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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (2) Show 2 proteins XML

Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2005-11-16 15:48:42 UTC

Update Date

2023-02-21 17:15:40 UTC

HMDB ID

HMDB0001398

Secondary Accession Numbers

HMDB01398

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

View in JSmol View NMR Assignments View Stereo Labels

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

Sweet

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 15598481)

Excreta

Biofluid or Excreta

Urine (PMID: 22284503)
Feces (PMID: 17314143)

Cellular substructure

Cytoplasm (HMDB: HMDB0001398)
Extracellular (HMDB: HMDB0001398)

Source

Exogenous

Exogenous (HMDB: HMDB0001398)

Food

Beverage

Fermented beverage

Beer (FooDB: FOOD00268)
White wine (FooDB: FOOD00917)

Vegetable

Shoot vegetable

Asparagus (FooDB: FOOD00021)

Fruit vegetable

Stalk vegetable

Celery stalks (FooDB: FOOD00215)

Herb and spice

Spice

Oilseed crop

Sesame (FooDB: FOOD00170)

Herb

Peppermint (FooDB: FOOD00113)

Coffee and coffee product

Coffee

Cereal and cereal product

Cereal

Corn (FooDB: FOOD00205)

Fruit

Other fruit

Fig (FooDB: FOOD00081)

Berry

Evergreen blackberry (FooDB: FOOD00901)
Blackberry (FooDB: FOOD00906)

Tea

Snack

Tortilla chip (FooDB: FOOD00721)

Pulse

Pulses (FooDB: FOOD00867)

Milk and milk product

Milk and milk products (FooDB: FOOD00863)

Endogenous

Endogenous (HMDB: HMDB0001398)

Process

Naturally occurring process

Biological process

Biochemical pathway

Metabolic pathway

Tyrosine Metabolism (PathBank: SMP0087328)

Disease pathway

Tyrosinemia, Transient, of the Newborn (PathBank: SMP0120779)
Hawkinsinuria (PathBank: SMP0120711)
Tyrosinemia Type I (PathBank: SMP0120729)
Alkaptonuria (PathBank: SMP0120453)
Dopamine beta-Hydroxylase Deficiency (PathBank: SMP0120563)
Monoamine Oxidase-A Deficiency (MAO-A) (PathBank: SMP0120817)

Drug action pathway

Disulfiram Action Pathway (PathBank: SMP0000429)

Role

Industrial application

Pharmaceutical industry

Antimicrobial agent

Disinfectant (HMDB: HMDB0001398)

Manufacturing industry

Material processing agent

Coloring agent

Fluorescent agent

Expectorant (HMDB: HMDB0001398)

Food and nutrition

Food additive

Flavoring agent

Flavor (HMDB: HMDB0001398)

Agriculture

Pesticide (HMDB: HMDB0001398)

Biological role

Plant metabolite (HMDB: HMDB0001398)
Prostaglandin synthesis inhibitor (HMDB: HMDB0001398)
Anesthetic (HMDB: HMDB0001398)
Anti bacterial (HMDB: HMDB0001398)
Anti dermatitic (HMDB: HMDB0001398)
Anti eczemic (HMDB: HMDB0001398)
Anti esophagitic (HMDB: HMDB0001398)
Anti septic (HMDB: HMDB0001398)
Anti tuberculic (HMDB: HMDB0001398)
Cardiodepressant (HMDB: HMDB0001398)
Cardiotonic (HMDB: HMDB0001398)
Dermal (HMDB: HMDB0001398)
Emetic (HMDB: HMDB0001398)
Insectifuge (HMDB: HMDB0001398)
Irritant (HMDB: HMDB0001398)
Transdermal (HMDB: HMDB0001398)

Modulator

Inhibitor

EC 1.1.1.25 (shikimate dehydrogenase) inhibitor (HMDB: HMDB0001398)

Physical Properties

State

Solid

Experimental Molecular 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)

