juglone
Sign in to saveAlso known as 5-hydroxy-1,4-naphthalenedione, 8-hydroxy-1,4-naphthoquinone, C.I. Natural Brown 7, C.I. 75500, Natural Brown 7
Juglone, also called 5-hydroxy-1,4-naphthalenedione (IUPAC) is a phenolic organic compound with the molecular formula C10H6O3. In the food industry, juglone is also known as C.I. Natural Brown 7 and C.I. 75500. It is insoluble in benzene but soluble in dioxane, from which it crystallizes as yellow needles. It is an isomer of lawsone, which is the active dye compound in the henna leaf.
Research
830 papers- Juglone in Oxidative Stress and Cell Signaling.Antioxidants (Basel, Switzerland) · 2019
- Juglone: A Versatile Natural Platform for Obtaining New Bioactive Compounds.Current topics in medicinal chemistry · 2021
- Juglone suppresses vasculogenic mimicry in glioma through inhibition of HuR-mediated VEGF-A expression.Biochemical pharmacology · 2024
- Juglone promotes spinal cord injury recovery by suppressing pyroptosis and necroptosis through FOS/USP53/ubiquitination.Phytomedicine : international journal of phytotherapy and phytopharmacology · 2025
- Juglone alleviates pelvic pain and prostatic inflammation via inhibiting the activation of NLRP3 inflammasome and alleviating oxidative stress in EAP mice.Phytomedicine : international journal of phytotherapy and phytopharmacology · 2025
via PubMed
Wikidata facts
- Mass
- 174.032
- Has use
- pigment
Show 8 more facts
- found in taxon
- Carya ovata
- chemical formula
- C₁₀H₆O₃
- subject has role
- enzyme inhibitor
- canonical SMILES
- C1=CC2=C(C(=O)C=CC2=O)C(=C1)O
- natural product of taxon
- Juglandaceae
- Commons category
- Juglone
- melting point
- 162
- described by source
- Brockhaus and Efron Encyclopedic Dictionary
via Wikidata · CC0
~6 min read
Encyclopedic overview
10 sectionsContents
- History
- Chemistry
- Synthesis
- Extraction
- Degradation
- Spectral data
- Biological effects
- Uses
- See also
- References
Juglone, also called 5-hydroxy-1,4-naphthalenedione (IUPAC) is a phenolic organic compound with the molecular formula C10H6O3. In the food industry, juglone is also known as C.I. Natural Brown 7 and C.I. 75500. It is insoluble in benzene but soluble in dioxane, from which it crystallizes as yellow needles. It is an isomer of lawsone, which is the active dye compound in the henna leaf.
Juglone occurs naturally in the leaves, roots, husks, fruit (the epicarp), and bark of plants in the Juglandaceae family, particularly the black walnut (Juglans nigra), and is toxic or growth-stunting to many types of plants. It is sometimes used as an herbicide, as a dye for cloth and inks, and as a coloring agent for foods and cosmetics.
Excerpted from Wikipedia’s “juglone” article, available under the CC BY-SA 4.0 licence.