Juglone

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Structural formula
Structure of juglone
General
Surname Juglone
other names
  • 5-hydroxy-1,4-naphthoquinone ( IUPAC )
  • 5-hydroxy-1,4-dihydronaphthalene-1,4-dione
  • CI Natural Brown 7
  • CI 75500
Molecular formula C 10 H 6 O 3
Brief description

yellow-brown, odorless, crystalline powder

External identifiers / databases
CAS number 481-39-0
EC number 207-567-5
ECHA InfoCard 100.006.880
PubChem 3806
ChemSpider 3674
Wikidata Q900912
properties
Molar mass 174.16 g mol −1
Physical state

firmly

Melting point

155 ° C

solubility

heavy in water

safety instructions
GHS labeling of hazardous substances
06 - Toxic or very toxic 09 - Dangerous for the environment

danger

H and P phrases H: 301-315-319-335-400
P: 261-273-301 + 310-305 + 351 + 338
As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Juglone is the simplest naturally occurring dye . It is derived from 1,4-naphthoquinone and belongs to the group of carbonyl dyes .

Extraction and presentation

The reaction of 1,5-dihydroxynaphthalene with peracetic acid in excess yields a mixture of juglone and 2-hydroxy-1,4-naphthoquinone .

Occurrence and characteristics

The green pods of the unripe fruits of the walnut tree ( Juglans regia L.) contain juglone.
Juglone from the peel, crystallized from xylene

Juglone can be isolated from walnut shells and also produced synthetically. Precursors of juglone are found in the leaves and can get into the soil when they decay, which hinders the formation of roots in other plants. In this way, competitors for water and nutrients grow sparsely under walnut trees. Juglone has antibacterial and fungitoxic action and acts bleeding breastfeeding ( antihämorrhagisch ). Animal studies have shown that juglone is also mutagenic .

Juglone is isomeric to 2-hydroxy-1,4-naphthoquinone (Lawson), the dye found in henna leaves .

See also

literature

  • Paul Karrer: Textbook of Organic Chemistry . 10th edition. Thieme Verlag, Stuttgart 1948.
  • Dietrich Frohne, Uwe Jensen: Systematics of the Plant Kingdom , 5th edition, Wissenschaftliche Verlagsgesellschaft mbH, Stuttgart 1998.

Individual evidence

  1. ↑ Juglon data sheet (PDF) from Carl Roth , accessed on December 14, 2010.
  2. ^ The Merck Index . An Encyclopaedia of Chemicals, Drugs and Biologicals , 14th Edition, 2006, p. 911, ISBN 978-0-911910-00-1 .
  3. ↑ a b c Entry on 5-hydroxy-1,4-naphthoquinone in the GESTIS substance database of the IFA , accessed on February 7, 2017(JavaScript required) .
  4. ^ Heinrich Zollinger: Color Chemistry: Syntheses, Properties, and Applications of Organic Dyes and Pigments . 3. Edition. WILEY-VCH Verlag, Weinheim 2003, ISBN 3-906390-23-3 , p. 347 ( limited preview in Google Book search).
  5. ^ Christoph Grundmann : A New Synthesis of Juglone . In: Synthesis . tape 1977 , no. 9 , September 1977, p. 644-645 , doi : 10.1055 / s-1977-24517 ( PDF ).
  6. ^ Albert Gossauer: Structure and reactivity of biomolecules , Verlag Helvetica Chimica Acta, Zurich, 2006, p. 277, ISBN 978-3-906390-29-1 .
  7. ↑ Botany-online: Influence of individual species on others; Competition, coexistence ( Memento from February 13, 2013 in the Internet Archive )