A redox-active hydroxyquinone
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Tetrahydroxyquinone

Item No. 32908

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
2,3,5,6-tetrahydroxy-2,5-cyclohexadiene-1,4-dione
CAS Number
319-89-1
Synonyms
  • NSC 112931
  • THQ
Molecular Formula
C6H4O6
Formula Weight
172.1
Purity
≥98%
Formulation (Request formulation change)
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: Slightly solubleDMSO: Slightly solublePBS (pH 7.2): 1 mg/ml
λmax
312 nm
SMILES
O=C1C(O)=C(C(C(O)=C1O)=O)O
InChi Code
InChI=1S/C6H4O6/c7-1-2(8)4(10)6(12)5(11)3(1)9/h7-8,11-12H
InChi Key
DGQOCLATAPFASR-UHFFFAOYSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    5 g

    $103

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    10 g

    $194

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    Cayman Chemical
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    Product Description

    Tetrahydroxyquinone is a redox-active hydroxyquinone.1,2 It inhibits HIV-1 proteinase (IC50 = 575 µM) and is active against T. brucei brucei (MIC100 = 100 µg/ml).1,3 Tetrahydroxyquinone (100 µM) induces the formation of reactive oxygen species (ROS) in, as well as apoptosis of, HL-60 leukemia cells.2 It has also been used in the manufacturing of lithium-ion batteries.4

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Brinkworth, R.I., and Fairlie, D.P. Hydroxyquinones are competitive non-peptide inhibitors of HIV-1 proteinase. Biochim. Biophys. Acta 1253(1), 5-8 (1995).

    2. Cavagis, A.D.M., Ferreira, C.V., Versteeg, H.H., et al. Tetrahydroxyquinone induces apoptosis of leukemia cells through diminished survival signaling. Exp. Hematol. 34(2), 188-196 (2006).

    3. Shapiro, A., Nathan, H.C., Hutner, S.H., et al. In vivo and in vitro activity by diverse chelators against Trypanosoma brucei brucei. J. Protozool. 29(1), 85-90 (1982).

    4. Chen, H., Armand, M., Courty, M., et al. Lithium salt of tetrahydroxybenzoquinone: Toward the development of a sustainable Li-ion battery. J. Am. Chem. Soc. 131(25), 8984-8988 (2009).