Guaiacol

Identification

Name
Guaiacol
Accession Number
DB11359
Type
Small Molecule
Groups
Approved
Description

Guaiacol is an agent thought to have disinfectant properties and used as an expectorant. Guaiacol is a phenolic natural product first isolated from Guaiac resin and the oxidation of lignin. Guaiacol is also present in wood smoke, as a product of pyrolysis of lignin. Guaiacol has been found in the urine of patients with neuroblastoma and pheochromocytoma.

Structure
Thumb
Synonyms
  • 1-hydroxy-2-methoxybenzene
  • 2-methoxyl-4-vinylphenol
  • 2-methoxyphenol
  • o-guaiacol
  • o-hydroxyanisole
  • o-Methoxyphenol
  • Pyrocatechol monomethyl ether
  • Pyroguaiac acid
External IDs
Fema no. 2532 / NSC-3815
Product Ingredients
IngredientUNIICASInChI Key
Guaiacol carbonateQ71XPQ6R29553-17-3ORUJFMPWKPVXLZ-UHFFFAOYSA-N
Guaiacol hydrochlorideNot AvailableNot AvailableAXHWIVKRWPJSOF-UHFFFAOYSA-N
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
Analgesic BalmGuaiacol (1.25 %) + Eucalyptus oil (2.5 %) + Menthol (3.12 %) + Methyl salicylate (25 %)OintmentTopicalStanley Pharmaceuticals, A Division Of Vita Health Products Inc.1965-12-312000-07-27Canada
Creo-rectal AdulteGuaiacol carbonate (600 mg) + Camphor (5 mg) + Diphenylpyraline hydrochloride (1.5 mg)SuppositoryRectalSandoz Canada Incorporated1951-12-31Not applicableCanada
Creo-rectal Enfants/childrenGuaiacol carbonate (200 mg) + Camphor (2 mg) + Diphenylpyraline hydrochloride (0.5 mg)SuppositoryRectalSandoz Canada Incorporated1951-12-31Not applicableCanada
Creo-rectal NourrissonGuaiacol carbonate (100 mg) + Camphor (1 mg) + Diphenylpyraline hydrochloride (0.25 mg)SuppositoryRectalSandoz Canada Incorporated1951-12-312012-11-02Canada
Demo Cineol InjGuaiacol (167 mg) + Camphor (20 mg) + Eucalyptol (184 mg)LiquidIntramuscularSabex Inc1951-12-311998-08-12Canada
Demo-cineol Adultes/adultsGuaiacol carbonate (200 mg) + Guaiacol (180 mg) + Camphor (40 mg) + Eucalyptol (370 mg)SuppositoryRectalSandoz Canada Incorporated1986-12-31Not applicableCanada
Demo-cineol Adultes/adultsGuaiacol carbonate (200 mg) + Guaiacol (180 mg) + Camphor (40 mg) + Eucalyptol (370 mg)SuppositoryRectalSandoz Canada Incorporated1986-12-31Not applicableCanada
Demo-cineol Enfants/childrenGuaiacol carbonate (100 mg) + Guaiacol (90 mg) + Camphor (20 mg) + Eucalyptol (185 mg)SuppositoryRectalSandoz Canada Incorporated1977-12-31Not applicableCanada
Demo-cineol Enfants/childrenGuaiacol carbonate (100 mg) + Guaiacol (90 mg) + Camphor (20 mg) + Eucalyptol (185 mg)SuppositoryRectalSandoz Canada Incorporated1977-12-31Not applicableCanada
Dentalgar LiqGuaiacol (1.98 g) + Benzocaine (54 mg) + Camphor (1.98 g) + Clove oil (1.98 ml) + Menthol (54 mg)LiquidDentalProduits Marc O (1987) Inc., Division Of Technilab Inc.1982-05-311999-09-17Canada
Unapproved/Other Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
Dry SocketGuaiacol (0.0416 g/1g) + Eugenol (0.0416 g/1g)PasteDentalDentsply Llc, Professional Division, Trading As "Sultan Healthcare"1900-01-01Not applicableUs
Categories
UNII
6JKA7MAH9C
CAS number
90-05-1
Weight
Average: 124.139
Monoisotopic: 124.052429498
Chemical Formula
C7H8O2
InChI Key
LHGVFZTZFXWLCP-UHFFFAOYSA-N
InChI
InChI=1S/C7H8O2/c1-9-7-5-3-2-4-6(7)8/h2-5,8H,1H3
IUPAC Name
2-methoxyphenol
SMILES
COC1=C(O)C=CC=C1

Pharmacology

Indication

It is used medicinally as an expectorant, antiseptic, and local anesthetic. Guaiacol is used in traditional dental pulp sedation, and has the property of inducing cell proliferation; guaiacol is a potent scavenger of reactive oxygen radicals and its radical scavenging activity may be associated with its effect on cell proliferation.

Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
USerum albuminNot AvailableHuman
Absorption

In rats, guaiacol is rapidly absorbed, being present in the blood 5 minutes after oral administration, and reaching its peak plasma concentration in about 10 minutes. Its elimination from the blood is usually as rapid.

