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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-12 00:19:54 UTC

Update Date

2023-02-21 17:26:49 UTC

HMDB ID

HMDB0038984

Secondary Accession Numbers

HMDB38984

Metabolite Identification

Common Name

4-Ethyl-2-methylphenol

Description

4-Ethyl-2-methylphenol belongs to the class of organic compounds known as ortho cresols. These are organic compounds containing an ortho-cresol moiety, which consists of a benzene bearing one hydroxyl group at ring positions 1 and 2, respectively. 4-Ethyl-2-methylphenol has been detected, but not quantified in, a few different foods, such as arabica coffees (Coffea arabica), coffee and coffee products, and robusta coffees (Coffea canephora). This could make 4-ethyl-2-methylphenol a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on 4-Ethyl-2-methylphenol.

Structure

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

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
2-Methyl-4-ethylphenol	HMDB
4-Ethyl-2-methyl-phenol	HMDB
4-Ethyl-O-cresol	HMDB
4-Ethyl-O-cresol, 8ci	HMDB

Chemical Formula

C₉H₁₂O

Average Molecular Weight

136.191

Monoisotopic Molecular Weight

136.088815006

IUPAC Name

4-ethyl-2-methylphenol

Traditional Name

4-ethyl-2-methylphenol

CAS Registry Number

2219-73-0

SMILES

CCC1=CC=C(O)C(C)=C1

InChI Identifier

InChI=1S/C9H12O/c1-3-8-4-5-9(10)7(2)6-8/h4-6,10H,3H2,1-2H3

InChI Key

QDQMEHXIUFCIGR-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as ortho cresols. These are organic compounds containing an ortho-cresol moiety, which consists of a benzene bearing one hydroxyl group at ring positions 1 and 2, respectively.

Kingdom

Super Class

Class

Sub Class

Direct Parent

Alternative Parents

Substituents

O-cresol
1-hydroxy-2-unsubstituted benzenoid
Toluene
Monocyclic benzene moiety
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Membrane (HMDB: HMDB0038984)
Cell membrane (HMDB: HMDB0038984)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0038984)

Source

Exogenous

Food

Food (HMDB: HMDB0038984)

Coffee and coffee product

Coffee

Arabica coffee (FooDB: FOOD00059)
Robusta coffee (FooDB: FOOD00060)

Coffee and coffee products (FooDB: FOOD00861)

Endogenous

Plant

Coffea (HMDB: HMDB0038984)

Process

Not Available

Role

Biological role

Nutrient (HMDB: HMDB0038984)

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	223.00 °C. @ 760.00 mm Hg (est)	The Good Scents Company Information System
Water Solubility	745.7 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	3.006 (est)	The Good Scents Company Information System

