4923-61-9

Basic information

• Product Name: 8-Methoxy-1,4-naphthoquinone
• Synonyms: 5-Methoxy-1,4-naphthoquinone;8-Methoxy-1,4-naphthoquinone
• CAS NO: 4923-61-9
• Molecular Formula: C₁₁H₈O₃
• Molecular Weight: 188.18
• Mol File: 4923-61-9.mol
• Article Data: 45

Chemical Properties

• Melting Point: 189 °C
• Boiling Point: 374.7°C at 760 mmHg
• Flash Point: 170.5°C
• Appearance: /
• Density: 1.284g/cm³
• Vapor Pressure: 8.17E-06mmHg at 25°C
• Refractive Index: 1.591
• CAS DataBase Reference: 8-Methoxy-1,4-naphthoquinone(CAS DataBase Reference)
• NIST Chemistry Reference: 8-Methoxy-1,4-naphthoquinone(4923-61-9)
• EPA Substance Registry System: 8-Methoxy-1,4-naphthoquinone(4923-61-9)

Safety Data

• Hazardous Substances Data: 4923-61-9(Hazardous Substances Data)

Usage

Synthesis Reference(s)

The Journal of Organic Chemistry, 46, p. 1814, 1981 DOI: 10.1021/jo00322a013Tetrahedron Letters, 31, p. 4871, 1990 DOI: 10.1016/S0040-4039(00)97755-4

InChI:InChI=1/C11H8O3/c1-14-10-4-2-3-7-8(12)5-6-9(13)11(7)10/h2-6H,1H3

Upstream product

• 3588-80-5 5-methoxynaphthalen-1-ol 
• 481-39-0 5-hydroxynaphtho-1,4-quinone 
• 74-88-4 methyl iodide 
• 74555-12-7 1,4-dihydro-4,4-(ethylenedioxy)-5-methoxy-1-oxonaphthalene 
• 3588-75-8 8-methoxy-naphthalen-1-ol 
• 10075-63-5 1,5-dimethoxynaphthalene 
• 64636-39-1 1,4,5-Trimethoxynaphthalene 
• 3843-55-8 4,8-dimethoxy-1-naphthol 
• 69833-14-3 4-Hydroxy-8-methoxynaphthalene-1-carbaldehyde 
• 24000-38-2 1,4-dimethoxy-1,3-butadiene 
• 106-51-4 p-benzoquinone 
• 93087-44-6 1-Methoxy-1,4-ethano-1,4-dihydro-naphthalindion-(5,8) 
• 77-78-1 dimethyl sulfate 
• 412041-47-5 2,3-diethynyl-1-methoxybenzene 

Downstream Products

• 109696-97-1 5-methoxy-3-(p-tolylthio)-1,4-naphthoquinone 
• 481-39-0 5-hydroxynaphtho-1,4-quinone 
• 188031-61-0 8-hydroxy-2-phenyl-1,4-naphthoquinone 
• 82-39-3 1-methoxyanthracene-9,10-dione 
• 1620126-91-1 2-methyl (2-(1,4-dihydro-5-methoxy-1,4-dioxonaphthalen-3-ylthio)acetamido)-3-phenylpropanoate 
• 1607448-12-3 C₂₈H₂₁NO₃ 
• 101600-87-7 8-methoxy-2-(phenylamino)-1,4-naphthoquinone 
• 1399290-45-9 (R)-tert-butyl-3-(5-methoxy-1,4-dioxo-1,4-dihydronaphthalen-2-yl)-2-oxo-3-phenylindoline-1-carboxylate 
• 1402705-62-7 (R)-tert-butyl-3-(8-methoxy-1,4-dioxo-1,4-dihydronaphthalen-2-yl)-2-oxo-3-phenylindoline-1-carboxylate 
• 1201635-11-1 2-bromobenzoic acid 4-hydroxy-5-methoxynaphthalen-1-yl ester 
• 1192354-83-8 8-methoxy-2-phenylnaphthalene-1,4-dione 

Relevant articles and documents

Cytotoxic activity of naphthoquinones with special emphasis on juglone and its 5-O-methyl derivative

The cytotoxicity of nine naphthoquinones (NQ) was assayed against HL-60 (leukaemia), MDA-MB-435 (melanoma), SF-295 (brain) and HCT-8 (colon), all human cancer cell lines, and peripheral blood mononuclear cells (PBMC), as representatives of normal cells, after 72h of incubation. 5-Methoxy-1,4-naphthoquinone was the most active compound, showing IC50 values in the range of 0.31 (1.7μM) in HL-60 to 0.88μg/mL (4.7μM) in SF-295 and IC50 of 0.69μg/mL (3.7μM) against PBMC. With the introduction of a bromo-substituent in position 2 or 3 of juglone, the IC50 significantly decreased, regardless of the position on the NQ moiety. However, compared with juglone methyl ether, the halogen substitution decreased the activity. To further understand the mechanism underlying the cytotoxicity of 5-methoxy-1,4-naphthoquinone, studies involving DNA fragmentation, cell cycle analysis, phosphatidyl serine externalization, mitochondrial depolarization and activation of caspases 8 and 3/7 were performed in HL-60 cell line, using doxorubicin as a positive control. The results indicate that the cytotoxic 5-methoxy-1,4-naphthoquinone activates caspases 8 and 3/7 and thus induces apoptosis independent of mitochondria.

Carbocyclic frenolicin analogues: Novel anticoccidial agents

Carbocyclic analogues of the antibacterial natural product frenolicin B have been synthesised. These analogues were active against parasitic protozoa of the genus Eimeria and represent a new series of anticoccidial agents. The synthesis of simplified analogues helped to define a possible pharmacophore for frenolicin.

Synthesis, biological evaluation, and correlation of cytotoxicity versus redox potential of 1,4-naphthoquinone derivatives

A series of 1,4-naphthoquinone derivatives of lawsone (1), 6-hydroxy-1,4-naphthoquinone (2), and juglone (3) were synthesized by alkylation, acylation, and sulfonylation reactions. The yields of lawsone derivatives 1a-1k (type A), 6-hydroxy-1,4-naphthoqui

Anti-novel coronavirus naphthoquinone compound and medical application thereof

The invention discloses an anti-novel coronavirus naphthoquinone compound and a medical application of the naphthoquinone compound. The structure of the compound is shown as a formula (I), wherein R1is hydrogen, methyl, ethyl, acetyl or propionyl; and R2 is hydrogen, methyl or ethyl. The compound disclosed by the invention has very strong activity of resisting the novel coronavirus, and can be used for inhibiting 3CL hydrolase (3C-like proteinase, 3CLpro) of the 2019-nCoV novel coronavirus. The in-vitro activity determination experiments show that the enzyme inhibition rate of part of the compounds reaches 99% under the concentration of 1 [mu] M. The naphthoquinone compound disclosed by the invention is clear in structure, simple and convenient in preparation method and high in yield, andhas important significance for developing efficient and low-toxicity novel anti-novel coronavirus drugs.