57620-99-2

Basic information

• Product Name: 3-(3-methylbut-2-en-1-yl)-1,4-dioxo-1,4-dihydronaphthalen-2-yl acetate
• Synonyms: 1,4-naphthalenedione, 2-(acetyloxy)-3-(3-methyl-2-buten-1-yl)-
• CAS NO: 57620-99-2
• Molecular Formula: C₁₇H₁₆O₄
• Molecular Weight: 284.3065
• Mol File: 57620-99-2.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 419.7°C at 760 mmHg
• Flash Point: 185.3°C
• Density: 1.21g/cm³
• Vapor Pressure: 2.98E-07mmHg at 25°C
• Refractive Index: 1.569
• CAS DataBase Reference: 3-(3-methylbut-2-en-1-yl)-1,4-dioxo-1,4-dihydronaphthalen-2-yl acetate(CAS DataBase Reference)
• NIST Chemistry Reference: 3-(3-methylbut-2-en-1-yl)-1,4-dioxo-1,4-dihydronaphthalen-2-yl acetate(57620-99-2)
• EPA Substance Registry System: 3-(3-methylbut-2-en-1-yl)-1,4-dioxo-1,4-dihydronaphthalen-2-yl acetate(57620-99-2)

Safety Data

• Hazardous Substances Data: 57620-99-2(Hazardous Substances Data)

Upstream product

• 84-79-7 Lapachol 
• 75-36-5 acetyl chloride 
• 504-85-8 4-methyl-pent-3-enoic acid 
• 1785-65-5 2-acetoxy-1,4-naphthoquinone 
• 108-24-7 acetic anhydride 
• 127-09-3 sodium acetate 

Downstream Products

• 41019-50-5 3'-bromo-β-lapachone 
• 74693-34-8 4'-bromo-iso-β-lapachone 
• 84-79-7 Lapachol 

Relevant articles and documents

Growth inhibitory activity for cancer cell lines of lapachol and its natural and semi-synthetic derivatives

A series of 17 selected natural and semisynthetic 1,4-naphthoquinones were synthesized, and their growth inhibitory activity was evaluated in vitro. The compounds were tested on six human cancer cell lines using the MTT colorimetric assay. The data revealed that of the chemicals under study only lapachol, its acetate and 3-geranyllawsone displayed the highest activity, recording mean IC50 values ranging from 15 to 22 μM.

Synthesis and pharmacophore modeling of naphthoquinone derivatives with cytotoxic activity in human promyelocytic leukemia HL-60 cell line

Catalyst/HypoGen pharmacophore modeling approach and three-dimensional quantitative structure-activity relationship (3D-QSAR)/comparative molecular similarity indices analysis (CoMSIA) methods have been successfully applied to explain the cytotoxic activity of a set of 51 natural and synthesized naphthoquinone derivatives tested in human promyelocytic leukemia HL-60 cell line. The computational models have facilitated the identification of structural elements of the ligands that are key for antitumoral properties. The four most salient features of the highly active β-cycled-pyran-1,2-naphthoquinones [0.1 μM 50 0.6 μM] are the hydrogen-bond interactions of the carbonyl groups at C-1 (HBA1) and C-2 (HBA2), the hydrogen-bond interaction of the oxygen atom of the pyran ring (HBA3), and the interaction of methyl groups (HYD) at the pyran ring with a hydrophobic area at the receptor. The moderately active 1,4-naphthoquinone derivatives accurately fulfill only three of these features. The results of our study provide a valuable tool in designing new and more potent cytotoxic analogues.

Synthesis of lapachol derivatives and their antibacterial activity

Several lapachol derivatives were synthesized from lapachol and tested for their antibacterial activity.