MiMeDB: Showing metabocard for Guaiacol (MMDBc0053306)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2022-05-16 21:20:22 UTC

Update Date

2024-09-28 00:38:52 UTC

Metabolite ID

MMDBc0053306

Metabolite Identification

Common Name

Guaiacol

Description

Guaiacol is a phenolic compound with a methoxy group and is the monomethyl ether of catechol. 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. Guaiacol is also 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

MOL 3D MOL SDF 3D SDF PDB 3D 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

Molecular Formula

C₇H₈O₂

Average Mass

124.139

Monoisotopic Mass

124.052429498

IUPAC Name

2-methoxyphenol

Traditional Name

guaiacol

CAS Registry Number

Not Available

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 )

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
Water Solubility	67.4 g/L	ALOGPS
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	No	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0a4i-6900000000-49cb804087a42b1d1a22	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0ab9-5900000000-b580cbc25d4176ce3894	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0pir-9700000000-f1436b3de82cff342b65	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-05fr-4900000000-c09a31d9523d2eab5598	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-014i-0900000000-283fdedfda9e853e0cac	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0a4i-6900000000-49cb804087a42b1d1a22	2018-05-18	View Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0ab9-5900000000-b580cbc25d4176ce3894	2018-05-18	View Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0pir-9700000000-f1436b3de82cff342b65	2018-05-18	View Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-05fr-4900000000-c09a31d9523d2eab5598	2018-05-18	View Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-014i-0900000000-283fdedfda9e853e0cac	2018-05-18	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-00di-8900000000-562c1e6a4f3289578f75	2016-09-22	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive	splash10-0fl0-7900000000-93aa107b2b3f584b3e44	2017-10-06	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - EI-B (HITACHI RMU-6E) , Positive	splash10-0a4i-6900000000-49cb804087a42b1d1a22	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - EI-B (HITACHI RMU-6L) , Positive	splash10-0ab9-5900000000-b580cbc25d4176ce3894	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - EI-B (HITACHI M-80B) , Positive	splash10-0pir-9700000000-12606badb77d4257635d	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - n/a 8V, negative	splash10-0a4i-0900000000-053a1c4e865e710614d5	2020-07-21	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-004i-0900000000-6b7a2fdf4e9a28ec6045	2015-04-24	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-004i-2900000000-ff014b7b55a5237cf91e	2015-04-24	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0udi-9100000000-8785b2e2d86c6294a754	2015-04-24	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-00di-0900000000-8856c60866e810389af7	2015-04-25	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-00di-1900000000-8db14d5e5710471f76a7	2015-04-25	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4i-9400000000-bc0d3592d62ec26dad6f	2015-04-25	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-004i-1900000000-7b4303f129d3e70a570e	2021-09-24	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00kb-9100000000-3ec9cfe154e8a98b3596	2021-09-24	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0w29-9000000000-ba9e4cd4adef59feb26e	2021-09-24	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-00di-0900000000-ee9e9b8403f62cfc7fdf	2021-09-24	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-00di-4900000000-d36c74cf39c4ddda0024	2021-09-24	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0gbc-9000000000-1b43386dae7e3252cd81	2021-09-24	View Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-0ac0-9800000000-5e89a9881e848e1b6c90	2015-03-01	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, experimental)		2012-12-04	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, CDCl₃, experimental)		2015-03-01	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 25.16 MHz, CDCl₃, experimental)		2015-03-12	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)		2021-09-16	View Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)		2012-12-05	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood
Urine

Tissue Locations

Not Available

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species
MMDBp0191942	Catechol O-methyltransferase	Unknown	P21964	Homo sapiens
MMDBp0195914	Transmembrane O-methyltransferase	Enzyme	Q8WZ04	Homo sapiens

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Bacteria	Actinobacteria	2
Eukaryota/Fungi	Basidiomycota	4	Human feces
Bacteria	Firmicutes	1	Human feces
Bacteria	Proteobacteria	1
Eukaryota/Fungi	Ascomycota	2	Human feces; Human saliva	Unknown

Exposure Sources

Source Type	Source Sub-type	Species	Data Source	Reference

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Min	Max	Units	Age	Sex	Health Condition	Data Source	Reference
Human Blood	Detected and Quantified	8.5	1.0			uM	Adult (>18 years old)	Both	Normal	HMDB	15598481
Human Urine	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	22284503

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

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

Pruitt KM, Kamau DN, Miller K, Mansson-Rahemtulla B, Rahemtulla F: Quantitative, standardized assays for determining the concentrations of bovine lactoperoxidase, human salivary peroxidase, and human myeloperoxidase. Anal Biochem. 1990 Dec;191(2):278-86. doi: 10.1016/0003-2697(90)90220-4. [PubMed:1964765 ]
Tsibris JC, Virgin SD, Khan-Dawood FS, Langenberg PW, Thomason JL, Spellacy WN: Cervicovaginal peroxidases: markers of the fertile period. Obstet Gynecol. 1986 Mar;67(3):316-20. [PubMed:3003635 ]
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 ]
Kupfer A, Lawson J, Branch RA: Stereoselectivity of the arene epoxide pathway of mephenytoin hydroxylation in man. Epilepsia. 1984 Feb;25(1):1-7. doi: 10.1111/j.1528-1157.1984.tb04148.x. [PubMed:6420144 ]
Mutlib AE, Klein JT: Application of liquid chromatography/mass spectrometry in accelerating the identification of human liver cytochrome P450 isoforms involved in the metabolism of iloperidone. J Pharmacol Exp Ther. 1998 Sep;286(3):1285-93. [PubMed:9732390 ]
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 ]
Bieniek G, Kurkiewicz S, Wilczok T, Klimek K, Swiatkowska L, Lusiak A: occupational exposure to aromatic hydrocarbons at a coke plant: Part II. Exposure assessment of volatile organic compounds. J Occup Health. 2004 May;46(3):181-6. doi: 10.1539/joh.46.181. [PubMed:15215658 ]
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 ]

Showing metabocard for Guaiacol (MMDBc0053306)

MOL for #<Metabolite:0x00007f46aeaeb2c0>

3D MOL for #<Metabolite:0x00007f46aeaeb2c0>

3D SDF for #<Metabolite:0x00007f46aeaeb2c0>

3D-SDF for #<Metabolite:0x00007f46aeaeb2c0>

PDB for #<Metabolite:0x00007f46aeaeb2c0>

3D PDB for #<Metabolite:0x00007f46aeaeb2c0>

SMILES for #<Metabolite:0x00007f46aeaeb2c0>

INCHI for #<Metabolite:0x00007f46aeaeb2c0>

Structure for #<Metabolite:0x00007f46aeaeb2c0>

3D Structure for #<Metabolite:0x00007f46aeaeb2c0>