MiMeDB: Showing metabocard for 4-Ethyl-2-methoxyphenol (MMDBc0033581)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-11-19 04:54:27 UTC

Update Date

2024-09-28 04:11:40 UTC

Metabolite ID

MMDBc0033581

Metabolite Identification

Common Name

4-Ethyl-2-methoxyphenol

Description

4-Ethyl-2-methoxyphenol is a volatile phenol found in wines spoiled with the Brettanomyces wild yeast. It is produced by Brettanomyces as a result of enzymatic conversion of vinylphenols derived from cinnamic acids naturally present in the grape must. At low concentrations, this compound is thought to add to wine complexity, but at high concentrations the wine is considered spoiled and has been described as animal, barnyard, stable, phenolic, and mousy. [PMID: 17850808 , PMID: 17676867 ]

Structure

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

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

Molecular Formula

C₉H₁₂O₂

Average Mass

152.1904

Monoisotopic Mass

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 )

Functional Ontology

Not Available

Physical Properties

State

Solid

Predicted 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

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0fe0-1900000000-309cbcd4c3b5c618be96	2016-09-22	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive	splash10-05fr-7970000000-0c5781b2a64e9da81fc1	2017-10-06	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0udi-0900000000-2a9371bb243c77e192e6	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0udi-1900000000-85d8006a41fe7e064e95	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0ufr-9200000000-22e200002e86f96c1187	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0udi-0900000000-0f4955d3a66c1c69cc27	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0udi-0900000000-acb830966ea966b2ef30	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0553-7900000000-03acff5e7f7c4a1400a3	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0uk9-0900000000-5da9cfbe875826c8990f	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0ufr-4900000000-a3c7ad0be273d13bb026	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0fvr-9000000000-81e6db59083c8f5d738f	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0udi-0900000000-3cd265ceef2fb5f5db20	2021-09-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0udr-0900000000-037544de7548b6280b04	2021-09-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-054o-9300000000-ef78296cecf47c0a1643	2021-09-23	View Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-000i-9700000000-746fbad678716b9e066e	2015-03-01	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)		2021-09-24	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Extracellular

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species
MMDBp0192140	UDP-glucuronosyltransferase 1-1	Enzyme	P22309	Homo sapiens
MMDBp0197061	Sulfotransferase 1A3	Enzyme	P0DMM9	Homo sapiens

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Not Available

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Eukaryota/Fungi	Ascomycota	1	Human feces; Human saliva	Unknown

Exposure Sources

Source Type	Source Sub-type	Species	Data Source	Reference
Food		Coffea arabica	FooDB	31437929
Food		Coffea canephora	FooDB	31437929
Food		Coffea arabica	FooDB	31437929
Food		Coffea canephora	FooDB	31437929
Food			FooDB	31437929
Food			FooDB	31437929
Food			FooDB	31437929
Plant	Leaves	Camellia sinensis	FooDB	31437929
Plant	Fruit	Capsicum annuum	FooDB	31437929
Plant	Seed	Sesamum orientale	FooDB	31437929
Plant	Plant	Cinnamomum aromaticum	FooDB	31437929
Plant	Leaves		FooDB	31437929
Plant	Leaves		FooDB	31437929
Plant	Leaves		FooDB	31437929
Plant	Seed	Coffea arabica	FooDB	31437929

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Min	Max	Units	Age	Sex	Health Condition	Data Source	Reference

External Links

HMDB ID

HMDB0040175

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

References

Synthesis Reference

Not Available

General References

Loscos N, Hernandez-Orte P, Cacho J, Ferreira V: Release and formation of varietal aroma compounds during alcoholic fermentation from nonfloral grape odorless flavor precursors fractions. J Agric Food Chem. 2007 Aug 8;55(16):6674-84. doi: 10.1021/jf0702343. Epub 2007 Jul 7. [PubMed:17616208 ]
Yannai, Shmuel (2004). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. Boca Raton: Chapman & Hall/CRC..

Showing metabocard for 4-Ethyl-2-methoxyphenol (MMDBc0033581)

MOL for #<Metabolite:0x00007f46caac5a68>

3D MOL for #<Metabolite:0x00007f46caac5a68>

3D SDF for #<Metabolite:0x00007f46caac5a68>

3D-SDF for #<Metabolite:0x00007f46caac5a68>

PDB for #<Metabolite:0x00007f46caac5a68>

3D PDB for #<Metabolite:0x00007f46caac5a68>

SMILES for #<Metabolite:0x00007f46caac5a68>

INCHI for #<Metabolite:0x00007f46caac5a68>

Structure for #<Metabolite:0x00007f46caac5a68>

3D Structure for #<Metabolite:0x00007f46caac5a68>