Jump To Section:

Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References XML

Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2012-09-11 17:47:27 UTC

Update Date

2022-03-07 02:53:13 UTC

HMDB ID

HMDB0032048

Secondary Accession Numbers

HMDB32048

Metabolite Identification

Common Name

2,6-Di-tert-butyl-4-hydroxymethylphenol

Description

2,6-Di-tert-butyl-4-hydroxymethylphenol, also known as BHT-OH, 3,5-di-tert-butyl-4-hydroxy-benzyl alcohol, or 4-hydroxymethyl-2,6-di-tert-butylphenol, belongs to the class of organic compounds known as phenylpropanes. These are organic compounds containing a phenylpropane moiety. BHT-OH is an extremely weak basic (essentially neutral) compound (based on its pKa). BHT-OH 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

HMDB0032048
     RDKit          3D
2,6-Di-tert-butyl-4-hydroxymethylphenol
 41 41  0  0  0  0  0  0  0  0999 V2000
    3.6069    0.5540   -0.2869 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5172   -0.5017   -0.2456 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5894   -1.2767   -1.5449 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7405   -1.4782    0.8858 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1953    0.1494   -0.0725 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1194    1.5312    0.0231 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1009    2.1496    0.1840 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1924    3.6219    0.2869 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3531    4.2201   -0.9698 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2438    1.3778    0.2488 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1561   -0.0108    0.1516 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3736   -0.8379    0.2230 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3572   -1.8181    1.3769 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5956   -1.5658   -1.1024 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6169    0.0416    0.4207 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0577   -0.6268   -0.0086 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1972   -1.9907   -0.1096 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5738   -0.0023   -0.3726 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6526    1.1512    0.6327 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4381    1.1978   -1.1603 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7556   -0.9346   -2.2171 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5676   -2.3700   -1.3914 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5234   -1.0490   -2.0978 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1854   -1.1528    1.7892 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8214   -1.5293    1.1346 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3972   -2.4780    0.5536 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9926    2.1715   -0.0231 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0172    3.9186    0.9714 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7638    4.0193    0.6996 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0894    5.1673   -0.9439 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1825    1.8702    0.3736 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6160   -2.8344    1.0410 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1396   -1.5667    2.1536 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3986   -1.7504    1.9302 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4690   -1.1949   -1.6422 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7108   -1.4678   -1.7632 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7762   -2.6235   -0.8628 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5626    0.5467    1.3861 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4773   -0.6637    0.4169 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7582    0.7217   -0.4372 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5083   -2.6860   -0.0850 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  1  0
  7 10  2  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 12 14  1  0
 12 15  1  0
 11 16  2  0
 16 17  1  0
 16  5  1  0
  1 18  1  0
  1 19  1  0
  1 20  1  0
  3 21  1  0
  3 22  1  0
  3 23  1  0
  4 24  1  0
  4 25  1  0
  4 26  1  0
  6 27  1  0
  8 28  1  0
  8 29  1  0
  9 30  1  0
 10 31  1  0
 13 32  1  0
 13 33  1  0
 13 34  1  0
 14 35  1  0
 14 36  1  0
 14 37  1  0
 15 38  1  0
 15 39  1  0
 15 40  1  0
 17 41  1  0
M  END


  Mrv1652304282018402D          

 17 17  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
  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
M  END
> <DATABASE_ID>
HMDB0032048

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C15H24O2/c1-14(2,3)11-7-10(9-16)8-12(13(11)17)15(4,5)6/h7-8,16-17H,9H2,1-6H3

> <INCHI_KEY>
HNURKXXMYARGAY-UHFFFAOYSA-N

> <FORMULA>
C15H24O2

> <MOLECULAR_WEIGHT>
236.3499

> <EXACT_MASS>
236.177630012

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
41

> <JCHEM_AVERAGE_POLARIZABILITY>
28.30917936611583

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2,6-di-tert-butyl-4-(hydroxymethyl)phenol

> <ALOGPS_LOGP>
4.00

> <JCHEM_LOGP>
3.9924432683333335

> <ALOGPS_LOGS>
-3.21

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
15.231099032059376

> <JCHEM_PKA_STRONGEST_ACIDIC>
10.727963046886996

> <JCHEM_PKA_STRONGEST_BASIC>
-2.7664658927568455

> <JCHEM_POLAR_SURFACE_AREA>
40.46

> <JCHEM_REFRACTIVITY>
72.1866

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.46e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2,6-di-tert-butyl-4-(hydroxymethyl)phenol

