TETRABROMOBISPHENOL A

Details

Stereochemistry	ACHIRAL
Molecular Formula	C15H12Br4O2
Molecular Weight	543.871
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CC(C)(C1=CC(Br)=C(O)C(Br)=C1)C2=CC(Br)=C(O)C(Br)=C2

InChI

InChIKey=VEORPZCZECFIRK-UHFFFAOYSA-N

InChI=1S/C15H12Br4O2/c1-15(2,7-3-9(16)13(20)10(17)4-7)8-5-11(18)14(21)12(19)6-8/h3-6,20-21H,1-2H3

HIDE SMILES / InChI

Molecular Formula	C15H12Br4O2
Molecular Weight	543.871
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Approval Year

PubMed

Title	Date	PubMed
Protective effects of puerarin against tetrabromobisphenol a-induced apoptosis and cardiac developmental toxicity in zebrafish embryo-larvae.	2015-09	24596333
Structurally-diverse, PPARγ-activating environmental toxicants induce adipogenesis and suppress osteogenesis in bone marrow mesenchymal stromal cells.	2015-05-04	25777084
Advanced morphological - behavioral test platform reveals neurodevelopmental defects in embryonic zebrafish exposed to comprehensive suite of halogenated and organophosphate flame retardants.	2015-05	25711236
Environmental contaminants activate human and polar bear (Ursus maritimus) pregnane X receptors (PXR, NR1I2) differently.	2015-04-01	25680588
Structural bisphenol analogues differentially target steroidogenesis in murine MA-10 Leydig cells as well as the glucocorticoid receptor.	2015-03-02	25576683
Evaluation of the toxic effects of brominated compounds (BDE-47, 99, 209, TBBPA) and bisphenol A (BPA) using a zebrafish liver cell line, ZFL.	2015-02	25544063
Comparing the effects of tetrabromobisphenol-A, bisphenol A, and their potential replacement alternatives, TBBPA-bis(2,3-dibromopropyl ether) and bisphenol S, on cell viability and messenger ribonucleic acid expression in chicken embryonic hepatocytes.	2015-02	25470364
Characterizing the peroxisome proliferator-activated receptor (PPARγ) ligand binding potential of several major flame retardants, their metabolites, and chemical mixtures in house dust.	2015-02	25314719
Modulation of estradiol synthesis and aromatase activity in human choriocarcinoma JEG-3 cells exposed to tetrabromobisphenol A.	2015-02	25223798
Tetrabromobisphenol A activates inflammatory pathways in human first trimester extravillous trophoblasts in vitro.	2014-12	25461914
Toxicogenomic analysis of the ability of brominated flame retardants TBBPA and BDE-209 to disrupt thyroid hormone signaling in neural cells.	2014-11-05	25172293
Halogenated bisphenol-A analogs act as obesogens in zebrafish larvae (Danio rerio).	2014-05	24591153
PBDE: structure-activity studies for the inhibition of hepatitis C virus NS3 helicase.	2014-04-02	24699145
Ioxynil and tetrabromobisphenol A suppress thyroid-hormone-induced activation of transcriptional elongation mediated by histone modifications and RNA polymerase II phosphorylation.	2014-04	24449421
Endocrine disruptors differentially target ATP-binding cassette transporters in the blood-testis barrier and affect Leydig cell testosterone secretion in vitro.	2013-12	24014645
Brominated flame retardants stimulate mouse immune cells in vitro.	2013-12	22972382
In vitro study on the agonistic and antagonistic activities of bisphenol-S and other bisphenol-A congeners and derivatives via nuclear receptors.	2013-10-01	23714657
Mimicking of estradiol binding by flame retardants and their metabolites: a crystallographic analysis.	2013-10	23959441
Comparative antioxidant status in freshwater fish Carassius auratus exposed to six current-use brominated flame retardants: a combined experimental and theoretical study.	2013-09-15	23880106
Toxicity assessment and vitellogenin expression in zebrafish (Danio rerio) embryos and larvae acutely exposed to bisphenol A, endosulfan, heptachlor, methoxychlor and tetrabromobisphenol A.	2013-07	22351617
Evaluation of aggregating brain cell cultures for the detection of acute organ-specific toxicity.	2013-06	22954530
Similarities in the endocrine-disrupting potencies of indoor dust and flame retardants by using human osteosarcoma (U2OS) cell-based reporter gene assays.	2013-03-19	23398518
Effect of tetrabrombisphenol A on induction of apoptosis in the testes and changes in expression of selected testicular genes in CD1 mice.	2013-01	22677475
Modulation of human α4β2 nicotinic acetylcholine receptors by brominated and halogen-free flame retardants as a measure for in vitro neurotoxicity.	2012-09-03	22750351
Multiple novel modes of action involved in the in vitro neurotoxic effects of tetrabromobisphenol-A.	2012-07	22547355
Metabolism of polybrominated diphenyl ethers and tetrabromobisphenol A by fish liver subcellular fractions in vitro.	2012-06-15	22417763
Tetrabromobisphenol-A disrupts thyroid hormone receptor alpha function in vitro: use of fluorescence polarization to assay corepressor and coactivator peptide binding.	2012-05	22277881
Disruption of the hypothalamic-pituitary-thyroid axis in zebrafish embryo-larvae following waterborne exposure to BDE-47, TBBPA and BPA.	2012-02	22100034
Parallel biotransformation of tetrabromobisphenol A in Xenopus laevis and mammals: Xenopus as a model for endocrine perturbation studies.	2012-02	22086976
An improved thyroid hormone reporter assay to determine the thyroid hormone-like activity of amiodarone, bithionol, closantel and rafoxanide.	2012-01-05	22015988
Some commonly used brominated flame retardants cause Ca2+-ATPase inhibition, beta-amyloid peptide release and apoptosis in SH-SY5Y neuronal cells.	2012	22485137
Peroxisome proliferator-activated receptor γ is a target for halogenated analogs of bisphenol A.	2011-09	21561829
Characterization of novel ligands of ERα, Erβ, and PPARγ: the case of halogenated bisphenol A and their conjugated metabolites.	2011-08	21622942
Molecular Mechanism of Tetrabromobisphenol A (TBBPA)-induced Target Organ Toxicity in Sprague-Dawley Male Rats.	2011-06	24278553
Embryonic exposure to tetrabromobisphenol A and its metabolites, bisphenol A and tetrabromobisphenol A dimethyl ether disrupts normal zebrafish (Danio rerio) development and matrix metalloproteinase expression.	2010-11-01	20728951
Some flame retardants and the antimicrobials triclosan and triclocarban enhance the androgenic activity in vitro.	2010-11	20943248
Disruption of thyroid hormone-dependent hypothalamic set-points by environmental contaminants.	2010-07-29	20399831
Effects of tetrabromobisphenol A, a brominated flame retardant, on the immune response to respiratory syncytial virus infection in mice.	2010-04	20074668
Nuclear hormone receptor activity of polybrominated diphenyl ethers and their hydroxylated and methoxylated metabolites in transactivation assays using Chinese hamster ovary cells.	2009-08	19672399
Anti-thyroid hormone activity of bisphenol A, tetrabromobisphenol A and tetrachlorobisphenol A in an improved reporter gene assay.	2009-08	19457453
Assessing the toxicity of TBBPA and HBCD by zebrafish embryo toxicity assay and biomarker analysis.	2009-08	18767142
Risk assessment of tetrabromobisphenol A on cyclooxygenase-2 expression via MAP kinase/NF-kappaB/AP-1 signaling pathways in murine macrophages.	2009	20077215
Molecular targets of TBBPA in zebrafish analysed through integration of genomic and proteomic approaches.	2008-12	18976794
Gender-specific proteomic responses in zebrafish liver following exposure to a selected mixture of brominated flame retardants.	2008-10	18258299
Tetrabromobisphenol A (TBBPA), induces cell death in TM4 Sertoli cells by modulating Ca2+ transport proteins and causing dysregulation of Ca2+ homeostasis.	2008-06	18329244
Effects of fifteen PBDE metabolites, DE71, DE79 and TBBPA on steroidogenesis in the H295R cell line.	2008-05	18313098
Screening of 397 chemicals and development of a quantitative structure--activity relationship model for androgen receptor antagonism.	2008-04	18324785
The widely utilized brominated flame retardant tetrabromobisphenol A (TBBPA) is a potent inhibitor of the SERCA Ca2+ pump.	2007-12-15	17784851
A new bioluminescent cellular assay to measure the transcriptional effects of chemicals that modulate the alpha-1 thyroid hormone receptor.	2007-09	17532181
Disruption of thyroid hormone binding to sea bream recombinant transthyretin by ioxinyl and polybrominated diphenyl ethers.	2007-08	17553549

Patents

Substance Class	Chemical Created by `admin` on `Mon Mar 31 19:18:54 GMT 2025` Edited by `admin` on `Mon Mar 31 19:18:54 GMT 2025`
Record UNII	FQI02RFC3A
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

TETRABROMOBISPHENOL A

Systematic Name

English

CP-2000

Preferred Name

English

TETRABROMOBISPHENOL A, 3,3',5,5'-

Common Name

English

TBBPA

Common Name

English

NSC-59775

Code

English

4,4'-(1-METHYLETHYLIDENE)BIS(2,6-DIBROMOPHENOL)

Systematic Name

English

2,2',6,6'-TETRABROMOBISPHENOL A [HSDB]

Common Name

English

2,2-BIS(3,5-DIBROMO-4-HYDROXYPHENYL)PROPANE

Systematic Name

English

TETRABROMOBISPHENOL A [IARC]

Common Name

English

TETRABROMOBISPHENOL A [MI]

Common Name

English

4,4'-ISOPROPYLIDENEBIS(2,6-DIBROMOPHENOL)

Systematic Name

English

3,3',5,5'-TETRABROMOBISPHENOL A

Common Name

English

Code System Code Type Description

PUBCHEM

6618