6223-31-0

Basic information

• Product Name: 2-hydroxy-6-Methoxy-1,4-dihydronaphthalene-1,4-dione
• Synonyms: 2-hydroxy-6-Methoxy-1,4-dihydronaphthalene-1,4-dione;2-Hydroxy-6-Methoxynaphthalene-1,4-dione;1,4-Naphthalenedione, 2-hydroxy-6-Methoxy-
• CAS NO: 6223-31-0
• Molecular Formula: C₁₁H₈O₄
• Molecular Weight: 204.17882
• Mol File: 6223-31-0.mol

Chemical Properties

• Appearance: /
• Storage Temp.: Sealed in dry,Room Temperature
• CAS DataBase Reference: 2-hydroxy-6-Methoxy-1,4-dihydronaphthalene-1,4-dione(CAS DataBase Reference)
• NIST Chemistry Reference: 2-hydroxy-6-Methoxy-1,4-dihydronaphthalene-1,4-dione(6223-31-0)
• EPA Substance Registry System: 2-hydroxy-6-Methoxy-1,4-dihydronaphthalene-1,4-dione(6223-31-0)

Safety Data

• Hazardous Substances Data: 6223-31-0(Hazardous Substances Data)

Usage

Uses

Used in Cosmetic Industry:
2-hydroxy-6-Methoxy-1,4-dihydronaphthalene-1,4-dione is used as a natural dye in the cosmetic industry for coloring hair and skin. It provides a reddish-brown hue when applied, making it a popular choice for those seeking a natural alternative to synthetic dyes.
Used in Traditional Medicine:
In traditional medicine, 2-hydroxy-6-Methoxy-1,4-dihydronaphthalene-1,4-dione is used for its potential anti-inflammatory and antimicrobial properties. Its long history of use suggests that it may offer health benefits in various medicinal applications.
Used in Food Industry:
2-hydroxy-6-Methoxy-1,4-dihydronaphthalene-1,4-dione is used as a colorant and flavoring agent in the food industry. Its natural reddish-brown color and unique properties make it a suitable ingredient for enhancing the appearance and taste of various food products.
Used in Pharmaceutical Research:
2-hydroxy-6-Methoxy-1,4-dihydronaphthalene-1,4-dione is used as a subject of pharmaceutical research for its potential anti-cancer and antioxidant effects. Studies are ongoing to explore its therapeutic potential and to develop novel drug delivery systems to enhance its bioavailability and efficacy in treating various health conditions.

Upstream product

• 21905-91-9 6-Methoxy-1,2-naphthochinon 
• 1078-19-9 6-methoxy-3,4-dihydro-1(2H)-naphthalenone 
• 6836-19-7 7-Methoxy-1-tetralone 

Downstream Products

• 31039-62-0 2,6-dihydroxynaphthalene-1,4-dione 
• 1308657-38-6 (S)-2-hydroxy-6-methoxy-3-(2-nitro-1-phenylethyl)naphthalene-1,4-dione 

Relevant articles and documents

A convenient synthesis of monpain trimethylether

A high yield synthesis of various 2-hydroxy-1,4-naphtoquinones was achieved by SeO2 oxidation of 1-tetralones into the corresponding 1,2-quinones, followed by heterogeneous phase KO2 mediated oxidation. Application of this synthesis to 5,7,8-trimethoxy-1-tetralone gave 2-hydroxy-5,7,8-trimethoxy-1,4-naphtoquinone 3d or monpain trimethylether.

Synthesis and biological evaluation of β-lapachone-monastrol hybrids as potential anticancer agents

A series of novel β-lapachone analogs was designed and synthesized by replacing pyran ring of β-lapachone with tetrahydropyrimidinethione moiety of monastrol. These hybrids had potent antiproliferative activity against NQO1-rich cell lines (HepG2 and A549

Bifunctional Naphtho[2,3- d][1,2,3]triazole-4,9-dione Compounds Exhibit Antitumor Effects in Vitro and in Vivo by Inhibiting Dihydroorotate Dehydrogenase and Inducing Reactive Oxygen Species Production

Human dihydroorotate dehydrogenase (hDHODH) is an attractive target for cancer therapy. Based on its crystal structure, we designed and synthesized a focused compound library containing the structural moiety of 1,4-benzoquinone, which possesses reactive oxygen species (ROS) induction capacity. Compound 3s with a naphtho[2,3-d][1,2,3]triazole-4,9-dione scaffold exhibited inhibitory activity against hDHODH. Further optimization led to compounds 11k and 11l, which inhibited hDHODH activity with IC50 values of 9 and 4.5 nM, respectively. Protein-ligand cocrystal structures clearly depicted hydrogen bond and hydrophobic interactions of 11k and 11l with hDHODH. Compounds 11k and 11l significantly inhibited leukemia cell and solid tumor cell proliferation and induced ROS production, mitochondrial dysfunction, apoptosis, and cell cycle arrest. Nanocrystallization of compound 11l displayed significant in vivo antitumor effects in the Raji xenograft model. Overall, this study provides a novel bifunctional compound 11l with hDHODH inhibition and ROS induction efficacy, which represents a promising anticancer lead worthy of further exploration.

