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Details

Stereochemistry ACHIRAL
Molecular Formula C15H24O
Molecular Weight 220.3505
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of BUTYLATED HYDROXYTOLUENE

SMILES

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

InChI

InChIKey=NLZUEZXRPGMBCV-UHFFFAOYSA-N
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

HIDE SMILES / InChI
Butylated hydroxytoluene, commonly known as BHT, is an organic compound that is used in the food, cosmetic, and pharmaceutical industry as an antioxidant. BHT is a substituted derivative of phenol. BHT helps to prevent the formation of free radicals and oxidation. When used in food products, it delays oxidative rancidity of fats and oils, and prevents loss of activity of oil-soluble vitamins. It may be found in pharmaceutical gels, creams and liquid or gelatin capsules, tablets and other pharmaceutical dosage forms. The ability of oral BHT to lead to cancer is a controversial topic, but most food industries have replaced it with butylated hydroxyanisole (BHA). BHT was first used as an antioxidant food additive in 1954. BHT does have other commercial uses, as in animal feeds and in the manufacture of synthetic rubber and plastics, where it also acts as an antioxidant. The U.S. Food and Drug Administration has deemed that BHT is safe enough when used in limited concentrations. It currently permits its use in concentrations of about 0.01% to 0.02% in most foods. As an emulsion stabilizer in shortening, it may be used in a somewhat higher concentration, 200 parts per million.

CNS Activity

Curator's Comment: It may cross the blood brain barrier, causing psychotropic symptoms

Approval Year

PubMed

PubMed

TitleDatePubMed
Inhibition by butylated hydroxytoluene and its oxidative metabolites of DMBA-induced mammary tumorigenesis and of mammary DMBA-DNA adduct formation in vivo in the female rat.
1992 Jun
Elastin gene expression is upregulated during pulmonary fibrosis.
1999
Nrf2 is essential for protection against acute pulmonary injury in mice.
1999 Oct 26
Chemoprevention of heterocyclic amine-induced carcinogenesis by phenolic compounds in rats.
1999 Sep 1
Examination of selected food additives and organochlorine food contaminants for androgenic activity in vitro.
2000 Feb
Differential expression and localization of the mRNA binding proteins, AU-rich element mRNA binding protein (AUF1) and Hu antigen R (HuR), in neoplastic lung tissue.
2000 Jun
Glycation amplifies lipoprotein(a)-induced alterations in the generation of fibrinolytic regulators from human vascular endothelial cells.
2000 Jun
Direct interaction of GD3 ganglioside with mitochondria generates reactive oxygen species followed by mitochondrial permeability transition, cytochrome c release, and caspase activation.
2000 May
MAP: microwave-assisted extraction of fatty acids and Py/GC/MS analysis of selected insects.
2001
Differential expression of forkhead box transcription factors following butylated hydroxytoluene lung injury.
2001 Apr
Studies using structural analogs and inbred strain differences to support a role for quinone methide metabolites of butylated hydroxytoluene (BHT) in mouse lung tumor promotion.
2001 Mar 7
Use of an automated on-line SPE-HPLC method to monitor caffeine and selected aniline and phenol compounds in aquatic systems of Macedonia-Thrace, Greece.
2001 Oct
Butylhydroxytoluene (BHT) increases susceptibility of transgenic rasH2 mice to lung carcinogenesis.
2001 Oct
The mouse rasH2/BHT model as an in vivo rapid assay for lung carcinogens.
2002 Aug
[Determination of 2,6-di-tertbutyl-4-methylphenol in an aviation jet fuel by high performance liquid chromatography].
2002 Jul
Hydrogen bonding between phenols and fatty acid esters: (1)H NMR study and ab initio calculations.
2002 Jul 11
Quantitative trait loci that regulate susceptibility to both butylated hydroxytoluene-induced pulmonary inflammation and lung tumor promotion in CXB recombinant inbred mice.
2002 Mar
Analysis of the antioxidant butylated hydroxytoluene (BHT) in water by means of solid phase extraction combined with GC/MS.
2002 May
Design and synthesis of 2,6-diprenyl-4-iodophenol TX-1952 with a novel and potent anti-peroxidative activity.
2002 May
A convenient method for determination of the C20-22 PUFA composition of glycerolipids in blood and breast milk.
2002 May
Screening chemical composition and in vitro antioxidant and antimicrobial activities of the essential oils from Origanum syriacum L. growing in Turkey.
2003 Dec
Sequestering ability of butylated hydroxytoluene, propyl gallate, resveratrol, and vitamins C and E against ABTS, DPPH, and hydroxyl free radicals in chemical and biological systems.
2003 Feb 12
Control of Clostridium perfringens germination and outgrowth by buffered sodium citrate during chilling of roast beef and injected pork.
2003 Mar
Reactive oxygen species mediate the down-regulation of mitochondrial transcripts and proteins by tumour necrosis factor-alpha in L929 cells.
2003 Mar 1
Effects of dietary butylated hydroxytoluene on aflatoxin B1-relevant metabolic enzymes in turkeys.
2003 May
Ubiquitous expression of the forkhead box M1B transgene accelerates proliferation of distinct pulmonary cell types following lung injury.
2003 Sep 26
Inhibition of glutathione S-transferase P1-1 in mouse lung epithelial cells by the tumor promoter 2,6-di-tert-butyl-4-methylene-2,5-cyclohexadienone (BHT-quinone methide): protein adducts investigated by electrospray mass spectrometry.
2004 Dec
Structure and generation mechanism of a novel degradation product formed by oxidatively induced coupling of miconazole nitrate with butylated hydroxytoluene in a topical ointment studied by HPLC-ESI-MS and organic synthesis.
2004 Feb
Inactivation of endoplasmic reticulum bound Ca2+-independent phospholipase A2 in renal cells during oxidative stress.
2004 Jun
Effect of thiabendazole on some rat hepatic xenobiotic metabolising enzymes.
2004 Jun
[Contact sensitization to pharmaceutic aids in dermatologic cosmetic and external use preparations].
2004 May
Malondialdehyde, a lipoperoxidation-derived aldehyde, can bring about secondary oxidative damage to proteins.
2004 Sep
Method development and validation for monitoring in vivo oxidative stress: evaluation of lipid peroxidation and fat-soluble vitamin status by HPLC in rat plasma.
2005 Aug 5
Iron-ascorbic acid-induced oxidant stress and its quenching by paraoxonase 1 in HDL and the liver: comparison between humans and rats.
2005 Oct 1
Enhancement of tumor invasion depends on transdifferentiation of skin fibroblasts mediated by reactive oxygen species.
2006 Jul 1
Synthesis and antioxidant activity of [60]fullerene-BHT conjugates.
2006 Jun 2
Cytokine response to lipoprotein lipid loading in human monocyte-derived macrophages.
2006 Jun 26
Prediction of estrogen receptor agonists and characterization of associated molecular descriptors by statistical learning methods.
2006 Nov
Quantitative analysis of early chemically-induced pulmonary lesions in mice of varying susceptibilities to lung tumorigenesis.
2006 Sep 28
Does immune stimulation or antioxidant therapy reduce MNU-induced placental damage via activation of Jak-STAT and NFkappaB signaling pathways?
2007 May-Jun
Patents