Experimental Chromatographic Properties

Not Available

Predicted Molecular 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

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	125.181	31661259
DarkChem	[M-H]-	122.475	31661259
DarkChem	[M+H]+	125.181	31661259
DarkChem	[M-H]-	122.475	31661259
AllCCS	[M+H]+	125.447	32859911
AllCCS	[M-H]-	122.088	32859911
DeepCCS	[M+H]+	126.607	30932474
DeepCCS	[M-H]-	123.189	30932474
DeepCCS	[M-2H]-	160.472	30932474
DeepCCS	[M+Na]+	135.53	30932474
AllCCS	[M+H]+	125.4	32859911
AllCCS	[M+H-H2O]+	120.6	32859911
AllCCS	[M+NH4]+	130.0	32859911
AllCCS	[M+Na]+	131.3	32859911
AllCCS	[M-H]-	122.1	32859911
AllCCS	[M+Na-2H]-	124.2	32859911
AllCCS	[M+HCOO]-	126.5	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	2.76 minutes	32390414
Predicted by Siyang on May 30, 2022	10.9294 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	2.63 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1471.3 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	378.9 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	139.8 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	238.0 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	207.4 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	471.5 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	436.0 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	150.4 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	972.9 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	342.8 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	955.1 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	295.1 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	384.3 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	502.0 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	308.4 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	110.1 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Guaiacol	COC1=C(O)C=CC=C1	1765.6	Standard polar	33892256
Guaiacol	COC1=C(O)C=CC=C1	1047.9	Standard non polar	33892256
Guaiacol	COC1=C(O)C=CC=C1	1102.7	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Guaiacol,1TMS,isomer #1	COC1=CC=CC=C1O[Si](C)(C)C	1225.1	Semi standard non polar	33892256
Guaiacol,1TBDMS,isomer #1	COC1=CC=CC=C1O[Si](C)(C)C(C)(C)C	1463.5	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - Guaiacol EI-B (Non-derivatized)	splash10-0a4i-6900000000-49cb804087a42b1d1a22	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Guaiacol EI-B (Non-derivatized)	splash10-0ab9-5900000000-b580cbc25d4176ce3894	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Guaiacol EI-B (Non-derivatized)	splash10-0pir-9700000000-f1436b3de82cff342b65	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Guaiacol EI-B (Non-derivatized)	splash10-05fr-4900000000-c09a31d9523d2eab5598	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Guaiacol GC-EI-TOF (Non-derivatized)	splash10-014i-0900000000-283fdedfda9e853e0cac	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Guaiacol EI-B (Non-derivatized)	splash10-0a4i-6900000000-49cb804087a42b1d1a22	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Guaiacol EI-B (Non-derivatized)	splash10-0ab9-5900000000-b580cbc25d4176ce3894	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Guaiacol EI-B (Non-derivatized)	splash10-0pir-9700000000-f1436b3de82cff342b65	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Guaiacol EI-B (Non-derivatized)	splash10-05fr-4900000000-c09a31d9523d2eab5598	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Guaiacol GC-EI-TOF (Non-derivatized)	splash10-014i-0900000000-283fdedfda9e853e0cac	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Guaiacol GC-MS (Non-derivatized) - 70eV, Positive	splash10-00di-8900000000-562c1e6a4f3289578f75	2016-09-22	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Guaiacol GC-MS (1 TMS) - 70eV, Positive	splash10-0fl0-7900000000-93aa107b2b3f584b3e44	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Guaiacol GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-0ac0-9800000000-5e89a9881e848e1b6c90	2015-03-01	Not Available	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - Guaiacol EI-B (HITACHI RMU-6E) , Positive-QTOF	splash10-0a4i-6900000000-49cb804087a42b1d1a22	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Guaiacol EI-B (HITACHI RMU-6L) , Positive-QTOF	splash10-0ab9-5900000000-b580cbc25d4176ce3894	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Guaiacol EI-B (HITACHI M-80B) , Positive-QTOF	splash10-0pir-9700000000-12606badb77d4257635d	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Guaiacol n/a 8V, negative-QTOF	splash10-0a4i-0900000000-053a1c4e865e710614d5	2020-07-21	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Guaiacol 10V, Positive-QTOF	splash10-004i-0900000000-6b7a2fdf4e9a28ec6045	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Guaiacol 20V, Positive-QTOF	splash10-004i-2900000000-ff014b7b55a5237cf91e	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Guaiacol 40V, Positive-QTOF	splash10-0udi-9100000000-8785b2e2d86c6294a754	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Guaiacol 10V, Negative-QTOF	splash10-00di-0900000000-8856c60866e810389af7	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Guaiacol 20V, Negative-QTOF	splash10-00di-1900000000-8db14d5e5710471f76a7	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Guaiacol 40V, Negative-QTOF	splash10-0a4i-9400000000-bc0d3592d62ec26dad6f	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Guaiacol 10V, Positive-QTOF	splash10-004i-1900000000-7b4303f129d3e70a570e	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Guaiacol 20V, Positive-QTOF	splash10-00kb-9100000000-3ec9cfe154e8a98b3596	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Guaiacol 40V, Positive-QTOF	splash10-0w29-9000000000-ba9e4cd4adef59feb26e	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Guaiacol 10V, Negative-QTOF	splash10-00di-0900000000-ee9e9b8403f62cfc7fdf	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Guaiacol 20V, Negative-QTOF	splash10-00di-4900000000-d36c74cf39c4ddda0024	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Guaiacol 40V, Negative-QTOF	splash10-0gbc-9000000000-1b43386dae7e3252cd81	2021-09-24	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Experimental 1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, experimental)	2012-12-04	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Experimental 2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)	2012-12-05	Wishart Lab	View Spectrum

IR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-)	2023-02-03	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)	2023-02-03	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)	2023-02-03	FELIX lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood
Feces
Urine

Tissue Locations

Not Available

Pathways

Name	SMPDB/PathBank	KEGG
Tyrosine metabolism	Not Available
Alkaptonuria		Not Available
Hawkinsinuria		Not Available
Tyrosinemia Type I		Not Available
Tyrosinemia, transient, of the newborn		Not Available

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	8.5 +/- 1.0 uM	Adult (>18 years old)	Both	Normal	15598481	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	22284503	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Clostridium difficile infection	17314143	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Intestinal infections	14684577	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Breast cancer	22284503	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Bladder cancer	28157703	details

Associated Disorders and Diseases

Disease References

Enteritis
Probert CS, Jones PR, Ratcliffe NM: A novel method for rapidly diagnosing the causes of diarrhoea. Gut. 2004 Jan;53(1):58-61. [PubMed:14684577 ]
Perillyl alcohol administration for cancer treatment
Silva CL, Passos M, Camara JS: Solid phase microextraction, mass spectrometry and metabolomic approaches for detection of potential urinary cancer biomarkers--a powerful strategy for breast cancer diagnosis. Talanta. 2012 Jan 30;89:360-8. doi: 10.1016/j.talanta.2011.12.041. Epub 2011 Dec 22. [PubMed:22284503 ]

Associated OMIM IDs

None

External Links

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

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

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)

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General References

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 ]
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. [PubMed:15215658 ]
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 ]
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 ]
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. [PubMed:4344880 ]
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. [PubMed:1964765 ]
Kupfer A, Lawson J, Branch RA: Stereoselectivity of the arene epoxide pathway of mephenytoin hydroxylation in man. Epilepsia. 1984 Feb;25(1):1-7. [PubMed:6420144 ]
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. [PubMed:16152729 ]

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

Reactions

Pyrocatechol → Guaiacol	details

Enzyme Details

2. 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

Showing metabocard for Guaiacol (HMDB0001398)

MOL for HMDB0001398 (Guaiacol)

3D MOL for HMDB0001398 (Guaiacol)

3D SDF for HMDB0001398 (Guaiacol)

3D-SDF for HMDB0001398 (Guaiacol)

PDB for HMDB0001398 (Guaiacol)

3D PDB for HMDB0001398 (Guaiacol)

SMILES for HMDB0001398 (Guaiacol)

INCHI for HMDB0001398 (Guaiacol)

Structure for HMDB0001398 (Guaiacol)

3D Structure for HMDB0001398 (Guaiacol)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra

Enzymes

Reactions