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	1.77 g/L	ALOGPS
logP	2.91	ALOGPS
logP	3.14	ChemAxon
logS	-1.9	ALOGPS
pKa (Strongest Acidic)	10.68	ChemAxon
pKa (Strongest Basic)	-5.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	20.23 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	42.72 m³·mol⁻¹	ChemAxon
Polarizability	15.91 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]+	129.825	31661259
DarkChem	[M-H]-	128.57	31661259
DeepCCS	[M+H]+	129.928	30932474
DeepCCS	[M-H]-	126.096	30932474
DeepCCS	[M-2H]-	163.316	30932474
DeepCCS	[M+Na]+	138.856	30932474
AllCCS	[M+H]+	126.7	32859911
AllCCS	[M+H-H2O]+	121.9	32859911
AllCCS	[M+NH4]+	131.1	32859911
AllCCS	[M+Na]+	132.3	32859911
AllCCS	[M-H]-	128.3	32859911
AllCCS	[M+Na-2H]-	130.0	32859911
AllCCS	[M+HCOO]-	132.0	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
4-Ethyl-2-methylphenol	CCC1=CC=C(O)C(C)=C1	2102.5	Standard polar	33892256
4-Ethyl-2-methylphenol	CCC1=CC=C(O)C(C)=C1	1180.3	Standard non polar	33892256
4-Ethyl-2-methylphenol	CCC1=CC=C(O)C(C)=C1	1258.7	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
4-Ethyl-2-methylphenol,1TMS,isomer #1	CCC1=CC=C(O[Si](C)(C)C)C(C)=C1	1287.2	Semi standard non polar	33892256
4-Ethyl-2-methylphenol,1TBDMS,isomer #1	CCC1=CC=C(O[Si](C)(C)C(C)(C)C)C(C)=C1	1535.3	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - 4-Ethyl-2-methylphenol EI-B (Non-derivatized)	splash10-00di-2900000000-24b0d5f4681821d3e156	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - 4-Ethyl-2-methylphenol EI-B (Non-derivatized)	splash10-00di-2900000000-24b0d5f4681821d3e156	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 4-Ethyl-2-methylphenol GC-MS (Non-derivatized) - 70eV, Positive	splash10-059i-2900000000-4573f4e3365a1901802f	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 4-Ethyl-2-methylphenol GC-MS (1 TMS) - 70eV, Positive	splash10-006x-6900000000-306058ff2fbd2fae0932	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 4-Ethyl-2-methylphenol GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Ethyl-2-methylphenol 10V, Positive-QTOF	splash10-000i-0900000000-b85dd702ac90fb9ff257	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Ethyl-2-methylphenol 20V, Positive-QTOF	splash10-000i-3900000000-7d4166d587a3f3051852	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Ethyl-2-methylphenol 40V, Positive-QTOF	splash10-0v00-9200000000-81ebb2aa5d538a68a898	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Ethyl-2-methylphenol 10V, Negative-QTOF	splash10-000i-0900000000-bef6b7b29fcca75a2d61	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Ethyl-2-methylphenol 20V, Negative-QTOF	splash10-000i-0900000000-ba57fd6314e5cf13074f	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Ethyl-2-methylphenol 40V, Negative-QTOF	splash10-0670-6900000000-3d7a958c6eb6a7fc616e	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Ethyl-2-methylphenol 10V, Negative-QTOF	splash10-000i-0900000000-3d153ee27562ca42735c	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Ethyl-2-methylphenol 20V, Negative-QTOF	splash10-000i-0900000000-67938e2abf4f421366c2	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Ethyl-2-methylphenol 40V, Negative-QTOF	splash10-014i-9700000000-5e312e4451e16075c03f	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Ethyl-2-methylphenol 10V, Positive-QTOF	splash10-000i-0900000000-d9ecf8c64d69f1282b98	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Ethyl-2-methylphenol 20V, Positive-QTOF	splash10-0573-9800000000-76e7f7e4f975b90f56cb	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Ethyl-2-methylphenol 40V, Positive-QTOF	splash10-00or-9000000000-d276f9def5c2f57948a9	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)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-24	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

Membrane

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

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

FDB018470

KNApSAcK ID

Not Available

Chemspider ID

32079

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

34857

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1559241

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 4-Ethyl-2-methylphenol (HMDB0038984)

MOL for HMDB0038984 (4-Ethyl-2-methylphenol)

3D MOL for HMDB0038984 (4-Ethyl-2-methylphenol)

3D SDF for HMDB0038984 (4-Ethyl-2-methylphenol)

3D-SDF for HMDB0038984 (4-Ethyl-2-methylphenol)

PDB for HMDB0038984 (4-Ethyl-2-methylphenol)

3D PDB for HMDB0038984 (4-Ethyl-2-methylphenol)

SMILES for HMDB0038984 (4-Ethyl-2-methylphenol)

INCHI for HMDB0038984 (4-Ethyl-2-methylphenol)

Structure for HMDB0038984 (4-Ethyl-2-methylphenol)

3D Structure for HMDB0038984 (4-Ethyl-2-methylphenol)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra