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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:47:32 UTC

Update Date

2023-02-21 17:21:35 UTC

HMDB ID

HMDB0032062

Secondary Accession Numbers

HMDB32062

Metabolite Identification

Common Name

2-tert-Butyl-1,4-benzenediol

Description

2-tert-Butyl-1,4-benzenediol, also known as MTBHQ or 2-t-butylhydroquinone, belongs to the class of organic compounds known as phenylpropanes. These are organic compounds containing a phenylpropane moiety. Based on a literature review a small amount of articles have been published on 2-tert-Butyl-1,4-benzenediol.

Structure

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

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: EYK                                               
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0       2.985   1.631   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.651   0.861   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.881   2.195   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.421  -0.472   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.318   0.091   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.318  -1.449   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -1.016  -2.219   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      -1.016  -3.759   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0      -2.350  -1.449   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -2.350   0.091   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -1.016   0.861   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      -1.016   2.401   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4    5                                             
CONECT    3    2                                                            
CONECT    4    2                                                            
CONECT    5    2    6   11                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10                                                       
CONECT   10    9   11                                                       
CONECT   11    5   10   12                                                  
CONECT   12   11                                                            
MASTER        0    0    0    0    0    0    0    0   12    0   24    0
END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
2-(1,1-Dimethylethyl)-1,4-benzenediol	ChEBI
2-t-Butyl-1,4-benzenediol	ChEBI
2-t-Butylhydroquinone	ChEBI
2-Tert-butyl(1,4)hydroquinone	ChEBI
2-Tertiary-butylhydroquinone	ChEBI
mono-Tert-butylhydroquinone	ChEBI
mono-Tertiarybutylhydroquinone	ChEBI
MTBHQ	ChEBI
t-Butyl hydroquinone	ChEBI
t-Butylhydroquinone	ChEBI
TBHQ	ChEBI
Tert-butyl-1,4-benzenediol	ChEBI
Tert-butylhydroquinone	ChEBI
Tertiary-butylhydroquinone	ChEBI
2-(1,1-Dimethylethyl)-1,4-benzenediol, 9ci	HMDB
2-(1,1-Dimethylethyl)benzene-1,4-diol	HMDB
2-Tert-butylbenzene-1,4-diol	HMDB
2-Tert-butylhydroquinone	HMDB
Banox 20ba	HMDB
Eastman MTBHQ	HMDB
EYK	HMDB
Monotertiary butyl hydroquinone	HMDB
Sustane	HMDB
Sustane TBHQ	HMDB
T-BHQ	HMDB
t-Butyl-hydroquinone	HMDB
Tenox 20	HMDB
Tenox tbho	HMDB
Tenox TBHQ	HMDB
Tenox TBHQTBHQ	HMDB
Tert-butyl-hydroquinone	HMDB
Tert-butylhydrochinone	HMDB
2-Tert-butyl-1,4-benzenediol	ChEBI

Chemical Formula

C₁₀H₁₄O₂

Average Molecular Weight

166.217

Monoisotopic Molecular Weight

166.099379692

IUPAC Name

2-tert-butylbenzene-1,4-diol

Traditional Name

tert-butylhydroquinone

CAS Registry Number

1948-33-0

SMILES

CC(C)(C)C1=CC(O)=CC=C1O

InChI Identifier

InChI=1S/C10H14O2/c1-10(2,3)8-6-7(11)4-5-9(8)12/h4-6,11-12H,1-3H3

InChI Key

BGNXCDMCOKJUMV-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as phenylpropanes. These are organic compounds containing a phenylpropane moiety.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Phenylpropanes

Direct Parent

Phenylpropanes

Alternative Parents

Substituents

Phenylpropane
Hydroquinone
1-hydroxy-2-unsubstituted benzenoid
Phenol
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

hydroquinones (CHEBI:78886 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Membrane (HMDB: HMDB0032062)
Cell membrane (HMDB: HMDB0032062)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0032062)

Source

Exogenous

Exogenous (HMDB: HMDB0032062)

Food

Food (HMDB: HMDB0032062)

Fat and oil

Fats and oils (FooDB: FOOD00864)

Endogenous

Endogenous (HMDB: HMDB0032062)

Process

Not Available

Role

Industrial application

Pharmaceutical industry

Pharmaceutical (HMDB: HMDB0032062)

Food and nutrition

Food and nutrition (HMDB: HMDB0032062)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	127 - 129 °C	Not Available
Boiling Point	291.35 °C. @ 760.00 mm Hg (est)	The Good Scents Company Information System
Water Solubility	748.2 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	2.257 (est)	The Good Scents Company Information System

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	2.75 g/L	ALOGPS
logP	2.61	ALOGPS
logP	2.91	ChemAxon
logS	-1.8	ALOGPS
pKa (Strongest Acidic)	9.94	ChemAxon
pKa (Strongest Basic)	-5.4	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	48.69 m³·mol⁻¹	ChemAxon
Polarizability	18.38 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]+	137.69	31661259
DarkChem	[M-H]-	135.619	31661259
DeepCCS	[M+H]+	139.755	30932474
DeepCCS	[M-H]-	137.334	30932474
DeepCCS	[M-2H]-	173.317	30932474
DeepCCS	[M+Na]+	148.532	30932474
AllCCS	[M+H]+	132.7	32859911
AllCCS	[M+H-H2O]+	128.4	32859911
AllCCS	[M+NH4]+	136.8	32859911
AllCCS	[M+Na]+	138.0	32859911
AllCCS	[M-H]-	133.9	32859911
AllCCS	[M+Na-2H]-	135.0	32859911
AllCCS	[M+HCOO]-	136.3	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
2-tert-Butyl-1,4-benzenediol	CC(C)(C)C1=CC(O)=CC=C1O	2455.3	Standard polar	33892256
2-tert-Butyl-1,4-benzenediol	CC(C)(C)C1=CC(O)=CC=C1O	1462.9	Standard non polar	33892256
2-tert-Butyl-1,4-benzenediol	CC(C)(C)C1=CC(O)=CC=C1O	1567.8	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
2-tert-Butyl-1,4-benzenediol,1TMS,isomer #1	CC(C)(C)C1=CC(O[Si](C)(C)C)=CC=C1O	1499.8	Semi standard non polar	33892256
2-tert-Butyl-1,4-benzenediol,1TMS,isomer #2	CC(C)(C)C1=CC(O)=CC=C1O[Si](C)(C)C	1576.7	Semi standard non polar	33892256
2-tert-Butyl-1,4-benzenediol,2TMS,isomer #1	CC(C)(C)C1=CC(O[Si](C)(C)C)=CC=C1O[Si](C)(C)C	1611.1	Semi standard non polar	33892256
2-tert-Butyl-1,4-benzenediol,1TBDMS,isomer #1	CC(C)(C)C1=CC(O[Si](C)(C)C(C)(C)C)=CC=C1O	1739.4	Semi standard non polar	33892256
2-tert-Butyl-1,4-benzenediol,1TBDMS,isomer #2	CC(C)(C)C1=CC(O)=CC=C1O[Si](C)(C)C(C)(C)C	1807.4	Semi standard non polar	33892256
2-tert-Butyl-1,4-benzenediol,2TBDMS,isomer #1	CC(C)(C)C1=CC(O[Si](C)(C)C(C)(C)C)=CC=C1O[Si](C)(C)C(C)(C)C	2086.0	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-tert-Butyl-1,4-benzenediol GC-MS (Non-derivatized) - 70eV, Positive	splash10-0udi-2900000000-f1c81ea618f29937b9db	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2-tert-Butyl-1,4-benzenediol GC-MS (2 TMS) - 70eV, Positive	splash10-0072-5290000000-a66d84718b6ad3740c7f	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2-tert-Butyl-1,4-benzenediol GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-0fk9-3900000000-b2a502fc1214548205d4	2014-09-20	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-tert-Butyl-1,4-benzenediol 10V, Positive-QTOF	splash10-014i-0900000000-c8c9ce2ba695603664e0	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-tert-Butyl-1,4-benzenediol 20V, Positive-QTOF	splash10-02t9-1900000000-60b2cdcb6f62608be562	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-tert-Butyl-1,4-benzenediol 40V, Positive-QTOF	splash10-0540-9600000000-c632f069846be5a5631e	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-tert-Butyl-1,4-benzenediol 10V, Negative-QTOF	splash10-014i-0900000000-a87a87005aabcae88abb	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-tert-Butyl-1,4-benzenediol 20V, Negative-QTOF	splash10-014i-0900000000-944286023e85118a003e	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-tert-Butyl-1,4-benzenediol 40V, Negative-QTOF	splash10-0api-5900000000-0b55de568076ecc543d6	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-tert-Butyl-1,4-benzenediol 10V, Positive-QTOF	splash10-066r-4900000000-4e458a1e12011a878c7f	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-tert-Butyl-1,4-benzenediol 20V, Positive-QTOF	splash10-0a4i-9700000000-dbaf67fa3a2eadaf141b	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-tert-Butyl-1,4-benzenediol 40V, Positive-QTOF	splash10-0a4i-9300000000-9a7c98eebcf85d0a0656	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-tert-Butyl-1,4-benzenediol 10V, Negative-QTOF	splash10-014i-0900000000-349584a3f625d5b5807f	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-tert-Butyl-1,4-benzenediol 20V, Negative-QTOF	splash10-0159-5900000000-5a27aa1cd764288a4c77	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-tert-Butyl-1,4-benzenediol 40V, Negative-QTOF	splash10-0aos-9700000000-31963d7453ec788e62df	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

Membrane

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

DB07726

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB008771

KNApSAcK ID

Not Available

Chemspider ID

15235

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Tert-Butylhydroquinone

METLIN ID

Not Available

PubChem Compound

16043

PDB ID

EYK

ChEBI ID

78886

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1050641

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Hsu SS, Chou CT: Deltamethrin-Induced [Ca (2)(+) ]i Rise and Death in HGB Human Glioblastoma Cells. Chin J Physiol. 2012 Aug 31;55(4):294-304. doi: 10.4077/CJP.2012.BAB114. [PubMed:23282171 ]
Stolze K, Nohl H: Free radical formation and erythrocyte membrane alterations during MetHb formation induced by the BHA metabolite, tert-butylhydroquinone. Free Radic Res. 1999 Apr;30(4):295-303. [PubMed:10230808 ]
Gunaseelan K, Romsted LS, Gonzalez-Romero E, Bravo-Diaz C: Determining partition constants of polar organic molecules between the oil/interfacial and water/interfacial regions in emulsions: a combined electrochemical and spectrometric method. Langmuir. 2004 Apr 13;20(8):3047-55. [PubMed:15875828 ]
Surak JG: Monotertiarybutylhydroquinone effects on Tetrahymena pyriformis. Life Sci. 1977 May 15;20(10):1735-40. [PubMed:406489 ]
Astill BD, Terhaar CJ, Krasavage WJ, Wlof GL, Roudabush RL, Fassett DW: Safety evaluation and biochemical behavior of monotertiarybutylhydroquinone. J Am Oil Chem Soc. 1975 Feb;52(2):53-8. [PubMed:1133430 ]
(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Showing metabocard for 2-tert-Butyl-1,4-benzenediol (HMDB0032062)

MOL for HMDB0032062 (2-tert-Butyl-1,4-benzenediol)

3D MOL for HMDB0032062 (2-tert-Butyl-1,4-benzenediol)

3D SDF for HMDB0032062 (2-tert-Butyl-1,4-benzenediol)

3D-SDF for HMDB0032062 (2-tert-Butyl-1,4-benzenediol)

PDB for HMDB0032062 (2-tert-Butyl-1,4-benzenediol)

3D PDB for HMDB0032062 (2-tert-Butyl-1,4-benzenediol)

SMILES for HMDB0032062 (2-tert-Butyl-1,4-benzenediol)

INCHI for HMDB0032062 (2-tert-Butyl-1,4-benzenediol)

Structure for HMDB0032062 (2-tert-Butyl-1,4-benzenediol)

3D Structure for HMDB0032062 (2-tert-Butyl-1,4-benzenediol)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra