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Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2020-04-28 16:57:56 UTC

Update Date

2022-03-07 03:18:20 UTC

HMDB ID

HMDB0240643

Secondary Accession Numbers

None

Metabolite Identification

Common Name

3,5-Di-tert-butyl-4-hydroxybenzaldehyde

Description

3,5-Di-tert-butyl-4-hydroxybenzaldehyde, also known as BHT-CHO or 4-formyl-2,6-di-tert-butylphenol, belongs to the class of organic compounds known as hydroxybenzaldehydes. These are organic aromatic compounds containing a benzene ring carrying an aldehyde group and a hydroxyl group. BHT-CHO 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-CHO was detected in human urine (PMID: 31265952 ).

Structure

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

HMDB0240643
     RDKit          3D
3,5-Di-tert-butyl-4-hydroxybenzaldehyde
 39 39  0  0  0  0  0  0  0  0999 V2000
   -2.7387   -1.6550    0.6015 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5114   -0.1754    0.4263 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6213    0.3639   -0.4419 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6657    0.5005    1.7907 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2187    0.1412   -0.1918 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1939    0.8266   -1.3820 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0011    1.1636   -2.0305 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0093    1.8875   -3.2858 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1017    2.2117   -3.7899 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2030    0.7979   -1.4602 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1741    0.1088   -0.2632 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4789   -0.2715    0.3393 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6809    0.3375    1.7061 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6152   -1.7755    0.4604 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6176    0.1876   -0.5430 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0052   -0.2208    0.3712 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0462   -0.9030    1.5555 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8473   -1.8058    0.6762 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3255   -2.0463    1.5536 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3955   -2.2115   -0.2777 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6173    0.1362    0.0071 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5716    1.4782   -0.5357 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6343   -0.1035   -1.4538 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1566   -0.1289    2.5680 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1946    1.5064    1.7430 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7420    0.6607    2.0384 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0918    1.1517   -1.8979 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9121    2.1351   -3.7646 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1225    1.0633   -1.9696 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5247    1.0513    1.6469 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9701   -0.4191    2.4622 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7813    0.9258    1.9971 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4218   -2.1895   -0.2055 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6968   -2.3165    0.1542 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9229   -2.0641    1.4863 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5668   -0.0977   -0.0027 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6647    1.2944   -0.6360 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5797   -0.3193   -1.5198 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7546   -1.2265    2.0676 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
  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
 10 29  1  0
 13 30  1  0
 13 31  1  0
 13 32  1  0
 14 33  1  0
 14 34  1  0
 14 35  1  0
 15 36  1  0
 15 37  1  0
 15 38  1  0
 17 39  1  0
M  END


  Mrv1652304282019012D          

 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
 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  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0240643

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C15H22O2/c1-14(2,3)11-7-10(9-16)8-12(13(11)17)15(4,5)6/h7-9,17H,1-6H3

> <INCHI_KEY>
DOZRDZLFLOODMB-UHFFFAOYSA-N

> <FORMULA>
C15H22O2

> <MOLECULAR_WEIGHT>
234.339

> <EXACT_MASS>
234.161979948

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
39

> <JCHEM_AVERAGE_POLARIZABILITY>
27.432508312141408

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3,5-di-tert-butyl-4-hydroxybenzaldehyde

> <ALOGPS_LOGP>
4.47

> <JCHEM_LOGP>
4.4722953803333345

> <ALOGPS_LOGS>
-3.75

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.590528030457019

> <JCHEM_PKA_STRONGEST_BASIC>
-6.545999518655894

> <JCHEM_POLAR_SURFACE_AREA>
37.3

> <JCHEM_REFRACTIVITY>
71.95469999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.20e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3,5-di-tert-butyl-4-hydroxybenzaldehyde

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0240643
     RDKit          3D
3,5-Di-tert-butyl-4-hydroxybenzaldehyde
 39 39  0  0  0  0  0  0  0  0999 V2000
   -2.7387   -1.6550    0.6015 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5114   -0.1754    0.4263 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6213    0.3639   -0.4419 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6657    0.5005    1.7907 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2187    0.1412   -0.1918 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1939    0.8266   -1.3820 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0011    1.1636   -2.0305 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0093    1.8875   -3.2858 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1017    2.2117   -3.7899 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2030    0.7979   -1.4602 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1741    0.1088   -0.2632 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4789   -0.2715    0.3393 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6809    0.3375    1.7061 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6152   -1.7755    0.4604 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6176    0.1876   -0.5430 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0052   -0.2208    0.3712 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0462   -0.9030    1.5555 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8473   -1.8058    0.6762 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3255   -2.0463    1.5536 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3955   -2.2115   -0.2777 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6173    0.1362    0.0071 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5716    1.4782   -0.5357 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6343   -0.1035   -1.4538 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1566   -0.1289    2.5680 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1946    1.5064    1.7430 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7420    0.6607    2.0384 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0918    1.1517   -1.8979 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9121    2.1351   -3.7646 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1225    1.0633   -1.9696 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5247    1.0513    1.6469 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9701   -0.4191    2.4622 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7813    0.9258    1.9971 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4218   -2.1895   -0.2055 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6968   -2.3165    0.1542 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9229   -2.0641    1.4863 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5668   -0.0977   -0.0027 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6647    1.2944   -0.6360 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5797   -0.3193   -1.5198 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7546   -1.2265    2.0676 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
  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
 10 29  1  0
 13 30  1  0
 13 31  1  0
 13 32  1  0
 14 33  1  0
 14 34  1  0
 14 35  1  0
 15 36  1  0
 15 37  1  0
 15 38  1  0
 17 39  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    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                                                       
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    HMDB0240643
HETATM    1  C1  UNL     1      -2.739  -1.655   0.602  1.00  0.00           C  
HETATM    2  C2  UNL     1      -2.511  -0.175   0.426  1.00  0.00           C  
HETATM    3  C3  UNL     1      -3.621   0.364  -0.442  1.00  0.00           C  
HETATM    4  C4  UNL     1      -2.666   0.501   1.791  1.00  0.00           C  
HETATM    5  C5  UNL     1      -1.219   0.141  -0.192  1.00  0.00           C  
HETATM    6  C6  UNL     1      -1.194   0.827  -1.382  1.00  0.00           C  
HETATM    7  C7  UNL     1       0.001   1.164  -2.031  1.00  0.00           C  
HETATM    8  C8  UNL     1      -0.009   1.887  -3.286  1.00  0.00           C  
HETATM    9  O1  UNL     1      -1.102   2.212  -3.790  1.00  0.00           O  
HETATM   10  C9  UNL     1       1.203   0.798  -1.460  1.00  0.00           C  
HETATM   11  C10 UNL     1       1.174   0.109  -0.263  1.00  0.00           C  
HETATM   12  C11 UNL     1       2.479  -0.272   0.339  1.00  0.00           C  
HETATM   13  C12 UNL     1       2.681   0.338   1.706  1.00  0.00           C  
HETATM   14  C13 UNL     1       2.615  -1.776   0.460  1.00  0.00           C  
HETATM   15  C14 UNL     1       3.618   0.188  -0.543  1.00  0.00           C  
HETATM   16  C15 UNL     1      -0.005  -0.221   0.371  1.00  0.00           C  
HETATM   17  O2  UNL     1      -0.046  -0.903   1.555  1.00  0.00           O  
HETATM   18  H1  UNL     1      -3.847  -1.806   0.676  1.00  0.00           H  
HETATM   19  H2  UNL     1      -2.325  -2.046   1.554  1.00  0.00           H  
HETATM   20  H3  UNL     1      -2.395  -2.211  -0.278  1.00  0.00           H  
HETATM   21  H4  UNL     1      -4.617   0.136   0.007  1.00  0.00           H  
HETATM   22  H5  UNL     1      -3.572   1.478  -0.536  1.00  0.00           H  
HETATM   23  H6  UNL     1      -3.634  -0.104  -1.454  1.00  0.00           H  
HETATM   24  H7  UNL     1      -2.157  -0.129   2.568  1.00  0.00           H  
HETATM   25  H8  UNL     1      -2.195   1.506   1.743  1.00  0.00           H  
HETATM   26  H9  UNL     1      -3.742   0.661   2.038  1.00  0.00           H  
HETATM   27  H10 UNL     1      -2.092   1.152  -1.898  1.00  0.00           H  
HETATM   28  H11 UNL     1       0.912   2.135  -3.765  1.00  0.00           H  
HETATM   29  H12 UNL     1       2.123   1.063  -1.970  1.00  0.00           H  
HETATM   30  H13 UNL     1       3.525   1.051   1.647  1.00  0.00           H  
HETATM   31  H14 UNL     1       2.970  -0.419   2.462  1.00  0.00           H  
HETATM   32  H15 UNL     1       1.781   0.926   1.997  1.00  0.00           H  
HETATM   33  H16 UNL     1       3.422  -2.189  -0.206  1.00  0.00           H  
HETATM   34  H17 UNL     1       1.697  -2.317   0.154  1.00  0.00           H  
HETATM   35  H18 UNL     1       2.923  -2.064   1.486  1.00  0.00           H  
HETATM   36  H19 UNL     1       4.567  -0.098  -0.003  1.00  0.00           H  
HETATM   37  H20 UNL     1       3.665   1.294  -0.636  1.00  0.00           H  
HETATM   38  H21 UNL     1       3.580  -0.319  -1.520  1.00  0.00           H  
HETATM   39  H22 UNL     1       0.755  -1.227   2.068  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    9   28
CONECT   10   11   29
CONECT   11   12   16   16
CONECT   12   13   14   15
CONECT   13   30   31   32
CONECT   14   33   34   35
CONECT   15   36   37   38
CONECT   16   17
CONECT   17   39
END

