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Details

Stereochemistry ACHIRAL
Molecular Formula C11H16O2
Molecular Weight 180.2435
Optical Activity NONE
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 No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

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
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
Prediction of estrogen receptor agonists and characterization of associated molecular descriptors by statistical learning methods.
2006 Nov
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
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 Chemical
Created
by admin
on Fri Dec 15 15:52:40 UTC 2023
Edited
by admin
on Fri Dec 15 15:52:40 UTC 2023
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 Fri Dec 15 15:52:40 UTC 2023 , Edited by admin on Fri Dec 15 15:52:40 UTC 2023
PRIMARY
ECHA (EC/EINECS)
204-442-7
Created by admin on Fri Dec 15 15:52:40 UTC 2023 , Edited by admin on Fri Dec 15 15:52:40 UTC 2023
PRIMARY
CAS
121-00-6
Created by admin on Fri Dec 15 15:52:40 UTC 2023 , Edited by admin on Fri Dec 15 15:52:40 UTC 2023
PRIMARY
RS_ITEM_NUM
1083100
Created by admin on Fri Dec 15 15:52:40 UTC 2023 , Edited by admin on Fri Dec 15 15:52:40 UTC 2023
PRIMARY
EPA CompTox
DTXSID7040788
Created by admin on Fri Dec 15 15:52:40 UTC 2023 , Edited by admin on Fri Dec 15 15:52:40 UTC 2023
PRIMARY
FDA UNII
62RAC24292
Created by admin on Fri Dec 15 15:52:40 UTC 2023 , Edited by admin on Fri Dec 15 15:52:40 UTC 2023
PRIMARY
CHEBI
76358
Created by admin on Fri Dec 15 15:52:40 UTC 2023 , Edited by admin on Fri Dec 15 15:52:40 UTC 2023
PRIMARY
PUBCHEM
8456
Created by admin on Fri Dec 15 15:52:40 UTC 2023 , Edited by admin on Fri Dec 15 15:52:40 UTC 2023
PRIMARY
HSDB
2750
Created by admin on Fri Dec 15 15:52:40 UTC 2023 , Edited by admin on Fri Dec 15 15:52:40 UTC 2023
PRIMARY
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