NP-MRD: Showing NP-Card for 2,6-Di-tert-butyl-4-methylphenol (NP0000821)

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Record Information

Version

2.0

Created at

2012-09-11 18:36:03 UTC

Updated at

2024-09-03 04:16:53 UTC

NP-MRD ID

NP0000821

Natural Product DOI

https://doi.org/10.57994/0845

Secondary Accession Numbers

None

Natural Product Identification

Common Name

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

Description

2,6-Di-tert-butyl-4-methylphenol, also known as butylated hydroxytoluene or BHT, belongs to the class of organic compounds known as phenylpropanes. These are organic compounds containing a phenylpropane moiety. BHT is a mild, camphor, and musty tasting compound. It has been detected, but not quantified, in soft-necked garlic. This could make BHT a potential biomarker for the consumption of this food. BHT 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. BHT was detected in human urine (PMID:31265952 ).

Structure

MOL SDF PDB SMILES InChI


  Mrv1652304282018152D          

 16 16  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
 9989.5420 9991.8056    0.0000 C   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
 9988.8275 9991.3931    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
 9989.9534 9992.5213    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
  1  2  1  0  0  0  0
  1  3  1  0  0  0  0
  1  4  1  0  0  0  0
  6  8  1  0  0  0  0
  6  9  1  0  0  0  0
  6 10  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 11  1  0  0  0  0
  1 11  1  0  0  0  0
 12  5  1  0  0  0  0
 13  6  1  0  0  0  0
 15  7  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0000821

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1=CC(=C(O)C(=C1)C(C)(C)C)C(C)(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C15H24O/c1-10-8-11(14(2,3)4)13(16)12(9-10)15(5,6)7/h8-9,16H,1-7H3

> <INCHI_KEY>
NLZUEZXRPGMBCV-UHFFFAOYSA-N

> <FORMULA>
C15H24O

> <MOLECULAR_WEIGHT>
220.3505

> <EXACT_MASS>
220.18271539

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
40

> <JCHEM_AVERAGE_POLARIZABILITY>
27.348201983235235

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2,6-di-tert-butyl-4-methylphenol

> <ALOGPS_LOGP>
5.25

> <JCHEM_LOGP>
5.273214425000001

> <ALOGPS_LOGS>
-4.16

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.602391152527046

> <JCHEM_PKA_STRONGEST_BASIC>
-4.559361293068014

> <JCHEM_POLAR_SURFACE_AREA>
20.23

> <JCHEM_REFRACTIVITY>
70.41189999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.52e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
ional

> <JCHEM_VEBER_RULE>
1

$$$$

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    8647.1458651.370   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0    8649.8168646.751   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0    8645.8118650.600   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0    8646.3738652.706   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0    8647.9138652.706   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0    8651.1468650.600   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0    8649.8138651.370   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0    8648.4818650.600   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0    8648.4808649.062   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0    8649.8138648.293   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0    8651.1468649.062   0.000  0.00  0.00           C+0
CONECT    1    2    3    4   11                                             
CONECT    2    1                                                            
CONECT    3    1                                                            
CONECT    4    1                                                            
CONECT    5   12                                                            
CONECT    6    8    9   10   13                                             
CONECT    7   15                                                            
CONECT    8    6                                                            
CONECT    9    6                                                            
CONECT   10    6                                                            
CONECT   11   12   16    1                                                  
CONECT   12   11   13    5                                                  
CONECT   13   12   14    6                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16    7                                                  
CONECT   16   15   11                                                       
MASTER        0    0    0    0    0    0    0    0   16    0   32    0
END

View in JSmol

Synonyms

Value	Source
2,6-Bis(1,1-dimethylethyl)-4-methylphenol	ChEBI
2,6-Di-t-butyl-4-methylphenol	ChEBI
2,6-Di-tert-butyl-1-hydroxy-4-methylbenzene	ChEBI
2,6-Di-tert-butyl-4-cresol	ChEBI
2,6-Di-tert-butyl-p-cresol	ChEBI
BHT	ChEBI
Butylated hydroxytoluene	ChEBI
Butylhydroxytoluene	ChEBI
2,6-Bis(1,1-dimethylethyl)-4-methylphenol, 9ci	HMDB
2,6-Di-tert-butyl-p-cresol, 8ci	HMDB
Butyl hydroxy toluene	HMDB
e321	HMDB
FEMA 2184	HMDB
Ionol	HMDB
Popol	HMDB
2,6 Di t butyl 4 methylphenol	HMDB
4-Methyl-2,6-ditertbutylphenol	HMDB
Hydroxytoluene, butylated	HMDB
Ionol (BHT)	HMDB
2,6 Di tert butyl p cresol	HMDB
4 Methyl 2,6 ditertbutylphenol	HMDB
Dibunol	HMDB
Di-tert-butyl-methylphenol	MeSH
2,6 Di tert butyl 4 methylphenol	MeSH
Di tert butyl methylphenol	MeSH
2,6-Bis(tert-butyl)-4-methylphenol	HMDB
2,6-Di(tert-butyl)hydroxytoluene	HMDB
2,6-Di-tert-butyl-4-hydroxytoluene	HMDB
2,6-Di-tert-butyl-4-methyl phenol	HMDB
2,6-Di-tert-butyl-4-methyl-1-hydroxybenzene	HMDB
2,6-Di-tert-butyl-4-methylhydroxybenzene	HMDB
2,6-Di-tert-butyl-4-methylphenol	HMDB
2,6-Di-tert-butyl-p-cresole	HMDB
2,6-Di-tert-butyl-p-methylphenol	HMDB
2,6-Di-tert-butylcresol	HMDB
2,6-Di-tert-butylmethylphenol	HMDB
2,6-Ditertbutyl paracresol	HMDB
2,6-tert-Butyl-4-methylphenol	HMDB
3,5-Bis(1,1-dimethylethyl)-4-hydroxytoluene	HMDB
3,5-Di-tert-butyl-4-hydroxytoluene	HMDB
3,5-Di-tert-butyl-p-hydroxytoluene	HMDB
4-Hydroxy-3,5-di-tert-butyltoluene	HMDB
4-Methyl-2,6-bis(1,1-dimethylethyl)phenol	HMDB
4-Methyl-2,6-di-tert-butylphenol	HMDB
4-Methyl-2,6-ditertbutyl phenol	HMDB
Di-tert-Butyl-4-methylphenol	HMDB
Di-tert-butyl-p-cresol	HMDB
Di-tert-butylcresol	HMDB
Dibutyl paracresol	HMDB
Dibutylated hydroxytoluene	HMDB
Dibutylcresol	HMDB
Dibutylhydroxytoluene	HMDB
o-Di-tert-butyl-p-methylphenol	HMDB

Chemical Formula

C₁₅H₂₄O

Average Mass

220.3505 Da

Monoisotopic Mass

220.18272 Da

IUPAC Name

2,6-di-tert-butyl-4-methylphenol

Traditional Name

ional

CAS Registry Number

128-37-0

SMILES

CC1=CC(=C(O)C(=C1)C(C)(C)C)C(C)(C)C

InChI Identifier

InChI=1S/C15H24O/c1-10-8-11(14(2,3)4)13(16)12(9-10)15(5,6)7/h8-9,16H,1-7H3

InChI Key

NLZUEZXRPGMBCV-UHFFFAOYSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CD3OD, experimental)	bgnzk@missouri.edu	Not Available	Not Available	2024-05-09	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CD3OD, experimental)	bgnzk@missouri.edu	Not Available	Not Available	2024-05-09	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 90 MHz, CDCl₃, experimental)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 25.16 MHz, CDCl₃, experimental)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View

Chemical Shift Submissions

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹H NMR Spectrum (1D, 600.133705802, CD₃OD, simulated)	bgnzk@missouri.edu	Sumner Lab, MU Metabolomics Center, University of Missouri, Columbia. MO, USA	Dr. Bharat Goel	2024-05-09	View Spectrum

Species

Species of Origin

Species Name	Source	Reference
Allium sativum	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Betula platyphylla		LOTUS database
Microcystis aeruginosa	-	KNApSAcK
Polysiphonia urceolata		LOTUS database
Teucrium leucocladum		LOTUS database
Thymus longicaulis		LOTUS database

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
P-cresol
Toluene
Phenol
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

phenols (CHEBI:34247 )

Physical Properties

State

Solid

Experimental Properties

Property	Value	Reference
Melting Point	71 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.0006 mg/mL at 25 °C	Not Available
LogP	5.10	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	0.015 g/L	ALOGPS
logP	5.25	ALOGPS
logP	5.27	ChemAxon
logS	-4.2	ALOGPS
pKa (Strongest Acidic)	11.6	ChemAxon
pKa (Strongest Basic)	-4.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	20.23 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	70.41 m³·mol⁻¹	ChemAxon
Polarizability	27.35 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0033826

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Butylated_hydroxytoluene

METLIN ID

Not Available

PubChem Compound

31404

PDB ID

Not Available

ChEBI ID

34247

Good Scents ID

Not Available

References

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 ]
Saleem A, Ahotupa M, Pihlaja K: Total phenolics concentration and antioxidant potential of extracts of medicinal plants of Pakistan. Z Naturforsch C J Biosci. 2001 Nov-Dec;56(11-12):973-8. doi: 10.1515/znc-2001-11-1211. [PubMed:11837686 ]
Merino O, Aguaguina WE, Esponda P, Risopatron J, Isachenko E, Isachenko V, Sanchez R: Protective effect of butylated hydroxytoluene on sperm function in human spermatozoa cryopreserved by vitrification technique. Andrologia. 2015 Mar;47(2):186-93. doi: 10.1111/and.12246. Epub 2014 Feb 24. [PubMed:24612426 ]
da Silva Santos V, Bisen-Hersh E, Yu Y, Cabral IS, Nardini V, Culbreth M, Teixeira da Rocha JB, Barbosa F Jr, Aschner M: Anthocyanin-rich acai (Euterpe oleracea Mart.) extract attenuates manganese-induced oxidative stress in rat primary astrocyte cultures. J Toxicol Environ Health A. 2014;77(7):390-404. doi: 10.1080/15287394.2014.880392. [PubMed:24617543 ]
(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Showing NP-Card for 2,6-Di-tert-butyl-4-methylphenol (NP0000821)

MOL for NP0000821 (2,6-Di-tert-butyl-4-methylphenol)

3D MOL for NP0000821 (2,6-Di-tert-butyl-4-methylphenol)

3D SDF for NP0000821 (2,6-Di-tert-butyl-4-methylphenol)

3D-SDF for NP0000821 (2,6-Di-tert-butyl-4-methylphenol)

PDB for NP0000821 (2,6-Di-tert-butyl-4-methylphenol)

3D PDB for NP0000821 (2,6-Di-tert-butyl-4-methylphenol)

SMILES for NP0000821 (2,6-Di-tert-butyl-4-methylphenol)

INCHI for NP0000821 (2,6-Di-tert-butyl-4-methylphenol)

Structure for NP0000821 (2,6-Di-tert-butyl-4-methylphenol)

3D Structure for NP0000821 (2,6-Di-tert-butyl-4-methylphenol)