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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2006-10-16 11:31:22 UTC
Update Date2023-02-21 17:17:06 UTC
HMDB IDHMDB0004998
Secondary Accession Numbers
  • HMDB04998
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
Data?1676999826
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 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 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
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point78.5 °CNot Available
Boiling Point356.77 °C. @ 760.00 mm Hg (est)The Good Scents Company Information System
Water Solubility2904 mg/L @ 25 °C (est)The Good Scents Company Information System
LogP1.39SMITH,JT & VINJAMOORI,DT (1995)
Experimental Chromatographic PropertiesNot Available
Predicted Molecular 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
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+144.69131661259
DarkChem[M-H]-140.77631661259
DeepCCS[M+H]+141.04930932474
DeepCCS[M-H]-137.36130932474
DeepCCS[M-2H]-174.59730932474
DeepCCS[M+Na]+150.13530932474
AllCCS[M+H]+145.132859911
AllCCS[M+H-H2O]+141.232859911
AllCCS[M+NH4]+148.832859911
AllCCS[M+Na]+149.932859911
AllCCS[M-H]-144.132859911
AllCCS[M+Na-2H]-145.032859911
AllCCS[M+HCOO]-146.032859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
GuaifenesinCOC1=CC=CC=C1OCC(O)CO2423.9Standard polar33892256
GuaifenesinCOC1=CC=CC=C1OCC(O)CO1660.6Standard non polar33892256
GuaifenesinCOC1=CC=CC=C1OCC(O)CO1675.2Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Guaifenesin,1TMS,isomer #1COC1=CC=CC=C1OCC(CO)O[Si](C)(C)C1748.3Semi standard non polar33892256
Guaifenesin,1TMS,isomer #2COC1=CC=CC=C1OCC(O)CO[Si](C)(C)C1736.4Semi standard non polar33892256
Guaifenesin,2TMS,isomer #1COC1=CC=CC=C1OCC(CO[Si](C)(C)C)O[Si](C)(C)C1791.7Semi standard non polar33892256
Guaifenesin,1TBDMS,isomer #1COC1=CC=CC=C1OCC(CO)O[Si](C)(C)C(C)(C)C1992.8Semi standard non polar33892256
Guaifenesin,1TBDMS,isomer #2COC1=CC=CC=C1OCC(O)CO[Si](C)(C)C(C)(C)C1976.4Semi standard non polar33892256
Guaifenesin,2TBDMS,isomer #1COC1=CC=CC=C1OCC(CO[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C2256.1Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Guaifenesin GC-MS (Non-derivatized) - 70eV, Positivesplash10-02h9-9700000000-9c7025c23632b898d4012017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Guaifenesin GC-MS (2 TMS) - 70eV, Positivesplash10-0fmi-9432000000-342d4da0e22ae9b9aeec2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Guaifenesin GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Guaifenesin GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Guaifenesin GC-MS (TMS_1_1) - 70eV, PositiveNot Available2021-11-03Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Guaifenesin GC-MS (TMS_1_2) - 70eV, PositiveNot Available2021-11-03Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Guaifenesin GC-MS (TBDMS_1_1) - 70eV, PositiveNot Available2021-11-03Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Guaifenesin GC-MS (TBDMS_1_2) - 70eV, PositiveNot Available2021-11-03Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Guaifenesin GC-MS (TBDMS_2_1) - 70eV, PositiveNot Available2021-11-03Wishart LabView Spectrum
MSMass Spectrum (Electron Ionization)splash10-00di-3900000000-022756bf476e39b7c0be2014-09-20Not AvailableView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Guaifenesin LC-ESI-qTof , Positive-QTOFsplash10-0hb9-2900000000-261d308d57fa6814ad4e2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Guaifenesin , positive-QTOFsplash10-0hb9-2900000000-261d308d57fa6814ad4e2017-09-14HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Guaifenesin 10V, Negative-QTOFsplash10-006t-0900000000-0f11215eb276a39fd06b2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Guaifenesin 20V, Negative-QTOFsplash10-05fr-1900000000-4b965972285b96b9e5dc2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Guaifenesin 40V, Negative-QTOFsplash10-0a4i-7900000000-4bcd84a8adc005d133142016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Guaifenesin 10V, Negative-QTOFsplash10-00di-1900000000-b243c8d4b91c351588932021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Guaifenesin 20V, Negative-QTOFsplash10-0a4i-9700000000-d4d9707e69287ac032f62021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Guaifenesin 40V, Negative-QTOFsplash10-0a4i-9400000000-774a7e43dd3c0931c38f2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Guaifenesin 10V, Positive-QTOFsplash10-0002-1900000000-27c5135862d6c8167c732016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Guaifenesin 20V, Positive-QTOFsplash10-005a-5900000000-9b8da4dd94b7fb1f45142016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Guaifenesin 40V, Positive-QTOFsplash10-0a4i-9600000000-73302276ee78da40b3532016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Guaifenesin 10V, Positive-QTOFsplash10-004i-1900000000-eb412f483f86ec8f705d2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Guaifenesin 20V, Positive-QTOFsplash10-0a4i-9700000000-4723ff7a6d82ffc57f342021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Guaifenesin 40V, Positive-QTOFsplash10-0apj-9200000000-199acc3684b3ffda62642021-09-22Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Experimental 2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, CD3OD, experimental)2012-12-05Wishart LabView Spectrum

IR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-)2023-02-03FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)2023-02-03FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)2023-02-03FELIX labView Spectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Predicted Concentrations
BiospecimenValueOriginal ageOriginal sexOriginal conditionComments
Blood0.000 uMAdult (>18 years old)BothNormalPredicted based on drug qualities
Blood0.000 umol/mmol creatinineAdult (>18 years old)BothNormalPredicted based on drug qualities
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB00874
Phenol Explorer Compound IDNot Available
FooDB IDFDB023575
KNApSAcK IDNot Available
Chemspider ID3396
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkGuaifenesin
METLIN ID4057
PubChem Compound3516
PDB IDNot Available
ChEBI ID200157
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1382601
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. [PubMed:13418392 ]