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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2012-09-11 17:48:04 UTC

Update Date

2023-02-21 17:21:38 UTC

HMDB ID

HMDB0032136

Secondary Accession Numbers

HMDB32136

Metabolite Identification

Common Name

2-Methoxy-4-methylphenol

Description

2-Methoxy-4-methylphenol, also known as 4-methylguaiacol or creosol, 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. Creosol reacts with hydrogen halides to give a catechol. Compared with phenol, creosol is a less toxic disinfectant. It is one of the components of creosote. 2-Methoxy-4-methylphenol is a bacon, bitter, and carnation tasting compound. 2-Methoxy-4-methylphenol has been detected, but not quantified, in several different foods, such as red bell peppers, green bell peppers, orange bell peppers, corns, and pepper (c. annuum). Sources of creosol include: Coal tar, creosote Wood, creosoteReduction product of vanillin using zinc powder in strong hydrochloric acidFound as glycosides in green vanilla beans. It is also found in tequila.

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
4-Methylguaiacol	MeSH
Creosol	MeSH
1-Hydroxy-2-methoxy-4-methylbenzene	HMDB
2-Hydroxy-5-methylanisole	HMDB
2-Methoxy-4-cresol	HMDB
2-Methoxy-4-methyl-phenol	HMDB
2-Methoxy-4-methylphenol (4-methylguaiacol)	HMDB
2-Methoxy-4-methylphenol (creosol)	HMDB
2-Methoxy-4-methylphenol, 9ci	HMDB
2-Methoxy-P-cresol	HMDB
3-Methoxy-4-hydroxytoluene	HMDB
3-Methoxy-4-methyl-phenol	HMDB
4-Hydroxy-3-methoxy-1-methylbenzene	HMDB
4-Hydroxy-3-methoxytoluene	HMDB
4-Methyl guaiacol	HMDB
4-Methyl-2-methoxyphenol	HMDB
4-Methyl-2-methoxyphenol (4-methylguaiacol)	HMDB
5-Methylguaiacol	HMDB
Cresolum drudum	HMDB
FEMA 2671	HMDB
Homocatechol methyl ester	HMDB
Homocatechol monomethyl ether	HMDB
Homoguaiacol	HMDB
Kreosol	HMDB
P-Creosol	HMDB
P-Methylguaiacol	HMDB
P-Methylguaicol	HMDB
Phenol, 4-methyl-2-methoxy	HMDB
Rohkcrsol	HMDB
Valspice	HMDB

Chemical Formula

C₈H₁₀O₂

Average Molecular Weight

138.1638

Monoisotopic Molecular Weight

138.068079564

IUPAC Name

2-methoxy-4-methylphenol

Traditional Name

creosol

CAS Registry Number

93-51-6

SMILES

COC1=C(O)C=CC(C)=C1

InChI Identifier

InChI=1S/C8H10O2/c1-6-3-4-7(9)8(5-6)10-2/h3-5,9H,1-2H3

InChI Key

PETRWTHZSKVLRE-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
P-cresol
Anisole
1-hydroxy-2-unsubstituted benzenoid
Toluene
Alkyl aryl ether
Monocyclic benzene moiety
Ether
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

Not Available

Ontology

Bitter

Feces (PMID: 17314143)

Cellular substructure

Extracellular (HMDB: HMDB0032136)
Cytoplasm (HMDB: HMDB0032136)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0032136)

Source

Endogenous

Endogenous (HMDB: HMDB0032136)

Plant

Plant (HMDB: HMDB0032136)
Poaceae (HMDB: HMDB0032136)

Exogenous

Food

Food (HMDB: HMDB0032136)

Beverage

Fermented beverage

White wine (FooDB: FOOD00917)

Cereal and cereal product

Cereal

Corn (FooDB: FOOD00205)

Anise (FooDB: FOOD00137)

Exogenous (HMDB: HMDB0032136)

Process

Not Available

Role

Industrial application

Food and nutrition

Food additive

Flavoring agent

Flavoring Agent (HMDB: HMDB0032136)

Physical Properties

State

Liquid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	5.5 °C	Not Available
Boiling Point	221.00 to 222.00 °C. @ 760.00 mm Hg	The Good Scents Company Information System
Water Solubility	2093 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	1.925 (est)	The Good Scents Company Information System

