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Showing Compound Guaifenesin (FDB023575)

Record Information
Version1.0
Creation date2011-09-21 00:31:50 UTC
Update date2015-10-09 22:33:02 UTC
Primary IDFDB023575
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameGuaifenesin
DescriptionGuaifenesin (INN) or guaiphenesin (former BAN) 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. [HMDB]
CAS Number93-14-1
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
SynonymSource
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
3-(o-Methoxyphenoxy)-1,2-propanediolhmdb
3-(o-Methoxyphenoxy)-propanediol-1,2hmdb
3-o-Methoxyphenoxypropane 1:2-diolhmdb
Benylin-Ehmdb
glycerin etherhmdb
Glycerol a-(o-methoxyphenyl)etherhmdb
Guaifenesinhmdb
o-Methoxyphenyl glyceryl etherhmdb
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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC10H14O4
IUPAC name3-(2-methoxyphenoxy)propane-1,2-diol
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
Isomeric SMILESCOC1=CC=CC=C1OCC(O)CO
Average Molecular Weight198.2158
Monoisotopic Molecular Weight198.089208936
Classification
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
Ontology
Role

Industrial application:

Physico-Chemical Properties
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionNot Available
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
EI-MSMass Spectrum (Electron Ionization)splash10-00di-3900000000-022756bf476e39b7c0be2014-09-20View Spectrum
Predicted GC-MSGuaifenesin, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-02h9-9700000000-9c7025c23632b898d401Spectrum
Predicted GC-MSGuaifenesin, 2 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0fmi-9432000000-342d4da0e22ae9b9aeecSpectrum
Predicted GC-MSGuaifenesin, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSGuaifenesin, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSGuaifenesin, TMS_1_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSGuaifenesin, TMS_1_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSGuaifenesin, TBDMS_1_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSGuaifenesin, TBDMS_1_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSGuaifenesin, TBDMS_2_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - LC-ESI-qTof , Positivesplash10-0hb9-2900000000-261d308d57fa6814ad4e2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - , positivesplash10-0hb9-2900000000-261d308d57fa6814ad4e2017-09-14View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-006t-0900000000-0f11215eb276a39fd06b2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-05fr-1900000000-4b965972285b96b9e5dc2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-7900000000-4bcd84a8adc005d133142016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-1900000000-b243c8d4b91c351588932021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-9700000000-d4d9707e69287ac032f62021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9400000000-774a7e43dd3c0931c38f2021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-1900000000-27c5135862d6c8167c732016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-005a-5900000000-9b8da4dd94b7fb1f45142016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-9600000000-73302276ee78da40b3532016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-1900000000-eb412f483f86ec8f705d2021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-9700000000-4723ff7a6d82ffc57f342021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0apj-9200000000-199acc3684b3ffda62642021-09-22View Spectrum
NMR
TypeDescriptionView
1D NMR1H NMR Spectrum (1D, 600 MHz, CD3OD, experimental)Spectrum
1D NMR1H NMR Spectrum (1D, 90 MHz, CDCl3, experimental)Spectrum
1D NMR13C NMR Spectrum (1D, 25.16 MHz, CDCl3, experimental)Spectrum
1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, CD3OD, experimental)Spectrum
ChemSpider ID3396
ChEMBL IDCHEMBL980
KEGG Compound IDNot Available
Pubchem Compound ID3516
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDDB00874
HMDB IDHMDB04998
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDGuaifenesin
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
Flavours
FlavorCitations
bitter
  1. Ayana Wiener, Marina Shudler, Anat Levit, Masha Y. Niv. BitterDB: a database of bitter compounds. Nucleic Acids Res 2012, 40(Database issue):D413-419. DOI:10.1093/nar/gkr755
Files
MSDSshow
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference