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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-12 01:43:10 UTC

Update Date

2023-02-21 17:27:50 UTC

HMDB ID

HMDB0040177

Secondary Accession Numbers

HMDB40177

Metabolite Identification

Common Name

3-Ethyl-1,2-benzenediol

Description

3-Ethyl-1,2-benzenediol, also known as 2,3-dihydroxyethylbenzene, belongs to the class of organic compounds known as catechols. Catechols are compounds containing a 1,2-benzenediol moiety. 3-Ethyl-1,2-benzenediol has been detected, but not quantified in, a few different foods, such as arabica coffees (Coffea arabica), coffee and coffee products, and robusta coffees (Coffea canephora). This could make 3-ethyl-1,2-benzenediol a potential biomarker for the consumption of these foods. 3-Ethyl-1,2-benzenediol is a primary metabolite. Primary metabolites are metabolically or physiologically essential metabolites. They are directly involved in an organism’s growth, development or reproduction. Based on a literature review very few articles have been published on 3-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
2,3-Dihydroxyethylbenzene	ChEBI
3-Ethyl-benzene-1,2-diol	ChEBI
3-Ethyl-pyrocatechol	HMDB
3-Ethylbenzene-1,2-diol	HMDB
3-Ethylcatechol	HMDB
3-Ethylpyrocatechol	HMDB
Ethyl-benzenediol	HMDB
Ethylpyrocatechol	HMDB

Chemical Formula

C₈H₁₀O₂

Average Molecular Weight

138.1638

Monoisotopic Molecular Weight

138.068079564

IUPAC Name

3-ethylbenzene-1,2-diol

Traditional Name

3-ethylcatechol

CAS Registry Number

933-99-3

SMILES

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

InChI Identifier

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

InChI Key

UUCQGNWZASKXNN-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

3-ethylcatechols (CHEBI:16572 )
a catechol (3-ETHYLCATECHOL )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Extracellular (HMDB: HMDB0040177)
Cytoplasm (HMDB: HMDB0040177)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0040177)

Source

Exogenous

Food

Food (HMDB: HMDB0040177)

Coffee and coffee product

Coffee

Arabica coffee (FooDB: FOOD00059)
Robusta coffee (FooDB: FOOD00060)

Coffee and coffee products (FooDB: FOOD00861)

Endogenous

Plant

Coffea (HMDB: HMDB0040177)

Process

Not Available

Role

Biological role

Nutrient (HMDB: HMDB0040177)

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	257.00 to 258.00 °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	1.736 (est)	The Good Scents Company Information System