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	6.71 g/L	ALOGPS
logP	1.79	ALOGPS
logP	2.03	ChemAxon
logS	-1.3	ALOGPS
pKa (Strongest Acidic)	10.34	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	39.54 m³·mol⁻¹	ChemAxon
Polarizability	14.77 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]+	129.829	31661259
DarkChem	[M-H]-	127.139	31661259
DeepCCS	[M+H]+	130.373	30932474
DeepCCS	[M-H]-	126.541	30932474
DeepCCS	[M-2H]-	163.764	30932474
DeepCCS	[M+Na]+	139.304	30932474
AllCCS	[M+H]+	126.8	32859911
AllCCS	[M+H-H2O]+	122.1	32859911
AllCCS	[M+NH4]+	131.2	32859911
AllCCS	[M+Na]+	132.5	32859911
AllCCS	[M-H]-	125.1	32859911
AllCCS	[M+Na-2H]-	126.8	32859911
AllCCS	[M+HCOO]-	128.7	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
2-Methoxy-4-methylphenol	COC1=C(O)C=CC(C)=C1	1940.5	Standard polar	33892256
2-Methoxy-4-methylphenol	COC1=C(O)C=CC(C)=C1	1159.5	Standard non polar	33892256
2-Methoxy-4-methylphenol	COC1=C(O)C=CC(C)=C1	1197.6	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
2-Methoxy-4-methylphenol,1TMS,isomer #1	COC1=CC(C)=CC=C1O[Si](C)(C)C	1297.3	Semi standard non polar	33892256
2-Methoxy-4-methylphenol,1TBDMS,isomer #1	COC1=CC(C)=CC=C1O[Si](C)(C)C(C)(C)C	1549.1	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - 2-Methoxy-4-methylphenol EI-B (Non-derivatized)	splash10-0079-8900000000-c42e8911b7e5bb460b86	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - 2-Methoxy-4-methylphenol EI-B (Non-derivatized)	splash10-0079-8900000000-c42e8911b7e5bb460b86	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2-Methoxy-4-methylphenol GC-MS (Non-derivatized) - 70eV, Positive	splash10-0079-2900000000-15a46b79f8391d6c6966	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2-Methoxy-4-methylphenol GC-MS (1 TMS) - 70eV, Positive	splash10-0072-5910000000-30cf6b8fe2b454aa0a7f	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2-Methoxy-4-methylphenol GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2-Methoxy-4-methylphenol GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-0079-9800000000-79f6c5643ac065193b94	2015-03-01	Not Available	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Methoxy-4-methylphenol 10V, Positive-QTOF	splash10-000i-0900000000-d79622f054761511961f	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Methoxy-4-methylphenol 20V, Positive-QTOF	splash10-000i-1900000000-186bb7a1a13b13310f72	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Methoxy-4-methylphenol 40V, Positive-QTOF	splash10-1000-9300000000-8f2b34f63ad1fd835b6e	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Methoxy-4-methylphenol 10V, Negative-QTOF	splash10-000i-0900000000-df50a00e5dc8e9a1f2ec	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Methoxy-4-methylphenol 20V, Negative-QTOF	splash10-000i-0900000000-41c1e559c847063fb1e4	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Methoxy-4-methylphenol 40V, Negative-QTOF	splash10-05fr-9600000000-7e3c4dbc7d1fd009db5b	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Methoxy-4-methylphenol 10V, Positive-QTOF	splash10-0a4i-1900000000-3649f7c79a19e4bc82a9	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Methoxy-4-methylphenol 20V, Positive-QTOF	splash10-0ar0-9500000000-1a0f4d510ef798661ce1	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Methoxy-4-methylphenol 40V, Positive-QTOF	splash10-014i-9000000000-fab9fd9e596db561d31e	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Methoxy-4-methylphenol 10V, Negative-QTOF	splash10-000i-0900000000-08ef9d705ca98ce39abf	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Methoxy-4-methylphenol 20V, Negative-QTOF	splash10-00dr-2900000000-09cc2771d42e461513a0	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Methoxy-4-methylphenol 40V, Negative-QTOF	splash10-014l-9000000000-7718ec98bccb51b6db7a	2021-09-24	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	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]-)	2023-02-04	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)	2023-02-04	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)	2023-02-04	FELIX lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Extracellular

Biospecimen Locations

Feces

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

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

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB008862

KNApSAcK ID

Not Available

Chemspider ID

21105936

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Creosol

METLIN ID

Not Available

PubChem Compound

7144

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1020341

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Showing metabocard for 2-Methoxy-4-methylphenol (HMDB0032136)

MOL for HMDB0032136 (2-Methoxy-4-methylphenol)

3D MOL for HMDB0032136 (2-Methoxy-4-methylphenol)

3D SDF for HMDB0032136 (2-Methoxy-4-methylphenol)

3D-SDF for HMDB0032136 (2-Methoxy-4-methylphenol)

PDB for HMDB0032136 (2-Methoxy-4-methylphenol)

3D PDB for HMDB0032136 (2-Methoxy-4-methylphenol)

SMILES for HMDB0032136 (2-Methoxy-4-methylphenol)

INCHI for HMDB0032136 (2-Methoxy-4-methylphenol)

Structure for HMDB0032136 (2-Methoxy-4-methylphenol)

3D Structure for HMDB0032136 (2-Methoxy-4-methylphenol)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra