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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:31:58 UTC

Update Date

2023-02-21 17:19:01 UTC

HMDB ID

HMDB0029673

Secondary Accession Numbers

HMDB29673

Metabolite Identification

Common Name

2,6-Dimethoxy-1,4-benzoquinone

Description

2,6-Dimethoxy-1,4-benzoquinone belongs to the class of organic compounds known as p-benzoquinones. These are benzoquinones where the two C=O groups are attached at the 1- and 4-positions, respectively. 2,6-Dimethoxy-1,4-benzoquinone has been detected, but not quantified in, common wheats (Triticum aestivum) and green vegetables. This could make 2,6-dimethoxy-1,4-benzoquinone a potential biomarker for the consumption of these foods. Based on a literature review a significant number of articles have been published on 2,6-Dimethoxy-1,4-benzoquinone.

Structure

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

HEADER    PROTEIN                                 24-SEP-17   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 2,6-Dimethoxybenzoquinone                         
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-SEP-17         0                                  
HETATM    1  O   UNK     0       9.748   1.540   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0       4.414   1.540   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0       7.081   3.080   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0       7.081  -3.080   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       8.415   0.770   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.747   0.770   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       7.081   1.540   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.747  -0.770   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       8.415  -0.770   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       7.081  -1.540   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       3.080   0.770   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      11.082   0.770   0.000  0.00  0.00           C+0
CONECT    1    5   12                                                       
CONECT    2    6   11                                                       
CONECT    3    7                                                            
CONECT    4   10                                                            
CONECT    5    1    7    9                                                  
CONECT    6    2    7    8                                                  
CONECT    7    3    5    6                                                  
CONECT    8    6   10                                                       
CONECT    9    5   10                                                       
CONECT   10    4    8    9                                                  
CONECT   11    2                                                            
CONECT   12    1                                                            
MASTER        0    0    0    0    0    0    0    0   12    0   24    0
END

View in JSmol View Stereo Labels

Synonyms

Value	Source
2,6-Dimetoxy-p-benzoquinone	Kegg
2, 6-Dimethoxy-1,4-benzoquinone	HMDB
2, 6-Dimethoxy-P-benzoquinone	HMDB
2, 6-Dimethoxyquinone	HMDB
2,5-Cyclohexadiene-1,4-dione, 2,6-dimethoxy- (9ci)	HMDB
2,6-Dimethoxy-2,5-cyclohexadiene-1,4-dione	HMDB
2,6-Dimethoxy-P-benzoquinone	HMDB, MeSH
2,6-Dimethoxy-P-quinone	HMDB
2,6-dimethoxybenzo-1,4-Quinone	HMDB
2,6-Dimethoxybenzoquinone	HMDB
2,6-Dimethoxyquinone	HMDB
2,6-Dimethoxysemiquinone anions	HMDB
2,6-Dimethoxysemiquinone radicals	HMDB
DMBQ	HMDB
Ghl.PD_Mitscher_leg0.4	HMDB
2,6-Dimethoxy-1,4-benzoquinone	MeSH

Chemical Formula

C₈H₈O₄

Average Molecular Weight

168.1467

Monoisotopic Molecular Weight

168.042258744

IUPAC Name

2,6-dimethoxycyclohexa-2,5-diene-1,4-dione

Traditional Name

2,6-dimethoxy-1,4-benzoquinone

CAS Registry Number

530-55-2

SMILES

COC1=CC(=O)C=C(OC)C1=O

InChI Identifier

InChI=1S/C8H8O4/c1-11-6-3-5(9)4-7(12-2)8(6)10/h3-4H,1-2H3

InChI Key

OLBNOBQOQZRLMP-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as p-benzoquinones. These are benzoquinones where the two C=O groups are attached at the 1- and 4-positions, respectively.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbonyl compounds

Direct Parent

P-benzoquinones

Alternative Parents

Substituents

P-benzoquinone
Vinylogous ester
Organic oxide
Hydrocarbon derivative
Aliphatic homomonocyclic compound

Molecular Framework

Aliphatic homomonocyclic compounds

External Descriptors

benzoquinones (CHEBI:27651 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Extracellular (HMDB: HMDB0029673)
Cytoplasm (HMDB: HMDB0029673)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0029673)

Source

Endogenous

Endogenous (HMDB: HMDB0029673)

Plant

Plant (HMDB: HMDB0029673)
Poaceae (HMDB: HMDB0029673)

Exogenous

Food

Food (HMDB: HMDB0029673)

Cereal and cereal product

Cereal

Common wheat (FooDB: FOOD00187)

Vegetable

Leaf vegetable

Green vegetables (FooDB: FOOD00872)

