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H47003

Sigma-Aldrich

5-Hydroxy-1,4-naphthoquinone

97%

Synonym(s):

Juglone

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About This Item

Empirical Formula (Hill Notation):
C10H6O3
CAS Number:
481-39-0
Molecular Weight:
174.15
Beilstein/REAXYS Number:
1909764
EC Number:
207-567-5
MDL number:
MFCD00001684
UNSPSC Code:
12352100
PubChem Substance ID:
24895654
NACRES:
NA.22

Quality Level

100

assay

97%

mp

161-163 °C (lit.)

SMILES string

Oc1cccc2C(=O)C=CC(=O)c12

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

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Application

5-Hydroxy-1,4-naphthoquinone (juglone) can be used as a starting material for the synthesis of:
  • Trypanocidal drugs.
  • Tacrine-naphthoquinone hybrids with potential application in the treatment of Alzheimer′s disease.
  • Juglone-based electroactive polymer, poly(5-hydroxy-1,4-naphthoquinone-co-5-hydroxy-3-thioacetic acid-1,4-naphthoquinone), for the electrochemical detection of DNA hybridization.
  • Ent-nocardione A, naturally-occurring tyrosine phosphatase inhibitor.

Juglone can also be used as a dienophile in the Diels–Alder reaction for the synthesis of variety of C-aryl glycosides.

pictograms

Skull and crossbones
GHS06

signalword

Danger

hcodes

H301

Hazard Classifications

Acute Tox. 3 Oral

wgk_germany

WGK 3

ppe

Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Multitarget drug design strategy: quinone-tacrine hybrids designed to block amyloid-β aggregation and to exert anticholinesterase and antioxidant effects.
Nepovimova E, et al.
Journal of medicinal chemistry, 57(20), 8576-8589 (2014)
Application of an Enyne Metathesis/Diels-Alder Cycloaddition Sequence: A New Versatile Approach to the Syntheses of C-Aryl Glycosides and Spiro-C-Aryl Glycosides.
Subrahmanyam AV, et al.
Chemistry?A European Journal, 16(28), 8545-8556 (2010)
2-and 3-substituted 1, 4-naphthoquinone derivatives as subversive substrates of trypanothione reductase and lipoamide dehydrogenase from trypanosoma c ruzi: synthesis and correlation between redox cycling activities and in vitro cytotoxicity.
Salmon-Chemin L, et al.
Journal of Medicinal Chemistry, 44(4), 548-565 (2001)
Study of the DNA hybridization transduction behavior of a quinone-containing electroactive polymer by cyclic voltammetry and electrochemical impedance spectroscopy.
Piro B, et al.
Journal of Electroanalytical Chemistry, 577(1), 155-165 (2005)
Formal Radical Cyclization onto Benzene Rings: A General Method and Its Use in the Synthesis of ent-Nocardione A.
Clive DLJ, et al.
The Journal of Organic Chemistry, 69(10), 3282-3293 (2004)
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