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Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2013-03-20 21:10:32 UTC

Update Date

2023-02-21 17:29:37 UTC

HMDB ID

HMDB0059925

Secondary Accession Numbers

HMDB59925

Metabolite Identification

Common Name

3-tert-Butyl-4-hydroxyanisole

Description

3-tert-Butyl-4-hydroxyanisole (3-BHA), also known as BHA or 4-methoxy-2-tert-butylphenol, belongs to the class of organic compounds known as methoxyphenols. Methoxyphenols are compounds containing a methoxy group attached to the benzene ring of a phenol moiety. BHA is an extremely weak basic (essentially neutral) compound (based on its pKa). BHA is a waxy solid used as a food additive with the E number E320. BHA is 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. BHA was detected in human urine (PMID: 31265952 ).

Structure

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

HMDB0059925
     RDKit          3D
3-tert-Butyl-4-hydroxyanisole
 29 29  0  0  0  0  0  0  0  0999 V2000
    3.4546   -0.3870   -1.5923 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3609   -0.4631   -0.1942 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1473   -0.3428    0.4539 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1442   -0.4295    1.8303 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9444   -0.3124    2.5002 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2014   -0.1139    1.7718 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4131    0.0051    2.4369 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2402   -0.0215    0.3943 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4457    0.1873   -0.3869 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0985    1.5117    0.0240 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0951    0.3437   -1.8457 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4914   -0.8739   -0.2349 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9741   -0.1424   -0.2462 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2570    0.6616   -1.9313 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4587   -0.7275   -1.9350 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7228   -1.0460   -2.1050 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0380   -0.5858    2.4222 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9098   -0.3770    3.5925 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5090   -0.0453    3.4334 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5815    1.4408    1.0092 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2652    2.2369    0.1082 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8006    1.8714   -0.7691 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3657    1.1518   -2.0071 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9971    0.5804   -2.4650 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6688   -0.6413   -2.1806 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2010   -0.7604   -1.0885 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0637   -0.7346    0.6824 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0630   -1.8973   -0.3454 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0892   -0.0893   -1.3319 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  6  8  1  0
  8  9  1  0
  9 10  1  0
  9 11  1  0
  9 12  1  0
  8 13  2  0
 13  3  1  0
  1 14  1  0
  1 15  1  0
  1 16  1  0
  4 17  1  0
  5 18  1  0
  7 19  1  0
 10 20  1  0
 10 21  1  0
 10 22  1  0
 11 23  1  0
 11 24  1  0
 11 25  1  0
 12 26  1  0
 12 27  1  0
 12 28  1  0
 13 29  1  0
M  END

HMDB0059925
     RDKit          3D
3-tert-Butyl-4-hydroxyanisole
 29 29  0  0  0  0  0  0  0  0999 V2000
    3.4546   -0.3870   -1.5923 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3609   -0.4631   -0.1942 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1473   -0.3428    0.4539 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1442   -0.4295    1.8303 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9444   -0.3124    2.5002 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2014   -0.1139    1.7718 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4131    0.0051    2.4369 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2402   -0.0215    0.3943 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4457    0.1873   -0.3869 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0985    1.5117    0.0240 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0951    0.3437   -1.8457 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4914   -0.8739   -0.2349 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9741   -0.1424   -0.2462 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2570    0.6616   -1.9313 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4587   -0.7275   -1.9350 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7228   -1.0460   -2.1050 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0380   -0.5858    2.4222 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9098   -0.3770    3.5925 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5090   -0.0453    3.4334 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5815    1.4408    1.0092 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2652    2.2369    0.1082 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8006    1.8714   -0.7691 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3657    1.1518   -2.0071 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9971    0.5804   -2.4650 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6688   -0.6413   -2.1806 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2010   -0.7604   -1.0885 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0637   -0.7346    0.6824 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0630   -1.8973   -0.3454 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0892   -0.0893   -1.3319 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  6  8  1  0
  8  9  1  0
  9 10  1  0
  9 11  1  0
  9 12  1  0
  8 13  2  0
 13  3  1  0
  1 14  1  0
  1 15  1  0
  1 16  1  0
  4 17  1  0
  5 18  1  0
  7 19  1  0
 10 20  1  0
 10 21  1  0
 10 22  1  0
 11 23  1  0
 11 24  1  0
 11 25  1  0
 12 26  1  0
 12 27  1  0
 12 28  1  0
 13 29  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    8667.6188666.508   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0    8668.9518665.737   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0    8668.3898667.845   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0    8666.8488667.845   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0    8664.9528668.049   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0    8664.9528661.884   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0    8666.2828665.737   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0    8664.9498666.507   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0    8663.6158665.737   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0    8663.6158664.197   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0    8664.9498663.427   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0    8666.2828664.197   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0    8663.6208661.111   0.000  0.00  0.00           C+0
CONECT    1    2    3    4    7                                             
CONECT    2    1                                                            
CONECT    3    1                                                            
CONECT    4    1                                                            
CONECT    5    8                                                            
CONECT    6   11   13                                                       
CONECT    7    8   12    1                                                  
CONECT    8    7    9    5                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12    6                                                  
CONECT   12   11    7                                                       
CONECT   13    6                                                            
MASTER        0    0    0    0    0    0    0    0   13    0   26    0
END

COMPND    HMDB0059925
HETATM    1  C1  UNL     1       3.455  -0.387  -1.592  1.00  0.00           C  
HETATM    2  O1  UNL     1       3.361  -0.463  -0.194  1.00  0.00           O  
HETATM    3  C2  UNL     1       2.147  -0.343   0.454  1.00  0.00           C  
HETATM    4  C3  UNL     1       2.144  -0.430   1.830  1.00  0.00           C  
HETATM    5  C4  UNL     1       0.944  -0.312   2.500  1.00  0.00           C  
HETATM    6  C5  UNL     1      -0.201  -0.114   1.772  1.00  0.00           C  
HETATM    7  O2  UNL     1      -1.413   0.005   2.437  1.00  0.00           O  
HETATM    8  C6  UNL     1      -0.240  -0.022   0.394  1.00  0.00           C  
HETATM    9  C7  UNL     1      -1.446   0.187  -0.387  1.00  0.00           C  
HETATM   10  C8  UNL     1      -2.099   1.512   0.024  1.00  0.00           C  
HETATM   11  C9  UNL     1      -1.095   0.344  -1.846  1.00  0.00           C  
HETATM   12  C10 UNL     1      -2.491  -0.874  -0.235  1.00  0.00           C  
HETATM   13  C11 UNL     1       0.974  -0.142  -0.246  1.00  0.00           C  
HETATM   14  H1  UNL     1       3.257   0.662  -1.931  1.00  0.00           H  
HETATM   15  H2  UNL     1       4.459  -0.727  -1.935  1.00  0.00           H  
HETATM   16  H3  UNL     1       2.723  -1.046  -2.105  1.00  0.00           H  
HETATM   17  H4  UNL     1       3.038  -0.586   2.422  1.00  0.00           H  
HETATM   18  H5  UNL     1       0.910  -0.377   3.592  1.00  0.00           H  
HETATM   19  H6  UNL     1      -1.509  -0.045   3.433  1.00  0.00           H  
HETATM   20  H7  UNL     1      -2.581   1.441   1.009  1.00  0.00           H  
HETATM   21  H8  UNL     1      -1.265   2.237   0.108  1.00  0.00           H  
HETATM   22  H9  UNL     1      -2.801   1.871  -0.769  1.00  0.00           H  
HETATM   23  H10 UNL     1      -0.366   1.152  -2.007  1.00  0.00           H  
HETATM   24  H11 UNL     1      -1.997   0.580  -2.465  1.00  0.00           H  
HETATM   25  H12 UNL     1      -0.669  -0.641  -2.181  1.00  0.00           H  
HETATM   26  H13 UNL     1      -3.201  -0.760  -1.089  1.00  0.00           H  
HETATM   27  H14 UNL     1      -3.064  -0.735   0.682  1.00  0.00           H  
HETATM   28  H15 UNL     1      -2.063  -1.897  -0.345  1.00  0.00           H  
HETATM   29  H16 UNL     1       1.089  -0.089  -1.332  1.00  0.00           H  
CONECT    1    2   14   15   16
CONECT    2    3
CONECT    3    4    4   13
CONECT    4    5   17
CONECT    5    6    6   18
CONECT    6    7    8
CONECT    7   19
CONECT    8    9   13   13
CONECT    9   10   11   12
CONECT   10   20   21   22
CONECT   11   23   24   25
CONECT   12   26   27   28
CONECT   13   29
END

