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Key Documents

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:
Molecular Weight:
174.15
Beilstein:
1909764
EC Number:
MDL number:
UNSPSC Code:
12352100
PubChem Substance ID:
NACRES:
NA.22

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

Signal Word

Danger

Hazard Statements

Hazard Classifications

Acute Tox. 3 Oral

Storage Class Code

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

WGK

WGK 3

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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)
G Devagi et al.
Scientific reports, 8(1), 7688-7688 (2018-05-18)
New ruthenium(II) complexes were synthesised and characterized by various spectro analytical techniques. The structure of the complexes 3 and 4 has been confirmed by X-ray crystallography. The complexes were subjected to study their anti-oxidant profile and were exhibited significantly greater
Fu-Lan Hsu et al.
Journal of agricultural and food chemistry, 60(12), 3092-3097 (2012-03-03)
Cinnamomum osmophloeum Kaneh is an indigenous tree species in Taiwan. In this study, phytochemical characteristics and antioxidant activities of the essential oils and key constituents from the leaves of two C. osmophloeum clones were investigated. The two trees possess two
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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