationNot Available
PathwaysNot Available
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Predicted Concentrations
BiofluidValueOriginal ageOriginal sexOriginal conditionComments
Blood0-5 uMAdult (>18 years old)BothNormalPredicted based on drug qualities
Blood0-3 umol/mmol creatinineAdult (>18 years old)BothNormalPredicted based on drug qualities
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB023575
KNApSAcK IDNot Available
Chemspider ID3396
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkGuaifenesin
NuGOwiki LinkHMDB04998
Metagene LinkHMDB04998
METLIN ID4057
PubChem Compound3516
PDB IDNot Available
ChEBI ID200157
References
Synthesis ReferenceSkursky, J. Resyl, a new derivative of guaiacol. Actas Ciba (1940), 181-2. CODEN: ACBABM CAN 36:1427 AN 1942:1427
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. SABA GM: [Glyceroguaiacol ether as muscle relaxant in anesthesia for gynecological surgery]. Minerva Anestesiol. 1957 Jan;23(1):19-21. [13418392 ]