Naphtho[2,3-: B] furan-4,9-dione synthesis via palladium-catalyzed reverse hydrogenolysis

A reverse hydrogenolysis process has been developed for two-site coupling of 2-hydroxy-1,4-naphthoquinones with olefins to produce naphtha[2,3-b]furan-4,9-diones and hydrogen (H2). The reaction is catalyzed by commercially available Pd/C without oxidants and hydrogen acceptors, thereby providing an intrinsically waste-free approach for the synthesis of functionalized and potentially biologically relevant naphtha[2,3-b]furan-4,9-diones.

Identification of β-lapachone analogs as novel MALT1 inhibitors to treat an aggressive subtype of diffuse large B-cell lymphoma

The treatment of activated B cell-like DLBCL (ABC-DLBCL) is one of the urgent unmet medical needs because it is the most resistant DLBCL subtype to current therapies eagerly awaiting effective therapeutic strategies. Recently, the paracaspase MALT1 has emerged as a promising therapeutic target for the treatment of ABC-DLBCL. Herein, we report a new class of MALT1 inhibitors developed by high-throughput screening and structure-based drug design. The original hit, 4-amino-1,2-naphthoquinone series inhibited MALT1 activity but suffered from poor cellular activity. The extensive pharmacophore search led to the discovery of structurally similar β-lapachone that is a direct inhibitor of MALT1 and possesses favorable physicochemical properties. Molecular simulation studies suggested the possibility of the formation of a covalent bond between MALT1 and β-lapachone, which was corroborated by experimental wash-out studies. Inspired by this, we explored the structure-activity relationships by incorporating electron-withdrawing substituents at C8 position of β-lapachone. These MALT1 inhibitors exhibited potent antiproliferative activity to OCI-LY3 cell line and inhibited the cleavage of CYLD mediated MALT1.

Design, synthesis and biological evaluation of novel 7-alkylamino substituted benzo[ a[phenazin derivatives as dual topoisomerase I/II inhibitors

A novel series of benzo[a]phenazin derivatives bearing alkylamino side chains were designed, synthesized and evaluated for their topoisomerases inhibitory activity as well as cytotoxicity against four human cancer cell lines (HL-60, K-562, HeLa, and A549)

Synthesis and cytotoxicity on human leukemia cells of furonaphthoquinones isolated from Tabebuia plants

Furonaphthoquinones are promising skeletons for anticancer drug molecules. In particular, methoxylated furonaphthoquinones are characteristic constituents of Tabebuia plants. In this research, we synthesized the furonaphthoquinones by effective one-pot ca

Synthetic methods for the preparation of ARQ 501 (β-Lapachone) human blood metabolites

ARQ 501 (3,4-dihydro-2,2-dimethyl-2H-naphthol[1,2-b] pyran-5,6-dione), a synthetic version of β-Lapachone, is a promising anti-cancer agent currently in multiple Phase II clinical trials. Promising anti-cancer activity was observed in Phase I and Phase II trials. Metabolism by red blood cells of drugs is an understudied area of research and the metabolites arising from oxidative ring opening (M2 and M3), decarbonylation/ring contraction (M5), and decarbonylation/oxidation (M4 and M6) of ARQ 501 offer a unique opportunity to provide insight into these metabolic processes. Since these metabolites were not detected in in vitro incubations of ARQ 501 with liver microsomes and were structurally diverse, confirmation by chemical synthesis was considered essential. In this report, we disclose the synthetic routes employed and the characterization of the reference standards for these blood metabolites as well as additional postulated structures, which were not confirmed as metabolites.

Biomimetic synthesis of antimalarial naphthoquinones

The total synthesis of naphthoquinone natural products isolated from the Bignoniaceae plant family is described. Pinnatal, isopinnatal, sterekunthals A and B, pyranokunthones A and B, and anthrakunthone have been prepared along the lines of a biosynthetic

Method for dyeing keratinous fibres using a monohydroxyindole or dihydroxyindole and a non-oxidizing aromatic carbonyl derivative and dyeing agent

The present invention relates to a method for dyeing keratinous fibers, characterized in that the following are applied to the fibers: a) a composition (A) containing, in a medium appropriate for dyeing, at least one monohydroxyindole or dihydroxyindole, this application being preceded or followed by the application of b) a composition (B) containing, in a medium appropriate for dyeing, at least one aromatic carbonyl derivative chosen from hydroxyacetophenones, hydroxybenzophenones, 2-hydroxy-1,4-benzoquinones, hydroxy-1,4-naphthoquinones,amino-1,4-naphthoquinones,hydroxy-9,10-anthraquinones and amino-9,10-anthraquinones. It also relates to the dyeing agents for carrying it out.