H47003

5-Hydroxy-1,4-naphthoquinone

97%

• Synonym(s): Juglone
• 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

Properties

• 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

Description

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.

Safety Information

• Pictograms: GHS06
• Signal Word: Danger
• Hazard Statements: H301
• Precautionary Statements: P264 - P270 - P301 + P310 - P405 - P501
• 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