2348-82-5

Basic information

• Product Name: 2-METHOXY-1,4-NAPHTHOQUINONE
• Synonyms: 1,4-Naphthoquinone, 2-methoxy-;2-methoxy-1,4-naphthalenedione;2-methoxy-4-naphthalenedione;2-methoxy-4-naphthoquinone;2-Methoxynaphthoquinone;2-Methoxy-p-naphthoquinone;2-METHOXY-1,4-NAPHTHOQUINONE;2-METHOXY-1,4-NAPTHOQUINONE, 98+% SEE S 45484-2
• CAS NO: 2348-82-5
• Molecular Formula: C₁₁H₈O₃
• Molecular Weight: 188.18
• Product Categories: C11 to C12;Carbonyl Compounds;Ketones;Building Blocks;C11 to C12;Carbonyl Compounds;Chemical Synthesis;Organic Building Blocks;Inhibitors
• Mol File: 2348-82-5.mol
• Article Data: 5

Chemical Properties

• Melting Point: 184-187 °C(lit.)
• Boiling Point: 283.17°C (rough estimate)
• Flash Point: 152.7°C
• Appearance: /
• Density: 1.2100 (rough estimate)
• Vapor Pressure: 8.98E-05mmHg at 25°C
• Refractive Index: 1.6400 (estimate)
• Water Solubility: 31.23mg/L(temperature not stated)
• CAS DataBase Reference: 2-METHOXY-1,4-NAPHTHOQUINONE(CAS DataBase Reference)
• NIST Chemistry Reference: 2-METHOXY-1,4-NAPHTHOQUINONE(2348-82-5)
• EPA Substance Registry System: 2-METHOXY-1,4-NAPHTHOQUINONE(2348-82-5)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• RTECS: QL8960000
• Hazardous Substances Data: 2348-82-5(Hazardous Substances Data)

Usage

Description

2-Methoxy-1,4-naphthoquinone is a chemical compound belonging to the naphthoquinone family, characterized by its naphthalene-1,4-dione structure with a methoxy group at position 2. It has been isolated from various natural sources, such as the leaves of Impatiens glandulifera and the roots of Rubia yunnanensis. 2-METHOXY-1,4-NAPHTHOQUINONE holds potential therapeutic properties, particularly in the treatment of Helicobacter pylori infection-related diseases.

Uses

Used in Pharmaceutical Industry:
2-Methoxy-1,4-naphthoquinone is used as a therapeutic agent for treating Helicobacter pylori infection-related diseases. Its potential candidacy in this application is attributed to its ability to target and alleviate conditions associated with the infection, thus providing a promising avenue for pharmaceutical research and development.
Used in Chemical Synthesis:
In the field of chemical synthesis, 2-Methoxy-1,4-naphthoquinone serves as a key intermediate compound in the preparation of various naphthoquinone derivatives. Specifically, it is used in the synthesis of 2-(4-X-phenylene)amine-1,4-naphthoquinones, where X can represent different substituents such as ferrocenyl, OMe, Me, I, Cl, and NO2. These synthesized compounds find applications in various areas, including pharmaceuticals, dyes, and materials science.

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

Upstream product

• 41431-92-9 2-(2',3',4',6'-tetra-O-acetyl-β-D-glucopyranosyloxy)-1,4-naphthoquinone 
• 93-04-9 2-Methoxynaphthalene 
• 74-83-9 methyl bromide 
• 83-72-7 2-hydroxynaphtho-1,4-quinone 
• 57189-64-7 1,2-dimethoxynaphthalene 
• 2880-58-2 2-methoxy-1,4-benzoquinone 
• 123-73-9 crotonaldehyde 

Downstream Products

• 101439-43-4 2-(4-chloro-phenyl)-3-methoxy-[1,4]naphthoquinone 
• 57182-49-7 2-(p-toluidino)-1,4-naphthoquinone 
• 412018-05-4 1-hydroxy-1,4-diphenyl-1H-naphthalen-2-one 
• 38528-37-9 2-(2-morpholin-4-yl-ethylamino)-[1,4]naphthoquinone 
• 16526-86-6 3-Methoxy-4.5-diphenyl-tricyclo<6.4.0.0^3.6>dodecatetraen-(4.8.10.12)-on-(2.7) 
• 61705-19-9 8,8-Diphenyl-1-methoxy-3,4-benzobicyclo[4.2.0.]-octen-3-dion-(2,5) 
• 123475-71-8 2-(2-(4-hydroxyphenyl)ethylamino)-1,4-naphthoquinone 
• 17241-45-1 2-methoxylapachol 
• 123475-75-2 2-((3,5-dibromo-4-hydroxyphenethyl)amino)naphthalene-1,4-dione 
• 74785-21-0 2,3-benzo-1-hydroxy-1-(3-methyl-2-butenyl)-6-methoxycyclohexa-2,5-dien-4-one 
• 75500-26-4 2-((Z)-2-Carboxy-1-hydroxy-2-nitro-vinyl)-benzoic acid 
• 14422-99-2 2-(ethylamino)naphthalene-1,4-dione 
• 14422-78-7 2-(diethylamino)naphthalene-1,4-dione 
• 173912-74-8 2-<<2-(2-hydroxyphenyl)ethyl>amino>-1,4-naphthoquinone 

Relevant articles and documents

Formation of naphthoquinones and anthraquinones by carbonyl-hydroquinone/benzoquinone reactions: A potential route for the origin of 9,10-anthraquinone in tea

The reaction of 2-alkenals (crotonaldehyde and 2-pentenal) with hydroquinones (hydroquinone and tert-butylhydroquinone) and benzoquinones (benzoquinone, methylbenzoquinone, and methoxybenzoquinone) was studied as a potential route for the endogenous formation of naphthoquinones and anthraquinones in foods. Polycyclic quinones were produced at a low water activity, within a wide pH range, and in the presence of air. 9,10-Anthraquinone formation had an activation energy of 46.1 ± 0.1 kJ·mol?1, and a reaction pathway for the formation of the different naphthoquinones and anthraquinones is proposed. These reactions also took place in tea, therefore suggesting that the common tea pollutant 9,10-anthraquinone is also a process-induced contaminant. In fact, when four commercial teas (from a total of eight studied teas) were heated at 60 °C for 72 h, they significantly (p 0.05) increased the amount of this toxicant. Reduction of 9,10-anthraquinone formation in teas is suggested to be carried out by reducing/scavenging its precursors.

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.

SYNTHESIS OF GLUCOSIDES OF 3-ALKYL-2-HYDROXY-1,4-NAPHTHOQUINONES

The condensation of D-glucose (tert-butyl orthoacetate) with 3-alkyl-2-hydroxy-1,4-naphthoquinones has yielded a series of acetylated glycosides of hydroxynaphthoquinones.It has been established that the time of the glycosylation reaction lengthens with an increase in the length and in the degree of branching of the side chain of the quinone.It has been shown that when the glycosides obtained are deacetylated cleavage of the glycosidic bond takes place with the formation of glucose and the corresponding quinone methyl ethers.Details of IR and 1H and 13C NMR spectra are given.