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0032048
     RDKit          3D
2,6-Di-tert-butyl-4-hydroxymethylphenol
 41 41  0  0  0  0  0  0  0  0999 V2000
    3.6069    0.5540   -0.2869 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5172   -0.5017   -0.2456 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5894   -1.2767   -1.5449 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7405   -1.4782    0.8858 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1953    0.1494   -0.0725 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1194    1.5312    0.0231 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1009    2.1496    0.1840 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1924    3.6219    0.2869 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3531    4.2201   -0.9698 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2438    1.3778    0.2488 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1561   -0.0108    0.1516 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3736   -0.8379    0.2230 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3572   -1.8181    1.3769 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5956   -1.5658   -1.1024 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6169    0.0416    0.4207 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0577   -0.6268   -0.0086 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1972   -1.9907   -0.1096 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5738   -0.0023   -0.3726 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6526    1.1512    0.6327 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4381    1.1978   -1.1603 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7556   -0.9346   -2.2171 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5676   -2.3700   -1.3914 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5234   -1.0490   -2.0978 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1854   -1.1528    1.7892 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8214   -1.5293    1.1346 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3972   -2.4780    0.5536 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9926    2.1715   -0.0231 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0172    3.9186    0.9714 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7638    4.0193    0.6996 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0894    5.1673   -0.9439 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1825    1.8702    0.3736 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6160   -2.8344    1.0410 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1396   -1.5667    2.1536 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3986   -1.7504    1.9302 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4690   -1.1949   -1.6422 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7108   -1.4678   -1.7632 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7762   -2.6235   -0.8628 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5626    0.5467    1.3861 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4773   -0.6637    0.4169 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7582    0.7217   -0.4372 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5083   -2.6860   -0.0850 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  1  0
  7 10  2  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 12 14  1  0
 12 15  1  0
 11 16  2  0
 16 17  1  0
 16  5  1  0
  1 18  1  0
  1 19  1  0
  1 20  1  0
  3 21  1  0
  3 22  1  0
  3 23  1  0
  4 24  1  0
  4 25  1  0
  4 26  1  0
  6 27  1  0
  8 28  1  0
  8 29  1  0
  9 30  1  0
 10 31  1  0
 13 32  1  0
 13 33  1  0
 13 34  1  0
 14 35  1  0
 14 36  1  0
 14 37  1  0
 15 38  1  0
 15 39  1  0
 15 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    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
CONECT    1    2    3    4    7                                             
CONECT    2    1                                                            
CONECT    3    1                                                            
CONECT    4    1                                                            
CONECT    5    8                                                            
CONECT    6   11   17                                                       
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                                                            
MASTER        0    0    0    0    0    0    0    0   17    0   34    0
END

COMPND    HMDB0032048
HETATM    1  C1  UNL     1       3.607   0.554  -0.287  1.00  0.00           C  
HETATM    2  C2  UNL     1       2.517  -0.502  -0.246  1.00  0.00           C  
HETATM    3  C3  UNL     1       2.589  -1.277  -1.545  1.00  0.00           C  
HETATM    4  C4  UNL     1       2.740  -1.478   0.886  1.00  0.00           C  
HETATM    5  C5  UNL     1       1.195   0.149  -0.072  1.00  0.00           C  
HETATM    6  C6  UNL     1       1.119   1.531   0.023  1.00  0.00           C  
HETATM    7  C7  UNL     1      -0.101   2.150   0.184  1.00  0.00           C  
HETATM    8  C8  UNL     1      -0.192   3.622   0.287  1.00  0.00           C  
HETATM    9  O1  UNL     1      -0.353   4.220  -0.970  1.00  0.00           O  
HETATM   10  C9  UNL     1      -1.244   1.378   0.249  1.00  0.00           C  
HETATM   11  C10 UNL     1      -1.156  -0.011   0.152  1.00  0.00           C  
HETATM   12  C11 UNL     1      -2.374  -0.838   0.223  1.00  0.00           C  
HETATM   13  C12 UNL     1      -2.357  -1.818   1.377  1.00  0.00           C  
HETATM   14  C13 UNL     1      -2.596  -1.566  -1.102  1.00  0.00           C  
HETATM   15  C14 UNL     1      -3.617   0.042   0.421  1.00  0.00           C  
HETATM   16  C15 UNL     1       0.058  -0.627  -0.009  1.00  0.00           C  
HETATM   17  O2  UNL     1       0.197  -1.991  -0.110  1.00  0.00           O  
HETATM   18  H1  UNL     1       4.574  -0.002  -0.373  1.00  0.00           H  
HETATM   19  H2  UNL     1       3.653   1.151   0.633  1.00  0.00           H  
HETATM   20  H3  UNL     1       3.438   1.198  -1.160  1.00  0.00           H  
HETATM   21  H4  UNL     1       1.756  -0.935  -2.217  1.00  0.00           H  
HETATM   22  H5  UNL     1       2.568  -2.370  -1.391  1.00  0.00           H  
HETATM   23  H6  UNL     1       3.523  -1.049  -2.098  1.00  0.00           H  
HETATM   24  H7  UNL     1       2.185  -1.153   1.789  1.00  0.00           H  
HETATM   25  H8  UNL     1       3.821  -1.529   1.135  1.00  0.00           H  
HETATM   26  H9  UNL     1       2.397  -2.478   0.554  1.00  0.00           H  
HETATM   27  H10 UNL     1       1.993   2.172  -0.023  1.00  0.00           H  
HETATM   28  H11 UNL     1      -1.017   3.919   0.971  1.00  0.00           H  
HETATM   29  H12 UNL     1       0.764   4.019   0.700  1.00  0.00           H  
HETATM   30  H13 UNL     1      -0.089   5.167  -0.944  1.00  0.00           H  
HETATM   31  H14 UNL     1      -2.182   1.870   0.374  1.00  0.00           H  
HETATM   32  H15 UNL     1      -2.616  -2.834   1.041  1.00  0.00           H  
HETATM   33  H16 UNL     1      -3.140  -1.567   2.154  1.00  0.00           H  
HETATM   34  H17 UNL     1      -1.399  -1.750   1.930  1.00  0.00           H  
HETATM   35  H18 UNL     1      -3.469  -1.195  -1.642  1.00  0.00           H  
HETATM   36  H19 UNL     1      -1.711  -1.468  -1.763  1.00  0.00           H  
HETATM   37  H20 UNL     1      -2.776  -2.624  -0.863  1.00  0.00           H  
HETATM   38  H21 UNL     1      -3.563   0.547   1.386  1.00  0.00           H  
HETATM   39  H22 UNL     1      -4.477  -0.664   0.417  1.00  0.00           H  
HETATM   40  H23 UNL     1      -3.758   0.722  -0.437  1.00  0.00           H  
HETATM   41  H24 UNL     1      -0.508  -2.686  -0.085  1.00  0.00           H  
CONECT    1    2   18   19   20
CONECT    2    3    4    5
CONECT    3   21   22   23
CONECT    4   24   25   26
CONECT    5    6    6   16
CONECT    6    7   27
CONECT    7    8   10   10
CONECT    8    9   28   29
CONECT    9   30
CONECT   10   11   31
CONECT   11   12   16   16
CONECT   12   13   14   15
CONECT   13   32   33   34
CONECT   14   35   36   37
CONECT   15   38   39   40
CONECT   16   17
CONECT   17   41
END

