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

2022-09-01 02:19:52 UTC

MiMeDB 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 SDF PDB SMILES InChI

Synonyms

Not Available

Chemical Formula

C₇H₈O₂

Average Molecular Weight

124.139

Monoisotopic Molecular Weight

124.052429498

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

Not Available

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

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Not Available

Spectra

Not Available

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

Proteins

#<MetaboliteProteinLink:0x000055b76df8f398>

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Related Health Condition	Evidence Type	Measured in Matrix	Data Source	Reference

Microbial Sources

Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
	Actinobacteria	2
Fungi	Basidiomycota	4	Human Feces
	Firmicutes	1	Human Feces
	Proteobacteria	1
Fungi	Ascomycota	2	Human Feces	; Unknown

Exposure Sources

Source Type	Source Sub-type	Species	Data Source	Reference	Details

Host Biospecimen and Location

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

External Links

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:0x000055b76ddad020>

3D MOL for #<Metabolite:0x000055b76ddad020>

3D SDF for #<Metabolite:0x000055b76ddad020>

3D-SDF for #<Metabolite:0x000055b76ddad020>

PDB for #<Metabolite:0x000055b76ddad020>

3D PDB for #<Metabolite:0x000055b76ddad020>

SMILES for #<Metabolite:0x000055b76ddad020>

INCHI for #<Metabolite:0x000055b76ddad020>

Structure for #<Metabolite:0x000055b76ddad020>

3D Structure for #<Metabolite:0x000055b76ddad020>