U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS
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

Targets

Primary TargetPharmacologyConditionPotency
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
PubMed

PubMed

TitleDatePubMed
Estrogenic activity of phenolic additives determined by an in vitro yeast bioassay.
2001 Feb
Effects of some sterically hindered phenols on whole-cell Ca(2+) current of guinea-pig gastric fundus smooth muscle cells.
2001 Mar
[Simultaneous determination of five antioxidants in food by HPLC with fluorescence detection].
2002 Apr
Evaluation of the anti-oxidative effect (in vitro) of tea polyphenols.
2003 Feb
Solid-state nuclear magnetic resonance determination of the physical form of BHA on common pharmaceutical excipients.
2004 Jan
Induction of metallothionein I by phenolic antioxidants requires metal-activated transcription factor 1 (MTF-1) and zinc.
2004 Jun 15
Molecular mechanism of cell death induced by the antioxidant tert-butylhydroxyanisole in human monocytic leukemia U937 cells.
2004 Mar
Kinetic radical scavenging activity and cytotoxicity of 2-methoxy- and 2-t-butyl-substituted phenols and their dimers.
2004 Sep-Oct
Characterization of hydroxyaromatic compounds in vegetable oils by capillary electrophoresis with direct injection in an oil-miscible KOH/propanol/methanol medium.
2005 Sep
Prediction of estrogen receptor agonists and characterization of associated molecular descriptors by statistical learning methods.
2006 Nov
[Expression changes of Notch-related genes during the differentiation of human mesenchymal stem cells into neurons].
2007 Jun 25
Development and evaluation of an electrochemical method for studying reactive phase-I metabolites: correlation to in vitro drug metabolism.
2007 May
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
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
Sorption behavior of a synthetic antioxidant, polycyclic musk, and an organophosphate insecticide in wastewater sludge.
2009
Comparison of volatile profiles of nine litchi (Litchi chinensis Sonn.) cultivars from Southern China.
2009 Oct 28
Cameroonian medicinal plants: pharmacology and derived natural products.
2010
Determination of antioxidants in new and used lubricant oils by headspace-programmed temperature vaporization-gas chromatography-mass spectrometry.
2010 Dec
Radical-scavenging activity and cytotoxicity of p-methoxyphenol and p-cresol dimers.
2010 Feb 26
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
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
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.
Substance Class Mixture
Created
by admin
on Fri Dec 16 19:25:04 UTC 2022
Edited
by admin
on Fri Dec 16 19:25:04 UTC 2022
Record UNII
REK4960K2U
Record Status Validated (UNII)
Record Version
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Name Type Language
BUTYLATED HYDROXYANISOLE
FHFI   HSDB   II   MART.   MI   NF   VANDF   WHO-DD   WHO-IP  
Common Name English
BUTYLATED HYDROXYANISOLE [HSDB]
Common Name English
EMBANOX
Common Name English
BUTYLHYDROXYANISOLE
Common Name English
BUTYLATED HYDROXYANISOLE [FHFI]
Common Name English
BUTYLATED HYDROXYANISOLE [NF]
Common Name English
INS NO.320
Code English
Butylated hydroxyanisole [WHO-DD]
Common Name English
BUTYLATED HYDROXYANISOLE [VANDF]
Common Name English
BUTYLATED HYDROXYANISOLE [MART.]
Common Name English
BHA [INCI]
Common Name English
BUTYLATED HYDROXYANISOLE [II]
Common Name English
BUTYLATED HYDROXYANISOLE [IARC]
Common Name English
BUTYLHYDROXYANISOLUM [WHO-IP LATIN]
Common Name English
tert-Butyl-4-methoxyphenol
Common Name English
BUTYLHYDROXYANISOLE [EP MONOGRAPH]
Common Name English
(1,1-DIMETHYLETHYL)-4-METHOXYPHENOL
Common Name English
3-TERTIARY-BUTYL-4-HYDROXYANISOLE
Common Name English
BUTYLATED HYDROXYANISOLE [MI]
Common Name English
FEMA NO. 2183
Code English
2(3)-TERT-BUTYL-4-HYDROXYANISOLE
Common Name English
ANTIOXYNE B
Common Name English
BHA [FCC]
Common Name English
TERT-BUTYL-P-HYDROXYANISOLE
Common Name English
BUTYLATED HYDROXYANISOLE [WHO-IP]
Common Name English
PHENOL, (1,1-DIMETHYLETHYL)-4-METHOXY-
Common Name English
INS-320
Code English
BHA
FCC   INCI  
INCI  
Official Name English
E-320
Code English
Classification Tree Code System Code
JECFA EVALUATION INS-320
Created by admin on Fri Dec 16 19:25:04 UTC 2022 , Edited by admin on Fri Dec 16 19:25:04 UTC 2022
NCI_THESAURUS C45175
Created by admin on Fri Dec 16 19:25:04 UTC 2022 , Edited by admin on Fri Dec 16 19:25:04 UTC 2022
CODEX ALIMENTARIUS (GSFA) INS-320
Created by admin on Fri Dec 16 19:25:04 UTC 2022 , Edited by admin on Fri Dec 16 19:25:04 UTC 2022
CFR 21 CFR 171.110
Created by admin on Fri Dec 16 19:25:04 UTC 2022 , Edited by admin on Fri Dec 16 19:25:04 UTC 2022
Code System Code Type Description
MERCK INDEX
M2819
Created by admin on Fri Dec 16 19:25:04 UTC 2022 , Edited by admin on Fri Dec 16 19:25:04 UTC 2022
PRIMARY Merck Index
CHEBI
76359
Created by admin on Fri Dec 16 19:25:04 UTC 2022 , Edited by admin on Fri Dec 16 19:25:04 UTC 2022
PRIMARY
NCI_THESAURUS
C44347
Created by admin on Fri Dec 16 19:25:04 UTC 2022 , Edited by admin on Fri Dec 16 19:25:04 UTC 2022
PRIMARY
DAILYMED
REK4960K2U
Created by admin on Fri Dec 16 19:25:04 UTC 2022 , Edited by admin on Fri Dec 16 19:25:04 UTC 2022
PRIMARY
RXCUI
1362900
Created by admin on Fri Dec 16 19:25:04 UTC 2022 , Edited by admin on Fri Dec 16 19:25:04 UTC 2022
PRIMARY RxNorm
EVMPD
SUB11764MIG
Created by admin on Fri Dec 16 19:25:04 UTC 2022 , Edited by admin on Fri Dec 16 19:25:04 UTC 2022
PRIMARY
CAS
25013-16-5
Created by admin on Fri Dec 16 19:25:04 UTC 2022 , Edited by admin on Fri Dec 16 19:25:04 UTC 2022
PRIMARY
JECFA MONOGRAPH
INS-320
Created by admin on Fri Dec 16 19:25:04 UTC 2022 , Edited by admin on Fri Dec 16 19:25:04 UTC 2022
PRIMARY
EPA CompTox
DTXSID7020215
Created by admin on Fri Dec 16 19:25:04 UTC 2022 , Edited by admin on Fri Dec 16 19:25:04 UTC 2022
PRIMARY
ECHA (EC/EINECS)
246-563-8
Created by admin on Fri Dec 16 19:25:04 UTC 2022 , Edited by admin on Fri Dec 16 19:25:04 UTC 2022
PRIMARY
MESH
D002083
Created by admin on Fri Dec 16 19:25:04 UTC 2022 , Edited by admin on Fri Dec 16 19:25:04 UTC 2022
PRIMARY
FDA UNII
REK4960K2U
Created by admin on Fri Dec 16 19:25:04 UTC 2022 , Edited by admin on Fri Dec 16 19:25:04 UTC 2022
PRIMARY
WHO INTERNATIONAL PHARMACOPEIA
BUTYLATED HYDROXYANISOLE
Created by admin on Fri Dec 16 19:25:04 UTC 2022 , Edited by admin on Fri Dec 16 19:25:04 UTC 2022
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.
WIKIPEDIA
BUTYLATED HYDROXYANISOLE
Created by admin on Fri Dec 16 19:25:04 UTC 2022 , Edited by admin on Fri Dec 16 19:25:04 UTC 2022
PRIMARY
HSDB
3913
Created by admin on Fri Dec 16 19:25:04 UTC 2022 , Edited by admin on Fri Dec 16 19:25:04 UTC 2022
PRIMARY
ChEMBL
CHEMBL192451
Created by admin on Fri Dec 16 19:25:04 UTC 2022 , Edited by admin on Fri Dec 16 19:25:04 UTC 2022
PRIMARY
All of the following components must be present:
Related Record Type Details
METABOLITE -> PARENT
METABOLITE -> PARENT
Related Record Type Details
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
Related Record Type Details
ACTIVE MOIETY
http://apps.who.int/phint/pdf/b/Jb.6.1.64.pdf
Definition References