HMDB0032048
     RDKit          3D
2,6-Di-tert-butyl-4-hydroxymethylphenol
 41 41  0  0  0  0  0  0  0  0999 V2000
    3.6069    0.5540   -0.2869 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5172   -0.5017   -0.2456 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5894   -1.2767   -1.5449 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7405   -1.4782    0.8858 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1953    0.1494   -0.0725 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1194    1.5312    0.0231 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1009    2.1496    0.1840 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1924    3.6219    0.2869 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3531    4.2201   -0.9698 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2438    1.3778    0.2488 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1561   -0.0108    0.1516 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3736   -0.8379    0.2230 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3572   -1.8181    1.3769 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5956   -1.5658   -1.1024 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6169    0.0416    0.4207 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0577   -0.6268   -0.0086 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1972   -1.9907   -0.1096 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5738   -0.0023   -0.3726 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6526    1.1512    0.6327 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4381    1.1978   -1.1603 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7556   -0.9346   -2.2171 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5676   -2.3700   -1.3914 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5234   -1.0490   -2.0978 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1854   -1.1528    1.7892 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8214   -1.5293    1.1346 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3972   -2.4780    0.5536 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9926    2.1715   -0.0231 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0172    3.9186    0.9714 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7638    4.0193    0.6996 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0894    5.1673   -0.9439 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1825    1.8702    0.3736 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6160   -2.8344    1.0410 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1396   -1.5667    2.1536 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3986   -1.7504    1.9302 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4690   -1.1949   -1.6422 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7108   -1.4678   -1.7632 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7762   -2.6235   -0.8628 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5626    0.5467    1.3861 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4773   -0.6637    0.4169 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7582    0.7217   -0.4372 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5083   -2.6860   -0.0850 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  1  0
  7 10  2  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 12 14  1  0
 12 15  1  0
 11 16  2  0
 16 17  1  0
 16  5  1  0
  1 18  1  0
  1 19  1  0
  1 20  1  0
  3 21  1  0
  3 22  1  0
  3 23  1  0
  4 24  1  0
  4 25  1  0
  4 26  1  0
  6 27  1  0
  8 28  1  0
  8 29  1  0
  9 30  1  0
 10 31  1  0
 13 32  1  0
 13 33  1  0
 13 34  1  0
 14 35  1  0
 14 36  1  0
 14 37  1  0
 15 38  1  0
 15 39  1  0
 15 40  1  0
 17 41  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
2, 6-Di-tert-butyl-4-(hydroxymethyl)phenol	HMDB
2, 6-Di-tert-butyl-4-hydroxymethylphenol	HMDB
2,6-Bis(1,1-dimethylethyl)-4-(hydroxymethyl)phenol	HMDB
2,6-Di-t-butyl-4-hydroxymethylphenol	HMDB
2,6-Di-tert-butyl-4-(hydroxymethyl)phenol	HMDB
2,6-Di-tert-butyl-4-hydroxymethyl phenol	HMDB
3,5-Bis(1,1-dimethylethyl)-4-hydroxy-benzenemethanol	HMDB
3,5-Bis(1,1-dimethylethyl)-4-hydroxybenzenemethanol	HMDB
3,5-Bis(1,1-dimethylethyl)-4-hydroxybenzenemethanol, 9ci	HMDB
3,5-Di-t-butyl-4-hydroxybenzyl alcohol	HMDB
3,5-Di-tert-butyl-4-hydroxy-benzyl alcohol	HMDB
3,5-Di-tert-butyl-4-hydroxybenzyl alcohol	HMDB
3,5-Di-tert-butyl-4-hydroxybenzyl alcohol, 8ci	HMDB
4-Hydroxymethyl-2,6-di-tert-butylphenol	HMDB, MeSH
4-Hydroxymethyl-2,6-di-tertbutylphenol	HMDB
alpha-Hydroxy-2,6-di-tert-butyl-P-cresol	HMDB
Antioxidant 754	HMDB
Benzenemethanol, 4-hydroxy-3,5-di-tert.-butyl	HMDB
BHT Alcohol	HMDB
Butylated hydroxymethylphenol	HMDB
Di-tert-butyl-4-hydroxymethyl phenol	HMDB
Ionox 100	HMDB
Ionox 100 antioxidant	HMDB
4-HMDBP	MeSH, HMDB
BHTBzOH	MeSH, HMDB
2,6-Di-tert-butyl-4-hydroxymethylphenol	MeSH
3,5-Di-t-butyl-4-hidroxy-benzyl alcohol	HMDB
3,5-Di-tert-butyl-4-hydroxyphenylmethanol	HMDB
4-Hydroxy-3,5-di-tert-butylbenzyl alcohol	HMDB
BHT-OH	HMDB

Chemical Formula

C₁₅H₂₄O₂

Average Molecular Weight

236.3499

Monoisotopic Molecular Weight

236.177630012

IUPAC Name

2,6-di-tert-butyl-4-(hydroxymethyl)phenol

Traditional Name

2,6-di-tert-butyl-4-(hydroxymethyl)phenol

CAS Registry Number

88-26-6

SMILES

CC(C)(C)C1=CC(CO)=CC(=C1O)C(C)(C)C

InChI Identifier

InChI=1S/C15H24O2/c1-14(2,3)11-7-10(9-16)8-12(13(11)17)15(4,5)6/h7-8,16-17H,9H2,1-6H3

InChI Key

HNURKXXMYARGAY-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
Benzyl alcohol
Phenol
Organic oxygen compound
Hydrocarbon derivative
Aromatic alcohol
Primary alcohol
Organooxygen compound
Alcohol
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cell membrane (HMDB: HMDB0032048)

Biofluid or Excreta

Excreta

Urine (PMID: 31265952)

Cellular substructure

Membrane (HMDB: HMDB0032048)

Source

Exogenous

Food

Food (HMDB: HMDB0032048)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	141 °C	Not Available
Boiling Point	306.00 to 307.00 °C. @ 760.00 mm Hg (est)	The Good Scents Company Information System
Water Solubility	312.6 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	3.504 (est)	The Good Scents Company Information System

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.15 g/L	ALOGPS
logP	4	ALOGPS
logP	3.99	ChemAxon
logS	-3.2	ALOGPS
pKa (Strongest Acidic)	10.73	ChemAxon
pKa (Strongest Basic)	-2.8	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	3	ChemAxon
Refractivity	72.19 m³·mol⁻¹	ChemAxon
Polarizability	28.31 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]+	157.537	31661259
DarkChem	[M-H]-	155.474	31661259
DeepCCS	[M+H]+	169.224	30932474
DeepCCS	[M-H]-	166.866	30932474
DeepCCS	[M-2H]-	199.752	30932474
DeepCCS	[M+Na]+	175.317	30932474
AllCCS	[M+H]+	150.9	32859911
AllCCS	[M+H-H2O]+	147.3	32859911
AllCCS	[M+NH4]+	154.2	32859911
AllCCS	[M+Na]+	155.2	32859911
AllCCS	[M-H]-	161.6	32859911
AllCCS	[M+Na-2H]-	162.1	32859911
AllCCS	[M+HCOO]-	162.7	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
2,6-Di-tert-butyl-4-hydroxymethylphenol	CC(C)(C)C1=CC(CO)=CC(=C1O)C(C)(C)C	2113.8	Standard polar	33892256
2,6-Di-tert-butyl-4-hydroxymethylphenol	CC(C)(C)C1=CC(CO)=CC(=C1O)C(C)(C)C	1722.1	Standard non polar	33892256
2,6-Di-tert-butyl-4-hydroxymethylphenol	CC(C)(C)C1=CC(CO)=CC(=C1O)C(C)(C)C	1787.7	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
2,6-Di-tert-butyl-4-hydroxymethylphenol,1TMS,isomer #1	CC(C)(C)C1=CC(CO[Si](C)(C)C)=CC(C(C)(C)C)=C1O	1765.8	Semi standard non polar	33892256
2,6-Di-tert-butyl-4-hydroxymethylphenol,1TMS,isomer #2	CC(C)(C)C1=CC(CO)=CC(C(C)(C)C)=C1O[Si](C)(C)C	1813.8	Semi standard non polar	33892256
2,6-Di-tert-butyl-4-hydroxymethylphenol,2TMS,isomer #1	CC(C)(C)C1=CC(CO[Si](C)(C)C)=CC(C(C)(C)C)=C1O[Si](C)(C)C	1952.8	Semi standard non polar	33892256
2,6-Di-tert-butyl-4-hydroxymethylphenol,1TBDMS,isomer #1	CC(C)(C)C1=CC(CO[Si](C)(C)C(C)(C)C)=CC(C(C)(C)C)=C1O	1985.5	Semi standard non polar	33892256
2,6-Di-tert-butyl-4-hydroxymethylphenol,1TBDMS,isomer #2	CC(C)(C)C1=CC(CO)=CC(C(C)(C)C)=C1O[Si](C)(C)C(C)(C)C	2069.2	Semi standard non polar	33892256
2,6-Di-tert-butyl-4-hydroxymethylphenol,2TBDMS,isomer #1	CC(C)(C)C1=CC(CO[Si](C)(C)C(C)(C)C)=CC(C(C)(C)C)=C1O[Si](C)(C)C(C)(C)C	2428.1	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - 2,6-Di-tert-butyl-4-hydroxymethylphenol EI-B (Non-derivatized)	splash10-00di-5980000000-c4903b8c014660089b1f	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - 2,6-Di-tert-butyl-4-hydroxymethylphenol EI-B (Non-derivatized)	splash10-00di-5980000000-c4903b8c014660089b1f	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2,6-Di-tert-butyl-4-hydroxymethylphenol GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a4i-1590000000-c105d4c8edcd01f667b2	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2,6-Di-tert-butyl-4-hydroxymethylphenol GC-MS (2 TMS) - 70eV, Positive	splash10-0avi-8049000000-0266b8a9fd3717df38fa	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2,6-Di-tert-butyl-4-hydroxymethylphenol 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-hydroxymethylphenol 10V, Positive-QTOF	splash10-00kr-0090000000-c6e1869c905799e56672	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,6-Di-tert-butyl-4-hydroxymethylphenol 20V, Positive-QTOF	splash10-014i-0290000000-7738b3dee209e378e21d	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,6-Di-tert-butyl-4-hydroxymethylphenol 40V, Positive-QTOF	splash10-014r-1590000000-d4b4f40a51824b17d1da	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,6-Di-tert-butyl-4-hydroxymethylphenol 10V, Negative-QTOF	splash10-000i-0090000000-215a903d9c5e8b2bf4f8	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,6-Di-tert-butyl-4-hydroxymethylphenol 20V, Negative-QTOF	splash10-052r-0090000000-9fb4b7f36c9ac96700c3	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,6-Di-tert-butyl-4-hydroxymethylphenol 40V, Negative-QTOF	splash10-0a4r-0590000000-d4aefa264a3d261899e9	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,6-Di-tert-butyl-4-hydroxymethylphenol 10V, Negative-QTOF	splash10-000i-0090000000-c0031dc201eac6b6350a	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,6-Di-tert-butyl-4-hydroxymethylphenol 20V, Negative-QTOF	splash10-000i-0090000000-3387d858c61f65b3f554	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,6-Di-tert-butyl-4-hydroxymethylphenol 40V, Negative-QTOF	splash10-000i-0690000000-a17a93b7b3d961cbe117	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,6-Di-tert-butyl-4-hydroxymethylphenol 10V, Positive-QTOF	splash10-000i-1590000000-c33d33740f4d9b567ca9	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,6-Di-tert-butyl-4-hydroxymethylphenol 20V, Positive-QTOF	splash10-08fr-4940000000-1dea2fb5642c1a3c1f6c	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,6-Di-tert-butyl-4-hydroxymethylphenol 40V, Positive-QTOF	splash10-0a4i-9600000000-bf881e2fdcee13275509	2021-09-25	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Membrane

