SODIUM 2,4,6-TRIBROMOPHENOLATE

Details

Stereochemistry	ACHIRAL
Molecular Formula	C6H2Br3O.Na
Molecular Weight	352.781
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure of SODIUM 2,4,6-TRIBROMOPHENOLATE

Structure Search

SMILES

[Na+].[O-]C1=C(Br)C=C(Br)C=C1Br

InChI

InChIKey=SECJJZLOAVXJDP-UHFFFAOYSA-M

InChI=1S/C6H3Br3O.Na/c7-3-1-4(8)6(10)5(9)2-3;/h1-2,10H;/q;+1/p-1

HIDE SMILES / InChI

Molecular Formula	Na
Molecular Weight	22.9898
Charge	1
Count

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

Molecular Formula	C6H2Br3O
Molecular Weight	329.791
Charge	-1
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
Brominated flame retardants in plasma samples from three different occupational groups in Norway.	2001 Aug	11523435
Sorption of organic contaminants in a fractured chalk formation.	2001 Aug	11513399
Determination of phenolic flame-retardants in human plasma using solid-phase extraction and gas chromatography-electron-capture mass spectrometry.	2001 Jan 5	11204209
Identification of hydroxylated PCB metabolites and other phenolic halogenated pollutants in human blood plasma.	2002 Jan	11706375
Brominated phenols: characterization of estrogen-like activity in the human breast cancer cell-line MCF-7.	2002 Mar 24	11879974
Toxic epidermal necrolysis due to administration of celecoxib (Celebrex).	2002 Oct	12425513
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
Preliminary study on the occurrence of brominated organic compounds in Dutch marine organisms.	2003 Jul	12919829
Seasonal distribution of bromophenols in selected Hong Kong seafood.	2003 Nov 5	14582971
Identification and responsibility of 2,4,6-tribromoanisole in musty, corked odors in wine.	2004 Mar 10	14995130
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
Halogenated natural products in five species of Antarctic sponges: compounds with POP-like properties?	2005 Jun 1	15984761
Enhancement of bromophenol levels in aquacultured silver seabream (Sparus sarba).	2005 Mar 23	15769146
Two-dimensional distribution of microbial activity and flow patterns within naturally fractured chalk.	2005 Oct	16099071
Reductive dehalogenation of tetrabromobisphenol-A by sediment from a contaminated ephemeral streambed and an enrichment culture.	2006 Aug	16497360
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
Effects of brominated flame retardants and brominated dioxins on steroidogenesis in H295R human adrenocortical carcinoma cell line.	2007 Apr	17447562
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
Determination of halophenolic wood preservant traces in milk using headspace solid-phase microextraction and gas chromatography-mass spectrometry.	2008 Dec 26	19027907
Effects of pH on the water solubility and 1-octanol-water partition coefficient of 2,4,6-tribromophenol.	2008 Feb	18246214
Haloanisole and halophenol contamination in Spanish aged red wines.	2009 Jan	19680868
Multifunctional in situ photopolymerized semi-interpenetrating network system is an effective donor site dressing: a cross comparison study in a swine model.	2009 Jan-Feb	19131760
Uptake and biotransformation of structurally diverse brominated flame retardants in zebrafish (Danio rerio) after dietary exposure.	2009 May	19049262
Distribution and formation of chlorophenols and bromophenols in marine and riverine environments.	2009 Oct	19664797
Neutral and phenolic brominated organic compounds of natural and anthropogenic origin in northeast Atlantic Greenland shark (Somniosus microcephalus).	2010 Dec	20891018
Biodegradation kinetics of selected brominated flame retardants in aerobic and anaerobic soil.	2010 Jun	20227803
Oral exposure of adult zebrafish (Danio rerio) to 2,4,6-tribromophenol affects reproduction.	2010 Oct 1	20719397
Internal binding of halogenated phenols in dehaloperoxidase-hemoglobin inhibits peroxidase function.	2010 Sep 8	20816071
PBDE: structure-activity studies for the inhibition of hepatitis C virus NS3 helicase.	2014 Apr 2	24699145
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 18:30:33 GMT 2023` Edited by `admin` on `Fri Dec 15 18:30:33 GMT 2023`
Record UNII	N37IT16D3V
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

SODIUM 2,4,6-TRIBROMOPHENOLATE

Systematic Name

English

VELCIDE

Brand Name

English

PHENOL, 2,4,6-TRIBROMO-, SODIUM SALT

Common Name

English

2,4,6-TRIBROMOPHENOL SODIUM SALT [MI]

Common Name

English

2,4,6-TRIBROMOPHENOL SODIUM SALT

Common Name

English

Code System Code Type Description

CAS

2666-53-7