Sample Use Guides

The effect of topical therapy with 15% Butylated hydroxytoluene in mineral oil on the course of recurrent herpes simplex labialis was examined in 30 patients in a double-blind, placebo-controlled pilot study.
Route of Administration: Topical
In Vitro Use Guide
Curator's Comment: The effect of Butylated hydroxytoluene on the oxidation of low density lipoproteins in relation to prostacyclin synthesis was investigated in the prescence of rabbit smooth muscle cells (SMC) and Fe-containing culture medium.
Butylated hydroxytoluene (BHT) inhibited lipoprotein oxidation by IC50 values of 0.8 uM
Name Type Language
BUTYLATED HYDROXYTOLUENE
FHFI   HSDB   II   MART.   MI   NF   USP-RS   VANDF   WHO-DD   WHO-IP  
Common Name English
Butylated hydroxytoluene [WHO-DD]
Common Name English
BUTYLATED HYDROXYTOLUENE [USP-RS]
Common Name English
INS NO.321
Code English
BUTYLATED HYDROXYTOLUENE [II]
Common Name English
BUTYLHYDROXYTOLUENE [EP MONOGRAPH]
Common Name English
E-321
Code English
PHENOL, 2,6-BIS(1,1-DIMETHYLETHYL)-4-METHYL-
Systematic Name English
BUTYLATED HYDROXYTOLUENE [VANDF]
Common Name English
BUTYLATED HYDROXYTOLUENE (E 321)
Common Name English
BUTYLATED HYDROXYTOLUENE [FHFI]
Common Name English
BUTYLHYDROXYTOLUENE
EP  
Systematic Name English
2,6-BIS(1,1-DIMETHYLETHYL)-4-METHYLPHENOL
Systematic Name English
BUTYLATED HYDROXYTOLUENE [IARC]
Common Name English
BUTYLATED HYDROXYTOLUENE [MART.]
Common Name English
BHT [FCC]
Common Name English
2,6-DI-TERT-BUTYL-P-CRESOL
Common Name English
KERABIT
Common Name English
BUTYLATED HYDROXYTOLUENE [NF]
Common Name English
4-METHYL-2,6-DITERTIARY-BUTYL-PHENOL
Common Name English
2,6-DI-TERT-BUTYL-P-CRESOL2,6-BIS(1,1-DIMETHYLETHYL)-4-METHYL-PHENOL
Systematic Name English
NSC-6347
Code English
BUTYLATED HYDROXYTOLUENE [HSDB]
Common Name English
FEMA NO. 2184
Code English
BHT
FCC   INCI  
INCI  
Official Name English
BUTYLATED HYDROXYTOLUENE [MI]
Common Name English
INS-321
Code English
2,6-DITERTIARY-BUTYL-P-CRESOL
Common Name English
BUTYLATED HYDROXYTOLUENE [WHO-IP]
Common Name English
BHT [INCI]
Common Name English
BUTYLHYDROXYTOLUENUM [WHO-IP LATIN]
Common Name English
Classification Tree Code System Code
EPA PESTICIDE CODE 22105
Created by admin on Fri Dec 15 15:08:02 GMT 2023 , Edited by admin on Fri Dec 15 15:08:02 GMT 2023
JECFA EVALUATION INS-321
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CODEX ALIMENTARIUS (GSFA) INS-321
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NCI_THESAURUS C275
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CFR 21 CFR 172.115
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Code System Code Type Description
CHEBI
34247
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PRIMARY
MERCK INDEX
m2820
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PRIMARY Merck Index
SMS_ID
100000076384
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PRIMARY
ChEMBL
CHEMBL146
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PRIMARY
NSC
6347
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PRIMARY
MESH
D002084
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PRIMARY
EVMPD
SUB11765MIG
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PRIMARY
RS_ITEM_NUM
1082708
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PRIMARY
NCI_THESAURUS
C322
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PRIMARY
DAILYMED
1P9D0Z171K
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PRIMARY
FDA UNII
1P9D0Z171K
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PRIMARY
CAS
128-37-0
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PRIMARY
ECHA (EC/EINECS)
204-881-4
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PRIMARY
EPA CompTox
DTXSID2020216
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PRIMARY
WIKIPEDIA
BUTYLATED HYDROXYTOLUENE
Created by admin on Fri Dec 15 15:08:03 GMT 2023 , Edited by admin on Fri Dec 15 15:08:03 GMT 2023
PRIMARY
RXCUI
1848
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PRIMARY RxNorm
HSDB
1147
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PRIMARY
PUBCHEM
31404
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PRIMARY
WHO INTERNATIONAL PHARMACOPEIA
BUTYLATED HYDROXYTOLUENE
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PRIMARY Description: Colourless crystals or a white or almost white, crystalline powder; odour, faint and characteristic. Solubility: Practically insoluble in water; freely soluble in ethanol (~750 g/l) TS, acetone R, ether R, and arachis oil R. Category: Antioxidant. Storage: Butylated hydroxytoluene should be kept in a well-closed container, protected from light.