A toxic metabolite of benzene
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1,4-Benzoquinone

Item No. 27560

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
2,5-cyclohexadiene-1,4-dione
CAS Number
106-51-4
Synonyms
  • p-Benzoquinone
  • NSC 36324
  • p-Quinone
Molecular Formula
C6H4O2
Formula Weight
108.1
Purity
≥98%
Formulation (Request formulation change)
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 30 mg/mlDMSO: 30 mg/mlEthanol: 10 mg/mlPBS (pH 7.2): 1 mg/ml
λmax
243 nm
SMILES
O=C(C=C1)C=CC1=O
InChi Code
InChI=1S/C6H4O2/c7-5-1-2-6(8)4-3-5/h1-4H
InChi Key
AZQWKYJCGOJGHM-UHFFFAOYSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Wet ice in continental US; may vary elsewhere
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    100 g

    $40

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    Product Description

    1,4-Benzoquinone is a toxic metabolite of benzene.1 It is formed via hepatic metabolism of benzene to 1,4-hydroquinone followed by myeloperoxidase processing of 1,4-hydroquinone in bone marrow.2 1,4-Benzoquinone decreases levels of cytochrome P450 in a concentration-dependent manner in minipig liver microsomes.1 It induces DNA mutations in human W138-VA13 and mouse HL18 cells.3 1,4-Benzoquinone (10 and 20 μM) disrupts mitochondrial membrane potential and reduces viability, increases production of reactive oxygen species (ROS), and induces apoptosis in a concentration-dependent manner in HL-60 cells.4

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Kondrová, E., Stopka, P., and Soucek, P. Cytochrome P450 destruction by benzene metabolites 1,4-benzoquinone and 1,4-hydroquinone and the formation of hydroxyl radicals in minipig liver microsomes. Toxicol. In Vitro 21(4), 566-575 (2007).

    2. Lindsey, R.H., Jr. , Bromberg, K.D., Felix, C.A., et al. 1,4-Benzoquinone is a topoisomerase II poison. Biochemistry 43(23), 7563-7574 (2004).

    3. Nakayama, A., Koyoshi, S., Morisawa, S., et al. Comparison of the mutations induced by p-benzoquinone, a benzene metabolite, in human and mouse cells. Mutat. Res. 470(2), 147-153 (2000).

    4. Sun, S., Zhang, C., Gao, J., et al. Benzoquinone induces ROS-dependent mitochondria-mediated apoptosis in HL-60 cells. Toxicol. Ind. Health 34(4), 270-281 (2018).