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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2009-04-06 16:19:46 UTC
Update Date2023-02-21 17:17:38 UTC
HMDB IDHMDB0012133
Secondary Accession Numbers
  • HMDB12133
Metabolite Identification
Common Name1,2-Benzoquinone
Description1,2-Benzoquinone, also known as catechol quinone or O-quinone, belongs to the class of organic compounds known as o-benzoquinones. These are benzoquinones where the two C=O groups are attached at the 1- and 2-positions, respectively. 1,2-Benzoquinone has been detected, but not quantified in, several different foods, such as chickens (Gallus gallus), green tea, red tea, domestic pigs (Sus scrofa domestica), and black tea. This could make 1,2-benzoquinone a potential biomarker for the consumption of these foods. Based on a literature review a significant number of articles have been published on 1,2-Benzoquinone.
Structure
Data?1676999858
Synonyms
ValueSource
2-BenzoquinoneChEBI
3,5-Cyclohexadiene-1,2-dioneChEBI
Catechol quinoneChEBI
Cyclohexa-3,5-diene-1,2-dioneChEBI
O-BenzoquinoneChEBI
O-QuinoneChEBI
Ortho-benzoquinoneChEBI
3,5-Cyclohexadiene-1,2-dione (9ci)HMDB
benzo-1,2-QuinoneHMDB
1,2-BenzoquinoneKEGG
Chemical FormulaC6H4O2
Average Molecular Weight108.0948
Monoisotopic Molecular Weight108.021129372
IUPAC Namecyclohexa-3,5-diene-1,2-dione
Traditional Nameo-quinone
CAS Registry Number583-63-1
SMILES
O=C1C=CC=CC1=O
InChI Identifier
InChI=1S/C6H4O2/c7-5-3-1-2-4-6(5)8/h1-4H
InChI KeyWOAHJDHKFWSLKE-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as o-benzoquinones. These are benzoquinones where the two C=O groups are attached at the 1- and 2-positions, respectively.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbonyl compounds
Direct ParentO-benzoquinones
Alternative Parents
Substituents
  • O-benzoquinone
  • Organic oxide
  • Hydrocarbon derivative
  • Aliphatic homomonocyclic compound
Molecular FrameworkAliphatic homomonocyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility16.1 g/LALOGPS
logP0.86ALOGPS
logP1.33ChemAxon
logS-0.83ALOGPS
pKa (Strongest Basic)-8.7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area34.14 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity31.18 m³·mol⁻¹ChemAxon
Polarizability9.73 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]+121.30831661259
DarkChem[M-H]-115.431661259
DeepCCS[M+H]+122.6830932474
DeepCCS[M-H]-120.11930932474
DeepCCS[M-2H]-156.38630932474
DeepCCS[M+Na]+131.04530932474
AllCCS[M+H]+122.332859911
AllCCS[M+H-H2O]+117.432859911
AllCCS[M+NH4]+127.032859911
AllCCS[M+Na]+128.332859911
AllCCS[M-H]-117.732859911
AllCCS[M+Na-2H]-120.132859911
AllCCS[M+HCOO]-122.932859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
1,2-BenzoquinoneO=C1C=CC=CC1=O1707.7Standard polar33892256
1,2-BenzoquinoneO=C1C=CC=CC1=O925.4Standard non polar33892256
1,2-BenzoquinoneO=C1C=CC=CC1=O1058.5Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 1,2-Benzoquinone GC-MS (Non-derivatized) - 70eV, Positivesplash10-0pb9-9500000000-1a07fadb8f28ea959a282017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 1,2-Benzoquinone 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 - 1,2-Benzoquinone 10V, Negative-QTOFsplash10-0a4i-0900000000-4fb61a2d97ea508989e92016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1,2-Benzoquinone 20V, Negative-QTOFsplash10-0a4i-0900000000-13ff869a1a7e1a44c9702016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1,2-Benzoquinone 40V, Negative-QTOFsplash10-0pb9-9700000000-fc958adc5ffed240f9c22016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1,2-Benzoquinone 10V, Negative-QTOFsplash10-0a4i-0900000000-62ea0dd9303aae554ccd2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1,2-Benzoquinone 20V, Negative-QTOFsplash10-0a4i-1900000000-9766b1b7668b7abc65ba2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1,2-Benzoquinone 40V, Negative-QTOFsplash10-0gb9-9000000000-4b9fa2e26f51e3c17bd12021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1,2-Benzoquinone 10V, Positive-QTOFsplash10-0a4i-0900000000-59076600ed27ef7ff1ad2016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1,2-Benzoquinone 20V, Positive-QTOFsplash10-0a4i-1900000000-03f8747e1c9926da750a2016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1,2-Benzoquinone 40V, Positive-QTOFsplash10-0udi-9000000000-67fb84b6bf182032b41d2016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1,2-Benzoquinone 10V, Positive-QTOFsplash10-0a59-7900000000-f5250ef56d23d42dfc732021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1,2-Benzoquinone 20V, Positive-QTOFsplash10-0ue9-9100000000-8398e0fee857c36bfc0c2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1,2-Benzoquinone 40V, Positive-QTOFsplash10-0udi-9000000000-a7b4f3fc126101b3970d2021-09-24Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum

IR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)2023-02-03FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)2023-02-03FELIX labView Spectrum
Biological Properties
Cellular LocationsNot Available
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 IDNot Available
FooDB IDFDB004549
KNApSAcK IDNot Available
Chemspider ID10941
KEGG Compound IDC02351
BioCyc IDCPD-385
BiGG IDNot Available
Wikipedia Link1,2-Benzoquinone
METLIN IDNot Available
PubChem Compound11421
PDB IDNot Available
ChEBI ID17253
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Davila LY, Caldas MJ: Applicability of MNDO techniques AM1 and PM3 to ring-structured polymers. J Comput Chem. 2002 Sep;23(12):1135-42. [PubMed:12116382 ]
  2. TAPPI G, FORNI PV: [Mycostatic and mycocidal action of heterocyclic derivatives of obenzoquinone]. Farmaco Sci Tec. 1950 May-Jun;5(3):241-50. [PubMed:15435538 ]
  3. Acharya AS, Manjula BN, Murthy GS, Vithayathil PJ: The influence of esterification of carboxyl groups of ribonuclease-A on its structure and immunological activity. Int J Pept Protein Res. 1977;9(3):213-9. [PubMed:844939 ]
  4. Nicoll K, Robertson J, Lant N, Kelland LR, Rogers PM, Robins DJ: Synthesis and antimelanoma activity of reversed amide analogues of N-acetyl-4-S-cysteaminylphenol. Oncol Res. 2006;16(2):97-106. [PubMed:16898270 ]