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137723

Sigma-Aldrich

2,4,6-Triiodophenol

97%

Synonym(s):

Bobel 24

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About This Item

Linear Formula:
I3C6H2OH
CAS Number:
609-23-4
Molecular Weight:
471.80
EC Number:
210-186-7
MDL number:
MFCD00002179
UNSPSC Code:
12352100
PubChem Substance ID:
24848345
NACRES:
NA.22

Assay

97%

form

powder

mp

157-159 °C (lit.)

SMILES string

Oc1c(I)cc(I)cc1I

InChI

1S/C6H3I3O/c7-3-1-4(8)6(10)5(9)2-3/h1-2,10H

InChI key

VAPDZNUFNKUROY-UHFFFAOYSA-N

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General description

2,4,6-Triiodophenol is iodinated disinfection byproduct formed during chlorination of sewage effluents. It is a potent thyroid hormone disrupting chemical.

Application

2,4,6-Triiodophenol was used in an in vitro assay to investigate deiodinase activity in human hepatic microsomes.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Classifications

Acute Tox. 4 Dermal - Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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Tingting Gong et al.
Chemosphere, 163, 359-365 (2016-08-25)
Iodide is widely present in drinking water sources as well as wastewater effluents. Chlorination and chloramination are the most commonly used disinfection methods. During chlorination or chloramination of drinking water/wastewater effluents, iodide may be oxidized to hypoiodous acid, which may
Sarah M Heissler et al.
FEBS letters, 586(19), 3208-3214 (2012-08-14)
Myosin-6 is an actin-based motor protein that moves its cargo towards the minus-end of actin filaments. Mutations in the gene encoding the myosin-6 heavy chain and changes in the cellular abundance of the protein have been linked to hypertrophic cardiomyopathy
Craig M Butt et al.
Toxicological sciences : an official journal of the Society of Toxicology, 124(2), 339-347 (2011-05-14)
Halogenated contaminants, particularly brominated flame retardants, disrupt circulating levels of thyroid hormones (THs), potentially affecting growth and development. Disruption may be mediated by impacts on deiodinase (DI) activity, which regulate the levels of active hormones available to bind to nuclear
Matilde Parreño et al.
Molecular cancer therapeutics, 5(5), 1166-1175 (2006-05-30)
2,4,6-Triiodophenol (Bobel-24, AM-24) was originally described as a nonsteroid antiinflammatory molecule. We have synthesized three derivatives of Bobel-24 (Bobel-4, Bobel-16, and Bobel-30) and tested their activities as putative antileukemic agents. We have found that Bobel-24 and Bobel-16 were dual inhibitors
Iñaki F Trocóniz et al.
Pharmaceutical research, 23(7), 1533-1542 (2006-06-20)
The aim of this study was to explore the possibility of achieving a practical dosing regimen for 2,4,6-triiodophenol (AM-24), a new leukotriene B4 (LTB4) synthesis inhibitor. First, a model capable of dealing with the nonlinearity in its pharmacokinetic profile was
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