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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-12 00:19:59 UTC

Update Date

2023-02-21 17:26:50 UTC

HMDB ID

HMDB0038985

Secondary Accession Numbers

HMDB38985

Metabolite Identification

Common Name

3-Ethyl-5-methylphenol

Description

3-Ethyl-5-methylphenol belongs to the class of organic compounds known as meta cresols. These are aromatic compounds containing a meta-cresol moiety, which consists of a benzene ring bearing a methyl group and a hydroxyl group at ring positions 1 and 3, respectively. 3-Ethyl-5-methylphenol has been detected, but not quantified in, breakfast cereal and cereals and cereal products. This could make 3-ethyl-5-methylphenol a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on 3-Ethyl-5-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
1-Hydroxy-3-methyl-5-ethylbenzene	HMDB
3-Ethyl-5-methyl-phenol	HMDB
3-Methyl-5-ethylphenol	HMDB
5-Ethyl-m-cresol	HMDB
5-Ethyl-m-cresol, 8ci	HMDB
m-Cresol, 5-ethyl- (8ci)	HMDB
Phenol, 3-ethyl-5-methyl- (9ci)	HMDB

Chemical Formula

C₉H₁₂O

Average Molecular Weight

136.191

Monoisotopic Molecular Weight

136.088815006

IUPAC Name

3-ethyl-5-methylphenol

Traditional Name

3-ethyl-5-methylphenol

CAS Registry Number

698-71-5

SMILES

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

InChI Identifier

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

InChI Key

XTCHLXABLZQNNN-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as meta cresols. These are aromatic compounds containing a meta-cresol moiety, which consists of a benzene ring bearing a methyl group and a hydroxyl group at ring positions 1 and 3, respectively.

Kingdom

Super Class

Class

Sub Class

Direct Parent

Alternative Parents

Substituents

M-cresol
1-hydroxy-4-unsubstituted benzenoid
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: HMDB0038985)
Cell membrane (HMDB: HMDB0038985)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0038985)

Source

Exogenous

Exogenous (HMDB: HMDB0038985)

Food

Food (HMDB: HMDB0038985)

Cereal and cereal product

Cereal product

Breakfast cereal (FooDB: FOOD00270)

Cereals and cereal products (FooDB: FOOD00858)

Endogenous

Plant

Poaceae (HMDB: HMDB0038985)