HMDB0059925
     RDKit          3D
3-tert-Butyl-4-hydroxyanisole
 29 29  0  0  0  0  0  0  0  0999 V2000
    3.4546   -0.3870   -1.5923 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3609   -0.4631   -0.1942 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1473   -0.3428    0.4539 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1442   -0.4295    1.8303 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9444   -0.3124    2.5002 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2014   -0.1139    1.7718 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4131    0.0051    2.4369 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2402   -0.0215    0.3943 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4457    0.1873   -0.3869 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0985    1.5117    0.0240 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0951    0.3437   -1.8457 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4914   -0.8739   -0.2349 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9741   -0.1424   -0.2462 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2570    0.6616   -1.9313 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4587   -0.7275   -1.9350 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7228   -1.0460   -2.1050 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0380   -0.5858    2.4222 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9098   -0.3770    3.5925 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5090   -0.0453    3.4334 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5815    1.4408    1.0092 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2652    2.2369    0.1082 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8006    1.8714   -0.7691 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3657    1.1518   -2.0071 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9971    0.5804   -2.4650 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6688   -0.6413   -2.1806 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2010   -0.7604   -1.0885 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0637   -0.7346    0.6824 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0630   -1.8973   -0.3454 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0892   -0.0893   -1.3319 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  6  8  1  0
  8  9  1  0
  9 10  1  0
  9 11  1  0
  9 12  1  0
  8 13  2  0
 13  3  1  0
  1 14  1  0
  1 15  1  0
  1 16  1  0
  4 17  1  0
  5 18  1  0
  7 19  1  0
 10 20  1  0
 10 21  1  0
 10 22  1  0
 11 23  1  0
 11 24  1  0
 11 25  1  0
 12 26  1  0
 12 27  1  0
 12 28  1  0
 13 29  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
2-(1,1-Dimethylethyl)-4-methoxyphenol	ChEBI
3-(1,1-Dimethylethyl)-4-hydroxyanisole	ChEBI
3-BHA	ChEBI
3-Tert-butyl-p-hydroxyanisole	ChEBI
4-Hydroxy-3-tert-butylanisole	ChEBI
4-Methoxy-2-tert-butylphenol	ChEBI
4-Methoxy-6-tert-butylphenol	ChEBI
O-Tert-butyl-p-methoxyphenol	ChEBI
p-Methoxy-O-tert-butylphenol	ChEBI
(1,1-Dimethylethyl)-4-methoxyphenol	HMDB
Methoxyphenol, butyl	HMDB
AMIF72	HMDB
BHA	HMDB
Butylhydroxyanisole	HMDB
Nipantiox 1 F	HMDB
AMIF-72	HMDB
Hydroxyanisole, butylated	HMDB
Nipantiox 1-F	HMDB
Nipantiox 1F	HMDB
Tenox bha	HMDB
AMIF 72	HMDB
Butyl methoxyphenol	HMDB
Butylated hydroxyanisole	HMDB
Embanox	HMDB
2-Tert-butyl-4-methoxyphenol	HMDB
2-Tert-butyl-p-methoxyphenol	HMDB
Tert-butyl-2-methoxy-4-phenol	HMDB
3-tert-Butyl-4-hydroxyanisole	HMDB

Chemical Formula

C₁₁H₁₆O₂

Average Molecular Weight

180.2435

Monoisotopic Molecular Weight

180.115029756

IUPAC Name

2-tert-butyl-4-methoxyphenol

Traditional Name

3-tert-butyl-4-hydroxyanisole

CAS Registry Number

121-00-6

SMILES

COC1=CC(=C(O)C=C1)C(C)(C)C

InChI Identifier

InChI=1S/C11H16O2/c1-11(2,3)9-7-8(13-4)5-6-10(9)12/h5-7,12H,1-4H3

InChI Key

MRBKEAMVRSLQPH-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as methoxyphenols. Methoxyphenols are compounds containing a methoxy group attached to the benzene ring of a phenol moiety.

Kingdom

Super Class

Class

Sub Class

Direct Parent

Alternative Parents

Substituents

Methoxyphenol
4-alkoxyphenol
Phenylpropane
Phenoxy compound
Methoxybenzene
Phenol ether
Anisole
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Monocyclic benzene moiety
Ether
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

aromatic ether (CHEBI:76358 )
phenols (CHEBI:76358 )

Ontology

Not Available

Urine (PMID: 31265952)

Cellular substructure

Membrane (HMDB: HMDB0059925)

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
Water Solubility	0.97 g/L	ALOGPS
logP	3.25	ALOGPS
logP	3.06	ChemAxon
logS	-2.3	ALOGPS
pKa (Strongest Acidic)	10.57	ChemAxon
pKa (Strongest Basic)	-4.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	29.46 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	53.17 m³·mol⁻¹	ChemAxon
Polarizability	20.42 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
DarkChem	[M+H]+	141.142	31661259
DarkChem	[M-H]-	141.615	31661259
DeepCCS	[M+H]+	146.458	30932474
DeepCCS	[M-H]-	144.062	30932474
DeepCCS	[M-2H]-	178.049	30932474
DeepCCS	[M+Na]+	152.718	30932474
AllCCS	[M+H]+	136.5	32859911
AllCCS	[M+H-H2O]+	132.3	32859911
AllCCS	[M+NH4]+	140.4	32859911
AllCCS	[M+Na]+	141.6	32859911
AllCCS	[M-H]-	139.9	32859911
AllCCS	[M+Na-2H]-	140.9	32859911
AllCCS	[M+HCOO]-	141.9	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 × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	5.38 minutes	32390414
Predicted by Siyang on May 30, 2022	15.9084 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.55 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2166.1 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	522.2 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	202.7 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	310.3 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	276.6 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	702.8 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	720.7 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	82.5 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1262.0 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	519.5 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	1333.9 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	434.4 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	433.9 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	436.4 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	344.0 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	14.5 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
3-tert-Butyl-4-hydroxyanisole	COC1=CC(=C(O)C=C1)C(C)(C)C	2377.3	Standard polar	33892256
3-tert-Butyl-4-hydroxyanisole	COC1=CC(=C(O)C=C1)C(C)(C)C	1418.2	Standard non polar	33892256
3-tert-Butyl-4-hydroxyanisole	COC1=CC(=C(O)C=C1)C(C)(C)C	1493.7	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
3-tert-Butyl-4-hydroxyanisole,1TMS,isomer #1	COC1=CC=C(O[Si](C)(C)C)C(C(C)(C)C)=C1	1560.4	Semi standard non polar	33892256
3-tert-Butyl-4-hydroxyanisole,1TBDMS,isomer #1	COC1=CC=C(O[Si](C)(C)C(C)(C)C)C(C(C)(C)C)=C1	1806.7	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - 3-tert-Butyl-4-hydroxyanisole EI-B (Non-derivatized)	splash10-014i-4900000000-3f285fdccb9fbe4de2d2	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - 3-tert-Butyl-4-hydroxyanisole EI-B (Non-derivatized)	splash10-014i-4900000000-3f285fdccb9fbe4de2d2	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3-tert-Butyl-4-hydroxyanisole GC-MS (Non-derivatized) - 70eV, Positive	splash10-014r-2900000000-6e34e81692e6395c1afe	2017-09-20	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3-tert-Butyl-4-hydroxyanisole GC-MS ( TMS) - 70eV, Positive	splash10-0079-7980000000-87abe5aa52479d1bd461	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3-tert-Butyl-4-hydroxyanisole 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
Experimental LC-MS/MS	LC-MS/MS Spectrum - 3-tert-Butyl-4-hydroxyanisole 75V, Negative-QTOF	splash10-004i-0900000000-58f82fc5543c0d66c899	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 3-tert-Butyl-4-hydroxyanisole 45V, Negative-QTOF	splash10-004i-0900000000-6de1ada6e165cb9fddbe	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 3-tert-Butyl-4-hydroxyanisole 60V, Negative-QTOF	splash10-004i-0900000000-3f65bbae1c7c5e9e8a29	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 3-tert-Butyl-4-hydroxyanisole 30V, Negative-QTOF	splash10-004i-0900000000-9f05f550021e6570b637	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 3-tert-Butyl-4-hydroxyanisole 15V, Negative-QTOF	splash10-004i-0900000000-0fdac0b3ba8a4734505a	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-tert-Butyl-4-hydroxyanisole 10V, Positive-QTOF	splash10-001i-0900000000-63e540598f2fa990edf3	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-tert-Butyl-4-hydroxyanisole 20V, Positive-QTOF	splash10-001i-1900000000-8066217d99f73fa2ec65	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-tert-Butyl-4-hydroxyanisole 40V, Positive-QTOF	splash10-0l7r-4900000000-65da2551598499ee4dac	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-tert-Butyl-4-hydroxyanisole 10V, Negative-QTOF	splash10-004i-0900000000-114f004bbcdf6d4522fd	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-tert-Butyl-4-hydroxyanisole 20V, Negative-QTOF	splash10-004i-0900000000-6c34280448208d6da7b3	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-tert-Butyl-4-hydroxyanisole 40V, Negative-QTOF	splash10-08gj-4900000000-78c4ba94b80f66329158	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-tert-Butyl-4-hydroxyanisole 10V, Positive-QTOF	splash10-001i-0900000000-d1acfc4fe8cc20fdb3bf	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-tert-Butyl-4-hydroxyanisole 20V, Positive-QTOF	splash10-000t-2900000000-4a41c9b45ff018073785	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-tert-Butyl-4-hydroxyanisole 40V, Positive-QTOF	splash10-0a4i-7900000000-8a4f1f09112bf7710dfd	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-tert-Butyl-4-hydroxyanisole 10V, Negative-QTOF	splash10-004i-0900000000-ed614b6bd089f6f9641a	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-tert-Butyl-4-hydroxyanisole 20V, Negative-QTOF	splash10-004i-1900000000-a34b44e76c734ea442ea	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-tert-Butyl-4-hydroxyanisole 40V, Negative-QTOF	splash10-0bta-4900000000-08b175b62b67340b812a	2021-10-12	Wishart Lab	View Spectrum

