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Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2020-04-28 16:47:45 UTC

Update Date

2022-03-07 03:18:20 UTC

HMDB ID

HMDB0240642

Secondary Accession Numbers

None

Metabolite Identification

Common Name

3,5-Di-tert-butyl-4-hydroxybenzoic acid

Description

3,5-Di-tert-butyl-4-hydroxybenzoic acid, also known as BHT-COOH or 4-carboxy-2,6-di-tert-butylphenol, belongs to the class of organic compounds known as hydroxybenzoic acid derivatives. Hydroxybenzoic acid derivatives are compounds containing a hydroxybenzoic acid (or a derivative), which is a benzene ring bearing a carboxyl and a hydroxyl groups. BHT-COOH 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-OH was detected in human urine (PMID: 31265952 ).

Structure

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

HMDB0240642
     RDKit          3D
3,5-Di-tert-butyl-4-hydroxybenzoic acid
 40 40  0  0  0  0  0  0  0  0999 V2000
   -3.5662    0.5116    0.2932 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4973   -0.4380   -0.1715 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6116   -0.6622   -1.6644 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7543   -1.7652    0.4925 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1744    0.1180    0.0962 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0918    1.3552    0.6986 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1074    1.9706    0.9956 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1380    3.2785    1.6326 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2479    3.8297    1.8985 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0476    3.9304    1.9528 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2460    1.2845    0.6590 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2084    0.0435    0.0546 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4988   -0.6385   -0.2768 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6523   -1.9572    0.4123 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6121   -0.7807   -1.7915 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6514    0.2396    0.1550 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0040   -0.5365   -0.2252 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1053   -1.7729   -0.8276 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5727    0.0531    0.1315 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4622    1.4607   -0.2734 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5109    0.7124    1.3776 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9879    0.1104   -2.1706 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2633   -1.6857   -1.8797 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6732   -0.5030   -1.9417 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0769   -2.5704    0.1407 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8257   -1.7038    1.5922 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7816   -2.0855    0.1472 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9768    1.9393    0.9851 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1107    4.9161    1.6882 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1977    1.7821    0.8992 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7585   -2.2821    0.9785 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4812   -1.9406    1.1593 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8519   -2.7585   -0.3483 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3388   -0.0632   -2.2240 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6289   -0.5256   -2.2814 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9409   -1.7929   -2.0206 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6105   -0.2703   -0.0971 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6797    1.2095   -0.3786 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6188    0.3645    1.2569 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6173   -2.3765   -1.1251 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
  2  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
  7 11  2  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 13 15  1  0
 13 16  1  0
 12 17  2  0
 17 18  1  0
 17  5  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  3 22  1  0
  3 23  1  0
  3 24  1  0
  4 25  1  0
  4 26  1  0
  4 27  1  0
  6 28  1  0
 10 29  1  0
 11 30  1  0
 14 31  1  0
 14 32  1  0
 14 33  1  0
 15 34  1  0
 15 35  1  0
 15 36  1  0
 16 37  1  0
 16 38  1  0
 16 39  1  0
 18 40  1  0
M  END


  Mrv1652304282018502D          

 18 18  0  0  0  0            999 V2000
 9992.4001 9991.8056    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9993.1137 9991.3931    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9992.8126 9992.5213    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9991.9877 9992.5213    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9990.9729 9992.6306    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9990.9729 9989.3307    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9991.6851 9991.3931    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9990.9713 9991.8052    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9990.2574 9991.3930    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9990.2573 9990.5688    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9990.9712 9990.1567    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9991.6851 9990.5688    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9989.9534 9992.5213    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9989.1284 9992.5213    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9988.8275 9991.3931    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9989.5420 9991.8056    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9990.2599 9988.9170    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9991.6875 9988.9200    0.0000 O   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
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12  7  1  0  0  0  0
  1  7  1  0  0  0  0
  8  5  1  0  0  0  0
  9 16  1  0  0  0  0
 16 13  1  0  0  0  0
 16 14  1  0  0  0  0
 16 15  1  0  0  0  0
 11  6  1  0  0  0  0
  6 17  1  0  0  0  0
  6 18  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0240642

> <DATABASE_NAME>
hmdb

> <SMILES>
CC(C)(C)C1=CC(=CC(=C1O)C(C)(C)C)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C15H22O3/c1-14(2,3)10-7-9(13(17)18)8-11(12(10)16)15(4,5)6/h7-8,16H,1-6H3,(H,17,18)

> <INCHI_KEY>
YEXOWHQZWLCHHD-UHFFFAOYSA-N

> <FORMULA>
C15H22O3

> <MOLECULAR_WEIGHT>
250.338

> <EXACT_MASS>
250.156894568

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
40

> <JCHEM_AVERAGE_POLARIZABILITY>
28.437319958345405

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3,5-di-tert-butyl-4-hydroxybenzoic acid

> <ALOGPS_LOGP>
4.50

> <JCHEM_LOGP>
4.417375943666666

> <ALOGPS_LOGS>
-3.37

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
10.918793243960485

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.358935436585984

> <JCHEM_PKA_STRONGEST_BASIC>
-5.185493095008355

> <JCHEM_POLAR_SURFACE_AREA>
57.53

> <JCHEM_REFRACTIVITY>
72.6269

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.07e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3,5-di-tert-butyl-4-hydroxybenzoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0240642
     RDKit          3D
3,5-Di-tert-butyl-4-hydroxybenzoic acid
 40 40  0  0  0  0  0  0  0  0999 V2000
   -3.5662    0.5116    0.2932 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4973   -0.4380   -0.1715 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6116   -0.6622   -1.6644 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7543   -1.7652    0.4925 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1744    0.1180    0.0962 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0918    1.3552    0.6986 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1074    1.9706    0.9956 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1380    3.2785    1.6326 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2479    3.8297    1.8985 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0476    3.9304    1.9528 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2460    1.2845    0.6590 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2084    0.0435    0.0546 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4988   -0.6385   -0.2768 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6523   -1.9572    0.4123 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6121   -0.7807   -1.7915 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6514    0.2396    0.1550 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0040   -0.5365   -0.2252 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1053   -1.7729   -0.8276 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5727    0.0531    0.1315 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4622    1.4607   -0.2734 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5109    0.7124    1.3776 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9879    0.1104   -2.1706 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2633   -1.6857   -1.8797 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6732   -0.5030   -1.9417 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0769   -2.5704    0.1407 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8257   -1.7038    1.5922 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7816   -2.0855    0.1472 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9768    1.9393    0.9851 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1107    4.9161    1.6882 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1977    1.7821    0.8992 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7585   -2.2821    0.9785 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4812   -1.9406    1.1593 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8519   -2.7585   -0.3483 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3388   -0.0632   -2.2240 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6289   -0.5256   -2.2814 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9409   -1.7929   -2.0206 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6105   -0.2703   -0.0971 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6797    1.2095   -0.3786 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6188    0.3645    1.2569 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6173   -2.3765   -1.1251 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
  2  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
  7 11  2  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 13 15  1  0
 13 16  1  0
 12 17  2  0
 17 18  1  0
 17  5  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  3 22  1  0
  3 23  1  0
  3 24  1  0
  4 25  1  0
  4 26  1  0
  4 27  1  0
  6 28  1  0
 10 29  1  0
 11 30  1  0
 14 31  1  0
 14 32  1  0
 14 33  1  0
 15 34  1  0
 15 35  1  0
 15 36  1  0
 16 37  1  0
 16 38  1  0
 16 39  1  0
 18 40  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    8652.4808651.370   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0    8653.8128650.600   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0    8653.2508652.706   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0    8651.7108652.706   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0    8649.8168652.910   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0    8649.8168646.751   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0    8651.1468650.600   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0    8649.8138651.370   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0    8648.4818650.600   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0    8648.4808649.062   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0    8649.8138648.293   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0    8651.1468649.062   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0    8647.9138652.706   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0    8646.3738652.706   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0    8645.8118650.600   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0    8647.1458651.370   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0    8648.4858645.978   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0    8651.1508645.984   0.000  0.00  0.00           O+0
CONECT    1    2    3    4    7                                             
CONECT    2    1                                                            
CONECT    3    1                                                            
CONECT    4    1                                                            
CONECT    5    8                                                            
CONECT    6   11   17   18                                                  
CONECT    7    8   12    1                                                  
CONECT    8    7    9    5                                                  
CONECT    9    8   10   16                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12    6                                                  
CONECT   12   11    7                                                       
CONECT   13   16                                                            
CONECT   14   16                                                            
CONECT   15   16                                                            
CONECT   16    9   13   14   15                                             
CONECT   17    6                                                            
CONECT   18    6                                                            
MASTER        0    0    0    0    0    0    0    0   18    0   36    0
END

