2,4,6-TRIBROMOPHENOL

Details

Stereochemistry	ACHIRAL
Molecular Formula	C6H3Br3O
Molecular Weight	330.799
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

OC1=C(Br)C=C(Br)C=C1Br

InChI

InChIKey=BSWWXRFVMJHFBN-UHFFFAOYSA-N

InChI=1S/C6H3Br3O/c7-3-1-4(8)6(10)5(9)2-3/h1-2,10H

HIDE SMILES / InChI

Molecular Formula	C6H3Br3O
Molecular Weight	330.799
Charge	0
Count

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

Description
Sources: http://www.deroyal.com/filedisplay.aspx?id=69
Curator's Comment: Description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/27613672

The substance 2,4,6-Tribromophenol (TBP) is used as a flame retardant in electronic and electric devices, and is a replacement for pentachlorophenol in wood preservation. TBP is a contaminant in different environmental matrices, at levels where treatment is required. 2,4,6-Tribromophenol (bismuth tribromophenate) has been used individually and in combination to control microbial growth in burn wounds and on healing meshed skin graft.

Approval Year

Targets

Primary Target	Pharmacology	Potency
α-Glucosidase, Saccharomyces cerevisiae 2 Target ID: α-Glucosidase, Saccharomyces cerevisiae Sources: https://www.ncbi.nlm.nih.gov/pubmed/25962377	Inhibitor 8297	24.0 µM [IC50]
Estrogen receptor 75 Target ID: CHEMBL2093866 Sources: https://www.ncbi.nlm.nih.gov/pubmed/16601080	Antagonist 2778	8.3 µM [IC50]
Transthyretin 6 Target ID: CHEMBL3194 Sources: https://www.ncbi.nlm.nih.gov/pubmed/16601080	Binding Agent 1064	0.0048 µM [IC50]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Burn 40 Sources: http://www.deroyal.com/filedisplay.aspx?id=69	Primary		Approved 8429	Xeroform Petrolatum Wound Dressing Approved Use Minimally draining wounds, Surgical incisions, Lacerations, Donor sites, Burns
Lacerations 3 Sources: http://www.deroyal.com/filedisplay.aspx?id=69	Primary		Approved 8429	Xeroform Petrolatum Wound Dressing Approved Use Surgical incisions • Donor sites • Skin grafts • First and second degree burns • Lacerations • Abrasions

PubMed

Title	Date	PubMed
Seasonal variations of bromophenols in brown algae (Padina arborescens, Sargassum siliquastrum, and Lobophora variegata) collected in Hong Kong.	2003 Apr 23	12696947
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
Tribromophenol induces the differentiation of SH-SY5Y human neuroblastoma cells in vitro.	2003 Oct-Dec	14599456
Determination of simple bromophenols in marine fishes by reverse-phase high performance liquid chromatography (RP-HPLC).	2005 Dec 15	18970325
Enzyme function of the globin dehaloperoxidase from Amphitrite ornata is activated by substrate binding.	2005 Dec 6	16313166
Biodegradation of 2,4,6-tribromophenol during transport in fractured chalk.	2005 Feb 1	15757335
Enhancement of bromophenol levels in aquacultured silver seabream (Sparus sarba).	2005 Mar 23	15769146
Proximal cavity, distal histidine, and substrate hydrogen-bonding mutations modulate the activity of Amphitrite ornata dehaloperoxidase.	2006 Aug 1	16866354
Prediction of estrogen receptor agonists and characterization of associated molecular descriptors by statistical learning methods.	2006 Nov	16497524
The marine secondary metabolites 2,4-dibromophenol and 2,4,6-tribromophenol differentially modulate voltage dependent ion currents in neuroendocrine (PC12) cells.	2006 Oct 12	16911838
The pH dependence of the activity of dehaloperoxidase from Amphitrite ornata.	2007 Jan	17182294
Measurement of polybrominated diphenyl ethers and metabolites in mouse plasma after exposure to a commercial pentabromodiphenyl ether mixture.	2007 Jul	17637922
Synthesis and characterization of 2,3-dibromopropyl-2,4,6-tribromophenyl ether (DPTE) and structurally related compounds evidenced in seal blubber and brain.	2007 Mar 1	17396646
Optimisation of a headspace solid-phase microextraction with on-fiber derivatisation method for the direct determination of haloanisoles and halophenols in wine.	2007 Mar 2	17258751
Optimisation of a microwave-assisted extraction method for the simultaneous determination of haloanisoles and halophenols in cork stoppers.	2007 May 18	17386931
Effects of pH on the water solubility and 1-octanol-water partition coefficient of 2,4,6-tribromophenol.	2008 Feb	18246214
Measuring Ca2+-signalling at fertilization in the sea urchin Psammechinus miliaris: alterations of this Ca2+-signal by copper and 2,4,6-tribromophenol.	2009 Aug	19460461
Biodegradation of brominated aromatics by cultures and laccase of Trametes versicolor.	2009 Aug	19443012
Gas chromatography coupled to electron capture negative ion mass spectrometry with nitrogen as the reagent gas--an alternative method for the determination of polybrominated compounds.	2009 Dec	19904736
Haloanisole and halophenol contamination in Spanish aged red wines.	2009 Jan	19680868
Bromophenol concentrations in fish from Salvador, BA, Brazil.	2009 Jun	19488620
Distribution and formation of chlorophenols and bromophenols in marine and riverine environments.	2009 Oct	19664797
Biodegradation kinetics of selected brominated flame retardants in aerobic and anaerobic soil.	2010 Jun	20227803
Internal binding of halogenated phenols in dehaloperoxidase-hemoglobin inhibits peroxidase function.	2010 Sep 8	20816071
Characterizing the peroxisome proliferator-activated receptor (PPARγ) ligand binding potential of several major flame retardants, their metabolites, and chemical mixtures in house dust.	2015 Feb	25314719

Patents

Sample Use Guides

In Vivo Use Guide

Xeroform Petrolatum Wound Dressing is a sterile, fine mesh gauze impregnated with a blend of 3% 2,4,6-TRIBROMOPHENOL (Bismuth Tribromophenate) and USP Petrolatum 1. Irrigate / Cleanse wound with sterile saline solution or sterile water. Gently dry surrounding skin. 2. Peel open pouch and remove Xeroform Petrolatum Wound Dressing from package. 3. Place dressing directly over wound. 4. Cover with appropriate cover / secondary dressing. 5. Change dressing per physician instructions. Recommended for daily dressing change to maintain a moist, non-adherent environment.

Route of Administration: Topical

In Vitro Use Guide

2,4,6-tribromophenol showed a dose-dependent effect on fertilization rates of P. miliaris and significantly inhibited fertilization at 1 uM.

Substance Class	Chemical Created by `admin` on `Fri Dec 15 17:59:51 GMT 2023` Edited by `admin` on `Fri Dec 15 17:59:51 GMT 2023`
Record UNII	YS6K3EU393
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

2,4,6-TRIBROMOPHENOL

Systematic Name

English

PHENOL, 2,4,6-TRIBROMO-

Systematic Name

English

2,4,6-TRIBROMOPHENOL [HSDB]

Common Name

English

FLAMMEX 3BP

Brand Name

English

TRIBROMOPHENOL, 2,4,6-

Systematic Name

English

NSC-2136

Code

English

BROMOL

Systematic Name

English

BROMKAL PUR 3

Brand Name

English

2,4,6-TRIBROMOPHENOL [MI]

Common Name

English

2,4,6-TRIBROMO-1-HYDROXYBENZENE

Systematic Name

English

Code System Code Type Description

PUBCHEM

1483