Chloranil

• Description:

  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 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.

• Shipping Conditions:

  Room Temperature

• Storage Conditions:

  -20°C, 3 years; 4°C, 2 years (Powder)

• Scientific Category:

  Reference compound1

• Clinical Information:

  No Development Reported

• Isoform:

  TLR4

• CAS Number:

  [118-75-2]