605-89-0

Basic information

• Product Name: 1,5-naphthylene di(acetate)
• Synonyms: 1,5-naphthylene di(acetate);1,5-Diacetoxynaphthalene;1,5-Naphthalenediol diacetate;Diacetic acid=1,5-naphthylene ester;Naphthalene-1,5-diol diacetate;(5-acetyloxynaphthalen-1-yl) acetate;(5-acetyloxynaphthalen-1-yl) ethanoate;acetic acid (5-acetoxy-1-naphthyl) ester
• CAS NO: 605-89-0
• Molecular Formula: C₁₄H₁₂O₄
• Molecular Weight: 244.24268
• EINECS: 210-098-9
• Mol File: 605-89-0.mol
• Article Data: 19

Chemical Properties

• Melting Point: 158 °C
• Boiling Point: 386.5°C at 760 mmHg
• Flash Point: 196.2°C
• Appearance: /
• Density: 1.228g/cm³
• Vapor Pressure: 3.54E-06mmHg at 25°C
• Refractive Index: 1.586
• Solubility: Chloroform, Dichloromethane, Ethyl Acetate, Methanol
• CAS DataBase Reference: 1,5-naphthylene di(acetate)(CAS DataBase Reference)
• NIST Chemistry Reference: 1,5-naphthylene di(acetate)(605-89-0)
• EPA Substance Registry System: 1,5-naphthylene di(acetate)(605-89-0)

Safety Data

• Hazardous Substances Data: 605-89-0(Hazardous Substances Data)

Usage

Uses

1,5-Diacetoxynaphthalene is an intermediate in the synthesis of Plumbagin-d3 (P627002). Plumbagin-d3 is labelled Plumbagin (P627000) which induces apoptosis in cancer cells. It also inhibits NADPH oxidase 4 in a time- and dose-dependent manner.

InChI:InChI=1/C14H12O4/c1-9(15)17-13-7-3-6-12-11(13)5-4-8-14(12)18-10(2)16/h3-8H,1-2H3

Upstream product

• 83-56-7 1,5-dihydroxynaphthalene 
• 108-24-7 acetic anhydride 
• 108-05-4 vinyl acetate 
• 91-20-3 naphthalene 
• 75-36-5 acetyl chloride 
• 25543-68-4 1,5-dihydroxy-2,6-naphthalenedicarboxylic acid 
• 127-09-3 sodium acetate 

Downstream Products

• 77189-69-6 5-acetoxy-2-bromo-1,4-naphthoquinone 
• 83-56-7 1,5-dihydroxynaphthalene 
• 94807-85-9 5-hydroxynaphthalen-1-yl acetate 
• 109972-84-1 1-Benzyloxy-5-hydroxynaphthalene 
• 221461-63-8 acetic acid 5-benzyloxy-naphthalen-1-yl ester 
• 68963-23-5 1-hydroxy-7-methylanthracene-9,10-dione 
• 4923-55-1 2-Hydroxyjuglon 
• 1262052-80-1 3-hydroxy-2-(5-hydroxy-1,4-dioxo-1,4-dihydronaphthalen-2-yl)-5-methylbenzaldehyde 
• 1262052-77-6 2-(2-(1,3-dioxan-2-yl)-6-(methoxymethoxy)-4-methylphenyl)-5-hydroxynaphthalene-1,4-dione 
• 5196-28-1 juglone acetate 

Relevant articles and documents

Synthesis of Barleriaquinones-I & II

Synthesis of two naturally occurring anthraquinones, Barleriaquinone-I (BQ-I) and Barleriaquinone-II (BQ-II) is achieved from commercially available naphthalene-1,5-diol. The anthraquinone core is constructed by utilizing simultaneous Heck and cross coupling reaction as the key step.

Synthesis, molecular docking, and biological activity of thioether derived from juglone in preclinical models of chronic myeloid leukemia

In this work, 16 new thio-1,4-naphthoquinones were synthesized, and their antiproliferative effects against tumor cell lines SK-MEL-19, AGP-01, ACP-02, HL-60, K-562, K-562-Lucena-1, FEPS, and non-neoplastic human fibroblast MRC-5, were examined. The compounds were selective active against leukemia cell lines. Based on the screening results for cytotoxic activity, naphthoquinone 11a showed higher cytotoxicity on the chemoresistant leukemia (FEPS) cell line when compared to the chemosensitive (K-562) cell line. Moreover, naphthoquinone 11a presented excellent ADME/T and did not violate Lipinski's rule of five, indicating good oral absorption. Target prediction revealed DNA topoisomerase I (TOP1) as a possible target of 11a. The molecular docking prediction showed an ? 11.94 kcal/mol binding affinity interaction of 11a with TOP1, involving three hydrogen bonds to ARG364, A113, and G11 from the active site of the enzyme. In addition, naphthoquinone 11a significantly suppressed the expression of the TOP1 gene in K-562 and FEPS leukemia cell lines. The naphthoquinone 11a induced significant changes in cell morphology, demonstrating cell and nuclear shrinkage, blebbing formation as well and fragmentation of the cell into apoptotic bodies. Thus, 11a could be a drug that leads to a new set of TOP1 major inhibitors. In summary, the present study showed a cytotoxic effect of 11a against chemoresistant and chemosensitive leukemia cell lines with TOP1 as a possible target.

Na 2 CO 3-Catalyzed O-Acylation of Phenols for the Synthesis of Aryl Carboxylates with Use of Alkenyl Carboxylates

Inorganic base-catalyzed O-acylation of phenol and its derivatives has been developed. The procedure provides an efficient catalysis system for the preparation of aryl carboxylates with alkenyl carboxylates as acyl reagents. The reaction proceeded smoothly by using ?-Na 2 CO 3 as the catalyst in MeCN to produce the corresponding aryl carboxylates in good to excellent yields.