H47003
5-Hydroxy-1,4-naphthoquinone
97%
Synonym(s):
Juglone
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About This Item
Empirical Formula (Hill Notation):
C10H6O3
CAS Number:
Molecular Weight:
174.15
UNSPSC Code:
12352100
NACRES:
NA.22
PubChem Substance ID:
EC Number:
207-567-5
Beilstein/REAXYS Number:
1909764
MDL number:
Assay:
97%
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
Application
5-Hydroxy-1,4-naphthoquinone (juglone) can be used as a starting material for the synthesis of:
Juglone can also be used as a dienophile in the Diels–Alder reaction for the synthesis of variety of C-aryl glycosides.
- 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.
signalword
Danger
hcodes
Hazard Classifications
Acute Tox. 3 Oral
Storage Class
6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects
wgk
WGK 3
ppe
Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges
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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)
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)