HMDB0240643
     RDKit          3D
3,5-Di-tert-butyl-4-hydroxybenzaldehyde
 39 39  0  0  0  0  0  0  0  0999 V2000
   -2.7387   -1.6550    0.6015 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5114   -0.1754    0.4263 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6213    0.3639   -0.4419 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6657    0.5005    1.7907 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2187    0.1412   -0.1918 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1939    0.8266   -1.3820 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0011    1.1636   -2.0305 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0093    1.8875   -3.2858 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1017    2.2117   -3.7899 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2030    0.7979   -1.4602 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1741    0.1088   -0.2632 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4789   -0.2715    0.3393 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6809    0.3375    1.7061 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6152   -1.7755    0.4604 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6176    0.1876   -0.5430 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0052   -0.2208    0.3712 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0462   -0.9030    1.5555 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8473   -1.8058    0.6762 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3255   -2.0463    1.5536 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3955   -2.2115   -0.2777 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6173    0.1362    0.0071 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5716    1.4782   -0.5357 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6343   -0.1035   -1.4538 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1566   -0.1289    2.5680 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1946    1.5064    1.7430 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7420    0.6607    2.0384 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0918    1.1517   -1.8979 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9121    2.1351   -3.7646 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1225    1.0633   -1.9696 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5247    1.0513    1.6469 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9701   -0.4191    2.4622 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7813    0.9258    1.9971 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4218   -2.1895   -0.2055 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6968   -2.3165    0.1542 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9229   -2.0641    1.4863 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5668   -0.0977   -0.0027 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6647    1.2944   -0.6360 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5797   -0.3193   -1.5198 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7546   -1.2265    2.0676 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
  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
 10 29  1  0
 13 30  1  0
 13 31  1  0
 13 32  1  0
 14 33  1  0
 14 34  1  0
 14 35  1  0
 15 36  1  0
 15 37  1  0
 15 38  1  0
 17 39  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
BHT-CHO	HMDB
2,6-Di-tert-butyl-4-formylphenol	HMDB
3,5-Bis(1,1-dimethylethyl)-4-hydroxybenzaldehyde	HMDB
4-Formyl-2,6-di-tert-butylphenol	HMDB
4-Hydroxy-3,5-di-tert-butylbenzaldehyde	HMDB
3,5-Di-tert-butyl-4-hydroxybenzaldehyde	HMDB

Chemical Formula

C₁₅H₂₂O₂

Average Molecular Weight

234.339

Monoisotopic Molecular Weight

234.161979948

IUPAC Name

3,5-di-tert-butyl-4-hydroxybenzaldehyde

Traditional Name

3,5-di-tert-butyl-4-hydroxybenzaldehyde

CAS Registry Number

1620-98-0

SMILES

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

InChI Identifier

InChI=1S/C15H22O2/c1-14(2,3)11-7-10(9-16)8-12(13(11)17)15(4,5)6/h7-9,17H,1-6H3

InChI Key

DOZRDZLFLOODMB-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as hydroxybenzaldehydes. These are organic aromatic compounds containing a benzene ring carrying an aldehyde group and a hydroxyl group.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbonyl compounds

Direct Parent

Hydroxybenzaldehydes

Alternative Parents

Substituents

Hydroxybenzaldehyde
Phenylpropane
Benzoyl
Phenol
Benzenoid
Monocyclic benzene moiety
Organic oxide
Hydrocarbon derivative
Aromatic homomonocyclic compound