IR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-)	2023-02-04	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)	2023-02-04	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)	2023-02-04	FELIX lab	View Spectrum

Biological Properties

Cellular Locations

Membrane (predicted from logP)

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	0.000571 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

8145

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Butylated_hydroxyanisole

METLIN ID

Not Available

PubChem Compound

8456

PDB ID

Not Available

ChEBI ID

76358

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

Cummings SW, Ansari GA, Guengerich FP, Crouch LS, Prough RA: Metabolism of 3-tert-butyl-4-hydroxyanisole by microsomal fractions and isolated rat hepatocytes. Cancer Res. 1985 Nov;45(11 Pt 2):5617-24. [PubMed:4053035 ]
Castelli MG, Benfenati E, Pastorelli R, Salmona M, Fanelli R: Kinetics of 3-tert-butyl-4-hydroxyanisole (BHA) in man. Food Chem Toxicol. 1984 Nov;22(11):901-4. [PubMed:6542057 ]
Wattenberg LW, Coccia JB, Lam LK: Inhibitory effects of phenolic compounds on benzo(a)pyrene-induced neoplasia. Cancer Res. 1980 Aug;40(8 Pt 1):2820-3. [PubMed:7388831 ]
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-tert-Butyl-4-hydroxyanisole (HMDB0059925)

MOL for HMDB0059925 (3-tert-Butyl-4-hydroxyanisole)

3D MOL for HMDB0059925 (3-tert-Butyl-4-hydroxyanisole)

3D SDF for HMDB0059925 (3-tert-Butyl-4-hydroxyanisole)

3D-SDF for HMDB0059925 (3-tert-Butyl-4-hydroxyanisole)

PDB for HMDB0059925 (3-tert-Butyl-4-hydroxyanisole)

3D PDB for HMDB0059925 (3-tert-Butyl-4-hydroxyanisole)

SMILES for HMDB0059925 (3-tert-Butyl-4-hydroxyanisole)

INCHI for HMDB0059925 (3-tert-Butyl-4-hydroxyanisole)

Structure for HMDB0059925 (3-tert-Butyl-4-hydroxyanisole)

3D Structure for HMDB0059925 (3-tert-Butyl-4-hydroxyanisole)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

IR Spectra