Difference between revisions of "Juglone"

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===Storage===
 
===Storage===
Juglone should be kept in closed bottles, away from air.
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Juglone should be kept in closed bottles, away from air and other contaminants.
  
 
===Disposal===
 
===Disposal===

Latest revision as of 09:56, 10 August 2019

Juglone
Names
IUPAC name
5-hydroxy-1,4-naphthalenedione
Other names
5-Hydroxy-1,4-naphthoquinone
5-Hydroxy-p-naphthoquinone
5-Hydroxynaphthoquinone
C.I. 75500
C.I. Natural Brown 7
NCI 2323
Nucin
Oil Red BS
Regianin
Properties
C10H6O3
Molar mass 174.155 g/mol
Appearance Yellow solid
Density 1.42 g/cm3 (at 25 °C)[1]
Melting point 162–163 °C (324–325 °F; 435–436 K)
Boiling point 381–385 °C (718–725 °F; 654–658 K) (decomposes)
0.0052 g/100 ml[2]
Solubility Soluble in acetone, benzene, chloroform, diethyl ether, dioxane, DMSO, ethanol
Vapor pressure 0.9 mmHg at 25 °C
Hazards
Safety data sheet Sigma-Aldrich
Flash point 201.3 °C (394.34 °F; 474 K)
Lethal dose or concentration (LD, LC):
112 mg/kg (rat, oral)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Juglone (IUPAC: 5-hydroxy-1,4-naphthalenedione) is an organic compound with the molecular formula C10H6O3.

Properties

Chemical

Reduction of juglone yields hydroxyjuglone, which is the compound found in the walnut plant. Juglone appears when hydroxyjuglone oxidizes in air.

Aqueous solutions of juglone with alkali turn purpleish.[3]

Physical

Juglone is a yellowish solid, insoluble in water but more soluble in organic solvents.

Availability

Juglone occurs naturally in the leaves, roots, husks, fruit, and bark of plants (but not in the edible kernel) in the Juglandaceae family, like the common walnut, though it occurs in higher concentration in the black walnut (Juglans nigra). The average amount of juglone found in walnuts is between 2-4% by fresh weight.[4][5] Juglone is extracted from unripe walnut hulls with diethyl ether. The extract is left in air to dry and oxidize. Juglone is purified via sublimation.[6]

Pure juglone can be purchased from lab suppliers.

Preparation

Juglone can be synthesized by oxidation of the nontoxic hydrojuglone, 1,5-dihydroxynaphthalene.

Projects

  • Make dye and ink
  • Biodegradable herbicide

Handling

Safety

Juglone is harmful if ingested. It is highly toxic to many insect herbivores. Juglone will also stain the skin.

The compound is investigated in medicine due to its antitumoral and antimicrobial properties.

Storage

Juglone should be kept in closed bottles, away from air and other contaminants.

Disposal

Should be neutralized with an oxidizing mixture like Fenton's reagent.

References

  1. Borovikov; Sivachek; Makovetskii; Novikov; Borovikov; Russian Journal of General Chemistry; vol. 67; nb. 6; (1997); p. 936 - 941
  2. https://link.springer.com/article/10.1007/BF00982309
  3. Merck, 1997
  4. https://archive.org/stream/bulletindelasoc181frangoog#page/n810/mode/2up
  5. https://www.notulaebotanicae.ro/index.php/nbha/article/view/4624
  6. https://www.sciencedirect.com/science/article/pii/B978938030854850006X

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