A natural naphthoquinone
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Plumbagin

Item No. 14314

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
5-hydroxy-2-methyl-1,4-naphthalenedione
CAS Number
481-42-5
Synonyms
  • NSC 236613
  • NSC 688284
Molecular Formula
C11H8O3
Formula Weight
188.2
Purity
≥98%
Formulation (Request formulation change)
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMSO: 10 mg/mlEthanol: 5 mg/mlMethanol: 5 mg/ml
λmax
210, 264 nm
SMILES
CC1=CC(C(C(O)=CC=C2)=C2C1=O)=O
InChi Code
InChI=1S/C11H8O3/c1-6-5-9(13)10-7(11(6)14)3-2-4-8(10)12/h2-5,12H,1H3
InChi Key
VCMMXZQDRFWYSE-UHFFFAOYSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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Certificates of Analysis & Batch Specific Data

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    100 mg

    $40

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    250 mg

    $60

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    500 mg

    $105

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    Cayman Chemical
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    Product Description

    Plumbagin is a natural 1,4-naphthoquinone first isolated from plants of the genus Plumbago. It has diverse effects in cells and animals. Plumbagin causes the generation of reactive oxygen species and induces apoptosis in cancer cells.1,2 It activates signaling through Nrf2 and the antioxidant response element, inducing the expression of Nrf2 target genes, including NQO1 and heme oxygenase-1 in cultured neuronal cells.1 Plumbagin also inhibits NADPH oxidase 4 in a time- and dose-dependent manner.3 It can be protective against peroxide stress or deprivation of glucose or oxygen.1

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Klotz, L.O., Hou, X., and Jacob, C. 1,4-Naphthoquinones: From oxidative damage to cellular and inter-cellular signaling. Molecules 19(9), 14902-14918 (2014).

    2. Gupta, S.C., Kim, J.H., Prasad, S., et al. Regulation of survival, proliferation, invasion, angiogenesis, and metastasis of tumor cells through modulation of inflammatory pathways by nutraceuticals. Cancer Metastasis Rev. 29(3), 405-434 (2010).

    3. Schramm, A., Matusik, P., Osmenda, G., et al. Targeting NADPH oxidases in vascular pharmacology. Vascul. Pharmacol. 56(5-6), 216-231 (2012).