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Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2017-10-08 19:45:47 UTC

Update Date

2022-03-07 03:18:12 UTC

HMDB ID

HMDB0166723

Secondary Accession Numbers

None

Metabolite Identification

Common Name

2,6-Di-tert-butyl-4-hydroxy-4-methyl-2,5-cyclohexadienone

Description

2,6-Di-tert-butyl-4-hydroxy-4-methyl-2,5-cyclohexadienone, also known as BHT-quinol, belongs to the class of organic compounds known as monocyclic monoterpenoids. These are monoterpenoids containing 1 ring in the isoprene chain. BHT-quinol is a metabolite of 2,6-di-tert-butyl-4-methylphenol (BHA), a synthetic phenolic antioxidant (SPA). SPAs are a family of chemicals used widely in foods, polymers, and cosmetics as radical trapping agents to slow down degradation due to oxidation. Given their widespread use, human exposure is unavoidable and there is public concern regarding environmental contamination by these chemicals. BHT-quinol was detected in human urine (PMID: 31265952 ).

Structure

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

HMDB0166723
     RDKit          3D
2,6-Di-tert-butyl-4-hydroxy-4-methyl-2,5-cyclohexadienone
 41 41  0  0  0  0  0  0  0  0999 V2000
   -0.2465    3.0035   -1.3408 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1313    2.1919   -0.0456 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0499    3.1495    0.9904 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1488    1.4812   -0.0932 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2268    0.1667   -0.0052 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5296   -0.5417   -0.0547 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5847   -1.5126   -1.2236 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6831    0.4238   -0.2279 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7160   -1.3310    1.2244 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0285   -0.6478    0.1452 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1082   -1.9034    0.2288 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2821    0.0121    0.1988 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4722   -0.8372    0.3510 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4480   -1.6575    1.6235 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7315    0.0101    0.4007 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6053   -1.7689   -0.8385 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2973    1.3217    0.1063 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4907    2.3556   -2.1884 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7208    3.5365   -1.4947 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0162    3.8004   -1.2343 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6042    3.8461    0.7291 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0594    2.0679   -0.2051 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4066   -2.5418   -0.8832 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6132   -1.5078   -1.6843 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9065   -1.1980   -2.0541 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5304    0.9580   -1.2008 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8074    1.1108    0.6113 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6036   -0.1798   -0.3639 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6363   -2.4204    1.0595 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9144   -1.0628    1.9690 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6976   -1.1139    1.7043 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4336   -1.7467    2.0478 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8115   -2.6830    1.4303 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0764   -1.1848    2.4031 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7164    0.6748    1.2995 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8356    0.6380   -0.5071 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5829   -0.7047    0.4244 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1136   -2.7102   -0.4988 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6553   -2.0085   -1.3154 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2550   -1.2992   -1.6341 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2747    1.8132    0.1464 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  1  0
  6  8  1  0
  6  9  1  0
  5 10  1  0
 10 11  2  0
 10 12  1  0
 12 13  1  0
 13 14  1  0
 13 15  1  0
 13 16  1  0
 12 17  2  0
 17  2  1  0
  1 18  1  0
  1 19  1  0
  1 20  1  0
  3 21  1  0
  4 22  1  0
  7 23  1  0
  7 24  1  0
  7 25  1  0
  8 26  1  0
  8 27  1  0
  8 28  1  0
  9 29  1  0
  9 30  1  0
  9 31  1  0
 14 32  1  0
 14 33  1  0
 14 34  1  0
 15 35  1  0
 15 36  1  0
 15 37  1  0
 16 38  1  0
 16 39  1  0
 16 40  1  0
 17 41  1  0
M  END


  Mrv1652304282019152D          

 17 17  0  0  0  0            999 V2000
10000.0661 9999.4712    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.7803 9999.0583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.478910000.1874    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.653310000.1874    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.637810000.2967    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9999.3506 9999.0583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.6362 9999.4708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.9218 9999.0582    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.9217 9998.2334    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.3506 9998.2334    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.617510000.1874    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9996.791910000.1874    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9996.4908 9999.0583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.2058 9999.4712    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.1200 9997.1775    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9999.1622 9997.1874    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.6361 9997.8210    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  3  1  0  0  0  0
  1  4  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
 10  6  2  0  0  0  0
  1  6  1  0  0  0  0
  7  5  2  0  0  0  0
  8 14  1  0  0  0  0
 14 11  1  0  0  0  0
 14 12  1  0  0  0  0
 14 13  1  0  0  0  0
 17 16  1  0  0  0  0
  9 17  1  0  0  0  0
 17 10  1  0  0  0  0
 17 15  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0166723

> <DATABASE_NAME>
hmdb

> <SMILES>
CC(C)(C)C1=CC(C)(O)C=C(C1=O)C(C)(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C15H24O2/c1-13(2,3)10-8-15(7,17)9-11(12(10)16)14(4,5)6/h8-9,17H,1-7H3

> <INCHI_KEY>
DQBHJILNHNRDTM-UHFFFAOYSA-N

> <FORMULA>
C15H24O2

> <MOLECULAR_WEIGHT>
236.355

> <EXACT_MASS>
236.177630013

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
41

> <JCHEM_AVERAGE_POLARIZABILITY>
27.790832809967753

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2,6-di-tert-butyl-4-hydroxy-4-methylcyclohexa-2,5-dien-1-one

> <ALOGPS_LOGP>
3.82

> <JCHEM_LOGP>
3.543885046666668

> <ALOGPS_LOGS>
-3.36

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.195239066484039

> <JCHEM_PKA_STRONGEST_BASIC>
-3.150802432319881

> <JCHEM_POLAR_SURFACE_AREA>
37.3

> <JCHEM_REFRACTIVITY>
72.3973

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.03e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2,6-di-tert-butyl-4-hydroxy-4-methylcyclohexa-2,5-dien-1-one

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0166723
     RDKit          3D
2,6-Di-tert-butyl-4-hydroxy-4-methyl-2,5-cyclohexadienone
 41 41  0  0  0  0  0  0  0  0999 V2000
   -0.2465    3.0035   -1.3408 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1313    2.1919   -0.0456 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0499    3.1495    0.9904 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1488    1.4812   -0.0932 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2268    0.1667   -0.0052 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5296   -0.5417   -0.0547 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5847   -1.5126   -1.2236 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6831    0.4238   -0.2279 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7160   -1.3310    1.2244 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0285   -0.6478    0.1452 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1082   -1.9034    0.2288 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2821    0.0121    0.1988 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4722   -0.8372    0.3510 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4480   -1.6575    1.6235 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7315    0.0101    0.4007 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6053   -1.7689   -0.8385 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2973    1.3217    0.1063 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4907    2.3556   -2.1884 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7208    3.5365   -1.4947 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0162    3.8004   -1.2343 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6042    3.8461    0.7291 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0594    2.0679   -0.2051 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4066   -2.5418   -0.8832 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6132   -1.5078   -1.6843 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9065   -1.1980   -2.0541 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5304    0.9580   -1.2008 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8074    1.1108    0.6113 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6036   -0.1798   -0.3639 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6363   -2.4204    1.0595 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9144   -1.0628    1.9690 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6976   -1.1139    1.7043 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4336   -1.7467    2.0478 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8115   -2.6830    1.4303 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0764   -1.1848    2.4031 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7164    0.6748    1.2995 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8356    0.6380   -0.5071 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5829   -0.7047    0.4244 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1136   -2.7102   -0.4988 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6553   -2.0085   -1.3154 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2550   -1.2992   -1.6341 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2747    1.8132    0.1464 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  1  0
  6  8  1  0
  6  9  1  0
  5 10  1  0
 10 11  2  0
 10 12  1  0
 12 13  1  0
 13 14  1  0
 13 15  1  0
 13 16  1  0
 12 17  2  0
 17  2  1  0
  1 18  1  0
  1 19  1  0
  1 20  1  0
  3 21  1  0
  4 22  1  0
  7 23  1  0
  7 24  1  0
  7 25  1  0
  8 26  1  0
  8 27  1  0
  8 28  1  0
  9 29  1  0
  9 30  1  0
  9 31  1  0
 14 32  1  0
 14 33  1  0
 14 34  1  0
 15 35  1  0
 15 36  1  0
 15 37  1  0
 16 38  1  0
 16 39  1  0
 16 40  1  0
 17 41  1  0
M  END

HEADER    PROTEIN                                 28-APR-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-APR-20         0                                  
HETATM    1  C   UNK     0    8666.7908665.679   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0    8668.1238664.909   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0    8667.5618667.016   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0    8666.0208667.016   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0    8664.1248667.221   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0    8665.4548664.909   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0    8664.1218665.679   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0    8662.7878664.909   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0    8662.7878663.369   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0    8665.4548663.369   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0    8662.2198667.016   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0    8660.6788667.016   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0    8660.1168664.909   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0    8661.4518665.679   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0    8663.1578661.398   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0    8665.1038661.416   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0    8664.1218662.599   0.000  0.00  0.00           C+0
CONECT    1    2    3    4    6                                             
CONECT    2    1                                                            
CONECT    3    1                                                            
CONECT    4    1                                                            
CONECT    5    7                                                            
CONECT    6    7   10    1                                                  
CONECT    7    6    8    5                                                  
CONECT    8    7    9   14                                                  
CONECT    9    8   17                                                       
CONECT   10    6   17                                                       
CONECT   11   14                                                            
CONECT   12   14                                                            
CONECT   13   14                                                            
CONECT   14    8   11   12   13                                             
CONECT   15   17                                                            
CONECT   16   17                                                            
CONECT   17   16    9   10   15                                             
MASTER        0    0    0    0    0    0    0    0   17    0   34    0
END

COMPND    HMDB0166723
HETATM    1  C1  UNL     1      -0.246   3.003  -1.341  1.00  0.00           C  
HETATM    2  C2  UNL     1      -0.131   2.192  -0.046  1.00  0.00           C  
HETATM    3  O1  UNL     1      -0.050   3.149   0.990  1.00  0.00           O  
HETATM    4  C3  UNL     1       1.149   1.481  -0.093  1.00  0.00           C  
HETATM    5  C4  UNL     1       1.227   0.167  -0.005  1.00  0.00           C  
HETATM    6  C5  UNL     1       2.530  -0.542  -0.055  1.00  0.00           C  
HETATM    7  C6  UNL     1       2.585  -1.513  -1.224  1.00  0.00           C  
HETATM    8  C7  UNL     1       3.683   0.424  -0.228  1.00  0.00           C  
HETATM    9  C8  UNL     1       2.716  -1.331   1.224  1.00  0.00           C  
HETATM   10  C9  UNL     1       0.029  -0.648   0.145  1.00  0.00           C  
HETATM   11  O2  UNL     1       0.108  -1.903   0.229  1.00  0.00           O  
HETATM   12  C10 UNL     1      -1.282   0.012   0.199  1.00  0.00           C  
HETATM   13  C11 UNL     1      -2.472  -0.837   0.351  1.00  0.00           C  
HETATM   14  C12 UNL     1      -2.448  -1.657   1.624  1.00  0.00           C  
HETATM   15  C13 UNL     1      -3.732   0.010   0.401  1.00  0.00           C  
HETATM   16  C14 UNL     1      -2.605  -1.769  -0.839  1.00  0.00           C  
HETATM   17  C15 UNL     1      -1.297   1.322   0.106  1.00  0.00           C  
HETATM   18  H1  UNL     1      -0.491   2.356  -2.188  1.00  0.00           H  
HETATM   19  H2  UNL     1       0.721   3.536  -1.495  1.00  0.00           H  
HETATM   20  H3  UNL     1      -1.016   3.800  -1.234  1.00  0.00           H  
HETATM   21  H4  UNL     1       0.604   3.846   0.729  1.00  0.00           H  
HETATM   22  H5  UNL     1       2.059   2.068  -0.205  1.00  0.00           H  
HETATM   23  H6  UNL     1       2.407  -2.542  -0.883  1.00  0.00           H  
HETATM   24  H7  UNL     1       3.613  -1.508  -1.684  1.00  0.00           H  
HETATM   25  H8  UNL     1       1.906  -1.198  -2.054  1.00  0.00           H  
HETATM   26  H9  UNL     1       3.530   0.958  -1.201  1.00  0.00           H  
HETATM   27  H10 UNL     1       3.807   1.111   0.611  1.00  0.00           H  
HETATM   28  H11 UNL     1       4.604  -0.180  -0.364  1.00  0.00           H  
HETATM   29  H12 UNL     1       2.636  -2.420   1.059  1.00  0.00           H  
HETATM   30  H13 UNL     1       1.914  -1.063   1.969  1.00  0.00           H  
HETATM   31  H14 UNL     1       3.698  -1.114   1.704  1.00  0.00           H  
HETATM   32  H15 UNL     1      -1.434  -1.747   2.048  1.00  0.00           H  
HETATM   33  H16 UNL     1      -2.811  -2.683   1.430  1.00  0.00           H  
HETATM   34  H17 UNL     1      -3.076  -1.185   2.403  1.00  0.00           H  
HETATM   35  H18 UNL     1      -3.716   0.675   1.299  1.00  0.00           H  
HETATM   36  H19 UNL     1      -3.836   0.638  -0.507  1.00  0.00           H  
HETATM   37  H20 UNL     1      -4.583  -0.705   0.424  1.00  0.00           H  
HETATM   38  H21 UNL     1      -3.114  -2.710  -0.499  1.00  0.00           H  
HETATM   39  H22 UNL     1      -1.655  -2.009  -1.315  1.00  0.00           H  
HETATM   40  H23 UNL     1      -3.255  -1.299  -1.634  1.00  0.00           H  
HETATM   41  H24 UNL     1      -2.275   1.813   0.146  1.00  0.00           H  
CONECT    1    2   18   19   20
CONECT    2    3    4   17
CONECT    3   21
CONECT    4    5    5   22
CONECT    5    6   10
CONECT    6    7    8    9
CONECT    7   23   24   25
CONECT    8   26   27   28
CONECT    9   29   30   31
CONECT   10   11   11   12
CONECT   12   13   17   17
CONECT   13   14   15   16
CONECT   14   32   33   34
CONECT   15   35   36   37
CONECT   16   38   39   40
CONECT   17   41
END

HMDB0166723
     RDKit          3D
2,6-Di-tert-butyl-4-hydroxy-4-methyl-2,5-cyclohexadienone
 41 41  0  0  0  0  0  0  0  0999 V2000
   -0.2465    3.0035   -1.3408 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1313    2.1919   -0.0456 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0499    3.1495    0.9904 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1488    1.4812   -0.0932 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2268    0.1667   -0.0052 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5296   -0.5417   -0.0547 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5847   -1.5126   -1.2236 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6831    0.4238   -0.2279 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7160   -1.3310    1.2244 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0285   -0.6478    0.1452 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1082   -1.9034    0.2288 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2821    0.0121    0.1988 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4722   -0.8372    0.3510 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4480   -1.6575    1.6235 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7315    0.0101    0.4007 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6053   -1.7689   -0.8385 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2973    1.3217    0.1063 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4907    2.3556   -2.1884 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7208    3.5365   -1.4947 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0162    3.8004   -1.2343 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6042    3.8461    0.7291 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0594    2.0679   -0.2051 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4066   -2.5418   -0.8832 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6132   -1.5078   -1.6843 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9065   -1.1980   -2.0541 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5304    0.9580   -1.2008 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8074    1.1108    0.6113 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6036   -0.1798   -0.3639 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6363   -2.4204    1.0595 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9144   -1.0628    1.9690 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6976   -1.1139    1.7043 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4336   -1.7467    2.0478 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8115   -2.6830    1.4303 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0764   -1.1848    2.4031 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7164    0.6748    1.2995 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8356    0.6380   -0.5071 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5829   -0.7047    0.4244 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1136   -2.7102   -0.4988 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6553   -2.0085   -1.3154 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2550   -1.2992   -1.6341 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2747    1.8132    0.1464 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  1  0
  6  8  1  0
  6  9  1  0
  5 10  1  0
 10 11  2  0
 10 12  1  0
 12 13  1  0
 13 14  1  0
 13 15  1  0
 13 16  1  0
 12 17  2  0
 17  2  1  0
  1 18  1  0
  1 19  1  0
  1 20  1  0
  3 21  1  0
  4 22  1  0
  7 23  1  0
  7 24  1  0
  7 25  1  0
  8 26  1  0
  8 27  1  0
  8 28  1  0
  9 29  1  0
  9 30  1  0
  9 31  1  0
 14 32  1  0
 14 33  1  0
 14 34  1  0
 15 35  1  0
 15 36  1  0
 15 37  1  0
 16 38  1  0
 16 39  1  0
 16 40  1  0
 17 41  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
2,6-Di-tert-butyl-4-hydroxy-4-methyl-2,5-cyclohexadien-1-one	MeSH
2,6-Bis(1,1-dimethylethyl)-4-hydroxy-4-methyl-2,5-cyclohexadien-1-one	HMDB
2,6-Di(tert-butyl)-4-hydroxy-4-methyl-2,5-cyclohexadien-1-one	HMDB
2,6-Di-tert-butyl-4-hydroxy-4-methyl-2,5-cyclohexadienone	HMDB
2,6-Di-tert-butyl-4-methyl-4-hydroxy-2,5-cyclohexadien-1-one	HMDB
2,6-Ditert-butyl-4-hydroxy-4-methylcyclohexa-2,5-dien-1-one	HMDB
4-Hydroxy-4-methyl-2,6-di-tert-butyl-2,5-cyclohexadienone	HMDB
BHT-quinol	HMDB

Chemical Formula

C₁₅H₂₄O₂

Average Molecular Weight

236.355

Monoisotopic Molecular Weight

236.177630013

IUPAC Name

2,6-di-tert-butyl-4-hydroxy-4-methylcyclohexa-2,5-dien-1-one

Traditional Name

2,6-di-tert-butyl-4-hydroxy-4-methylcyclohexa-2,5-dien-1-one

CAS Registry Number

10396-80-2

SMILES

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

InChI Identifier

InChI=1S/C15H24O2/c1-13(2,3)10-8-15(7,17)9-11(12(10)16)14(4,5)6/h8-9,17H,1-7H3

InChI Key

DQBHJILNHNRDTM-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as monocyclic monoterpenoids. These are monoterpenoids containing 1 ring in the isoprene chain.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Monoterpenoids

Direct Parent

Monocyclic monoterpenoids

Alternative Parents

Substituents

Monocyclic monoterpenoid
Tertiary alcohol
Cyclic ketone
Ketone
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Alcohol
Aliphatic homomonocyclic compound

Molecular Framework

Aliphatic homomonocyclic compounds

External Descriptors

Not Available

Ontology

Not Available

Urine (PMID: 31265952)

Process

Not Available

Role

Not Available

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
logP	3.82	ALOGPS
logP	3.54	ChemAxon
logS	-3.4	ALOGPS
pKa (Strongest Acidic)	14.2	ChemAxon
pKa (Strongest Basic)	-3.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	37.3 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	72.4 m³·mol⁻¹	ChemAxon
Polarizability	27.79 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M+H]+	169.583	30932474
DeepCCS	[M-H]-	167.226	30932474
DeepCCS	[M-2H]-	200.111	30932474
DeepCCS	[M+Na]+	175.677	30932474
AllCCS	[M+H]+	151.3	32859911
AllCCS	[M+H-H2O]+	147.7	32859911
AllCCS	[M+NH4]+	154.6	32859911
AllCCS	[M+Na]+	155.5	32859911
AllCCS	[M-H]-	162.7	32859911
AllCCS	[M+Na-2H]-	163.4	32859911
AllCCS	[M+HCOO]-	164.2	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
2,6-Di-tert-butyl-4-hydroxy-4-methyl-2,5-cyclohexadienone	CC(C)(C)C1=CC(C)(O)C=C(C1=O)C(C)(C)C	2389.5	Standard polar	33892256
2,6-Di-tert-butyl-4-hydroxy-4-methyl-2,5-cyclohexadienone	CC(C)(C)C1=CC(C)(O)C=C(C1=O)C(C)(C)C	1548.3	Standard non polar	33892256
2,6-Di-tert-butyl-4-hydroxy-4-methyl-2,5-cyclohexadienone	CC(C)(C)C1=CC(C)(O)C=C(C1=O)C(C)(C)C	1443.5	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
2,6-Di-tert-butyl-4-hydroxy-4-methyl-2,5-cyclohexadienone,1TMS,isomer #1	CC1(O[Si](C)(C)C)C=C(C(C)(C)C)C(=O)C(C(C)(C)C)=C1	1572.4	Semi standard non polar	33892256
2,6-Di-tert-butyl-4-hydroxy-4-methyl-2,5-cyclohexadienone,1TBDMS,isomer #1	CC1(O[Si](C)(C)C(C)(C)C)C=C(C(C)(C)C)C(=O)C(C(C)(C)C)=C1	1795.0	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 - 2,6-Di-tert-butyl-4-hydroxy-4-methyl-2,5-cyclohexadienone GC-MS (Non-derivatized) - 70eV, Positive	splash10-02os-4940000000-74d1c19f1a4219cc3a55	2018-04-09	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2,6-Di-tert-butyl-4-hydroxy-4-methyl-2,5-cyclohexadienone 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-Di-tert-butyl-4-hydroxy-4-methyl-2,5-cyclohexadienone 10V, Positive-QTOF	splash10-014r-0090000000-ded3d904ebb9d67ef04e	2018-04-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,6-Di-tert-butyl-4-hydroxy-4-methyl-2,5-cyclohexadienone 20V, Positive-QTOF	splash10-02u9-2690000000-9a90dc3b253d4ea9380a	2018-04-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,6-Di-tert-butyl-4-hydroxy-4-methyl-2,5-cyclohexadienone 40V, Positive-QTOF	splash10-053r-9610000000-375c5f29d6f71a6b2453	2018-04-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,6-Di-tert-butyl-4-hydroxy-4-methyl-2,5-cyclohexadienone 10V, Negative-QTOF	splash10-000i-0090000000-c382ade86833a96572f4	2018-04-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,6-Di-tert-butyl-4-hydroxy-4-methyl-2,5-cyclohexadienone 20V, Negative-QTOF	splash10-000i-0090000000-17a554389c5b5527c9f3	2018-04-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,6-Di-tert-butyl-4-hydroxy-4-methyl-2,5-cyclohexadienone 40V, Negative-QTOF	splash10-07yr-3690000000-2df7a13aee3d603a41d6	2018-04-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,6-Di-tert-butyl-4-hydroxy-4-methyl-2,5-cyclohexadienone 10V, Positive-QTOF	splash10-000i-0190000000-7feaadbcc50ec3cbf0b7	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,6-Di-tert-butyl-4-hydroxy-4-methyl-2,5-cyclohexadienone 20V, Positive-QTOF	splash10-06si-9710000000-5709196b7a162be280fb	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,6-Di-tert-butyl-4-hydroxy-4-methyl-2,5-cyclohexadienone 40V, Positive-QTOF	splash10-0a4i-9400000000-ec314e2f09fa22bf80af	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,6-Di-tert-butyl-4-hydroxy-4-methyl-2,5-cyclohexadienone 10V, Negative-QTOF	splash10-000i-0090000000-c0031dc201eac6b6350a	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,6-Di-tert-butyl-4-hydroxy-4-methyl-2,5-cyclohexadienone 20V, Negative-QTOF	splash10-000i-0090000000-c0031dc201eac6b6350a	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,6-Di-tert-butyl-4-hydroxy-4-methyl-2,5-cyclohexadienone 40V, Negative-QTOF	splash10-0ik9-0790000000-dea4db79a24e1bd0484d	2021-09-23	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Urine

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Urine	Detected and Quantified	0.000387 umol/mmol creatinine	Adult (>18 years old)	Both	Normal	31265952	details

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

Not Available

KNApSAcK ID

Not Available

Chemspider ID

128880

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

146102

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Liu R, Mabury SA: Unexpectedly high concentrations of 2,4-di-tert-butylphenol in human urine. Environ Pollut. 2019 Sep;252(Pt B):1423-1428. doi: 10.1016/j.envpol.2019.06.077. Epub 2019 Jun 21. [PubMed:31265952 ]

Showing metabocard for 2,6-Di-tert-butyl-4-hydroxy-4-methyl-2,5-cyclohexadienone (HMDB0166723)

MOL for HMDB0166723 (2,6-Di-tert-butyl-4-hydroxy-4-methyl-2,5-cyclohexadienone)

3D MOL for HMDB0166723 (2,6-Di-tert-butyl-4-hydroxy-4-methyl-2,5-cyclohexadienone)

3D SDF for HMDB0166723 (2,6-Di-tert-butyl-4-hydroxy-4-methyl-2,5-cyclohexadienone)

3D-SDF for HMDB0166723 (2,6-Di-tert-butyl-4-hydroxy-4-methyl-2,5-cyclohexadienone)

PDB for HMDB0166723 (2,6-Di-tert-butyl-4-hydroxy-4-methyl-2,5-cyclohexadienone)

3D PDB for HMDB0166723 (2,6-Di-tert-butyl-4-hydroxy-4-methyl-2,5-cyclohexadienone)

SMILES for HMDB0166723 (2,6-Di-tert-butyl-4-hydroxy-4-methyl-2,5-cyclohexadienone)

INCHI for HMDB0166723 (2,6-Di-tert-butyl-4-hydroxy-4-methyl-2,5-cyclohexadienone)

Structure for HMDB0166723 (2,6-Di-tert-butyl-4-hydroxy-4-methyl-2,5-cyclohexadienone)

3D Structure for HMDB0166723 (2,6-Di-tert-butyl-4-hydroxy-4-methyl-2,5-cyclohexadienone)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra