475-38-7

Basic information

• Product Name: 5,8-Dihydroxy-1,4-naphthoquinone
• Synonyms: ,8-Dihydroxy-[1,4]naphthoquinone;,8-Dihydroxy-1,4-naphthalenedione;1,4-Naphthoquinone, 5,8-dihydroxy-;2,3-Dihydro-1,4,5,8-naphthalenetetrone;5,8-dihydroxy-4-naphthalenedione;5,8-dihydroxy-4-naphthoquinone;5,8-Dihydroxynaphthoquinone;Naphthazarine
• CAS NO: 475-38-7
• Molecular Formula: C₁₀H₆O₄
• Molecular Weight: 190.15
• EINECS: 207-495-4
• Product Categories: API intermediates
• Mol File: 475-38-7.mol
• Article Data: 30

Chemical Properties

• Melting Point: 220-230 °C(lit.)
• Boiling Point: 285.64°C (rough estimate)
• Flash Point: 269.2 °C
• Appearance: dark purple to brown-black powder
• Density: 1.3366 (rough estimate)
• Vapor Pressure: 1.51E-10mmHg at 25°C
• Refractive Index: 1.5280 (estimate)
• Storage Temp.: Sealed in dry,Room Temperature
• PKA: 6.98±0.20(Predicted)
• Water Solubility: Soluble in water (5520 mg/L 25.).
• BRN: 880561
• CAS DataBase Reference: 5,8-Dihydroxy-1,4-naphthoquinone(CAS DataBase Reference)
• NIST Chemistry Reference: 5,8-Dihydroxy-1,4-naphthoquinone(475-38-7)
• EPA Substance Registry System: 5,8-Dihydroxy-1,4-naphthoquinone(475-38-7)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 22-24/25-37/39-26
• WGK Germany: 3
• RTECS: QL7970000
• Hazardous Substances Data: 475-38-7(Hazardous Substances Data)

Usage

Chemical Properties

dark purple to brown-black powder

Definition

ChEBI: A naphthoquinone that is 1,4-naphthoquinone in which the hydrogens at positions 5 and 8 are replaced by hydroxy groups.

Preparation

1,8-Dinitronaphthalene and 1,5-Dinitronaphthalene mixture or both alone and one of sulfur 40% fuming sulfuric ACID reaction, the product (5, 8 – dihydroxy – naphthoquinone) into Sulfurous acid?hydrogen salt.

Properties and Applications

ash red to black. Soluble in water for red light brown, soluble in ethanol for yellow brown, with green fluorescence. In concentrated sulfuric acid to dark yellow green, heating to rouge red, dilution after brown black precipitation. Dye aqueous solution to join sodium hydroxide to red, the air oxidation into blue. Standard Ironing Fastness Light Fastness Fulling Persperation Fastness Soaping Water Alkali Acid ISO 5 6 5 4 5 5 5

Standard

Ironing Fastness

Alkali

Acid

ISO

5

Purification Methods

It crystallises in red-brown needles with a green shine from EtOH. It also crystallises from hexane and is further purified by sublimation at 2-10mm. [Huppert et al. J Phys Chem 89 5811 1985.] It is sparingly soluble in H2O but soluble in alkalis. The diacetate forms golden yellow prisms from CHCl3, m 192-193o and the 5,8-dimethoxy derivative has m 157o (155o) (from pet ether) [Bruce & Thompson J Chem Soc 1089 1955, IR: Schmand & Boldt J Am Chem Soc 97 447 1975, NMR: Brockmann & Zeeck Chem Ber 101 4221 1968]. The monothiosemicarbazone has m 168o(dec) from EtOH [Gardner et al. J Am Chem Soc 74 2106 1952]. [Beilstein 8 H 412, 8 III 3600.]

InChI:InChI=1/C10H6O4/c11-5-1-2-6(12)10-8(14)4-3-7(13)9(5)10/h1-4,11-12H

Upstream product

• 108-30-5 succinic acid anhydride 
• 123-31-9 hydroquinone 
• 23077-93-2 1,4,5,8-naphthalenediquinone 
• 64-19-7 acetic acid 
• 7647-01-0 hydrogenchloride 
• 90845-15-1 1,2,5,8-tetranitro-naphthalene 
• 6259-68-3 5-amino-8-hydroxy-[1,4]naphthoquinone-1-imine 
• 7664-93-9 sulfuric acid 
• 10075-63-5 1,5-dimethoxynaphthalene 
• 64636-39-1 1,4,5-Trimethoxynaphthalene 
• 108-31-6 maleic anhydride 
• 130-15-4 [1,4]naphthoquinone 
• 150-78-7 1,4-dimethoxybezene 
• 90-15-3 α-naphthol 

Downstream Products

• 14569-45-0 5,8-diacetoxy-1,4-naphthoquinone 
• 6047-49-0 1,4,5,8-Tetraacetoxy-naphthalin 
• 71639-99-1 5-(2',4'-dimethoxy-6'-methylbenzoyloxy)-8-hydroxy-1,4-naphthoquinone 
• 132632-70-3 4-(1-Cyclohexyl-ethoxy)-5,8-dihydroxy-3,4,4a,9a-tetrahydro-1H-anthracene-2,9,10-trione 
• 132632-77-0 5,8-Dihydroxy-4-(2-phenyl-propoxy)-3,4,4a,9a-tetrahydro-1H-anthracene-2,9,10-trione 
• 132632-72-5 5,8-Dihydroxy-4-(1-phenyl-propoxy)-3,4,4a,9a-tetrahydro-1H-anthracene-2,9,10-trione 
• 132632-73-6 5,8-Dihydroxy-4-(2-methyl-1-phenyl-propoxy)-3,4,4a,9a-tetrahydro-1H-anthracene-2,9,10-trione 
• 132632-81-6 5,8-Dihydroxy-4-[1-(4-methoxy-phenyl)-ethoxy]-3,4,4a,9a-tetrahydro-1H-anthracene-2,9,10-trione 
• 132632-80-5 5,8-Dihydroxy-4-[1-(4-trifluoromethyl-phenyl)-ethoxy]-3,4,4a,9a-tetrahydro-1H-anthracene-2,9,10-trione 
• 131627-67-3 5,8-Dihydroxy-4-(1-phenyl-ethoxy)-3,4,4a,9a-tetrahydro-1H-anthracene-2,9,10-trione 
• 518-80-9 helminthosporin 
• 95393-73-0 1,4-dihydroxy-8-methoxy-6-methylanthraquinone 
• 84525-49-5 Benzoic acid (1S,4R,4aS,9aR)-4-ethoxycarbonylamino-5,8-dihydroxy-9,10-dioxo-1,4,4a,9,9a,10-hexahydro-anthracen-1-yl ester 
• 94975-33-4 Carbonic acid 4-nitro-benzyl ester 4-(4-nitro-benzyloxycarbonyloxy)-5,8-dioxo-5,8-dihydro-naphthalen-1-yl ester 

Relevant articles and documents

A versatile synthesis of the 1,4-dihydroxynaphthoquinone nucleus

The electrochemical oxidation of different methoxynaphthalenes to afford the corresponding 5,8-dihydroxy-1,4-naphthoquinones has been examined. This method constitutes a new alternative and efficient route for the synthesis of the 5,8-dihydroxy-1,4-naphthoquinone nucleus. (C) 2000 Elsevier Science Ltd.

A hydrogen peroxide-activated Cu(II) pro-ionophore strategy for modifying naphthazarin as a promising anticancer agent with high selectivity for generating ROS in HepG2 cells over in L02 cells

Targeting redox vulnerability of cancer cells by pro-oxidants capable of generating reactive oxygen species (ROS) has surfaced as an important anticancer strategy. Due to the intrinsic narrow therapeutic window and other dangerous side effects of ROS generation, it is highly needed and challenging to develop pro-oxidative anticancer agents (PAAs) with high selectivity for generating ROS in cancer cells. Herein we report a hydrogen peroxide (H2O2)-activated Cu(II) pro-ionophore strategy to develop naphthazarin (Nap) as such type of PAAs based on the H2O2-mediated conversion of boronate to free phenol. The boronate-protected Nap (PNap) can exploit increased levels of H2O2 in HepG2 cells to in situ release Nap followed by its efflux via conjugation with reduced glutathione (GSH), allowing that the Nap-GSH adduct works as a Cu(II) ionophore to induce continuously GSH depletion via a reduction-dependent releasing of Cu(I) by GSH. This strategy endows PNap with the unprecedented ability to hit multi-redox characteristics (increased levels of H2O2, GSH and copper) of HepG2 cells, leading to ROS generation preferentially in HepG2 cells along with their selective death.

The compound 2-(naphthalene-2-thio)-5,8-dimethoxy-1,4-naphthoquinone induces apoptosis via reactive oxygen species-regulated mitogen-activated protein kinase, protein kinase B, and signal transducer and activator of transcription 3 signaling in human gastric cancer cells

(Table presented.). It is reported that 1,4-naphthoquinones and their derivatives have potent antitumor activity in various cancers, although their clinical application is limited by observed side effects. To improve the therapeutic efficacy of naphthoquinones in the treatment of cancer and to reduce side effects, we synthesized a novel naphthoquinone derivative, 2-(naphthalene-2-thio)-5,8-dimethoxy-1,4-naphthoquinone (NTDMNQ). In this study, we explored the effects of NTDMNQ on apoptosis in gastric cancer cells with a focus on reactive oxygen species (ROS) production. Our results demonstrated that NTDMNQ exhibited the cytotoxic effects on gastric cancer cells in a dose-dependent manner. NTDMNQ significantly induced mitochondrial-related apoptosis in AGS cells and increased the accumulation of ROS. However, pre-treatment with N-acetyl-L-cysteine (NAC), an ROS scavenger, inhibited the NTDMNQ-induced apoptosis. In addition, NTDMNQ increased the phosphorylation of p38 kinase and c-Jun N-terminal kinase (JNK) and decreased the phosphorylation of extracellular signal-regulated kinase (ERK), protein kinase B (Akt), and Signal Transducer and Activator of Transcription 3 (STAT3); these effects were blocked by mitogen-activated protein kinase (MAPK) inhibitor and NAC. Taken together, the present findings indicate that NTDMNQ-induced gastric cancer cell apoptosis via ROS-mediated regulation of the MAPK, Akt, and STAT3 signaling pathways. Therefore, NTDMNQ may be a potential treatment for gastric cancer as well as other tumor types.

Method for synthesizing 5,8-dihydroxy-1,4-naphthoquinone with molten salt method

The invention discloses a method for synthesizing 5,8-dihydroxy-1,4-naphthoquinone with a molten salt method. The method comprises the following main steps: step 1, a complex of 5,8-dihydroxy-1,4-naphthoquinone and AlCl3 is formed from hydroquinone and maleic anhydride as raw materials for synthesizing 5,8-dihydroxy-1,4-naphthoquinone as well as anhydrous AlCl3 as a catalyst and NaCl as molten salt through Friedel-Crafts acylation at high temperature and high pressure; step 2, free 5,8-dihydroxy-1,4-naphthoquinone is prepared from the complex of 5,8-dihydroxy-1,4-naphthoquinone and AlCl3 by digesting and then purified, and a 5,8-dihydroxy-1,4-naphthoquinone product is obtained. According to the method, the target product is obtained directly with one-step reaction on the basis of the molten salt method without an intermediate, so that the synthetic route is shortened greatly, aftertreatment is simple, a recrystallization step can be omitted, and extraction purity is guaranteed.