6320-73-6

Basic information

• Product Name: 3-decyl-4-hydroxynaphthalene-1,2-dione
• CAS NO: 6320-73-6
• Molecular Formula: C₂₀H₂₆O₃
• Molecular Weight: 314.4186
• Mol File: 6320-73-6.mol
• Article Data: 1

Chemical Properties

• Boiling Point: 457.9°C at 760 mmHg
• Flash Point: 244.8°C
• Density: 1.102g/cm³
• Vapor Pressure: 3.53E-09mmHg at 25°C
• Refractive Index: 1.55
• CAS DataBase Reference: 3-decyl-4-hydroxynaphthalene-1,2-dione(CAS DataBase Reference)
• NIST Chemistry Reference: 3-decyl-4-hydroxynaphthalene-1,2-dione(6320-73-6)
• EPA Substance Registry System: 3-decyl-4-hydroxynaphthalene-1,2-dione(6320-73-6)

Safety Data

• Hazardous Substances Data: 6320-73-6(Hazardous Substances Data)

Upstream product

• 130-15-4 [1,4]naphthoquinone 
• 2065-37-4 2-bromo-1,4-naphthoquinone 
• 41245-48-1 2-decyl-1,4-naphthoquinone 
• 112-37-8 undecylenic acid 
• 1504583-91-8 2-bromo-3-decyl-1,4-naphthoquinone 
• 17746-05-3 undecanoyl chloride 

Relevant articles and documents

Design, synthesis, and biological testing of novel naphthoquinones as substrate-based inhibitors of the quinol/fumarate reductase from Wolinella succinogenes

Novel naphthoquinones were designed, synthesized, and tested as substrate-based inhibitors against the membrane-embedded protein quinol/fumarate reductase (QFR) from Wolinella succinogenes, a target closely related to QFRs from the human pathogens Helicobacter pylori and Campylobacter jejuni. For a better understanding of the hitherto structurally unexplored substrate binding pocket, a structure-activity relationship (SAR) study was carried out. Analogues of lawsone (2-hydroxy-1,4-naphthoquinone 3a) were synthesized that vary in length and size of the alkyl side chains (3b-k). A combined study on the prototropic tautomerism of 2-hydroxy-1,4-naphthoquinones series indicated that the 1,4-tautomer is the more stable and biologically relevant isomer and that the presence of the hydroxyl group is crucial for inhibition. Furthermore, 2-bromine-1,4-naphthoquinone (4a-c) and 2-methoxy-1,4-naphthoquinone (5a-b) series were also discovered as novel and potent inhibitors. Compounds 4a and 4b showed IC50 values in low micromolar range in the primary assay and no activity in the counter DT-diaphorase assay.