Juglone

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
Names
Preferred IUPAC name
5-Hydroxynaphthalene-1,4-dione
Other names
  • 5-Hydroxy-1,4-naphthoquinone
  • 5-Hydroxy-p-naphthoquinone
  • Regianin
  • 5-Hydroxynaphthoquinone
  • Nucin
  • NCI 2323
  • Oil Red BS
  • C.I. Natural Brown 7
Identifiers
3D model (JSmol)
1909764
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.006.880
EC Number
  • 207-567-5
PubChem CID
RTECS number
  • QJ5775000
UNII
  • InChI=1S/C10H6O3/c11-7-4-5-9(13)10-6(7)2-1-3-8(10)12/h1-5,12H N
    Key: KQPYUDDGWXQXHS-UHFFFAOYSA-N N
  • InChI=1/C10H6O3/c11-7-4-5-9(13)10-6(7)2-1-3-8(10)12/h1-5,12H
    Key: KQPYUDDGWXQXHS-UHFFFAOYAH
SMILES
  • O=C\2c1c(c(O)ccc1)C(=O)/C=C/2
Properties
C10H6O3
Molar mass 174.155 g·mol−1
Appearance Yellow solid
Melting point 162 to 163 °C (324 to 325 °F; 435 to 436 K)
Slightly sol.
Related compounds
Related compounds
 quinone
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N verify (what is YN ?)
Infobox references

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.

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