Volume of distribution
Not Available
Protein binding
Not Available
Metabolism
Not Available
Route of elimination

Excreted by rabbits in combined form with sulfate (15%) and glucuronic acid (72%).

Half life
Not Available
Clearance
Not Available
Toxicity
Not Available
Affected organisms
Not Available
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
Not Available
Food Interactions
Not Available

References

General References
  1. Monograph [Link]
External Links
Human Metabolome Database
HMDB0001398
KEGG Drug
D00117
KEGG Compound
C01502
PubChem Compound
460
PubChem Substance
347827973
ChemSpider
447
BindingDB
50240369
ChEBI
28591
ChEMBL
CHEMBL13766
HET
JZ3
Wikipedia
Guaiacol
PDB Entries
3ht9 / 4a6z / 4a78 / 4g05 / 4qoq / 5ncb

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
3TerminatedTreatmentCoughing1
3Unknown StatusTreatmentCoughing1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
FormRouteStrength
OintmentTopical
SuppositoryRectal
LiquidIntramuscular
LiquidDental
PasteDental
LozengeOral
Prices
Not Available
Patents
Not Available

Properties

State
Not Available
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility67.4 mg/mLALOGPS
logP1.32ALOGPS
logP1.51ChemAxon
logS-0.27ALOGPS
pKa (Strongest Acidic)9.98ChemAxon
pKa (Strongest Basic)-4.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area29.46 Å2ChemAxon
Rotatable Bond Count1ChemAxon
Refractivity34.5 m3·mol-1ChemAxon
Polarizability12.69 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
GC-MS Spectrum - EI-BGC-MSsplash10-0a4i-6900000000-49cb804087a42b1d1a22
GC-MS Spectrum - EI-BGC-MSsplash10-0ab9-5900000000-b580cbc25d4176ce3894
GC-MS Spectrum - EI-BGC-MSsplash10-0pir-9700000000-f1436b3de82cff342b65
GC-MS Spectrum - EI-BGC-MSsplash10-05fr-4900000000-c09a31d9523d2eab5598
GC-MS Spectrum - GC-EI-TOFGC-MSsplash10-014i-0900000000-283fdedfda9e853e0cac
Mass Spectrum (Electron Ionization)MSsplash10-0ac0-9800000000-5e89a9881e848e1b6c90
MS/MS Spectrum - EI-B (HITACHI RMU-6E) , PositiveLC-MS/MSsplash10-0a4i-6900000000-49cb804087a42b1d1a22
MS/MS Spectrum - EI-B (HITACHI RMU-6L) , PositiveLC-MS/MSsplash10-0ab9-5900000000-b580cbc25d4176ce3894
MS/MS Spectrum - EI-B (HITACHI M-80B) , PositiveLC-MS/MSsplash10-0pir-9700000000-12606badb77d4257635d
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-004i-0900000000-6b7a2fdf4e9a28ec6045
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-004i-2900000000-ff014b7b55a5237cf91e
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0udi-9100000000-8785b2e2d86c6294a754
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-00di-0900000000-8856c60866e810389af7
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-00di-1900000000-8db14d5e5710471f76a7
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-0a4i-9400000000-bc0d3592d62ec26dad6f
1H NMR Spectrum1D NMRNot Applicable
1H NMR Spectrum1D NMRNot Applicable
13C NMR Spectrum1D NMRNot Applicable
[1H,13C] 2D NMR Spectrum2D NMRNot Applicable

Taxonomy

Description
This compound belongs to the class of organic compounds known as methoxyphenols. These are compounds containing a methoxy group attached to the benzene ring of a phenol moiety.
Kingdom
Organic compounds
Super Class
Benzenoids
Class
Phenols
Sub Class
Methoxyphenols
Direct Parent
Methoxyphenols
Alternative Parents
Phenoxy compounds / Methoxybenzenes / Anisoles / Alkyl aryl ethers / 1-hydroxy-4-unsubstituted benzenoids / 1-hydroxy-2-unsubstituted benzenoids / Hydrocarbon derivatives
Substituents
Methoxyphenol / Phenoxy compound / Methoxybenzene / Phenol ether / Anisole / 1-hydroxy-4-unsubstituted benzenoid / 1-hydroxy-2-unsubstituted benzenoid / Alkyl aryl ether / Monocyclic benzene moiety / Ether
Molecular Framework
Aromatic homomonocyclic compounds
External Descriptors
phenols, monomethoxybenzene (CHEBI:28591) / a guaiacol (CPD-400)

Targets

Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Toxic substance binding
Specific Function
Serum albumin, the main protein of plasma, has a good binding capacity for water, Ca(2+), Na(+), K(+), fatty acids, hormones, bilirubin and drugs. Its main function is the regulation of the colloid...
Gene Name
ALB
Uniprot ID
P02768
Uniprot Name
Serum albumin
Molecular Weight
69365.94 Da
References
  1. Ogata N, Shibata T: Binding of alkyl- and alkoxy-substituted simple phenolic compounds to human serum proteins. Res Commun Mol Pathol Pharmacol. 2000;107(1-2):167-73. [PubMed:11334365]

Drug created on December 03, 2015 09:52 / Updated on November 02, 2018 09:00