42164-69-2

Basic information

• Product Name: 2-[(3-methylbut-2-en-1-yl)oxy]naphthalene-1,4-dione
• CAS NO: 42164-69-2
• Molecular Formula: C₁₅H₁₄O₃
• Molecular Weight: 242.2699
• Mol File: 42164-69-2.mol
• Article Data: 6

Chemical Properties

• Boiling Point: 394.7°C at 760 mmHg
• Flash Point: 175.7°C
• Density: 1.18g/cm³
• Vapor Pressure: 1.95E-06mmHg at 25°C
• Refractive Index: 1.573
• CAS DataBase Reference: 2-[(3-methylbut-2-en-1-yl)oxy]naphthalene-1,4-dione(CAS DataBase Reference)
• NIST Chemistry Reference: 2-[(3-methylbut-2-en-1-yl)oxy]naphthalene-1,4-dione(42164-69-2)
• EPA Substance Registry System: 2-[(3-methylbut-2-en-1-yl)oxy]naphthalene-1,4-dione(42164-69-2)

Safety Data

• Hazardous Substances Data: 42164-69-2(Hazardous Substances Data)

Usage

General Description

2-[(3-methylbut-2-en-1-yl)oxy]naphthalene-1,4-dione is a chemical compound with the molecular formula C17H16O3. It is also known as juglone or 5-hydroxy-1,4-naphthoquinone. Juglone is a natural organic compound found in the roots, leaves, and bark of walnut trees, as well as in other plants in the Juglandaceae family. It is known for its allelopathic properties, meaning that it can inhibit the growth of other plants by releasing toxic chemicals into the soil. Juglone has also been studied for its potential use in medicine, as it has shown antibacterial, antiviral, and antitumor properties in laboratory tests. Additionally, juglone has been used in traditional medicine for its astringent and anti-inflammatory properties. However,

Upstream product

• 36417-25-1 2-hydroxy-1,4-naphthoquinone silver salt 
• 870-63-3 prenyl bromide 
• 83-72-7 2-hydroxynaphtho-1,4-quinone 

Downstream Products

• 521-49-3 dunnione 
• 83-72-7 2-hydroxynaphtho-1,4-quinone 

Relevant articles and documents

Synthesis and biological evaluation of lipophilic 1,4-naphthoquinone derivatives against human cancer cell lines

To examine the effect of hydrophobicity on the anticancer activity of 1,4-naphthoquinone derivatives, a series of compounds bearing a 2-O-alkyl-, 3-C-alkyl- or 2/3-N-morpholinoalkyl group were synthesized and evaluated for their anticancer activity against five human cancer cell lines in vitro. The cytotoxicity of these derivatives was assayed against HT-29, SW480, HepG2, MCF-7 and HL-60 cells by the MTT assay. Among them, 2-hydroxy-3-farnesyl-1,4-naphthoquinone (11a) was found to be the most cytotoxic against these cell lines. Our results showed that the effectiveness of compound 11a may be attributed to its suppression of the survival of HT-29. Secondly, in the Hoechst 33258 staining test, compound 11a-treated cells exhibited nuclear condensation typical of apoptosis. Additionally, cell cycle analysis by flow cytometry indicated that compound 11a arrested HT-29 cells in the S phase. Furthermore, cell death detected by Annexin V-FITC/propidium iodide staining showed that compound 11a efficiently induced apoptosis of HT-29 in a concentration-dependent manner. Taken together, compound 11a effectively inhibits colon cancer cell proliferation and may be a potent anticancer agent.

PHARMACEUTICAL COMPOSITION FOR THE TREATMENT AND PREVENTION OF DISEASES INVOLVING IMPOTENCE

Disclosed is a pharmaceutical composition for the treatment and/or prevention of erectile dysfunction, comprising (a) a therapeutically effective amount of a compound represented by Formula 1 or 2, and (b) a pharmaceutically acceptable carrier, a diluent or an excipient, or any combination thereof.

β-Lapachone: Synthesis of Derivatives and Activities in Tumor Models

In order to find a 3,4-dihydro-2H-naphthopyran-5,6-dione more potent than the naturally occurring 2,2-dimethyl derivative , we synthesized a series of analogous compounds with modifications at position 2 of the pyran ring or at positions 8 and 9 of the benzene ring.Of the compounds tested in vitro for inhibition of RNA-dependent DNA polymerase and in mice infected with Rauscher leukemia, all retained good enzyme activity.Inhibition of the reverse transcriptase activity of the 2,2-substituted derivatives 10b-e was as strong as 10a.However, only the 2-methyl-2-phenyl derivative 10e proved to be about as potent as 2,2-dimethyl reference compound 10a in prolonging the mean survival time of mice with Rauscher leukemia virus induced leukemia.