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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:48:04 UTC

Update Date

2023-02-21 17:21:39 UTC

HMDB ID

HMDB0032137

Secondary Accession Numbers

HMDB32137

Metabolite Identification

Common Name

2,6-Dimethyl-1,4-benzenediol

Description

2,6-Dimethyl-1,4-benzenediol, also known as 2, 6-dimethyl-p-benzohydroquinone or 2, 6-xylohydroquinone, belongs to the class of organic compounds known as hydroquinones. Hydroquinones are compounds containing a hydroquinone moiety, which consists of a benzene ring with a hydroxyl groups at positions 1 and 4. 2,6-Dimethyl-1,4-benzenediol has been detected, but not quantified, in a few different foods, such as broccoli, common pea, and pulses. This could make 2,6-dimethyl-1,4-benzenediol a potential biomarker for the consumption of these foods.

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, 6-Dimethyl-P-benzohydroquinone	HMDB
2, 6-Xylohydroquinone	HMDB
2,5-Dihydroxy-m-xylene	HMDB
2,6-Dimethyl-hydroquinone	HMDB
2,6-Dimethyl-P-benzohydroquinone	HMDB
2,6-Dimethylbenzene-1,4-diol	HMDB
2,6-Dimethylhydroquinone	HMDB
2,6-Dimethylhydroquinone, 8ci	HMDB
2,6-Dimethylquinol	HMDB
2,6-Xylohydroquinone	HMDB
2,6-Xyloquinol	HMDB
3,5-Dimethylhydroquinone	HMDB
DMHQ	HMDB
m-XHQ	HMDB
m-Xylene-2,5-diol	HMDB
m-Xylohydroquinone	HMDB
Metaxylohydroquinone	HMDB
MXHQ	HMDB
Poly(2,6-dimethyl-1,4-phenylene oxide)	HMDB

Chemical Formula

C₈H₁₀O₂

Average Molecular Weight

138.1638

Monoisotopic Molecular Weight

138.068079564

IUPAC Name

2,6-dimethylbenzene-1,4-diol

Traditional Name

1,4-benzenediol, 2,6-dimethyl-

CAS Registry Number

654-42-2

SMILES

CC1=CC(O)=CC(C)=C1O

InChI Identifier

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

InChI Key

SGWZVZZVXOJRAQ-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as hydroquinones. Hydroquinones are compounds containing a hydroquinone moiety, which consists of a benzene ring with a hydroxyl groups at positions 1 and 4.

Kingdom

Super Class

Class

Sub Class

Direct Parent

Alternative Parents

Substituents

M-xylene
Xylene
O-cresol
M-cresol
Hydroquinone
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: HMDB0032137)
Cytoplasm (HMDB: HMDB0032137)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0032137)

Source

Endogenous

Endogenous (HMDB: HMDB0032137)

Plant

Fabaceae (HMDB: HMDB0032137)

Exogenous

Food

Food (HMDB: HMDB0032137)

Vegetable

Cabbage

Broccoli (FooDB: FOOD00034)

Pulse

Pea

Common pea (FooDB: FOOD00141)

Pulses (FooDB: FOOD00867)

Exogenous (HMDB: HMDB0032137)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	149 - 151 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	45350 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	1.00	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	29.6 g/L	ALOGPS
logP	1.29	ALOGPS
logP	2.39	ChemAxon
logS	-0.67	ALOGPS
pKa (Strongest Acidic)	10.11	ChemAxon
pKa (Strongest Basic)	-5.9	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	0	ChemAxon
Refractivity	40.1 m³·mol⁻¹	ChemAxon
Polarizability	14.85 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]+	129.265	31661259
DarkChem	[M-H]-	125.49	31661259
DeepCCS	[M+H]+	132.262	30932474
DeepCCS	[M-H]-	129.774	30932474
DeepCCS	[M-2H]-	166.217	30932474
DeepCCS	[M+Na]+	141.232	30932474
AllCCS	[M+H]+	127.1	32859911
AllCCS	[M+H-H2O]+	122.4	32859911
AllCCS	[M+NH4]+	131.4	32859911
AllCCS	[M+Na]+	132.7	32859911
AllCCS	[M-H]-	124.8	32859911
AllCCS	[M+Na-2H]-	126.4	32859911
AllCCS	[M+HCOO]-	128.3	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
2,6-Dimethyl-1,4-benzenediol	CC1=CC(O)=CC(C)=C1O	2456.3	Standard polar	33892256
2,6-Dimethyl-1,4-benzenediol	CC1=CC(O)=CC(C)=C1O	1412.4	Standard non polar	33892256
2,6-Dimethyl-1,4-benzenediol	CC1=CC(O)=CC(C)=C1O	1433.9	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
2,6-Dimethyl-1,4-benzenediol,1TMS,isomer #1	CC1=CC(O[Si](C)(C)C)=CC(C)=C1O	1547.7	Semi standard non polar	33892256
2,6-Dimethyl-1,4-benzenediol,1TMS,isomer #2	CC1=CC(O)=CC(C)=C1O[Si](C)(C)C	1496.5	Semi standard non polar	33892256
2,6-Dimethyl-1,4-benzenediol,2TMS,isomer #1	CC1=CC(O[Si](C)(C)C)=CC(C)=C1O[Si](C)(C)C	1518.5	Semi standard non polar	33892256
2,6-Dimethyl-1,4-benzenediol,1TBDMS,isomer #1	CC1=CC(O[Si](C)(C)C(C)(C)C)=CC(C)=C1O	1722.3	Semi standard non polar	33892256
2,6-Dimethyl-1,4-benzenediol,1TBDMS,isomer #2	CC1=CC(O)=CC(C)=C1O[Si](C)(C)C(C)(C)C	1747.1	Semi standard non polar	33892256
2,6-Dimethyl-1,4-benzenediol,2TBDMS,isomer #1	CC1=CC(O[Si](C)(C)C(C)(C)C)=CC(C)=C1O[Si](C)(C)C(C)(C)C	2009.9	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-Dimethyl-1,4-benzenediol GC-MS (Non-derivatized) - 70eV, Positive	splash10-000i-1900000000-88ff73c8d1623ee40a29	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2,6-Dimethyl-1,4-benzenediol GC-MS (2 TMS) - 70eV, Positive	splash10-01b9-5490000000-f8ef259a1d967e78dd1c	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2,6-Dimethyl-1,4-benzenediol GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-000i-9700000000-540233787be2454eb216	2015-03-01	Not Available	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-Dimethyl-1,4-benzenediol 10V, Negative-QTOF	splash10-000i-0900000000-e4a9e1743830760fbb61	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,6-Dimethyl-1,4-benzenediol 20V, Negative-QTOF	splash10-000i-0900000000-dc1c84c5524e01153f43	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,6-Dimethyl-1,4-benzenediol 40V, Negative-QTOF	splash10-000i-9600000000-beafda0b0f54b42a956b	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,6-Dimethyl-1,4-benzenediol 10V, Negative-QTOF	splash10-000i-0900000000-08ef9d705ca98ce39abf	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,6-Dimethyl-1,4-benzenediol 20V, Negative-QTOF	splash10-000i-1900000000-2f78f289353ccbdd5534	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,6-Dimethyl-1,4-benzenediol 40V, Negative-QTOF	splash10-014l-9300000000-09309f2133472f16330f	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,6-Dimethyl-1,4-benzenediol 10V, Positive-QTOF	splash10-000i-0900000000-b1389ce8d1190e7088d0	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,6-Dimethyl-1,4-benzenediol 20V, Positive-QTOF	splash10-000i-1900000000-8d53d61708dd20fdb467	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,6-Dimethyl-1,4-benzenediol 40V, Positive-QTOF	splash10-0076-9300000000-13a8e5bb83e69dab8b90	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,6-Dimethyl-1,4-benzenediol 10V, Positive-QTOF	splash10-000i-0900000000-a988d5277867358ca91a	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,6-Dimethyl-1,4-benzenediol 20V, Positive-QTOF	splash10-00dl-9800000000-9e041e506c5c739100ab	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,6-Dimethyl-1,4-benzenediol 40V, Positive-QTOF	splash10-0f6x-9000000000-bdfa6ce17abc04785c51	2021-09-22	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	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

FDB008863

KNApSAcK ID

C00058169

Chemspider ID

62764

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

69560

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1430561

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-Dimethyl-1,4-benzenediol (HMDB0032137)

MOL for HMDB0032137 (2,6-Dimethyl-1,4-benzenediol)

3D MOL for HMDB0032137 (2,6-Dimethyl-1,4-benzenediol)

3D SDF for HMDB0032137 (2,6-Dimethyl-1,4-benzenediol)

3D-SDF for HMDB0032137 (2,6-Dimethyl-1,4-benzenediol)

PDB for HMDB0032137 (2,6-Dimethyl-1,4-benzenediol)

3D PDB for HMDB0032137 (2,6-Dimethyl-1,4-benzenediol)

SMILES for HMDB0032137 (2,6-Dimethyl-1,4-benzenediol)

INCHI for HMDB0032137 (2,6-Dimethyl-1,4-benzenediol)

Structure for HMDB0032137 (2,6-Dimethyl-1,4-benzenediol)

3D Structure for HMDB0032137 (2,6-Dimethyl-1,4-benzenediol)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra