15127-94-3

Basic information

• Product Name: 1,4-Naphthalenedione, 5-hydroxy-2-methoxy-
• CAS NO: 15127-94-3
• Molecular Formula: C11H8O4
• Mol File: 15127-94-3.mol
• Article Data: 4

Chemical Properties

• CAS DataBase Reference: 1,4-Naphthalenedione, 5-hydroxy-2-methoxy-(CAS DataBase Reference)
• NIST Chemistry Reference: 1,4-Naphthalenedione, 5-hydroxy-2-methoxy-(15127-94-3)
• EPA Substance Registry System: 1,4-Naphthalenedione, 5-hydroxy-2-methoxy-(15127-94-3)

Safety Data

• Hazardous Substances Data: 15127-94-3(Hazardous Substances Data)

Usage

Appearance

Yellow, crystalline solid

Natural occurrence

Found in black walnut trees and other plants of the Juglandaceae family

Uses

a. Organic synthesis
b. Dye and pigment in textile and paper industries
c. Traditional medicine for wound healing
d. Ingredient in natural hair dyes

Biological activities

a. Antibacterial
b. Antiviral
c. Cytotoxic

Potential applications

a. Treatment of cancer
b. Allelopathic agent (inhibiting growth of competing plant species)

Toxicity

Toxic to many plants, inhibiting their growth through allelopathy (released from roots and leaves of black walnut trees)

Upstream product

• 67-56-1 methanol 
• 4923-57-3 2-chlorojuglone 
• 69008-03-3 2-bromo-5-hydroxy-[1,4]naphthoquinone 
• 83-72-7 2-hydroxynaphtho-1,4-quinone 
• 2348-82-5 2-methoxy-1,4-naphthoquinone 
• 124-41-4 sodium methylate 
• 52431-65-9 3-Bromojuglone 
• 18855-92-0 3-chlorojuglone 
• 481-39-0 5-hydroxynaphtho-1,4-quinone 

Downstream Products

• 4923-55-1 2-Hydroxyjuglon 
• 4923-58-4 3,5-dihydroxy-2,3-dihydro-1,4-naphthoquinone 

Relevant articles and documents

1,4-Naphthoquinones. XV: Reaction of 2- and 3-chloro- or bromojuglone derivatives with OH in methanol. (Part I: Monomeric compounds)

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Ru(II)-Catalyzed Site-Selective Hydroxylation of Flavone and Chromone Derivatives: The Importance of the 5-Hydroxyl Motif for the Inhibition of Aurora Kinases

An efficient protocol for Ru(II)-catalyzed direct C-H oxygenation of a broad range of flavone and chromone substrates was developed. This convenient and powerful synthetic tool allows for the rapid installation of the hydroxyl group into the flavone, chromone, and other related scaffolds and opens the way for analog synthesis of highly potent Aurora kinase inhibitors. The molecular docking simulations indicate that the formation of bidentate H-bonding patterns in the hinge regions between the 5-hydroxyflavonoids and Ala213 was the significant binding force, which is consistent with experimental and computational findings.