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

Details

Stereochemistry ACHIRAL
Molecular Formula C11H16O2
Molecular Weight 180.2435
Optical Activity UNSPECIFIED
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of 3-TERT-BUTYL-4-HYDROXYANISOLE

SMILES

COC1=CC=C(O)C(=C1)C(C)(C)C

InChI

InChIKey=MRBKEAMVRSLQPH-UHFFFAOYSA-N
InChI=1S/C11H16O2/c1-11(2,3)9-7-8(13-4)5-6-10(9)12/h5-7,12H,1-4H3

HIDE SMILES / InChI

Molecular Formula C11H16O2
Molecular Weight 180.2435
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description

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
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

In Vivo Use Guide
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
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 Chemical
Created
by admin
on Tue Oct 22 08:28:20 UTC 2019
Edited
by admin
on Tue Oct 22 08:28:20 UTC 2019
Record UNII
62RAC24292
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
3-TERT-BUTYL-4-HYDROXYANISOLE
USP-RS  
Systematic Name English
3-TERT-BUTYL-4-HYDROXYANISOLE [USP-RS]
Common Name English
PHENOL, 2-(1,1-DIMETHYLETHYL)-4-METHOXY-
Systematic Name English
PHENOL, 2-TERT-BUTYL-4-METHOXY-
Systematic Name English
3-(1,1-DIMETHYLETHYL)-4-HYDROXYANISOLE
Systematic Name English
3-T-BUTYL-4-HYDROXYANISOLE [HSDB]
Common Name English
3-BHA
Common Name English
2-TERT-BUTYL-4-METHOXYPHENOL
Systematic Name English
Code System Code Type Description
MESH
C051362
Created by admin on Tue Oct 22 08:28:21 UTC 2019 , Edited by admin on Tue Oct 22 08:28:21 UTC 2019
PRIMARY
ECHA (EC/EINECS)
204-442-7
Created by admin on Tue Oct 22 08:28:21 UTC 2019 , Edited by admin on Tue Oct 22 08:28:21 UTC 2019
PRIMARY
CAS
121-00-6
Created by admin on Tue Oct 22 08:28:21 UTC 2019 , Edited by admin on Tue Oct 22 08:28:21 UTC 2019
PRIMARY
EPA CompTox
121-00-6
Created by admin on Tue Oct 22 08:28:21 UTC 2019 , Edited by admin on Tue Oct 22 08:28:21 UTC 2019
PRIMARY
PUBCHEM
8456
Created by admin on Tue Oct 22 08:28:21 UTC 2019 , Edited by admin on Tue Oct 22 08:28:21 UTC 2019
PRIMARY
HSDB
121-00-6
Created by admin on Tue Oct 22 08:28:21 UTC 2019 , Edited by admin on Tue Oct 22 08:28:21 UTC 2019
PRIMARY
Related Record Type Details
PARENT -> IMPURITY