Process

Not Available

Role

Biological role

Nutrient (HMDB: HMDB0038985)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	54 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	2.32 mg/mL at 25 °C	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	1.82 g/L	ALOGPS
logP	2.91	ALOGPS
logP	3.14	ChemAxon
logS	-1.9	ALOGPS
pKa (Strongest Acidic)	10.23	ChemAxon
pKa (Strongest Basic)	-5.5	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	15.98 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]+	130.223	31661259
DarkChem	[M-H]-	128.247	31661259
DeepCCS	[M+H]+	130.783	30932474
DeepCCS	[M-H]-	126.952	30932474
DeepCCS	[M-2H]-	164.198	30932474
DeepCCS	[M+Na]+	139.738	30932474
AllCCS	[M+H]+	125.9	32859911
AllCCS	[M+H-H2O]+	121.2	32859911
AllCCS	[M+NH4]+	130.3	32859911
AllCCS	[M+Na]+	131.6	32859911
AllCCS	[M-H]-	127.2	32859911
AllCCS	[M+Na-2H]-	128.9	32859911
AllCCS	[M+HCOO]-	130.8	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.	4.71 minutes	32390414
Predicted by Siyang on May 30, 2022	14.3175 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	3.63 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1724.3 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	491.7 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	191.3 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	324.6 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	308.6 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	626.2 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	610.6 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	105.7 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1209.4 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	489.5 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	1335.9 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	411.5 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	404.3 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	422.3 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	288.1 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	34.0 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
3-Ethyl-5-methylphenol	CCC1=CC(O)=CC(C)=C1	1925.4	Standard polar	33892256
3-Ethyl-5-methylphenol	CCC1=CC(O)=CC(C)=C1	1210.4	Standard non polar	33892256
3-Ethyl-5-methylphenol	CCC1=CC(O)=CC(C)=C1	1266.5	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
3-Ethyl-5-methylphenol,1TMS,isomer #1	CCC1=CC(C)=CC(O[Si](C)(C)C)=C1	1282.7	Semi standard non polar	33892256
3-Ethyl-5-methylphenol,1TBDMS,isomer #1	CCC1=CC(C)=CC(O[Si](C)(C)C(C)(C)C)=C1	1508.4	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - 3-Ethyl-5-methylphenol EI-B (Non-derivatized)	splash10-00dr-7900000000-80e62eab57b0f556d76d	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - 3-Ethyl-5-methylphenol EI-B (Non-derivatized)	splash10-00dr-7900000000-80e62eab57b0f556d76d	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3-Ethyl-5-methylphenol GC-MS (Non-derivatized) - 70eV, Positive	splash10-00dr-2900000000-4a41a8b4f8db4c19ad9c	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3-Ethyl-5-methylphenol GC-MS (1 TMS) - 70eV, Positive	splash10-006x-5900000000-35a11937235306d87ad3	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3-Ethyl-5-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 - 3-Ethyl-5-methylphenol 10V, Positive-QTOF	splash10-000i-0900000000-87c04c76e1a0ddad3723	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Ethyl-5-methylphenol 20V, Positive-QTOF	splash10-000i-3900000000-e9df6a7a926a18dca784	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Ethyl-5-methylphenol 40V, Positive-QTOF	splash10-0udl-9200000000-abe61868b33061d2064b	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Ethyl-5-methylphenol 10V, Negative-QTOF	splash10-000i-0900000000-cfcd2b5864d2130041b3	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Ethyl-5-methylphenol 20V, Negative-QTOF	splash10-000i-0900000000-4b210e2625f05c5628c7	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Ethyl-5-methylphenol 40V, Negative-QTOF	splash10-00kr-9800000000-3f569e16302635182ede	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Ethyl-5-methylphenol 10V, Negative-QTOF	splash10-000i-0900000000-3d153ee27562ca42735c	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Ethyl-5-methylphenol 20V, Negative-QTOF	splash10-000i-0900000000-9412b4e044a15d2566fb	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Ethyl-5-methylphenol 40V, Negative-QTOF	splash10-0006-9300000000-b51c7053f079fbcd8175	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Ethyl-5-methylphenol 10V, Positive-QTOF	splash10-000i-1900000000-8796ca63974eb7891302	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Ethyl-5-methylphenol 20V, Positive-QTOF	splash10-00mo-9500000000-ebf4633de1b16e252374	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Ethyl-5-methylphenol 40V, Positive-QTOF	splash10-00ou-9000000000-079babaf2e1226b8b248	2021-09-25	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

FDB018471

KNApSAcK ID

Not Available

Chemspider ID

12250

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

12775

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1043551

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 3-Ethyl-5-methylphenol (HMDB0038985)

MOL for HMDB0038985 (3-Ethyl-5-methylphenol)

3D MOL for HMDB0038985 (3-Ethyl-5-methylphenol)

3D SDF for HMDB0038985 (3-Ethyl-5-methylphenol)

3D-SDF for HMDB0038985 (3-Ethyl-5-methylphenol)

PDB for HMDB0038985 (3-Ethyl-5-methylphenol)

3D PDB for HMDB0038985 (3-Ethyl-5-methylphenol)

SMILES for HMDB0038985 (3-Ethyl-5-methylphenol)

INCHI for HMDB0038985 (3-Ethyl-5-methylphenol)

Structure for HMDB0038985 (3-Ethyl-5-methylphenol)

3D Structure for HMDB0038985 (3-Ethyl-5-methylphenol)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra