Chloranil

Chloranil (Tetrachloro-p-benzoquinone), an orally active metabolite of pentachlorophenol and hexachlorobenzene, is a widely used fungicide. Chloranil can induce ROS production. Chloranil induces neutrophil extracellular traps through the ROS-JNK-NOX2 pathway. Chloranil induces ferroptosis and neuroinflammation. Chloranil induces apoptosis of mouse embryonic stem cells[1][2][3][4][5] .

Product Specifications

CAS Number

[118-75-2]

Product Name Alternative

Tetrachloro-p-benzoquinone; TCBQ

UNSPSC

12352211

Hazard Statement

H315, H317, H318, H410

Target

Apoptosis; Ferroptosis; Fungal; JNK; MyD88; Reactive Oxygen Species (ROS) ; Toll-like Receptor (TLR)

Type

Reference compound

Related Pathways

Anti-infection; Apoptosis; Immunology/Inflammation; MAPK/ERK Pathway; Metabolic Enzyme/Protease; NF-κB

Applications

COVID-19-immunoregulation

Field of Research

Infection; Metabolic Disease; Inflammation/Immunology; Neurological Disease

Assay Protocol

https://www.medchemexpress.com/chloranil.html

Purity

99.51

Solubility

DMSO : 5 mg/mL (ultrasonic; warming; heat to 60°C)

Smiles

O=C1C(Cl)=C(Cl)C(C(Cl)=C1Cl)=O

Molecular Formula

C6Cl4O2

Molecular Weight

245.88

Precautions

H315, H317, H318, H410

References & Citations

[1]Fu J, et al.The acute exposure of tetrachloro-p-benzoquinone (a.k.a. chloranil) triggers inflammation and neurological dysfunction via Toll-like receptor 4 signaling: The protective role of melatonin preconditioning. Toxicology. 2017 Apr 15;381:39-50. |[2]Liu Z, et al. Tetrachlorobenzoquinone exposure triggers ferroptosis contributing to its neurotoxicity. Chemosphere. 2021 Feb;264 (Pt 1) :128413. |[3]Zuehlke A, et al. Elevated 5-hydroxymethycytosine and cell apoptosis induced by tetrachloro-1,4-benzoquinone in mouse embryonic stem cells. J Environ Sci (China) . 2017 Jan;51:1-4.|[4]Lv X, et al. Tetrachlorobenzoquinone exhibits immunotoxicity by inducing neutrophil extracellular traps through a mechanism involving ROS-JNK-NOX2 positive feedback loop. Environ Pollut. 2021 Jan 1;268 (Pt B) :115921. |[5]Xu D, et al. Tetrachlorobenzoquinone induces acute liver injury, up-regulates HO-1 and NQO1 expression in mice model: the protective role of chlorogenic acid. Environ Toxicol Pharmacol. 2014 May;37 (3) :1212-20.