BHA (E 320) is a synthetic antioxidant authorized as a food additive. BHA is a mixture of two isomers: 2-tert-butyl-4-hydroxyanisole and 3-tert-butyl-4-hydroxyanisole. BHA is known to have various beneficial activities such as antioxidant activity, anti-inflammatory effects, and anticancer potential although some reports suggested that this reagent induces cytotoxicity. In general, the majority of the genotoxicity studies indicate a lack of potential for BHA to induce point mutations or to interact with or damage DNA. It was banned in Japan in 1958, and it was recommended that it be banned in the UK, however, due to industry pressure it was not. The antioxidant properties of 3-tert-butyl-4-hydroxyanisole are achieved via inhibition of ROS generation. The experiments on mice have shown that pretreatment with compound prevented apoptotic cell death induced by oxidative stress in mouse hepatocytes that may be beneficial for treating liver diseases caused by oxidative stress.
Approval Year
Targets
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Target ID: GO:1903409 Sources: https://www.ncbi.nlm.nih.gov/pubmed/25798044 |
Conditions
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PubMed
Title | Date | PubMed |
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Estrogenic activity of phenolic additives determined by an in vitro yeast bioassay. | 2001 Feb |
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Effects of some sterically hindered phenols on whole-cell Ca(2+) current of guinea-pig gastric fundus smooth muscle cells. | 2001 Mar |
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[Simultaneous determination of five antioxidants in food by HPLC with fluorescence detection]. | 2002 Apr |
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Evaluation of the anti-oxidative effect (in vitro) of tea polyphenols. | 2003 Feb |
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Solid-state nuclear magnetic resonance determination of the physical form of BHA on common pharmaceutical excipients. | 2004 Jan |
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Induction of metallothionein I by phenolic antioxidants requires metal-activated transcription factor 1 (MTF-1) and zinc. | 2004 Jun 15 |
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Molecular mechanism of cell death induced by the antioxidant tert-butylhydroxyanisole in human monocytic leukemia U937 cells. | 2004 Mar |
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Kinetic radical scavenging activity and cytotoxicity of 2-methoxy- and 2-t-butyl-substituted phenols and their dimers. | 2004 Sep-Oct |
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Characterization of hydroxyaromatic compounds in vegetable oils by capillary electrophoresis with direct injection in an oil-miscible KOH/propanol/methanol medium. | 2005 Sep |
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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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[Expression changes of Notch-related genes during the differentiation of human mesenchymal stem cells into neurons]. | 2007 Jun 25 |
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Development and evaluation of an electrochemical method for studying reactive phase-I metabolites: correlation to in vitro drug metabolism. | 2007 May |
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Induction of endoplasmic reticulum stress by the pro-apoptotic retinoid N-(4-hydroxyphenyl)retinamide via a reactive oxygen species-dependent mechanism in human head and neck cancer cells. | 2007 May |
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Comparative study of the alkyl and peroxy radical-scavenging activity of 2-t-butyl-4-methoxyphenol (BHA) and its dimer, and their theoretical parameters. | 2008 May-Jun |
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Sorption behavior of a synthetic antioxidant, polycyclic musk, and an organophosphate insecticide in wastewater sludge. | 2009 |
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Comparison of volatile profiles of nine litchi (Litchi chinensis Sonn.) cultivars from Southern China. | 2009 Oct 28 |
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Cameroonian medicinal plants: pharmacology and derived natural products. | 2010 |
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Determination of antioxidants in new and used lubricant oils by headspace-programmed temperature vaporization-gas chromatography-mass spectrometry. | 2010 Dec |
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Radical-scavenging activity and cytotoxicity of p-methoxyphenol and p-cresol dimers. | 2010 Feb 26 |
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Potential involvement of F0F1-ATP(synth)ase and reactive oxygen species in apoptosis induction by the antineoplastic agent erucylphosphohomocholine in glioblastoma cell lines : a mechanism for induction of apoptosis via the 18 kDa mitochondrial translocator protein. | 2010 Jul |
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Antimicrobial and antioxidant effects of phenolic constituents from Klainedoxa gabonensis. | 2010 Oct |
Patents
Sample Use Guides
BHA (E 320) is a synthetic antioxidant authorised as a food additive. BHA is a mixture of two isomers with full chemical names 2-tert-butyl-4-hydroxyanisole and 3-tert-butyl-4-hydroxyanisole.
Route of Administration:
Oral
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/25798044
It was examined the effect of BHA against hydrogen peroxide (H2O2)-induced apoptosis in primary cultured mouse hepatocytes. Butylated hydroxyanisole (BHA; 3-tert-butyl 4-hydroxyanisole) is one of the most widely used synthetic phenolic compounds. To determine the effect of BHA on decreased cell viability caused by H2O2, cells were pretreated with various concentrations (0~10 µM) of BHA for 30 min and then treated with 1,000 µM H2O2. BHA prevented the decreases in cell viability caused by H2O2. These results indicate that BHA pretreatment protects primary cultured mouse hepatocytes from H2O2-induced apoptosis.
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Mixture
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JECFA EVALUATION |
INS-320
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NCI_THESAURUS |
C45175
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CODEX ALIMENTARIUS (GSFA) |
INS-320
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CFR |
21 CFR 171.110
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M2819
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BUTYLATED HYDROXYANISOLE
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PRIMARY | Description: A white or almost white, crystalline powder or a yellowish white solid; odour, faint and characteristic. Solubility: Practically insoluble in water; freely soluble in ethanol (~750 g/l) TS, ether R, propylene glycol R, and arachis oil R; dissolves in solutions of alkali hydroxides. Category: Antioxidant. Storage: Butylated hydroxyanisole should be kept in a well-closed container, protected from light. Definition: Butylated hydroxyanisole contains a variable amount of 3-tert-butyl-4-methoxyphenol. | ||
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BUTYLATED HYDROXYANISOLE
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CHEMBL192451
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CHROMATOGRAPHIC PURITY (HPLC/UV)
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ACTIVE MOIETY |
http://apps.who.int/phint/pdf/b/Jb.6.1.64.pdf
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