Showing metabocard for Guaiacol (BMDB0001398)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesenzymes (1) Show 1 proteinXML
Record Information
Version1.0
Creation Date2016-09-30 22:45:23 UTC
Update Date2020-05-19 22:01:22 UTC
BMDB IDBMDB0001398
Secondary Accession Numbers
  • BMDB01398
Metabolite Identification
Common NameGuaiacol
DescriptionGuaiacol, also known as Guaiacol or Guaiacol, 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 exists as a solid, possibly soluble (in water), and an extremely weak basic (essentially neutral) compound (based on its pKa) molecule. Guaiacol exists in all living species, ranging from bacteria to humans. Guaiacol participates in a number of enzymatic reactions, within cattle. In particular, Norepinephrine and guaiacol can be converted into normetanephrine and pyrocatechol; which is mediated by the enzyme catechol O-methyltransferase. In addition, Epinephrine and guaiacol can be converted into metanephrine and pyrocatechol; which is mediated by the enzyme catechol O-methyltransferase. In cattle, guaiacol is involved in the metabolic pathway called the tyrosine metabolism pathway. Guaiacol is a potentially toxic compound.
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 Weight124.139
Monoisotopic Molecular Weight124.052429498
IUPAC Name2-methoxyphenol
Traditional Nameguaiacol
CAS Registry Number90-05-1
SMILES
COC1=C(O)C=CC=C1
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
StatusExpected but not Quantified
Origin
  • Endogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cytoplasm
  • Mitochondria
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 FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Biological Properties
Cellular Locations
  • Cytoplasm
  • Mitochondria
Biospecimen LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
HMDB IDHMDB0001398
DrugBank IDDB11359
Phenol Explorer Compound ID650
FooDB 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
Synthesis ReferenceChen, Jiehua; Xu, Baocai; Zhang, Hong; Ye, Jianfeng. Method for preparing guaiacol from catechol and dimethyl carbonate. Faming Zhuanli Shenqing Gongkai Shuomingshu (2007), 6pp.
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

Enzyme Details
1. Catechol O-methyltransferase
General function:
Involved in catechol O-methyltransferase activity
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 (By similarity).
Gene Name:
COMT
Uniprot ID:
A7MBI7
Molecular weight:
30485.0
Reactions
Norepinephrine + Guaiacol → Normetanephrine + Pyrocatecholdetails
Epinephrine + Guaiacol → Metanephrine + Pyrocatecholdetails
3,4-Dihydroxyphenylglycol + Guaiacol → Vanylglycol + Pyrocatecholdetails
3,4-Dihydroxymandelic acid + Guaiacol → Vanillylmandelic acid + Pyrocatecholdetails
Dopamine + Guaiacol → 3-Methoxytyramine + Pyrocatecholdetails
3,4-Dihydroxybenzeneacetic acid + Guaiacol → Homovanillic acid + Pyrocatecholdetails