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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-12 01:43:04 UTC
Update Date2022-03-07 02:56:29 UTC
HMDB IDHMDB0040175
Secondary Accession Numbers
  • HMDB40175
Metabolite Identification
Common Name4-Ethyl-2-methoxyphenol
Description4-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
Data?1563863501
Synonyms
ValueSource
P-EthylguaiacolMetaCyc, HMDB
1-Hydroxy-2-methoxy-4-ethylbenzeneHMDB
2-Methoxy-4-ethylphenolHMDB, MeSH
4-Ethyl guiacolHMDB
4-Ethyl-2-methoxy-phenolHMDB
4-Ethyl-2-methoxyphenol (4-ethylguaiacol)HMDB
4-Ethyl-2-metoxy phenolHMDB
4-Ethyl-guaiacolHMDB
4-EthylguaiacolHMDB, MeSH
4-Hydroxy-3-methoxy ethylbenzeneHMDB
4-Hydroxy-3-methoxyethylbenzeneHMDB
4-Hydroxy-3-methoxyphenylethaneHMDB
Ethylguiacol (4-ethyl-2-methoxyphenol)HMDB
FEMA 2436HMDB
Guaiacol, 4-ethylHMDB
Guaiacyl ethaneHMDB
HomocresolHMDB
P-Ethyl-2-methoxyphenolHMDB
Phenol, 2-methoxy-4-ethylHMDB
Chemical FormulaC9H12O2
Average Molecular Weight152.1904
Monoisotopic Molecular Weight152.083729628
IUPAC Name4-ethyl-2-methoxyphenol
Traditional Name4-ethylguaiacol
CAS Registry Number2785-89-9
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 KeyCHWNEIVBYREQRF-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.
KingdomOrganic compounds
Super ClassBenzenoids
ClassPhenols
Sub ClassMethoxyphenols
Direct ParentMethoxyphenols
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 FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
Disposition

Biological location

Source

Physical Properties
StateLiquid
Experimental Molecular Properties
PropertyValueReference
Melting Point-7 °CNot Available
Boiling Point235.00 to 236.00 °C. @ 760.00 mm HgThe Good Scents Company Information System
Water Solubility693.8 mg/L @ 25 °C (est)The Good Scents Company Information System
LogP2.434 (est)The Good Scents Company Information System
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility2.41 g/LALOGPS
logP2.36ALOGPS
logP2.47ChemAxon
logS-1.8ALOGPS
pKa (Strongest Acidic)10.3ChemAxon
pKa (Strongest Basic)-4.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area29.46 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity44.14 m³·mol⁻¹ChemAxon
Polarizability16.75 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+134.10731661259
DarkChem[M-H]-132.77931661259
DeepCCS[M+H]+135.39730932474
DeepCCS[M-H]-131.56930932474
DeepCCS[M-2H]-169.24830932474
DeepCCS[M+Na]+144.78730932474
AllCCS[M+H]+131.632859911
AllCCS[M+H-H2O]+127.032859911
AllCCS[M+NH4]+135.932859911
AllCCS[M+Na]+137.132859911
AllCCS[M-H]-131.932859911
AllCCS[M+Na-2H]-133.332859911
AllCCS[M+HCOO]-134.932859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
4-Ethyl-2-methoxyphenolCCC1=CC(OC)=C(O)C=C12024.5Standard polar33892256
4-Ethyl-2-methoxyphenolCCC1=CC(OC)=C(O)C=C11251.1Standard non polar33892256
4-Ethyl-2-methoxyphenolCCC1=CC(OC)=C(O)C=C11294.5Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
4-Ethyl-2-methoxyphenol,1TMS,isomer #1CCC1=CC=C(O[Si](C)(C)C)C(OC)=C11343.8Semi standard non polar33892256
4-Ethyl-2-methoxyphenol,1TBDMS,isomer #1CCC1=CC=C(O[Si](C)(C)C(C)(C)C)C(OC)=C11593.9Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 4-Ethyl-2-methoxyphenol GC-MS (Non-derivatized) - 70eV, Positivesplash10-0fe0-1900000000-309cbcd4c3b5c618be962016-09-22Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 4-Ethyl-2-methoxyphenol GC-MS (1 TMS) - 70eV, Positivesplash10-05fr-7970000000-0c5781b2a64e9da81fc12017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 4-Ethyl-2-methoxyphenol GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
MSMass Spectrum (Electron Ionization)splash10-000i-9700000000-746fbad678716b9e066e2015-03-01Not AvailableView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Ethyl-2-methoxyphenol 10V, Positive-QTOFsplash10-0udi-0900000000-2a9371bb243c77e192e62016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Ethyl-2-methoxyphenol 20V, Positive-QTOFsplash10-0udi-1900000000-85d8006a41fe7e064e952016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Ethyl-2-methoxyphenol 40V, Positive-QTOFsplash10-0ufr-9200000000-22e200002e86f96c11872016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Ethyl-2-methoxyphenol 10V, Negative-QTOFsplash10-0udi-0900000000-0f4955d3a66c1c69cc272016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Ethyl-2-methoxyphenol 20V, Negative-QTOFsplash10-0udi-0900000000-acb830966ea966b2ef302016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Ethyl-2-methoxyphenol 40V, Negative-QTOFsplash10-0553-7900000000-03acff5e7f7c4a1400a32016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Ethyl-2-methoxyphenol 10V, Positive-QTOFsplash10-0uk9-0900000000-5da9cfbe875826c8990f2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Ethyl-2-methoxyphenol 20V, Positive-QTOFsplash10-0ufr-4900000000-a3c7ad0be273d13bb0262021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Ethyl-2-methoxyphenol 40V, Positive-QTOFsplash10-0fvr-9000000000-81e6db59083c8f5d738f2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Ethyl-2-methoxyphenol 10V, Negative-QTOFsplash10-0udi-0900000000-3cd265ceef2fb5f5db202021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Ethyl-2-methoxyphenol 20V, Negative-QTOFsplash10-0udr-0900000000-037544de7548b6280b042021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Ethyl-2-methoxyphenol 40V, Negative-QTOFsplash10-054o-9300000000-ef78296cecf47c0a16432021-09-23Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound ID633
FooDB IDFDB019887
KNApSAcK IDNot Available
Chemspider ID56245
KEGG Compound IDNot Available
BioCyc IDCPD-10601
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound62465
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1028451
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Enzymes

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 aciddetails
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 aciddetails