Showing Compound Card for Guajol (CDB000452)

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Record Information
Version1.0
Created at2020-03-19 00:37:42 UTC
Updated at2020-12-07 19:07:26 UTC
CannabisDB IDCDB000452
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common NameGuajol
DescriptionGuajol or Guaiacol, also known as 2-hydroxyanisole or 2-methoxyphenol, belongs to the class of organic compounds known as methoxyphenols. Methoxyphenols are compounds containing a methoxy group attached to the benzene ring of a phenol moiety. Guaiacol is a phenolic compound with a methoxy group and is the monomethyl ether of catechol. Guaiacol is a sweet, medicinal, and phenolic tasting compound. Guaiacol is found in the highest concentration within a few different foods, such as sesames, coffee, and white wines and in a lower concentration in peppermints. Guaiacol has also been detected, but not quantified in white mustards, peppers, red bell peppers, cherry tomato, turmerics, and Cannabis sativa ( Ref:DOI ). Guaiacol is also a constituent of cannabis smoke and is volatilized during the combustion of cannabis ( Ref:DOI ). Guaiacol is readily oxidized by the heme iron of peroxidases including the peroxidase of cyclooxygenase (COX) enzymes. It therefore serves as a reducing co-substrate for COX reactions. Guaiacol is a phenolic natural product first isolated from Guaiac resin and the oxidation of lignin. It is a yellowish aromatic oil that is now commonly derived from guaiacum or wood creosote. 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 (PMID: 16152729 ). Guaiacol is used in the preparation of synthetic vanillin. 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. (PMID 4344880 , 16152729 )
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
1-Hydroxy-2-methoxybenzeneChEBI
2-HydroxyanisoleChEBI
Catechol monomethyl etherChEBI
O-MethoxyphenolChEBI
CreodonKegg
2-MethoxyphenolHMDB
2-Methoxy-phenolHMDB
AnastilHMDB
Guaiacol (liquid) extra pureHMDB
GuaiastilHMDB
GuaicolHMDB
GuaicolinaHMDB
GuajakolHMDB
GuajolHMDB
GuasolHMDB
GuiacolHMDB
MethoxyphenolHMDB
MethylcatacholHMDB
MethylcatecholHMDB
O-GuaiacolHMDB
O-HydroxyanisoleHMDB
O-Methoxy-phenolHMDB
O-Methyl catecholHMDB
Pyrocatechol monomethyl etherHMDB
Pyroguaiac acidHMDB
2-Hydroxy-anisoleHMDB
Catechol, methylHMDB
Methyl catecholHMDB
2-Methoxyl-4-vinylphenolHMDB
GuaiacolHMDB
Chemical FormulaC7H8O2
Average Molecular Weight124.14
Monoisotopic Molecular Weight124.0524
IUPAC Name2-methoxyphenol
Traditional Nameguaiacol
CAS Registry Number8021-39-4
SMILES
COC1=CC=CC=C1O
InChI Identifier
InChI=1S/C7H8O2/c1-9-7-5-3-2-4-6(7)8/h2-5,8H,1H3
InChI KeyLHGVFZTZFXWLCP-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as methoxyphenols. Methoxyphenols are compounds containing a methoxy group attached to the benzene ring of a phenol moiety.
KingdomOrganic compounds
Super ClassBenzenoids
ClassPhenols
Sub ClassMethoxyphenols
Direct ParentMethoxyphenols
Alternative Parents
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
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

Biological location:

Source:

Role

Environmental role:

Industrial application:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point28 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility18.7 mg/mL at 15 °CNot Available
logP1.32HANSCH,C ET AL. (1995)
Predicted Properties
PropertyValueSource
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 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity34.5 m³·mol⁻¹ChemAxon
Polarizability12.69 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
EI-MSMass Spectrum (Electron Ionization)splash10-0ac0-9800000000-5e89a9881e848e1b6c902015-03-01View Spectrum
GC-MSGuajol, non-derivatized, GC-MS Spectrumsplash10-0a4i-6900000000-49cb804087a42b1d1a22Spectrum
GC-MSGuajol, non-derivatized, GC-MS Spectrumsplash10-0ab9-5900000000-b580cbc25d4176ce3894Spectrum
GC-MSGuajol, non-derivatized, GC-MS Spectrumsplash10-0pir-9700000000-f1436b3de82cff342b65Spectrum
GC-MSGuajol, non-derivatized, GC-MS Spectrumsplash10-05fr-4900000000-c09a31d9523d2eab5598Spectrum
GC-MSGuajol, non-derivatized, GC-MS Spectrumsplash10-014i-0900000000-283fdedfda9e853e0cacSpectrum
GC-MSGuajol, non-derivatized, GC-MS Spectrumsplash10-0a4i-6900000000-49cb804087a42b1d1a22Spectrum
GC-MSGuajol, non-derivatized, GC-MS Spectrumsplash10-0ab9-5900000000-b580cbc25d4176ce3894Spectrum
GC-MSGuajol, non-derivatized, GC-MS Spectrumsplash10-0pir-9700000000-f1436b3de82cff342b65Spectrum
GC-MSGuajol, non-derivatized, GC-MS Spectrumsplash10-05fr-4900000000-c09a31d9523d2eab5598Spectrum
GC-MSGuajol, non-derivatized, GC-MS Spectrumsplash10-014i-0900000000-283fdedfda9e853e0cacSpectrum
Predicted GC-MSGuajol, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-00di-8900000000-562c1e6a4f3289578f75Spectrum
Predicted GC-MSGuajol, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0fl0-7900000000-93aa107b2b3f584b3e44Spectrum
Predicted GC-MSGuajol, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - EI-B (HITACHI RMU-6E) , Positivesplash10-0a4i-6900000000-49cb804087a42b1d1a222012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - EI-B (HITACHI RMU-6L) , Positivesplash10-0ab9-5900000000-b580cbc25d4176ce38942012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - EI-B (HITACHI M-80B) , Positivesplash10-0pir-9700000000-12606badb77d4257635d2012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - n/a 8V, negativesplash10-0a4i-0900000000-053a1c4e865e710614d52020-07-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-0900000000-6b7a2fdf4e9a28ec60452015-04-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-004i-2900000000-ff014b7b55a5237cf91e2015-04-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0udi-9100000000-8785b2e2d86c6294a7542015-04-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-0900000000-8856c60866e810389af72015-04-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00di-1900000000-8db14d5e5710471f76a72015-04-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9400000000-bc0d3592d62ec26dad6f2015-04-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-1900000000-7b4303f129d3e70a570e2021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00kb-9100000000-3ec9cfe154e8a98b35962021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0w29-9000000000-ba9e4cd4adef59feb26e2021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-0900000000-ee9e9b8403f62cfc7fdf2021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00di-4900000000-d36c74cf39c4ddda00242021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0gbc-9000000000-1b43386dae7e3252cd812021-09-24View Spectrum
NMR
TypeDescriptionView
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, experimental)Spectrum
1D NMR1H NMR Spectrum (1D, 400 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, 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
1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)Spectrum
Pathways
Pathways
Protein Targets
Enzymes
Protein NameGene NameLocusUniprot IDDetails
Catechol O-methyltransferaseCOMT22q11.21P21964 details
Prostaglandin G/H synthase 1PTGS19q32-q33.3P23219 details
Transmembrane O-methyltransferaseLRTOMT11q13.4Q8WZ04 details
TransportersNot Available
Metal Bindings
Protein NameGene NameLocusUniprot IDDetails
Catechol O-methyltransferaseCOMT22q11.21P21964 details
Prostaglandin G/H synthase 1PTGS19q32-q33.3P23219 details
Receptors
Protein NameGene NameLocusUniprot IDDetails
Prostaglandin G/H synthase 1PTGS19q32-q33.3P23219 details
Transmembrane O-methyltransferaseLRTOMT11q13.4Q8WZ04 details
Transcriptional FactorsNot Available
Concentrations Data
Not Available
HMDB IDHMDB0001398
DrugBank IDDB11359
Phenol Explorer Compound ID650
FoodDB IDFDB011885
KNApSAcK IDC00029459
Chemspider ID447
KEGG Compound IDC15572
BioCyc IDCPD-400
BiGG IDNot Available
Wikipedia LinkGuaiacol
METLIN ID6217
PubChem Compound460
PDB IDNot Available
ChEBI ID28591
References
General References
  1. Rogers LE, Lyon GM Jr, Porter FS: Spot test for vanillylmandelic acid and other guaiacols in urine of patients with neuroblastoma. Am J Clin Pathol. 1972 Oct;58(4):383-7. doi: 10.1093/ajcp/58.5.383. [PubMed:4344880 ]
  2. Mimurai T, Yazaki K, Sawaki K, Ozawa T, Kawaguchi M: Hydroxyl radical scavenging effects of guaiacol used in traditional dental pulp sedation: reaction kinetic study. Biomed Res. 2005 Aug;26(4):139-45. doi: 10.2220/biomedres.26.139. [PubMed:16152729 ]
  3. Duffey SS, Aldrich JR, Blum MS: Biosynthesis of phenol and guaiacol by the hemipteran Leptoglossus phyllopus. Comp Biochem Physiol B. 1977;56(2):101-2. doi: 10.1016/0305-0491(77)90029-3. [PubMed:830476 ]
  4. Dorfner R, Ferge T, Kettrup A, Zimmermann R, Yeretzian C: Real-time monitoring of 4-vinylguaiacol, guaiacol, and phenol during coffee roasting by resonant laser ionization time-of-flight mass spectrometry. J Agric Food Chem. 2003 Sep 10;51(19):5768-73. doi: 10.1021/jf0341767. [PubMed:12952431 ]
  5. Rice S, Koziel JA: Characterizing the Smell of Marijuana by Odor Impact of Volatile Compounds: An Application of Simultaneous Chemical and Sensory Analysis. PLoS One. 2015 Dec 10;10(12):e0144160. doi: 10.1371/journal.pone.0144160. eCollection 2015. [PubMed:26657499 ]

Enzymes

Enzyme Details
1. Catechol O-methyltransferase
General function:
Involved in magnesium ion binding
Specific function:
Catalyzes the O-methylation, and thereby the inactivation, of catecholamine neurotransmitters and catechol hormones. Also shortens the biological half-lives of certain neuroactive drugs, like L-DOPA, alpha-methyl DOPA and isoproterenol.
Gene Name:
COMT
Uniprot ID:
P21964
Molecular weight:
30036.77
Enzyme Details
2. Prostaglandin G/H synthase 1
General function:
Involved in peroxidase activity
Specific function:
May play an important role in regulating or promoting cell proliferation in some normal and neoplastically transformed cells.
Gene Name:
PTGS1
Uniprot ID:
P23219
Molecular weight:
68685.82
Enzyme Details
3. Transmembrane O-methyltransferase
General function:
Involved in O-methyltransferase activity
Specific function:
Catalyzes the O-methylation, and thereby the inactivation, of catecholamine neurotransmitters and catechol hormones (By similarity). Required for auditory function.
Gene Name:
LRTOMT
Uniprot ID:
Q8WZ04
Molecular weight:
32154.43