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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

Expected but not Quantified

Creation Date

2012-09-12 01:43:04 UTC

Update Date

2023-02-21 17:27:49 UTC

HMDB ID

HMDB0040175

Secondary Accession Numbers

HMDB40175

Metabolite Identification

Common Name

4-Ethyl-2-methoxyphenol

Description

4-Ethyl-2-methoxyphenol 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. 4-Ethyl-2-methoxyphenol is a bacon, clove, and phenolic tasting compound. 4-Ethyl-2-methoxyphenol is found, on average, in the highest concentration within a few different foods, such as red wine, robusta coffees (Coffea canephora), and coffees (Coffea) and in a lower concentration in arabica coffees (Coffea arabica). 4-Ethyl-2-methoxyphenol has also been detected, but not quantified in, several different foods, such as beer, chinese cinnamons (Cinnamomum aromaticum), red bell peppers (Capsicum annuum), yellow bell peppers (Capsicum annuum), and green tea. This could make 4-ethyl-2-methoxyphenol a potential biomarker for the consumption of these foods. Based on a literature review a significant number of articles have been published on 4-Ethyl-2-methoxyphenol.

Structure

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

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
P-Ethylguaiacol	MetaCyc, HMDB
1-Hydroxy-2-methoxy-4-ethylbenzene	HMDB
2-Methoxy-4-ethylphenol	HMDB, MeSH
4-Ethyl guiacol	HMDB
4-Ethyl-2-methoxy-phenol	HMDB
4-Ethyl-2-methoxyphenol (4-ethylguaiacol)	HMDB
4-Ethyl-2-metoxy phenol	HMDB
4-Ethyl-guaiacol	HMDB
4-Ethylguaiacol	HMDB, MeSH
4-Hydroxy-3-methoxy ethylbenzene	HMDB
4-Hydroxy-3-methoxyethylbenzene	HMDB
4-Hydroxy-3-methoxyphenylethane	HMDB
Ethylguiacol (4-ethyl-2-methoxyphenol)	HMDB
FEMA 2436	HMDB
Guaiacol, 4-ethyl	HMDB
Guaiacyl ethane	HMDB
Homocresol	HMDB
P-Ethyl-2-methoxyphenol	HMDB
Phenol, 2-methoxy-4-ethyl	HMDB

Chemical Formula

C₉H₁₂O₂

Average Molecular Weight

152.1904

Monoisotopic Molecular Weight

152.083729628

IUPAC Name

4-ethyl-2-methoxyphenol

Traditional Name

4-ethylguaiacol

CAS Registry Number

2785-89-9

SMILES

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

InChI Identifier

InChI=1S/C9H12O2/c1-3-7-4-5-8(10)9(6-7)11-2/h4-6,10H,3H2,1-2H3

InChI Key

CHWNEIVBYREQRF-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-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

an aromatic compound (CPD-10601 )

Ontology

Cellular substructure

Extracellular (HMDB: HMDB0040175)
Cytoplasm (HMDB: HMDB0040175)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0040175)

Source

Exogenous

Exogenous (HMDB: HMDB0040175)

Food

Food (HMDB: HMDB0040175)

Beverage

Fermented beverage

Red wine (FooDB: FOOD00911)
Beer (FooDB: FOOD00268)

Coffee and coffee product

Coffee

Cereal and cereal product

Cereal

Corn (FooDB: FOOD00205)

Herb and spice

Oilseed crop

Sesame (FooDB: FOOD00170)

Spice

Chinese cinnamon (FooDB: FOOD00050)

Not Available

Industrial application

Food and nutrition

Food additive

Flavoring agent

Flavoring Agent (HMDB: HMDB0040175)

Biological role

Nutrient (HMDB: HMDB0040175)

Physical Properties

State

Liquid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	-7 °C	Not Available
Boiling Point	235.00 to 236.00 °C. @ 760.00 mm Hg	The Good Scents Company Information System
Water Solubility	693.8 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	2.434 (est)	The Good Scents Company Information System

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	2.41 g/L	ALOGPS
logP	2.36	ALOGPS
logP	2.47	ChemAxon
logS	-1.8	ALOGPS
pKa (Strongest Acidic)	10.3	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	2	ChemAxon
Refractivity	44.14 m³·mol⁻¹	ChemAxon
Polarizability	16.75 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]+	134.107	31661259
DarkChem	[M-H]-	132.779	31661259
DeepCCS	[M+H]+	135.397	30932474
DeepCCS	[M-H]-	131.569	30932474
DeepCCS	[M-2H]-	169.248	30932474
DeepCCS	[M+Na]+	144.787	30932474
AllCCS	[M+H]+	131.6	32859911
AllCCS	[M+H-H2O]+	127.0	32859911
AllCCS	[M+NH4]+	135.9	32859911
AllCCS	[M+Na]+	137.1	32859911
AllCCS	[M-H]-	131.9	32859911
AllCCS	[M+Na-2H]-	133.3	32859911
AllCCS	[M+HCOO]-	134.9	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.	4.18 minutes	32390414
Predicted by Siyang on May 30, 2022	12.7116 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	4.83 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1758.3 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	405.2 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	161.5 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	245.2 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	184.7 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	560.7 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	541.7 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	104.5 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1135.8 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	421.5 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	1143.4 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	350.3 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	403.4 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	401.7 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	318.0 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	38.7 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
4-Ethyl-2-methoxyphenol	CCC1=CC(OC)=C(O)C=C1	2024.5	Standard polar	33892256
4-Ethyl-2-methoxyphenol	CCC1=CC(OC)=C(O)C=C1	1251.1	Standard non polar	33892256
4-Ethyl-2-methoxyphenol	CCC1=CC(OC)=C(O)C=C1	1294.5	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
4-Ethyl-2-methoxyphenol,1TMS,isomer #1	CCC1=CC=C(O[Si](C)(C)C)C(OC)=C1	1343.8	Semi standard non polar	33892256
4-Ethyl-2-methoxyphenol,1TBDMS,isomer #1	CCC1=CC=C(O[Si](C)(C)C(C)(C)C)C(OC)=C1	1593.9	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 4-Ethyl-2-methoxyphenol GC-MS (Non-derivatized) - 70eV, Positive	splash10-0fe0-1900000000-309cbcd4c3b5c618be96	2016-09-22	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 4-Ethyl-2-methoxyphenol GC-MS (1 TMS) - 70eV, Positive	splash10-05fr-7970000000-0c5781b2a64e9da81fc1	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 4-Ethyl-2-methoxyphenol GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-000i-9700000000-746fbad678716b9e066e	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 - 4-Ethyl-2-methoxyphenol 10V, Positive-QTOF	splash10-0udi-0900000000-2a9371bb243c77e192e6	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Ethyl-2-methoxyphenol 20V, Positive-QTOF	splash10-0udi-1900000000-85d8006a41fe7e064e95	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Ethyl-2-methoxyphenol 40V, Positive-QTOF	splash10-0ufr-9200000000-22e200002e86f96c1187	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Ethyl-2-methoxyphenol 10V, Negative-QTOF	splash10-0udi-0900000000-0f4955d3a66c1c69cc27	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Ethyl-2-methoxyphenol 20V, Negative-QTOF	splash10-0udi-0900000000-acb830966ea966b2ef30	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Ethyl-2-methoxyphenol 40V, Negative-QTOF	splash10-0553-7900000000-03acff5e7f7c4a1400a3	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Ethyl-2-methoxyphenol 10V, Positive-QTOF	splash10-0uk9-0900000000-5da9cfbe875826c8990f	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Ethyl-2-methoxyphenol 20V, Positive-QTOF	splash10-0ufr-4900000000-a3c7ad0be273d13bb026	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Ethyl-2-methoxyphenol 40V, Positive-QTOF	splash10-0fvr-9000000000-81e6db59083c8f5d738f	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Ethyl-2-methoxyphenol 10V, Negative-QTOF	splash10-0udi-0900000000-3cd265ceef2fb5f5db20	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Ethyl-2-methoxyphenol 20V, Negative-QTOF	splash10-0udr-0900000000-037544de7548b6280b04	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Ethyl-2-methoxyphenol 40V, Negative-QTOF	splash10-054o-9300000000-ef78296cecf47c0a1643	2021-09-23	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
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, 100 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, 1000 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, 200 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, 300 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, 400 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, 500 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, 600 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, 700 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, 800 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
Predicted 1D NMR	¹³C 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

Cytoplasm
Extracellular

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

633

FooDB ID

FDB019887

KNApSAcK ID

Not Available

Chemspider ID

56245

KEGG Compound ID

Not Available

BioCyc ID

CPD-10601

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

62465

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1028451

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.. .

Enzymes

Enzyme Details

1. UDP-glucuronosyltransferase 1-1

General function:: Involved in transferase activity, transferring hexosyl groups
Specific function:: UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform glucuronidates bilirubin IX-alpha to form both the IX-alpha-C8 and IX-alpha-C12 monoconjugates and diconjugate. Is also able to catalyze the glucuronidation of 17beta-estradiol, 17alpha-ethinylestradiol, 1-hydroxypyrene, 4-methylumbelliferone, 1-naphthol, paranitrophenol, scopoletin, and umbelliferone.
Gene Name:: UGT1A1
Uniprot ID:: P22309
Molecular weight:: 59590.91

Reactions

4-Ethyl-2-methoxyphenol → 6-(4-ethyl-2-methoxyphenoxy)-3,4,5-trihydroxyoxane-2-carboxylic acid	details

Enzyme Details

2. Sulfotransferase 1A3

General function:: sulfotransferase activity
Specific function:: Sulfotransferase that utilizes 3'-phospho-5'-adenylyl sulfate (PAPS) as sulfonate donor to catalyze the sulfate conjugation of phenolic monoamines (neurotransmitters such as dopamine, norepinephrine and serotonin) and phenolic and catechol drugs.
Gene Name:: SULT1A3
Uniprot ID:: P0DMM9
Molecular weight:: 34195.96

Reactions

4-Ethyl-2-methoxyphenol → (4-ethyl-2-methoxyphenyl)oxidanesulfonic acid	details

Showing metabocard for 4-Ethyl-2-methoxyphenol (HMDB0040175)

MOL for HMDB0040175 (4-Ethyl-2-methoxyphenol)

3D MOL for HMDB0040175 (4-Ethyl-2-methoxyphenol)

3D SDF for HMDB0040175 (4-Ethyl-2-methoxyphenol)

3D-SDF for HMDB0040175 (4-Ethyl-2-methoxyphenol)

PDB for HMDB0040175 (4-Ethyl-2-methoxyphenol)

3D PDB for HMDB0040175 (4-Ethyl-2-methoxyphenol)

SMILES for HMDB0040175 (4-Ethyl-2-methoxyphenol)

INCHI for HMDB0040175 (4-Ethyl-2-methoxyphenol)

Structure for HMDB0040175 (4-Ethyl-2-methoxyphenol)

3D Structure for HMDB0040175 (4-Ethyl-2-methoxyphenol)

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

Reactions