COMPND    HMDB0240642
HETATM    1  C1  UNL     1      -3.566   0.512   0.293  1.00  0.00           C  
HETATM    2  C2  UNL     1      -2.497  -0.438  -0.171  1.00  0.00           C  
HETATM    3  C3  UNL     1      -2.612  -0.662  -1.664  1.00  0.00           C  
HETATM    4  C4  UNL     1      -2.754  -1.765   0.493  1.00  0.00           C  
HETATM    5  C5  UNL     1      -1.174   0.118   0.096  1.00  0.00           C  
HETATM    6  C6  UNL     1      -1.092   1.355   0.699  1.00  0.00           C  
HETATM    7  C7  UNL     1       0.107   1.971   0.996  1.00  0.00           C  
HETATM    8  C8  UNL     1       0.138   3.278   1.633  1.00  0.00           C  
HETATM    9  O1  UNL     1       1.248   3.830   1.899  1.00  0.00           O  
HETATM   10  O2  UNL     1      -1.048   3.930   1.953  1.00  0.00           O  
HETATM   11  C9  UNL     1       1.246   1.285   0.659  1.00  0.00           C  
HETATM   12  C10 UNL     1       1.208   0.043   0.055  1.00  0.00           C  
HETATM   13  C11 UNL     1       2.499  -0.638  -0.277  1.00  0.00           C  
HETATM   14  C12 UNL     1       2.652  -1.957   0.412  1.00  0.00           C  
HETATM   15  C13 UNL     1       2.612  -0.781  -1.792  1.00  0.00           C  
HETATM   16  C14 UNL     1       3.651   0.240   0.155  1.00  0.00           C  
HETATM   17  C15 UNL     1       0.004  -0.536  -0.225  1.00  0.00           C  
HETATM   18  O3  UNL     1      -0.105  -1.773  -0.828  1.00  0.00           O  
HETATM   19  H1  UNL     1      -4.573   0.053   0.132  1.00  0.00           H  
HETATM   20  H2  UNL     1      -3.462   1.461  -0.273  1.00  0.00           H  
HETATM   21  H3  UNL     1      -3.511   0.712   1.378  1.00  0.00           H  
HETATM   22  H4  UNL     1      -1.988   0.110  -2.171  1.00  0.00           H  
HETATM   23  H5  UNL     1      -2.263  -1.686  -1.880  1.00  0.00           H  
HETATM   24  H6  UNL     1      -3.673  -0.503  -1.942  1.00  0.00           H  
HETATM   25  H7  UNL     1      -2.077  -2.570   0.141  1.00  0.00           H  
HETATM   26  H8  UNL     1      -2.826  -1.704   1.592  1.00  0.00           H  
HETATM   27  H9  UNL     1      -3.782  -2.086   0.147  1.00  0.00           H  
HETATM   28  H10 UNL     1      -1.977   1.939   0.985  1.00  0.00           H  
HETATM   29  H11 UNL     1      -1.111   4.916   1.688  1.00  0.00           H  
HETATM   30  H12 UNL     1       2.198   1.782   0.899  1.00  0.00           H  
HETATM   31  H13 UNL     1       1.759  -2.282   0.978  1.00  0.00           H  
HETATM   32  H14 UNL     1       3.481  -1.941   1.159  1.00  0.00           H  
HETATM   33  H15 UNL     1       2.852  -2.759  -0.348  1.00  0.00           H  
HETATM   34  H16 UNL     1       3.339  -0.063  -2.224  1.00  0.00           H  
HETATM   35  H17 UNL     1       1.629  -0.526  -2.281  1.00  0.00           H  
HETATM   36  H18 UNL     1       2.941  -1.793  -2.021  1.00  0.00           H  
HETATM   37  H19 UNL     1       4.611  -0.270  -0.097  1.00  0.00           H  
HETATM   38  H20 UNL     1       3.680   1.209  -0.379  1.00  0.00           H  
HETATM   39  H21 UNL     1       3.619   0.364   1.257  1.00  0.00           H  
HETATM   40  H22 UNL     1       0.617  -2.377  -1.125  1.00  0.00           H  
CONECT    1    2   19   20   21
CONECT    2    3    4    5
CONECT    3   22   23   24
CONECT    4   25   26   27
CONECT    5    6    6   17
CONECT    6    7   28
CONECT    7    8   11   11
CONECT    8    9    9   10
CONECT   10   29
CONECT   11   12   30
CONECT   12   13   17   17
CONECT   13   14   15   16
CONECT   14   31   32   33
CONECT   15   34   35   36
CONECT   16   37   38   39
CONECT   17   18
CONECT   18   40
END

