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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-12 01:43:01 UTC
Update Date2023-02-21 17:27:49 UTC
HMDB IDHMDB0040174
Secondary Accession Numbers
  • HMDB40174
Metabolite Identification
Common Name4-Ethyl-1,2-benzenediol
Description4-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
Data?1677000469
Synonyms
ValueSource
4-EthylcatecholHMDB
4-EthylpyrocatecholHMDB
4-Ethylpyrocatechol, 8ciHMDB
Chemical FormulaC8H10O2
Average Molecular Weight138.1638
Monoisotopic Molecular Weight138.068079564
IUPAC Name4-ethylbenzene-1,2-diol
Traditional Name4-ethylbenzene-1,2-diol
CAS Registry Number1124-39-6
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 KeyHFLGBNBLMBSXEM-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as catechols. Catechols are compounds containing a 1,2-benzenediol moiety.
KingdomOrganic compounds
Super ClassBenzenoids
ClassPhenols
Sub ClassBenzenediols
Direct ParentCatechols
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 FrameworkAromatic homomonocyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
Role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point41 °CNot Available
Boiling Point273.00 to 274.00 °C. @ 760.00 mm Hg (est)The Good Scents Company Information System
Water Solubility5520 mg/L @ 25 °C (est)The Good Scents Company Information System
LogP1.840 (est)The Good Scents Company Information System
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility11.5 g/LALOGPS
logP1.74ALOGPS
logP2.32ChemAxon
logS-1.1ALOGPS
pKa (Strongest Acidic)9.52ChemAxon
pKa (Strongest Basic)-6.2ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area40.46 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity39.66 m³·mol⁻¹ChemAxon
Polarizability14.77 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+129.59831661259
DarkChem[M-H]-127.49431661259
DeepCCS[M+H]+131.46130932474
DeepCCS[M-H]-127.63230932474
DeepCCS[M-2H]-165.02830932474
DeepCCS[M+Na]+140.56730932474
AllCCS[M+H]+128.532859911
AllCCS[M+H-H2O]+123.832859911
AllCCS[M+NH4]+132.932859911
AllCCS[M+Na]+134.232859911
AllCCS[M-H]-127.532859911
AllCCS[M+Na-2H]-129.232859911
AllCCS[M+HCOO]-131.032859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
4-Ethyl-1,2-benzenediolCCC1=CC(O)=C(O)C=C12371.7Standard polar33892256
4-Ethyl-1,2-benzenediolCCC1=CC(O)=C(O)C=C11274.7Standard non polar33892256
4-Ethyl-1,2-benzenediolCCC1=CC(O)=C(O)C=C11397.3Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
4-Ethyl-1,2-benzenediol,1TMS,isomer #1CCC1=CC=C(O)C(O[Si](C)(C)C)=C11360.5Semi standard non polar33892256
4-Ethyl-1,2-benzenediol,1TMS,isomer #2CCC1=CC=C(O[Si](C)(C)C)C(O)=C11366.7Semi standard non polar33892256
4-Ethyl-1,2-benzenediol,2TMS,isomer #1CCC1=CC=C(O[Si](C)(C)C)C(O[Si](C)(C)C)=C11410.4Semi standard non polar33892256
4-Ethyl-1,2-benzenediol,1TBDMS,isomer #1CCC1=CC=C(O)C(O[Si](C)(C)C(C)(C)C)=C11597.6Semi standard non polar33892256
4-Ethyl-1,2-benzenediol,1TBDMS,isomer #2CCC1=CC=C(O[Si](C)(C)C(C)(C)C)C(O)=C11609.2Semi standard non polar33892256
4-Ethyl-1,2-benzenediol,2TBDMS,isomer #1CCC1=CC=C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)=C11880.7Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 4-Ethyl-1,2-benzenediol GC-MS (Non-derivatized) - 70eV, Positivesplash10-0079-2900000000-2171b1eac2762a8afe242017-07-27Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 4-Ethyl-1,2-benzenediol GC-MS (2 TMS) - 70eV, Positivesplash10-01b9-5690000000-8473f1858712e3d482342017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 4-Ethyl-1,2-benzenediol GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 4-Ethyl-1,2-benzenediol GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Ethyl-1,2-benzenediol 10V, Positive-QTOFsplash10-000i-0900000000-cfd55c699b663d7c84332015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Ethyl-1,2-benzenediol 20V, Positive-QTOFsplash10-000i-2900000000-f1a5178e168369a01e4d2015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Ethyl-1,2-benzenediol 40V, Positive-QTOFsplash10-0ufr-9100000000-5c1a962eddfbaeaba15d2015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Ethyl-1,2-benzenediol 10V, Negative-QTOFsplash10-000i-0900000000-11ca02b796388914a6472015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Ethyl-1,2-benzenediol 20V, Negative-QTOFsplash10-000i-1900000000-0d3b6ab4226bac9a5cac2015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Ethyl-1,2-benzenediol 40V, Negative-QTOFsplash10-0673-9700000000-5597623aae19131d35912015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Ethyl-1,2-benzenediol 10V, Positive-QTOFsplash10-000i-0900000000-e2bbe2db2b145c67830a2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Ethyl-1,2-benzenediol 20V, Positive-QTOFsplash10-003f-9500000000-0e538033bebb0479e88e2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Ethyl-1,2-benzenediol 40V, Positive-QTOFsplash10-0fvr-9000000000-78228f0270dd35d8c8a42021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Ethyl-1,2-benzenediol 10V, Negative-QTOFsplash10-000i-0900000000-08ef9d705ca98ce39abf2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Ethyl-1,2-benzenediol 20V, Negative-QTOFsplash10-000i-2900000000-7dc219a6c51ca57e746b2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Ethyl-1,2-benzenediol 40V, Negative-QTOFsplash10-0006-9000000000-230580e07dc3f472caac2021-09-24Wishart 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

IR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-)2023-02-04FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)2023-02-04FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)2023-02-04FELIX 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 ID705
FooDB IDFDB019886
KNApSAcK IDC00056475
Chemspider ID63926
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound70761
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1539941
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 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-methoxyphenoldetails
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 aciddetails
4-Ethyl-1,2-benzenediol → 6-(4-ethyl-2-hydroxyphenoxy)-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-1,2-benzenediol → (5-ethyl-2-hydroxyphenyl)oxidanesulfonic aciddetails