Bovine Metabolome Database: Showing metabocard for Guaiacol (BMDB0001398)

Identification Taxonomy Physical properties Pathways Spectra Concentrations Links References enzymes (1) Show 1 protein XML

Record Information

Version

1.0

Creation Date

2016-09-30 22:45:23 UTC

Update Date

2020-05-19 22:01:22 UTC

BMDB ID

BMDB0001398

Secondary Accession Numbers

BMDB01398

Metabolite Identification

Common Name

Guaiacol

Description

Guaiacol, 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

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
1-Hydroxy-2-methoxybenzene	ChEBI
2-Hydroxyanisole	ChEBI
Catechol monomethyl ether	ChEBI
O-Methoxyphenol	ChEBI
Creodon	Kegg
2-Methoxyphenol	HMDB
2-Methoxy-phenol	HMDB
Anastil	HMDB
Guaiacol (liquid) extra pure	HMDB
Guaiastil	HMDB
Guaicol	HMDB
Guaicolina	HMDB
Guajakol	HMDB
Guajol	HMDB
Guasol	HMDB
Guiacol	HMDB
Methoxyphenol	HMDB
Methylcatachol	HMDB
Methylcatechol	HMDB
O-Guaiacol	HMDB
O-Hydroxyanisole	HMDB
O-Methoxy-phenol	HMDB
O-Methyl catechol	HMDB
Pyrocatechol monomethyl ether	HMDB
Pyroguaiac acid	HMDB
2-Hydroxy-anisole	HMDB
Catechol, methyl	HMDB
Methyl catechol	HMDB
2-Methoxyl-4-vinylphenol	HMDB
Guaiacol	HMDB

Chemical Formula

C₇H₈O₂

Average Molecular Weight

124.139

Monoisotopic Molecular Weight

124.052429498

IUPAC Name

2-methoxyphenol

Traditional Name

guaiacol

CAS Registry Number

90-05-1

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 Key

LHGVFZTZFXWLCP-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.

Kingdom

Super Class

Class

Sub Class

Direct Parent

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 Framework

Aromatic homomonocyclic compounds

External Descriptors

phenols (CHEBI:28591 )
monomethoxybenzene (CHEBI:28591 )
a guaiacol (CPD-400 )

Ontology

Status

Expected but not Quantified

Origin

Endogenous

Biofunction

Not Available

Application

Not Available

Cellular locations

Cytoplasm
Mitochondria

Physical Properties

State

Solid

Experimental Properties

Property	Value	Reference
Melting Point	28 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	18.7 mg/mL at 15 °C	Not Available
LogP	1.32	HANSCH,C ET AL. (1995)

Predicted Properties

Property	Value	Source
logP	1.32	ALOGPS
logP	1.51	ChemAxon
logS	-0.27	ALOGPS
pKa (Strongest Acidic)	9.98	ChemAxon
pKa (Strongest Basic)	-4.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	29.46 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	34.5 m³·mol⁻¹	ChemAxon
Polarizability	12.69 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Spectra

Spectrum Type	Description	Splash Key
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0a4i-6900000000-49cb804087a42b1d1a22	View in MoNA
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0ab9-5900000000-b580cbc25d4176ce3894	View in MoNA
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0pir-9700000000-f1436b3de82cff342b65	View in MoNA
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-05fr-4900000000-c09a31d9523d2eab5598	View in MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-014i-0900000000-283fdedfda9e853e0cac	View in MoNA
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0a4i-6900000000-49cb804087a42b1d1a22	View in MoNA
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0ab9-5900000000-b580cbc25d4176ce3894	View in MoNA
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0pir-9700000000-f1436b3de82cff342b65	View in MoNA
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-05fr-4900000000-c09a31d9523d2eab5598	View in MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-014i-0900000000-283fdedfda9e853e0cac	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-00di-8900000000-562c1e6a4f3289578f75	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive	splash10-0fl0-7900000000-93aa107b2b3f584b3e44	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	View in JSpectraViewer
LC-MS/MS	LC-MS/MS Spectrum - EI-B (HITACHI RMU-6E) , Positive	splash10-0a4i-6900000000-49cb804087a42b1d1a22	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - EI-B (HITACHI RMU-6L) , Positive	splash10-0ab9-5900000000-b580cbc25d4176ce3894	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - EI-B (HITACHI M-80B) , Positive	splash10-0pir-9700000000-12606badb77d4257635d	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - n/a 8V, negative	splash10-0a4i-0900000000-053a1c4e865e710614d5	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-004i-0900000000-6b7a2fdf4e9a28ec6045	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-004i-2900000000-ff014b7b55a5237cf91e	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0udi-9100000000-8785b2e2d86c6294a754	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-00di-0900000000-8856c60866e810389af7	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-00di-1900000000-8db14d5e5710471f76a7	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4i-9400000000-bc0d3592d62ec26dad6f	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-004i-1900000000-7b4303f129d3e70a570e	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00kb-9100000000-3ec9cfe154e8a98b3596	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0w29-9000000000-ba9e4cd4adef59feb26e	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-00di-0900000000-ee9e9b8403f62cfc7fdf	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-00di-4900000000-d36c74cf39c4ddda0024	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0gbc-9000000000-1b43386dae7e3252cd81	View in MoNA
MS	Mass Spectrum (Electron Ionization)	splash10-0ac0-9800000000-5e89a9881e848e1b6c90	View in MoNA
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, experimental)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 400 MHz, CDCl₃, experimental)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 25.16 MHz, CDCl₃, experimental)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)	Not Available	View in JSpectraViewer

Biological Properties

Cellular Locations

Cytoplasm
Mitochondria

Biospecimen Locations

Not Available

Pathways

Name	SMPDB/Pathwhiz	KEGG
Tyrosine Metabolism		Not Available

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

External Links

HMDB ID

HMDB0001398

DrugBank ID

DB11359

Phenol Explorer Compound ID

FooDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Not Available

Wikipedia Link

Guaiacol

METLIN ID

6217

PubChem Compound

460

PDB ID

Not Available

ChEBI ID

28591

References

Synthesis Reference

Chen, 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 References

Not 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 + Pyrocatechol	details
Epinephrine + Guaiacol → Metanephrine + Pyrocatechol	details
3,4-Dihydroxyphenylglycol + Guaiacol → Vanylglycol + Pyrocatechol	details
3,4-Dihydroxymandelic acid + Guaiacol → Vanillylmandelic acid + Pyrocatechol	details
Dopamine + Guaiacol → 3-Methoxytyramine + Pyrocatechol	details
3,4-Dihydroxybenzeneacetic acid + Guaiacol → Homovanillic acid + Pyrocatechol	details

Showing metabocard for Guaiacol (BMDB0001398)

Structure for BMDB0001398 (Guaiacol)

Enzymes

Reactions