Exogenous (HMDB: HMDB0029673)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	252 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	70600 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	-0.06	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	7.05 g/L	ALOGPS
logP	0.36	ALOGPS
logP	0.21	ChemAxon
logS	-1.4	ALOGPS
pKa (Strongest Basic)	-4.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	52.6 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	44.47 m³·mol⁻¹	ChemAxon
Polarizability	15.54 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	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]+	138.178	31661259
DarkChem	[M-H]-	137.444	31661259
DeepCCS	[M+H]+	134.28	30932474
DeepCCS	[M-H]-	130.452	30932474
DeepCCS	[M-2H]-	167.839	30932474
DeepCCS	[M+Na]+	143.378	30932474
AllCCS	[M+H]+	136.2	32859911
AllCCS	[M+H-H2O]+	131.9	32859911
AllCCS	[M+NH4]+	140.3	32859911
AllCCS	[M+Na]+	141.4	32859911
AllCCS	[M-H]-	133.0	32859911
AllCCS	[M+Na-2H]-	134.2	32859911
AllCCS	[M+HCOO]-	135.5	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
2,6-Dimethoxy-1,4-benzoquinone	COC1=CC(=O)C=C(OC)C1=O	2104.7	Standard polar	33892256
2,6-Dimethoxy-1,4-benzoquinone	COC1=CC(=O)C=C(OC)C1=O	1332.1	Standard non polar	33892256
2,6-Dimethoxy-1,4-benzoquinone	COC1=CC(=O)C=C(OC)C1=O	1369.2	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 - 2,6-Dimethoxy-1,4-benzoquinone GC-MS (Non-derivatized) - 70eV, Positive	splash10-0ap3-8900000000-8b7cfcabbf83c8748217	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2,6-Dimethoxy-1,4-benzoquinone GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2,6-Dimethoxy-1,4-benzoquinone 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 - 2,6-Dimethoxy-1,4-benzoquinone 10V, Positive-QTOF	splash10-014i-0900000000-d4f01c77fdc0297d8118	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,6-Dimethoxy-1,4-benzoquinone 20V, Positive-QTOF	splash10-014i-0900000000-6e32a3d9f4b7cdb957fc	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,6-Dimethoxy-1,4-benzoquinone 40V, Positive-QTOF	splash10-0a4r-9600000000-d5725919e94062776993	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,6-Dimethoxy-1,4-benzoquinone 10V, Negative-QTOF	splash10-014i-0900000000-2465b4da8838c4c61cc3	2016-08-04	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,6-Dimethoxy-1,4-benzoquinone 20V, Negative-QTOF	splash10-014i-0900000000-5fcc8e0ae08d407017a9	2016-08-04	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,6-Dimethoxy-1,4-benzoquinone 40V, Negative-QTOF	splash10-0a4r-7900000000-80fd932a3585df0b512a	2016-08-04	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,6-Dimethoxy-1,4-benzoquinone 10V, Positive-QTOF	splash10-014i-0900000000-f95c25c23dba001bba7b	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,6-Dimethoxy-1,4-benzoquinone 20V, Positive-QTOF	splash10-05n0-3900000000-b257d968c303e5abb106	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,6-Dimethoxy-1,4-benzoquinone 40V, Positive-QTOF	splash10-0aou-9000000000-13b511af9b51cff60361	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,6-Dimethoxy-1,4-benzoquinone 10V, Negative-QTOF	splash10-014i-0900000000-930f9ca2cc854ecca14e	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,6-Dimethoxy-1,4-benzoquinone 20V, Negative-QTOF	splash10-014i-0900000000-fdb500a379becee68e5c	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,6-Dimethoxy-1,4-benzoquinone 40V, Negative-QTOF	splash10-0ap0-4900000000-4c9648cf6476bd481443	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]+)	2023-02-03	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)	2023-02-03	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

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

2,6-Dimethoxybenzoquinone

METLIN ID

Not Available

PubChem Compound

68262

PDB ID

KIA

ChEBI ID

544013

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1339891

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 2,6-Dimethoxy-1,4-benzoquinone (HMDB0029673)

MOL for HMDB0029673 (2,6-Dimethoxy-1,4-benzoquinone)

3D MOL for HMDB0029673 (2,6-Dimethoxy-1,4-benzoquinone)

3D SDF for HMDB0029673 (2,6-Dimethoxy-1,4-benzoquinone)

3D-SDF for HMDB0029673 (2,6-Dimethoxy-1,4-benzoquinone)

PDB for HMDB0029673 (2,6-Dimethoxy-1,4-benzoquinone)

3D PDB for HMDB0029673 (2,6-Dimethoxy-1,4-benzoquinone)

SMILES for HMDB0029673 (2,6-Dimethoxy-1,4-benzoquinone)

INCHI for HMDB0029673 (2,6-Dimethoxy-1,4-benzoquinone)

Structure for HMDB0029673 (2,6-Dimethoxy-1,4-benzoquinone)

3D Structure for HMDB0029673 (2,6-Dimethoxy-1,4-benzoquinone)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra

IR Spectra