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	0.000493 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

FDB008752

KNApSAcK ID

Not Available

Chemspider ID

6663

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

6929

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1411991

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 ]
(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Showing metabocard for 2,6-Di-tert-butyl-4-hydroxymethylphenol (HMDB0032048)

MOL for HMDB0032048 (2,6-Di-tert-butyl-4-hydroxymethylphenol)

3D MOL for HMDB0032048 (2,6-Di-tert-butyl-4-hydroxymethylphenol)

3D SDF for HMDB0032048 (2,6-Di-tert-butyl-4-hydroxymethylphenol)

3D-SDF for HMDB0032048 (2,6-Di-tert-butyl-4-hydroxymethylphenol)

PDB for HMDB0032048 (2,6-Di-tert-butyl-4-hydroxymethylphenol)

3D PDB for HMDB0032048 (2,6-Di-tert-butyl-4-hydroxymethylphenol)

SMILES for HMDB0032048 (2,6-Di-tert-butyl-4-hydroxymethylphenol)

INCHI for HMDB0032048 (2,6-Di-tert-butyl-4-hydroxymethylphenol)

Structure for HMDB0032048 (2,6-Di-tert-butyl-4-hydroxymethylphenol)

3D Structure for HMDB0032048 (2,6-Di-tert-butyl-4-hydroxymethylphenol)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra