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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (3) Show 3 proteins XML

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-12 01:43:01 UTC

Update Date

2023-02-21 17:27:49 UTC

HMDB ID

HMDB0040174

Secondary Accession Numbers

HMDB40174

Metabolite Identification

Common Name

4-Ethyl-1,2-benzenediol

Description

4-Ethyl-1,2-benzenediol belongs to the class of organic compounds known as catechols. Catechols are compounds containing a 1,2-benzenediol moiety. 4-Ethyl-1,2-benzenediol is found, on average, in the highest concentration within a few different foods, such as arabica coffees (Coffea arabica), robusta coffees (Coffea canephora), and coffees (Coffea) and in a lower concentration in cocoa powder and beer. 4-Ethyl-1,2-benzenediol has also been detected, but not quantified in, a few different foods, such as coffee and coffee products, eggplants (Solanum melongena), and green vegetables. This could make 4-ethyl-1,2-benzenediol a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on 4-Ethyl-1,2-benzenediol.

Structure

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

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
4-Ethylcatechol	HMDB
4-Ethylpyrocatechol	HMDB
4-Ethylpyrocatechol, 8ci	HMDB

Chemical Formula

C₈H₁₀O₂

Average Molecular Weight

138.1638

Monoisotopic Molecular Weight

138.068079564

IUPAC Name

4-ethylbenzene-1,2-diol

Traditional Name

4-ethylbenzene-1,2-diol

CAS Registry Number

1124-39-6

SMILES

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

InChI Identifier

InChI=1S/C8H10O2/c1-2-6-3-4-7(9)8(10)5-6/h3-5,9-10H,2H2,1H3

InChI Key

HFLGBNBLMBSXEM-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as catechols. Catechols are compounds containing a 1,2-benzenediol moiety.

Kingdom

Super Class

Class

Sub Class

Direct Parent

Alternative Parents

Substituents

Catechol
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
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

Extracellular (HMDB: HMDB0040174)
Cytoplasm (HMDB: HMDB0040174)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0040174)

Source

Exogenous

Exogenous (HMDB: HMDB0040174)

Food

Food (HMDB: HMDB0040174)

Vegetable

Fruit vegetable

Eggplant (FooDB: FOOD00174)

Leaf vegetable

Green vegetables (FooDB: FOOD00872)

Beverage

Fermented beverage

Beer (FooDB: FOOD00268)

Cocoa and cocoa product

Cocoa product

Cocoa powder (FooDB: FOOD00685)

Coffee and coffee product

Coffee

Coffee and coffee products (FooDB: FOOD00861)

Not Available

Nutrient (HMDB: HMDB0040174)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	41 °C	Not Available
Boiling Point	273.00 to 274.00 °C. @ 760.00 mm Hg (est)	The Good Scents Company Information System
Water Solubility	5520 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	1.840 (est)	The Good Scents Company Information System

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	11.5 g/L	ALOGPS
logP	1.74	ALOGPS
logP	2.32	ChemAxon
logS	-1.1	ALOGPS
pKa (Strongest Acidic)	9.52	ChemAxon
pKa (Strongest Basic)	-6.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	40.46 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	39.66 m³·mol⁻¹	ChemAxon
Polarizability	14.77 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	129.598	31661259
DarkChem	[M-H]-	127.494	31661259
DeepCCS	[M+H]+	131.461	30932474
DeepCCS	[M-H]-	127.632	30932474
DeepCCS	[M-2H]-	165.028	30932474
DeepCCS	[M+Na]+	140.567	30932474
AllCCS	[M+H]+	128.5	32859911
AllCCS	[M+H-H2O]+	123.8	32859911
AllCCS	[M+NH4]+	132.9	32859911
AllCCS	[M+Na]+	134.2	32859911
AllCCS	[M-H]-	127.5	32859911
AllCCS	[M+Na-2H]-	129.2	32859911
AllCCS	[M+HCOO]-	131.0	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.	3.27 minutes	32390414
Predicted by Siyang on May 30, 2022	11.2968 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	5.32 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	33.6 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1392.6 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	359.2 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	139.4 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	227.0 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	178.1 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	521.4 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	467.9 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	99.2 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	915.3 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	372.6 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	1090.0 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	289.8 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	358.0 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	455.5 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	265.7 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	94.4 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
4-Ethyl-1,2-benzenediol	CCC1=CC(O)=C(O)C=C1	2371.7	Standard polar	33892256
4-Ethyl-1,2-benzenediol	CCC1=CC(O)=C(O)C=C1	1274.7	Standard non polar	33892256
4-Ethyl-1,2-benzenediol	CCC1=CC(O)=C(O)C=C1	1397.3	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
4-Ethyl-1,2-benzenediol,1TMS,isomer #1	CCC1=CC=C(O)C(O[Si](C)(C)C)=C1	1360.5	Semi standard non polar	33892256
4-Ethyl-1,2-benzenediol,1TMS,isomer #2	CCC1=CC=C(O[Si](C)(C)C)C(O)=C1	1366.7	Semi standard non polar	33892256
4-Ethyl-1,2-benzenediol,2TMS,isomer #1	CCC1=CC=C(O[Si](C)(C)C)C(O[Si](C)(C)C)=C1	1410.4	Semi standard non polar	33892256
4-Ethyl-1,2-benzenediol,1TBDMS,isomer #1	CCC1=CC=C(O)C(O[Si](C)(C)C(C)(C)C)=C1	1597.6	Semi standard non polar	33892256
4-Ethyl-1,2-benzenediol,1TBDMS,isomer #2	CCC1=CC=C(O[Si](C)(C)C(C)(C)C)C(O)=C1	1609.2	Semi standard non polar	33892256
4-Ethyl-1,2-benzenediol,2TBDMS,isomer #1	CCC1=CC=C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)=C1	1880.7	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-1,2-benzenediol GC-MS (Non-derivatized) - 70eV, Positive	splash10-0079-2900000000-2171b1eac2762a8afe24	2017-07-27	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 4-Ethyl-1,2-benzenediol GC-MS (2 TMS) - 70eV, Positive	splash10-01b9-5690000000-8473f1858712e3d48234	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 4-Ethyl-1,2-benzenediol GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 4-Ethyl-1,2-benzenediol 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-1,2-benzenediol 10V, Positive-QTOF	splash10-000i-0900000000-cfd55c699b663d7c8433	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Ethyl-1,2-benzenediol 20V, Positive-QTOF	splash10-000i-2900000000-f1a5178e168369a01e4d	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Ethyl-1,2-benzenediol 40V, Positive-QTOF	splash10-0ufr-9100000000-5c1a962eddfbaeaba15d	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Ethyl-1,2-benzenediol 10V, Negative-QTOF	splash10-000i-0900000000-11ca02b796388914a647	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Ethyl-1,2-benzenediol 20V, Negative-QTOF	splash10-000i-1900000000-0d3b6ab4226bac9a5cac	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Ethyl-1,2-benzenediol 40V, Negative-QTOF	splash10-0673-9700000000-5597623aae19131d3591	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Ethyl-1,2-benzenediol 10V, Positive-QTOF	splash10-000i-0900000000-e2bbe2db2b145c67830a	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Ethyl-1,2-benzenediol 20V, Positive-QTOF	splash10-003f-9500000000-0e538033bebb0479e88e	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Ethyl-1,2-benzenediol 40V, Positive-QTOF	splash10-0fvr-9000000000-78228f0270dd35d8c8a4	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Ethyl-1,2-benzenediol 10V, Negative-QTOF	splash10-000i-0900000000-08ef9d705ca98ce39abf	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Ethyl-1,2-benzenediol 20V, Negative-QTOF	splash10-000i-2900000000-7dc219a6c51ca57e746b	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Ethyl-1,2-benzenediol 40V, Negative-QTOF	splash10-0006-9000000000-230580e07dc3f472caac	2021-09-24	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

FooDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

70761

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1539941

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. Catechol O-methyltransferase

General function:: Involved in magnesium ion binding
Specific function:: Catalyzes the O-methylation, and thereby the inactivation, of catecholamine neurotransmitters and catechol hormones. Also shortens the biological half-lives of certain neuroactive drugs, like L-DOPA, alpha-methyl DOPA and isoproterenol.
Gene Name:: COMT
Uniprot ID:: P21964
Molecular weight:: 30036.77

Reactions

4-Ethyl-1,2-benzenediol → 4-Ethyl-2-methoxyphenol	details

Enzyme Details

2. 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-1,2-benzenediol → 6-(5-ethyl-2-hydroxyphenoxy)-3,4,5-trihydroxyoxane-2-carboxylic acid	details
4-Ethyl-1,2-benzenediol → 6-(4-ethyl-2-hydroxyphenoxy)-3,4,5-trihydroxyoxane-2-carboxylic acid	details

Enzyme Details

3. 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-1,2-benzenediol → (5-ethyl-2-hydroxyphenyl)oxidanesulfonic acid	details

Showing metabocard for 4-Ethyl-1,2-benzenediol (HMDB0040174)

MOL for HMDB0040174 (4-Ethyl-1,2-benzenediol)

3D MOL for HMDB0040174 (4-Ethyl-1,2-benzenediol)

3D SDF for HMDB0040174 (4-Ethyl-1,2-benzenediol)

3D-SDF for HMDB0040174 (4-Ethyl-1,2-benzenediol)

PDB for HMDB0040174 (4-Ethyl-1,2-benzenediol)

3D PDB for HMDB0040174 (4-Ethyl-1,2-benzenediol)

SMILES for HMDB0040174 (4-Ethyl-1,2-benzenediol)

INCHI for HMDB0040174 (4-Ethyl-1,2-benzenediol)

Structure for HMDB0040174 (4-Ethyl-1,2-benzenediol)

3D Structure for HMDB0040174 (4-Ethyl-1,2-benzenediol)

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

Reactions