Molecular Framework

Aromatic 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	4.47	ALOGPS
logP	4.47	ChemAxon
logS	-3.8	ALOGPS
pKa (Strongest Acidic)	8.59	ChemAxon
pKa (Strongest Basic)	-6.5	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	3	ChemAxon
Refractivity	71.95 m³·mol⁻¹	ChemAxon
Polarizability	27.43 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]+	163.444	30932474
DeepCCS	[M-H]-	161.086	30932474
DeepCCS	[M-2H]-	193.972	30932474
DeepCCS	[M+Na]+	169.537	30932474
AllCCS	[M+H]+	151.0	32859911
AllCCS	[M+H-H2O]+	147.6	32859911
AllCCS	[M+NH4]+	154.2	32859911
AllCCS	[M+Na]+	155.1	32859911
AllCCS	[M-H]-	158.9	32859911
AllCCS	[M+Na-2H]-	159.3	32859911
AllCCS	[M+HCOO]-	159.8	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
3,5-Di-tert-butyl-4-hydroxybenzaldehyde	CC(C)(C)C1=CC(C=O)=CC(=C1O)C(C)(C)C	2098.8	Standard polar	33892256
3,5-Di-tert-butyl-4-hydroxybenzaldehyde	CC(C)(C)C1=CC(C=O)=CC(=C1O)C(C)(C)C	1812.3	Standard non polar	33892256
3,5-Di-tert-butyl-4-hydroxybenzaldehyde	CC(C)(C)C1=CC(C=O)=CC(=C1O)C(C)(C)C	1788.0	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
3,5-Di-tert-butyl-4-hydroxybenzaldehyde,1TMS,isomer #1	CC(C)(C)C1=CC(C=O)=CC(C(C)(C)C)=C1O[Si](C)(C)C	1895.5	Semi standard non polar	33892256
3,5-Di-tert-butyl-4-hydroxybenzaldehyde,1TBDMS,isomer #1	CC(C)(C)C1=CC(C=O)=CC(C(C)(C)C)=C1O[Si](C)(C)C(C)(C)C	2124.8	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 - 3,5-Di-tert-butyl-4-hydroxybenzaldehyde 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 - 3,5-Di-tert-butyl-4-hydroxybenzaldehyde 10V, Positive-QTOF	splash10-000i-0090000000-2c991b2e45e9d7f068ec	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,5-Di-tert-butyl-4-hydroxybenzaldehyde 20V, Positive-QTOF	splash10-002r-1690000000-d79b8ed5d047d3b089e4	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,5-Di-tert-butyl-4-hydroxybenzaldehyde 40V, Positive-QTOF	splash10-0a5i-9880000000-90b4746c09e146631cd0	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,5-Di-tert-butyl-4-hydroxybenzaldehyde 10V, Negative-QTOF	splash10-001i-0090000000-fad9e20ea6c96fddad43	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,5-Di-tert-butyl-4-hydroxybenzaldehyde 20V, Negative-QTOF	splash10-001i-0190000000-8f081ea411cd3c3ae483	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,5-Di-tert-butyl-4-hydroxybenzaldehyde 40V, Negative-QTOF	splash10-0fc0-2970000000-55d230157bae7438bf58	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,5-Di-tert-butyl-4-hydroxybenzaldehyde 10V, Negative-QTOF	splash10-001i-0090000000-9087f47ed0ae51229a17	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,5-Di-tert-butyl-4-hydroxybenzaldehyde 20V, Negative-QTOF	splash10-001i-0090000000-400e602157ce1eab0ce2	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,5-Di-tert-butyl-4-hydroxybenzaldehyde 40V, Negative-QTOF	splash10-00kr-0950000000-c2fdca009d989142e2df	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,5-Di-tert-butyl-4-hydroxybenzaldehyde 10V, Positive-QTOF	splash10-000i-1490000000-2635b56a0da1455cd7bd	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,5-Di-tert-butyl-4-hydroxybenzaldehyde 20V, Positive-QTOF	splash10-0a4r-3890000000-f40569a3b6711fb5bb6c	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,5-Di-tert-butyl-4-hydroxybenzaldehyde 40V, Positive-QTOF	splash10-05ai-6900000000-b42c795013899011a284	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	0.000671 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

65974

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

73219

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-hydroxybenzaldehyde (HMDB0240643)

MOL for HMDB0240643 (3,5-Di-tert-butyl-4-hydroxybenzaldehyde)

3D MOL for HMDB0240643 (3,5-Di-tert-butyl-4-hydroxybenzaldehyde)

3D SDF for HMDB0240643 (3,5-Di-tert-butyl-4-hydroxybenzaldehyde)

3D-SDF for HMDB0240643 (3,5-Di-tert-butyl-4-hydroxybenzaldehyde)

PDB for HMDB0240643 (3,5-Di-tert-butyl-4-hydroxybenzaldehyde)

3D PDB for HMDB0240643 (3,5-Di-tert-butyl-4-hydroxybenzaldehyde)

SMILES for HMDB0240643 (3,5-Di-tert-butyl-4-hydroxybenzaldehyde)

INCHI for HMDB0240643 (3,5-Di-tert-butyl-4-hydroxybenzaldehyde)

Structure for HMDB0240643 (3,5-Di-tert-butyl-4-hydroxybenzaldehyde)

3D Structure for HMDB0240643 (3,5-Di-tert-butyl-4-hydroxybenzaldehyde)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra