An allelopathic naphthoquinone
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Juglone

Item No. 16216

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
5-hydroxy-1,4-naphthalenedione
CAS Number
481-39-0
Synonyms
  • 5-Hydroxy-1,4-naphthoquinone
  • NSC 34266
  • NSC 153189
  • NSC 622948
Molecular Formula
C10H6O3
Formula Weight
174.2
Purity
≥95%
Formulation
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMSO: 10 mg/mlEthanol: 10 mg/ml
λmax
209, 249, 424 nm
SMILES
O=C1C=CC(C2=CC=CC(O)=C21)=O
InChi Code
InChI=1S/C10H6O3/c11-7-4-5-9(13)10-6(7)2-1-3-8(10)12/h1-5,12H
InChi Key
KQPYUDDGWXQXHS-UHFFFAOYSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    500 mg

    $38

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    1 g

    $61

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    Product Description

    Juglone is a natural naphthoquinone found in the black walnut (J. nigra) and other plants in the Juglandaceae family. It has allelopathic actions, suppressing growth, photosynthesis, and respiration in plants and other organisms, although some bacteria can metabolize juglone.1,2 Juglone also irreversibly inhibits peptidyl-prolyl cis/trans isomerases of the parvulin family, including human Pin1, yeast Ess1/Ptf1, and E. coli parvulin (Ki = 55.9 nM).3 Juglone also blocks transcription by RNA polymerases I, II, and III (IC50s = 2-7 µM) and attenuates kidney fibrosis in rats treated with unilateral ureteral obstruction, both through Pin1-independent mechanisms.4,5

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Hejl, A.A., Einhellig, F.A., and Rasmussen, J.A. Effects of juglone on growth, photosynthesis, and respiration. J. Chem. Ecol. 19(3), 559-568 (1993).

    2. Williamson, G.B., and Weidenhamer, J.D. Bacterial degradation of juglone: Evidence against allelopathy? J. Chem. Ecol. 16(5), 1739-1742 (1990).

    3. Hennig, L., Christner, C., Kipping, M., et al. Selective inactivation of parvulin-like peptidyl-prolyl cis/trans isomerases by juglone. Biochemistry 37(17), 5953-5960 (1998).

    4. Chao, S.H., Greenlead, A.L., and Price, D.H. Juglone, an inhibitor of the peptidyl-prolyl isomerase Pin1, also directly blocks transcription. Nucleic Acids Res. 29(3), 767-773 (2001).

    5. Reese, S., Vidyasagar, A., Jacobson, L., et al. The Pin 1 inhibitor juglone attenuates kidney fibrogenesis via Pin 1-independent mechanisms in the unilateral ureteral occlusion model. Fibrogenesis Tissue Repair 3, 1 (2010).