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
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
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
Sources: http://naturaldatabase.therapeuticresearch.com/nd/PrintVersion.aspx?id=1071&AspxAutoDetectCookieSupport=1
Curator's Comment: It may cross the blood brain barrier, causing psychotropic symptoms
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
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Target ID: CHEMBL205 Sources: https://www.ncbi.nlm.nih.gov/pubmed/19231207 |
630.0 nM [Ki] | ||
Conditions
Condition | Modality | Targets | Highest Phase | Product |
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Primary | Unknown Approved UseUnknown |
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Primary | Unknown Approved UseUnknown |
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Inactive ingredient | A-TEAM Approved UseUSE HELPS PROTECT AGAINST SUNBURN Launch Date2014 |
PubMed
Title | Date | PubMed |
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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 |
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Elastin gene expression is upregulated during pulmonary fibrosis. | 1999 |
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Nrf2 is essential for protection against acute pulmonary injury in mice. | 1999 Oct 26 |
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Chemoprevention of heterocyclic amine-induced carcinogenesis by phenolic compounds in rats. | 1999 Sep 1 |
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Examination of selected food additives and organochlorine food contaminants for androgenic activity in vitro. | 2000 Feb |
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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 |
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Glycation amplifies lipoprotein(a)-induced alterations in the generation of fibrinolytic regulators from human vascular endothelial cells. | 2000 Jun |
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Direct interaction of GD3 ganglioside with mitochondria generates reactive oxygen species followed by mitochondrial permeability transition, cytochrome c release, and caspase activation. | 2000 May |
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MAP: microwave-assisted extraction of fatty acids and Py/GC/MS analysis of selected insects. | 2001 |
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Differential expression of forkhead box transcription factors following butylated hydroxytoluene lung injury. | 2001 Apr |
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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 |
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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 |
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Butylhydroxytoluene (BHT) increases susceptibility of transgenic rasH2 mice to lung carcinogenesis. | 2001 Oct |
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The mouse rasH2/BHT model as an in vivo rapid assay for lung carcinogens. | 2002 Aug |
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[Determination of 2,6-di-tertbutyl-4-methylphenol in an aviation jet fuel by high performance liquid chromatography]. | 2002 Jul |
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Hydrogen bonding between phenols and fatty acid esters: (1)H NMR study and ab initio calculations. | 2002 Jul 11 |
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Quantitative trait loci that regulate susceptibility to both butylated hydroxytoluene-induced pulmonary inflammation and lung tumor promotion in CXB recombinant inbred mice. | 2002 Mar |
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Analysis of the antioxidant butylated hydroxytoluene (BHT) in water by means of solid phase extraction combined with GC/MS. | 2002 May |
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Design and synthesis of 2,6-diprenyl-4-iodophenol TX-1952 with a novel and potent anti-peroxidative activity. | 2002 May |
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A convenient method for determination of the C20-22 PUFA composition of glycerolipids in blood and breast milk. | 2002 May |
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Screening chemical composition and in vitro antioxidant and antimicrobial activities of the essential oils from Origanum syriacum L. growing in Turkey. | 2003 Dec |
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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 |
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Control of Clostridium perfringens germination and outgrowth by buffered sodium citrate during chilling of roast beef and injected pork. | 2003 Mar |
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Reactive oxygen species mediate the down-regulation of mitochondrial transcripts and proteins by tumour necrosis factor-alpha in L929 cells. | 2003 Mar 1 |
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Effects of dietary butylated hydroxytoluene on aflatoxin B1-relevant metabolic enzymes in turkeys. | 2003 May |
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Ubiquitous expression of the forkhead box M1B transgene accelerates proliferation of distinct pulmonary cell types following lung injury. | 2003 Sep 26 |
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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 |
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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 |
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Inactivation of endoplasmic reticulum bound Ca2+-independent phospholipase A2 in renal cells during oxidative stress. | 2004 Jun |
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Effect of thiabendazole on some rat hepatic xenobiotic metabolising enzymes. | 2004 Jun |
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[Contact sensitization to pharmaceutic aids in dermatologic cosmetic and external use preparations]. | 2004 May |
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Malondialdehyde, a lipoperoxidation-derived aldehyde, can bring about secondary oxidative damage to proteins. | 2004 Sep |
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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 |
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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 |
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Enhancement of tumor invasion depends on transdifferentiation of skin fibroblasts mediated by reactive oxygen species. | 2006 Jul 1 |
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Synthesis and antioxidant activity of [60]fullerene-BHT conjugates. | 2006 Jun 2 |
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Cytokine response to lipoprotein lipid loading in human monocyte-derived macrophages. | 2006 Jun 26 |
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Prediction of estrogen receptor agonists and characterization of associated molecular descriptors by statistical learning methods. | 2006 Nov |
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Quantitative analysis of early chemically-induced pulmonary lesions in mice of varying susceptibilities to lung tumorigenesis. | 2006 Sep 28 |
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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
In Vivo Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/2988845
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
Sources: https://www.ncbi.nlm.nih.gov/pubmed/1900157
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
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Classification Tree | Code System | Code | ||
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EPA PESTICIDE CODE |
22105
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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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34247
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m2820
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100000076384
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CHEMBL146
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6347
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C322
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128-37-0
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204-881-4
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DTXSID2020216
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BUTYLATED HYDROXYTOLUENE
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1848
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1147
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31404
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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. |
ACTIVE MOIETY
METABOLITE (PARENT)