483-55-6

Basic information

• Product Name: 2-hydroxy-3-methyl-1,4-naphthoquinone
• Synonyms: 2-hydroxy-3-methyl-1,4-naphthoquinone;2-Hydroxy-3-methyl-1,4-benzoquinone;Q121 2-HYDROXY-3-METHYL-1,4-NAPHTHOQUINONE;2-HYDROXY-3-METHYL-1,4-NAPHTHOQUINONE(WXG00550)
• CAS NO: 483-55-6
• Molecular Formula: C₁₁H₈O₃
• Molecular Weight: 188.17942
• EINECS: 207-594-2
• Mol File: 483-55-6.mol
• Article Data: 43

Chemical Properties

• Melting Point: 173-174°
• Boiling Point: 283.17°C (rough estimate)
• Flash Point: 175.232 °C
• Appearance: /
• Density: 1.2100 (rough estimate)
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.6310 (estimate)
• PKA: 5.21±0.10(Predicted)
• CAS DataBase Reference: 2-hydroxy-3-methyl-1,4-naphthoquinone(CAS DataBase Reference)
• NIST Chemistry Reference: 2-hydroxy-3-methyl-1,4-naphthoquinone(483-55-6)
• EPA Substance Registry System: 2-hydroxy-3-methyl-1,4-naphthoquinone(483-55-6)

Safety Data

• Hazardous Substances Data: 483-55-6(Hazardous Substances Data)

Usage

Purification Methods

Crystallise the quinone from diethyl ether/pet ether. [Beilstein 8 III 2568, 8 IV 2375.]

InChI:InChI=1/C11H8O3/c1-6-9(12)7-4-2-3-5-8(7)11(14)10(6)13/h2-5,13H,1H3

Upstream product

• 83-72-7 2-hydroxynaphtho-1,4-quinone 
• 110-22-5 diacetyl peroxide 
• 64-17-5 ethanol 
• 573-20-6 menadiol di(acetate) 
• 141-52-6 sodium ethanolate 
• 14944-23-1 3-methyl-1-tetralone 
• 64-19-7 acetic acid 
• 6091-04-9 3-methyl-1,4-dioxo-1,4-dihydronaphthalen-2-yl acetate 
• 58-27-5 menadione 
• 7664-93-9 sulfuric acid 
• 7732-18-5 water 
• 604-86-4 1,2,4-triacetoxy-3-methylnaphthalene 
• 108-24-7 acetic anhydride 
• 17827-40-6 1,4-dimethoxynaphthalene-3-methyl-2-carboxaldehyde 

Downstream Products

• 83-72-7 2-hydroxynaphtho-1,4-quinone 
• 854676-10-1 (2-pyruvoyl-phenyl)-glyoxylic acid 
• 130180-05-1 {1-[(2,4-Dinitro-phenyl)-hydrazono]-3-methyl-4-oxo-1,4-dihydro-naphthalen-2-yloxy}-acetic acid ethyl ester 
• 130180-09-5 4-{N'-[2-Ethoxycarbonylmethoxy-3-methyl-4-oxo-4H-naphthalen-(1Z)-ylidene]-hydrazino}-2-hydroxy-benzoic acid ethyl ester 
• 130180-08-4 4-{N'-[2-Ethoxycarbonylmethoxy-3-methyl-4-oxo-4H-naphthalen-(1Z)-ylidene]-hydrazino}-benzoic acid ethyl ester 
• 130180-27-7 10-(2,4-Dinitro-phenyl)-6-methyl-10H-7-oxa-10,11-diaza-cyclohepta[a]naphthalene-5,9-dione 
• 130180-07-3 4-{N'-[2-Ethoxycarbonylmethoxy-3-methyl-4-oxo-4H-naphthalen-(1Z)-ylidene]-hydrazino}-2-hydroxy-benzoic acid 
• 130180-06-2 4-{N'-[2-Ethoxycarbonylmethoxy-3-methyl-4-oxo-4H-naphthalen-(1Z)-ylidene]-hydrazino}-benzoic acid 
• 130180-31-3 2-Hydroxy-4-(6-methyl-5,9-dioxo-8,9-dihydro-5H-7-oxa-10,11-diaza-cyclohepta[a]naphthalen-10-yl)-benzoic acid ethyl ester 
• 130180-29-9 2-Hydroxy-4-(6-methyl-5,9-dioxo-8,9-dihydro-5H-7-oxa-10,11-diaza-cyclohepta[a]naphthalen-10-yl)-benzoic acid 
• 130180-03-9 {1-[(4-Iodo-phenyl)-hydrazono]-3-methyl-4-oxo-1,4-dihydro-naphthalen-2-yloxy}-acetic acid ethyl ester 
• 130180-04-0 {1-[(4-Bromo-phenyl)-hydrazono]-3-methyl-4-oxo-1,4-dihydro-naphthalen-2-yloxy}-acetic acid ethyl ester 
• 130180-30-2 4-(6-Methyl-5,9-dioxo-8,9-dihydro-5H-7-oxa-10,11-diaza-cyclohepta[a]naphthalen-10-yl)-benzoic acid ethyl ester 
• 130180-28-8 4-(6-Methyl-5,9-dioxo-8,9-dihydro-5H-7-oxa-10,11-diaza-cyclohepta[a]naphthalen-10-yl)-benzoic acid 

Relevant articles and documents

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Synthesis and molecular structure of a zinc complex of the vitamin K 3 analogue phthiocol

The complex [Zn(phthiocol)2(H2O)2]; 1, where phthiocol is 2-hydroxy-3-methyl-1,4-naphthoquinone, has been synthesized and characterized by elemental analysis, FT-IR, 1H NMR, UV-vis spectroscopy, thermogravimetric (TG) analysis, electrochemical and single crystal X-ray diffraction studies. The mC=O stretch shifts to lower frequencies upon complexation of phthiocol to Zn2+. 1H NMR spectra show an upfield shift of the benzenoid ring protons in 1. There is a bathochromic shift of the LMCT band in the UV-vis spectra of 1. Single crystal X-ray structure of 1 show distorted octahedral geometry around Zn2+. Two phthiocol ligands are in plane with the metal, while water molecules are trans to this plane. Coordination of deprotonated phthiocol ligands is 'trans, trans' to Zn2+. Intra as well as intermolecular interactions are observed in 1. Molecules of 1 show three dimensional network through C-H...O and O-H...O interactions. Additional anodic peaks are observed in cyclic voltammogram of phthiocol ligand due to oxidation of reduced species formed during reduction. One-electron reduction of 1 is shown to be reversible and DFT studies define this redox event as ligand-centered.

Tridentate 3-Substituted Naphthoquinone Ruthenium Arene Complexes: Synthesis, Characterization, Aqueous Behavior, and Theoretical and Biological Studies

A series of nine RuII arene complexes bearing tridentate naphthoquinone-based N,O,O-ligands was synthesized and characterized. Aqueous stability and their hydrolysis mechanism were investigated via UV/vis photometry, HPLC-MS, and density functional theory calculations. Substituents with a positive inductive effect improved their stability at physiological pH (7.4) intensely, whereas substituents such as halogens accelerated hydrolysis and formation of dimeric pyrazolate and hydroxido bridged dimers. The observed cytotoxic profile is unusual, as complexes exhibited much higher cytotoxicity in SW480 colon cancer cells than in the broadly chemo- (incl. platinum-) sensitive CH1/PA-1 teratocarcinoma cells. This activity pattern as well as reduced or slightly enhanced ROS generation and the lack of DNA interactions indicate a mode of action different from established or previously investigated classes of metallodrugs.

Novel phthiocol-based organometallics with tridentate coordination motif and their unexpected cytotoxic behaviour

Novel phthiocol-based organometallics with in situ formed tridentate N,O,O-coordination motif were established via three-component microwave assisted one-pot reaction. These complexes exhibited enhanced stability in aqueous solution compared to the parental compound KP2048 and showed unexpected cytotoxic behaviour and selectivity in 2D and 3D cell cultures.