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	12.3 g/L	ALOGPS
logP	1.68	ALOGPS
logP	2.32	ChemAxon
logS	-1	ALOGPS
pKa (Strongest Acidic)	9.56	ChemAxon
pKa (Strongest Basic)	-6.3	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	14.6 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]+	128.646	31661259
DarkChem	[M-H]-	126.565	31661259
DeepCCS	[M+H]+	129.732	30932474
DeepCCS	[M-H]-	125.875	30932474
DeepCCS	[M-2H]-	163.533	30932474
DeepCCS	[M+Na]+	138.876	30932474
AllCCS	[M+H]+	128.6	32859911
AllCCS	[M+H-H2O]+	123.8	32859911
AllCCS	[M+NH4]+	133.0	32859911
AllCCS	[M+Na]+	134.3	32859911
AllCCS	[M-H]-	126.8	32859911
AllCCS	[M+Na-2H]-	128.5	32859911
AllCCS	[M+HCOO]-	130.4	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
3-Ethyl-1,2-benzenediol	CCC1=C(O)C(O)=CC=C1	2370.9	Standard polar	33892256
3-Ethyl-1,2-benzenediol	CCC1=C(O)C(O)=CC=C1	1227.3	Standard non polar	33892256
3-Ethyl-1,2-benzenediol	CCC1=C(O)C(O)=CC=C1	1352.5	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
3-Ethyl-1,2-benzenediol,1TMS,isomer #1	CCC1=CC=CC(O)=C1O[Si](C)(C)C	1351.1	Semi standard non polar	33892256
3-Ethyl-1,2-benzenediol,1TMS,isomer #2	CCC1=CC=CC(O[Si](C)(C)C)=C1O	1352.4	Semi standard non polar	33892256
3-Ethyl-1,2-benzenediol,2TMS,isomer #1	CCC1=CC=CC(O[Si](C)(C)C)=C1O[Si](C)(C)C	1411.5	Semi standard non polar	33892256
3-Ethyl-1,2-benzenediol,1TBDMS,isomer #1	CCC1=CC=CC(O)=C1O[Si](C)(C)C(C)(C)C	1592.3	Semi standard non polar	33892256
3-Ethyl-1,2-benzenediol,1TBDMS,isomer #2	CCC1=CC=CC(O[Si](C)(C)C(C)(C)C)=C1O	1587.5	Semi standard non polar	33892256
3-Ethyl-1,2-benzenediol,2TBDMS,isomer #1	CCC1=CC=CC(O[Si](C)(C)C(C)(C)C)=C1O[Si](C)(C)C(C)(C)C	1889.4	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 - 3-Ethyl-1,2-benzenediol GC-MS (Non-derivatized) - 70eV, Positive	splash10-0079-2900000000-36b9bcdfa090323af83f	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3-Ethyl-1,2-benzenediol GC-MS (2 TMS) - 70eV, Positive	splash10-01b9-5590000000-9da678b71fc5f29736e2	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3-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 - 3-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 - 3-Ethyl-1,2-benzenediol 10V, Positive-QTOF	splash10-000i-0900000000-bdf0496088698f171dca	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Ethyl-1,2-benzenediol 20V, Positive-QTOF	splash10-000i-1900000000-442196e73f41887963f4	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Ethyl-1,2-benzenediol 40V, Positive-QTOF	splash10-0ug3-9000000000-c3b6bb237787c5789e5f	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Ethyl-1,2-benzenediol 10V, Negative-QTOF	splash10-000i-0900000000-c76a144f545b48203ef2	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Ethyl-1,2-benzenediol 20V, Negative-QTOF	splash10-000i-0900000000-bf2ce51ba13e5399e115	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Ethyl-1,2-benzenediol 40V, Negative-QTOF	splash10-0a7i-9700000000-c37140612bbcd7f9c3db	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Ethyl-1,2-benzenediol 10V, Negative-QTOF	splash10-000i-0900000000-08ef9d705ca98ce39abf	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Ethyl-1,2-benzenediol 20V, Negative-QTOF	splash10-000i-2900000000-9b1096ccd22785585809	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Ethyl-1,2-benzenediol 40V, Negative-QTOF	splash10-000i-9800000000-6d4a02a59c6856ef7540	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Ethyl-1,2-benzenediol 10V, Positive-QTOF	splash10-0079-0900000000-868e9d99c314890d0bee	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Ethyl-1,2-benzenediol 20V, Positive-QTOF	splash10-000f-9700000000-73ec276d4b4f5c251815	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Ethyl-1,2-benzenediol 40V, Positive-QTOF	splash10-0fic-9100000000-421cb26da6c8840f5130	2021-09-22	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

Not Available

FooDB ID

FDB019889

KNApSAcK ID

Not Available

Chemspider ID

63462

KEGG Compound ID

C06728

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

70278

PDB ID

Not Available

ChEBI ID

16572

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1534511

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.. .

Showing metabocard for 3-Ethyl-1,2-benzenediol (HMDB0040177)

MOL for HMDB0040177 (3-Ethyl-1,2-benzenediol)

3D MOL for HMDB0040177 (3-Ethyl-1,2-benzenediol)

3D SDF for HMDB0040177 (3-Ethyl-1,2-benzenediol)

3D-SDF for HMDB0040177 (3-Ethyl-1,2-benzenediol)

PDB for HMDB0040177 (3-Ethyl-1,2-benzenediol)

3D PDB for HMDB0040177 (3-Ethyl-1,2-benzenediol)

SMILES for HMDB0040177 (3-Ethyl-1,2-benzenediol)

INCHI for HMDB0040177 (3-Ethyl-1,2-benzenediol)

Structure for HMDB0040177 (3-Ethyl-1,2-benzenediol)

3D Structure for HMDB0040177 (3-Ethyl-1,2-benzenediol)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra