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) 
• 860776-15-4 1-hydroxy-4,5-naphthylene phenylboronate 
• 186581-53-3 diazomethane 

Downstream Products

• 159497-29-7 N-(2-methoxy-4-methlphenyl)-3-amino-5-methoxy-1,4-napthoquinone 
• 129237-15-6 1-(N-Benzoyl-N-benzylamino)-5-methoxy-1,4,4a,9a-tetrahydro-9,10-anthraquinone 
• 3300-25-2 8-O-methylchrysophanol 
• 76695-93-7 1-hydroxy-5-methoxy-3-methyl-9,10 dihydroanthracene 9,10-dione 
• 22266-99-5 2-methyl-5-methoxy-1,4-naphthoquinone 
• 22273-29-6 8-methoxy-2-methylnaphthalene-1,4-dione 
• 90013-25-5 5-methoxy-2,3-dimethyl-1,4-naphtoquinone 
• 109696-97-1 5-methoxy-3-(p-tolylthio)-1,4-naphthoquinone 
• 95684-16-5 2-chloro-3-anilino-5-methoxy-1,4-naphthoquinone 
• 95684-15-4 2-anilino-3-chloro-5-methoxy-1,4-naphthoquinone 
• 82-39-3 1-methoxyanthracene-9,10-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.

2-Propargylamino-naphthoquinone derivatives as multipotent agents for the treatment of Alzheimer's disease

Alzheimer's disease is a progressive brain disorder with characteristic symptoms and several pathological hallmarks. The concept of “one drug, one target” has not generated any new drugs since 2004. The new era of drug development in the field of AD build

Synthesis and biological evaluation of novel isothiazoloquinoline quinone analogues

Natural quinones and their analogues have attracted growing attention because of their novel anticancer activities. A series of novel isothiazoloquinoline quinone analogues were synthesized and evaluated for antitumor activities against four different kind of cancer cells. Among them, isothiazoloquinolinoquinones inhibited cancer cells proliferation effectively with IC50 values in the nanomolar range, and isothiazoloquinolinoquinone 13a induced the cell apoptosis. Further exploration of possible mechanism of action indicates that 13a not only activates ROS production through NQO1-directed redox cycling but also inhibits the phosphorylation of STAT3. These findings indicate that 13a has potential use for the development of new skeleton drug candidate as an efficient substrate of NQO1 and STAT3 inhibitor.