Skip to Content
Merck
All Photos(1)

Key Documents

View All Documentation

Safety Information

H47003

Sigma-Aldrich

5-Hydroxy-1,4-naphthoquinone

97%

Synonym(s):

Juglone

Sign Into View Organizational & Contract Pricing
All Photos(1)

About This Item

Empirical Formula (Hill Notation):
C10H6O3
CAS Number:
481-39-0
Molecular Weight:
174.15
Beilstein:
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

Looking for similar products? Visit Product Comparison Guide

Related Categories

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

Signal Word

Danger

Hazard Statements

H301

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

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

JAN Code

H47003-5G:
H47003-VAR:
H47003-BULK:
H47003-1G:
H47003-100G:

Choose from one of the most recent versions:

Certificates of Analysis (COA)

Lot/Batch Number
STBL1178
STBK2768
STBJ6726
STBH9858
STBH2148

Don't see the Right Version?

If you require a particular version, you can look up a specific certificate by the Lot or Batch number.

Search for a COA

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

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)
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)
View All Related Papers

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service