A naphthoquinone with diverse biological activities
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(±)-Dunnione

Item No. 21943

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
2,3-dihydro-2,3,3-trimethyl-naphtho[1,2-b]furan-4,5-dione
CAS Number
521-49-3
Synonyms
  • NSC 95403
Molecular Formula
C15H14O3
Formula Weight
242.3
Purity
≥98%
Formulation (Request formulation change)
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 30 mg/mlDMSO: 30 mg/mlEthanol: 30 mg/ml
λmax
212, 261, 445 nm
SMILES
O=C(C1=CC=CC=C1C2=C3C(C)(C)C(C)O2)C3=O
InChi Code
InChI=1S/C15H14O3/c1-8-15(2,3)11-13(17)12(16)9-6-4-5-7-10(9)14(11)18-8/h4-8H,1-3H3
InChi Key
WGENOABUKBFVAA-UHFFFAOYSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    1 mg

    $69

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    5 mg

    $297

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    10 mg

    $525

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    25 mg

    $1,146

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    Product Description

    (±)-Dunnione is a naturally occurring naphthoquinone with diverse biological activities.1,2,3,4 (±)-Dunnione also reduces the growth of T. cruzi epimastigotes (IC50 = 4.01 μM).2 It is a substrate for NAD(P)H:quinone oxidoreductase 1 (NQO1) that increases production of reactive oxygen species (ROS) and induces cell death of A549 lung carcinoma cells (IC50 = 6.1 μM).3 (±)-Dunnione (20 mg/kg per day for 4 days) increases intracellular NAD+ (Item No. 16077) and prevents inflammatory cytokine production and small intestinal damage induced by cisplatin (Item No. 13119) in mice.4

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Khambay, B.P.S., Batty, D., Jewess, P.J., et al. Mode of action and pesticidal activity of the natural product dunnione and of some analogues. Pest. Manag. Sci. 59(2), 174-182 (2003).

    2. Salas, C.O., Faúndez, M., Morello, A., et al. Natural and synthetic naphthoquinones active against Trypanosoma cruzi: An initial step towards new drugs for Chagas disease. Curr. Med. Chem. 18(1), 144-161 (2011).

    3. Bian, J., Xu, L., Deng, B., et al. Synthesis and evaluation of (±)-dunnione and its ortho-quinone analogues as substrates for NAD(P)H:quinone oxidoreductase 1 (NQO1). Bioorg. Med. Chem. Lett. 25(6), 1244-1248 (2015).

    4. Pandit, A., Kim, H.-J., Oh, G.-S., et al. Dunnione ameliorates cisplatin-induced small intestinal damage by modulating NAD(+) metabolism. Biochem. Bioph. Res. Commun. 467(4), 697-703 (2015).