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

Approval Year

PubMed

Title	Date	PubMed
Anaerobic-aerobic process for microbial degradation of tetrabromobisphenol A.	2000 Jun	10831413
Effects of the environmental oestrogens bisphenol A, tetrachlorobisphenol A, tetrabromobisphenol A, 4-hydroxybiphenyl and 4,4'-dihydroxybiphenyl on oestrogen receptor binding, cell proliferation and regulation of oestrogen sensitive proteins in the human breast cancer cell line MCF-7.	2003 Apr	12753421
The flame retardants tetrabromobisphenol A and tetrabromobisphenol A-bisallylether suppress the induction of interleukin-2 receptor alpha chain (CD25) in murine splenocytes.	2003 Feb 14	12505372
Brominated dioxin-like compounds: in vitro assessment in comparison to classical dioxin-like compounds and other polyaromatic compounds.	2003 Sep	12850102
Inhibitory effects of environmental chemicals on protein disulfide isomerase in vitro.	2005 Dec	16617682
Anti-thyroid hormonal activity of tetrabromobisphenol A, a flame retardant, and related compounds: Affinity to the mammalian thyroid hormone receptor, and effect on tadpole metamorphosis.	2005 Feb 18	15680168
Biosensor recognition of thyroid-disrupting chemicals using transport proteins.	2006 Feb 15	16478101
In vitro profiling of the endocrine-disrupting potency of brominated flame retardants.	2006 Jul	16601080
Exposure to tetrabromobisphenol-A alters TH-associated gene expression and tadpole metamorphosis in the Pacific tree frog Pseudacris regilla.	2006 Jun 30	16678281
Prediction of estrogen receptor agonists and characterization of associated molecular descriptors by statistical learning methods.	2006 Nov	16497524
Cytotoxicity of TBBPA and effects on proliferation, cell cycle and MAPK pathways in mammalian cells.	2007 Apr	17254629
Disruption of thyroid hormone binding to sea bream recombinant transthyretin by ioxinyl and polybrominated diphenyl ethers.	2007 Aug	17553549
The widely utilized brominated flame retardant tetrabromobisphenol A (TBBPA) is a potent inhibitor of the SERCA Ca2+ pump.	2007 Dec 15	17784851
Screening of 397 chemicals and development of a quantitative structure--activity relationship model for androgen receptor antagonism.	2008 Apr	18324785
Gender-specific proteomic responses in zebrafish liver following exposure to a selected mixture of brominated flame retardants.	2008 Oct	18258299
Risk assessment of tetrabromobisphenol A on cyclooxygenase-2 expression via MAP kinase/NF-kappaB/AP-1 signaling pathways in murine macrophages.	2009	20077215
Disruption of the hypothalamic-pituitary-thyroid axis in zebrafish embryo-larvae following waterborne exposure to BDE-47, TBBPA and BPA.	2012 Feb	22100034
Parallel biotransformation of tetrabromobisphenol A in Xenopus laevis and mammals: Xenopus as a model for endocrine perturbation studies.	2012 Feb	22086976
Tetrabromobisphenol-A disrupts thyroid hormone receptor alpha function in vitro: use of fluorescence polarization to assay corepressor and coactivator peptide binding.	2012 May	22277881
Toxicity assessment and vitellogenin expression in zebrafish (Danio rerio) embryos and larvae acutely exposed to bisphenol A, endosulfan, heptachlor, methoxychlor and tetrabromobisphenol A.	2013 Jul	22351617
Similarities in the endocrine-disrupting potencies of indoor dust and flame retardants by using human osteosarcoma (U2OS) cell-based reporter gene assays.	2013 Mar 19	23398518
Mimicking of estradiol binding by flame retardants and their metabolites: a crystallographic analysis.	2013 Oct	23959441
In vitro study on the agonistic and antagonistic activities of bisphenol-S and other bisphenol-A congeners and derivatives via nuclear receptors.	2013 Oct 1	23714657
Ioxynil and tetrabromobisphenol A suppress thyroid-hormone-induced activation of transcriptional elongation mediated by histone modifications and RNA polymerase II phosphorylation.	2014 Apr	24449421
PBDE: structure-activity studies for the inhibition of hepatitis C virus NS3 helicase.	2014 Apr 2	24699145
Environmental contaminants activate human and polar bear (Ursus maritimus) pregnane X receptors (PXR, NR1I2) differently.	2015 Apr 1	25680588

Patents

Name

Type

Language

TETRABROMOBISPHENOL A

Systematic 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

CP-2000

Code

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