40815-72-3

Basic information

• Product Name: 2-(prop-2-en-1-yloxy)naphthalene-1,4-dione
• CAS NO: 40815-72-3
• Molecular Formula: C₁₃H₁₀O₃
• Molecular Weight: 214.2167
• Mol File: 40815-72-3.mol
• Article Data: 9

Chemical Properties

• Boiling Point: 369.4°C at 760 mmHg
• Flash Point: 165.7°C
• Density: 1.22g/cm³
• Vapor Pressure: 1.19E-05mmHg at 25°C
• Refractive Index: 1.584
• CAS DataBase Reference: 2-(prop-2-en-1-yloxy)naphthalene-1,4-dione(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(prop-2-en-1-yloxy)naphthalene-1,4-dione(40815-72-3)
• EPA Substance Registry System: 2-(prop-2-en-1-yloxy)naphthalene-1,4-dione(40815-72-3)

Safety Data

• Hazardous Substances Data: 40815-72-3(Hazardous Substances Data)

Usage

General Description

2-(prop-2-en-1-yloxy)naphthalene-1,4-dione, also known as naphthoquinone, is a chemical compound with a naphthalene backbone and two functional groups - a prop-2-en-1-yloxy and a dione group. It is commonly used in the production of dyes and pigments, as well as in the synthesis of pharmaceuticals and organic compounds. Naphthoquinone is also known for its antimicrobial, antifungal, and anticancer properties, and is used in some traditional medicine practices for its potential health benefits. However, it can be toxic in high concentrations and should be handled with caution. Overall, naphthoquinone is a versatile chemical with a range of industrial and potentially medicinal applications.

Upstream product

• 556-56-9 allyl iodid 
• 36417-25-1 2-hydroxy-1,4-naphthoquinone silver salt 
• 83-72-7 2-hydroxynaphtho-1,4-quinone 
• 107-18-6 allyl alcohol 
• 106-95-6 allyl bromide 
• 1010-60-2 2-chloro-1,4-naphthoquinone 
• 130-15-4 [1,4]naphthoquinone 
• 2065-37-4 2-bromo-1,4-naphthoquinone 
• 1785-67-7 1,2,4-triacetyloxynaphthalene 

Downstream Products

• 40815-76-7 3-allyl-2-hydroxy-1,4-naphthoquinone 
• 17112-93-5 2-methylnaphtho<1,2-b>furan-4,5-dione 

Relevant articles and documents

Synthesis and evaluation of (±)-dunnione and its ortho-quinone analogues as substrates for NAD(P)H:quinone oxidoreductase 1 (NQO1)

Natural product (±)-dunnione (2) and its ortho-quinone analogues (3-8) were synthesized and found to be substrates for NQO1. The structure-activity relationship study revealed that the biological activity was favored by the presence of methyl group at the C ring and methoxy group at the A ring. The docking studies supported the rationalization of the metabolic studies. Deeper location in the active site of NQO1, interactions with hydrophobic pocket and C-H...π interactions with the adjacent Phe178 residue contributed to the better catalytic efficiency and specificity to NQO1. Cytotoxicity studies and determination of superoxide (O2-) production in the presence and absence of the NOQ1 inhibitor dicoumarol confirmed that the ortho-quinones exerted their antitumor activity through NQO1-mediated ROS production by redox cycling.

Microwave-induced Selective Alkoxylation of 1,4-Naphthoquinones

A new efficient alkoxylation of 1,4-naphthoquinones at the active quinonoid position is reported using alkanols and an alkenol in the presence of cerium chloride and iodine under microwave irradiation.

Discovery of quinone-directed antitumor agents selectively bioactivated by NQO1 over CPR with improved safety profile

In this work, we mainly focused on discovering compounds with good selectivity for NQO1 over CPR. The NQO1-mediated two-electron reduction of compounds would kill cancer cells selectively, while CPR-mediated one-electron reduction would induce potential hepatotoxicity. Several novel quinone-directed antitumor agents were discovered as specific NQO1 substrates through structure-activity relationship studies. Among them, compound 3,7,8-trimethylnaphtho[1,2-b]furan-4,5-dione (12b) emerged as the most specific substrate of the two-electron oxidoreductase NQO1 and could hardly be reduced by CPR. It afforded the highest selectivity between NQO1/CPR (selectivity ratio = 6.37), much higher than the control β-lapachone (selectivity ratio = 1.36), indicated 12b may possess superior safety profile. The electrochemical studies provided a reasonable explanation to the good selectivity toward NQO1. Molecular docking studies supported that 12b was capable of forming additional C-H … π interactions with Trp105 and Phe178 residues compared to the control β-lap. In addition, compound 12b was shown to kill cancer cells efficiently both in vitro and in vivo model. This work gave us a promising and novel scaffold for further investigation.