HMDB0240642
     RDKit          3D
3,5-Di-tert-butyl-4-hydroxybenzoic acid
 40 40  0  0  0  0  0  0  0  0999 V2000
   -3.5662    0.5116    0.2932 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4973   -0.4380   -0.1715 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6116   -0.6622   -1.6644 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7543   -1.7652    0.4925 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1744    0.1180    0.0962 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0918    1.3552    0.6986 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1074    1.9706    0.9956 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1380    3.2785    1.6326 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2479    3.8297    1.8985 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0476    3.9304    1.9528 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2460    1.2845    0.6590 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2084    0.0435    0.0546 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4988   -0.6385   -0.2768 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6523   -1.9572    0.4123 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6121   -0.7807   -1.7915 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6514    0.2396    0.1550 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0040   -0.5365   -0.2252 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1053   -1.7729   -0.8276 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5727    0.0531    0.1315 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4622    1.4607   -0.2734 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5109    0.7124    1.3776 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9879    0.1104   -2.1706 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2633   -1.6857   -1.8797 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6732   -0.5030   -1.9417 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0769   -2.5704    0.1407 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8257   -1.7038    1.5922 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7816   -2.0855    0.1472 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9768    1.9393    0.9851 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1107    4.9161    1.6882 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1977    1.7821    0.8992 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7585   -2.2821    0.9785 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4812   -1.9406    1.1593 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8519   -2.7585   -0.3483 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3388   -0.0632   -2.2240 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6289   -0.5256   -2.2814 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9409   -1.7929   -2.0206 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6105   -0.2703   -0.0971 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6797    1.2095   -0.3786 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6188    0.3645    1.2569 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6173   -2.3765   -1.1251 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
  2  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
  7 11  2  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 13 15  1  0
 13 16  1  0
 12 17  2  0
 17 18  1  0
 17  5  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  3 22  1  0
  3 23  1  0
  3 24  1  0
  4 25  1  0
  4 26  1  0
  4 27  1  0
  6 28  1  0
 10 29  1  0
 11 30  1  0
 14 31  1  0
 14 32  1  0
 14 33  1  0
 15 34  1  0
 15 35  1  0
 15 36  1  0
 16 37  1  0
 16 38  1  0
 16 39  1  0
 18 40  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
3,5-Di-tert-butyl-4-hydroxybenzoate	Generator
BHT-COOH	HMDB
2,6-Di-tert-butyl-4-carboxyphenol	HMDB
3,5-Bis(1,1-dimethylethyl)-4-hydroxybenzoic acid	HMDB
4-Carboxy-2,6-di-tert-butylphenol	HMDB
4-Hydroxy-3,5-di-tert-butylbenzoic acid	HMDB
3,5-Di-tert-butyl-4-hydroxybenzoic acid	MeSH

Chemical Formula

C₁₅H₂₂O₃

Average Molecular Weight

250.338

Monoisotopic Molecular Weight

250.156894568

IUPAC Name

3,5-di-tert-butyl-4-hydroxybenzoic acid

Traditional Name

3,5-di-tert-butyl-4-hydroxybenzoic acid

CAS Registry Number

1421-49-4

SMILES

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

InChI Identifier

InChI=1S/C15H22O3/c1-14(2,3)10-7-9(13(17)18)8-11(12(10)16)15(4,5)6/h7-8,16H,1-6H3,(H,17,18)

InChI Key

YEXOWHQZWLCHHD-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as hydroxybenzoic acid derivatives. Hydroxybenzoic acid derivatives are compounds containing a hydroxybenzoic acid (or a derivative), which is a benzene ring bearing a carboxyl and a hydroxyl groups.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Benzoic acids and derivatives

Direct Parent

Hydroxybenzoic acid derivatives

Alternative Parents

Substituents

Hydroxybenzoic acid
Phenylpropane
Benzoic acid
Benzoyl
Phenol
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

Not Available

Ontology

Not Available

Urine (PMID: 31265952)

Source

Exogenous

Exogenous (HMDB: HMDB0240642)

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	4.5	ALOGPS
logP	4.42	ChemAxon
logS	-3.4	ALOGPS
pKa (Strongest Acidic)	4.36	ChemAxon
pKa (Strongest Basic)	-5.2	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	57.53 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	72.63 m³·mol⁻¹	ChemAxon
Polarizability	28.44 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
DeepCCS	[M+H]+	165.661	30932474
DeepCCS	[M-H]-	163.304	30932474
DeepCCS	[M-2H]-	196.19	30932474
DeepCCS	[M+Na]+	171.755	30932474
AllCCS	[M+H]+	153.3	32859911
AllCCS	[M+H-H2O]+	149.9	32859911
AllCCS	[M+NH4]+	156.6	32859911
AllCCS	[M+Na]+	157.5	32859911
AllCCS	[M-H]-	163.0	32859911
AllCCS	[M+Na-2H]-	163.2	32859911
AllCCS	[M+HCOO]-	163.6	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm √ó 2.1 mm; 1.7 Œºmparticle diameter). Predicted by Afia on May 17, 2022.	6.88 minutes	32390414
Predicted by Siyang on May 30, 2022	16.252 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.04 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2357.7 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	476.5 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	182.7 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	239.8 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	144.6 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	782.8 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	842.5 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	79.3 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1170.8 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	591.1 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	1573.9 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	421.9 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	397.5 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	368.8 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	308.2 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	8.0 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
3,5-Di-tert-butyl-4-hydroxybenzoic acid	CC(C)(C)C1=CC(=CC(=C1O)C(C)(C)C)C(O)=O	2422.4	Standard polar	33892256
3,5-Di-tert-butyl-4-hydroxybenzoic acid	CC(C)(C)C1=CC(=CC(=C1O)C(C)(C)C)C(O)=O	1894.0	Standard non polar	33892256
3,5-Di-tert-butyl-4-hydroxybenzoic acid	CC(C)(C)C1=CC(=CC(=C1O)C(C)(C)C)C(O)=O	1945.7	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
3,5-Di-tert-butyl-4-hydroxybenzoic acid,1TMS,isomer #1	CC(C)(C)C1=CC(C(=O)O)=CC(C(C)(C)C)=C1O[Si](C)(C)C	2015.1	Semi standard non polar	33892256
3,5-Di-tert-butyl-4-hydroxybenzoic acid,1TMS,isomer #2	CC(C)(C)C1=CC(C(=O)O[Si](C)(C)C)=CC(C(C)(C)C)=C1O	1906.7	Semi standard non polar	33892256
3,5-Di-tert-butyl-4-hydroxybenzoic acid,2TMS,isomer #1	CC(C)(C)C1=CC(C(=O)O[Si](C)(C)C)=CC(C(C)(C)C)=C1O[Si](C)(C)C	2078.1	Semi standard non polar	33892256
3,5-Di-tert-butyl-4-hydroxybenzoic acid,1TBDMS,isomer #1	CC(C)(C)C1=CC(C(=O)O)=CC(C(C)(C)C)=C1O[Si](C)(C)C(C)(C)C	2243.9	Semi standard non polar	33892256
3,5-Di-tert-butyl-4-hydroxybenzoic acid,1TBDMS,isomer #2	CC(C)(C)C1=CC(C(=O)O[Si](C)(C)C(C)(C)C)=CC(C(C)(C)C)=C1O	2143.5	Semi standard non polar	33892256
3,5-Di-tert-butyl-4-hydroxybenzoic acid,2TBDMS,isomer #1	CC(C)(C)C1=CC(C(=O)O[Si](C)(C)C(C)(C)C)=CC(C(C)(C)C)=C1O[Si](C)(C)C(C)(C)C	2507.8	Semi standard non polar	33892256

Spectra

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	0.00187 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

14285

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

15007

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 3,5-Di-tert-butyl-4-hydroxybenzoic acid (HMDB0240642)

MOL for HMDB0240642 (3,5-Di-tert-butyl-4-hydroxybenzoic acid)

3D MOL for HMDB0240642 (3,5-Di-tert-butyl-4-hydroxybenzoic acid)

3D SDF for HMDB0240642 (3,5-Di-tert-butyl-4-hydroxybenzoic acid)

3D-SDF for HMDB0240642 (3,5-Di-tert-butyl-4-hydroxybenzoic acid)

PDB for HMDB0240642 (3,5-Di-tert-butyl-4-hydroxybenzoic acid)

3D PDB for HMDB0240642 (3,5-Di-tert-butyl-4-hydroxybenzoic acid)

SMILES for HMDB0240642 (3,5-Di-tert-butyl-4-hydroxybenzoic acid)

INCHI for HMDB0240642 (3,5-Di-tert-butyl-4-hydroxybenzoic acid)

Structure for HMDB0240642 (3,5-Di-tert-butyl-4-hydroxybenzoic acid)

3D Structure for HMDB0240642 (3,5-Di-tert-butyl-4-hydroxybenzoic acid)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized