29366-44-7

Basic information

• Product Name: 1,4-Naphthalenedione, 2-ethyl-3-hydroxy- (9CI)
• Synonyms: 1,4-Naphthalenedione, 2-ethyl-3-hydroxy- (9CI);2-Ethyl-3-hydroxy-1,4-naphthoquinone
• CAS NO: 29366-44-7
• Molecular Formula: C₁₂H₁₀O₃
• Molecular Weight: 202.206
• Product Categories: ALCOHOL
• Mol File: 29366-44-7.mol
• Article Data: 11

Chemical Properties

• Boiling Point: 363.7°Cat760mmHg
• Flash Point: 187.9°C
• Appearance: /
• Density: 1.32g/cm³
• Vapor Pressure: 6.32E-06mmHg at 25°C
• Refractive Index: 1.62
• CAS DataBase Reference: 1,4-Naphthalenedione, 2-ethyl-3-hydroxy- (9CI)(CAS DataBase Reference)
• NIST Chemistry Reference: 1,4-Naphthalenedione, 2-ethyl-3-hydroxy- (9CI)(29366-44-7)
• EPA Substance Registry System: 1,4-Naphthalenedione, 2-ethyl-3-hydroxy- (9CI)(29366-44-7)

Safety Data

• Hazardous Substances Data: 29366-44-7(Hazardous Substances Data)

Usage

Derivative

1,4-naphthoquinone

Synonyms

Menadione

Category

Synthetic form of vitamin K

Uses

a. Nutritional supplement
b. Production of vitamin K supplements
c. Precursor for synthesis of dyes and pigments

Research

Potential antiproliferative and anticancer properties

Safety

Toxic in high doses, handle with caution

InChI:InChI=1/C12H10O3/c1-2-7-10(13)8-5-3-4-6-9(8)12(15)11(7)14/h3-6,13H,2H2,1H3

Upstream product

• 100121-60-6 1-(2-acetyl-phenyl)-butan-1-one 
• 67-56-1 methanol 
• 63688-80-2 2,3-epoxy-2,3-diethyl-2,3-dihydro-[1,4]naphthoquinone 
• 83-72-7 2-hydroxynaphtho-1,4-quinone 
• 3248-28-0 dipropionyl peroxide 
• 51015-30-6 3-ethyl-1-oxo-1,2,3,4-tetrahydronaphthalene 
• 858436-33-6 2-ethyl-naphthalene-1,3-diol 
• 53948-59-7 2,3-epoxi-2-etil-2,3-dihidro-1,4-naftoquinona 
• 75-07-0 acetaldehyde 
• 27699-93-0 2‐hydroxy‐1,4‐naphthoquinone 
• 802294-64-0 propionic acid 
• 2065-37-4 2-bromo-1,4-naphthoquinone 
• 13984-88-8 2-bromo-3-ethyl-1,4-naphthoquinone 
• 35028-12-7 1-(2-ethyl-phenyl)-butan-1-one 

Downstream Products

• 62830-41-5 4-{N'-[3-Ethyl-2-hydroxy-4-oxo-4H-naphthalen-(1Z)-ylidene]-hydrazino}-3-iodo-benzoic acid ethyl ester 
• 62830-36-8 4-{N'-[3-Ethyl-2-hydroxy-4-oxo-4H-naphthalen-(1Z)-ylidene]-hydrazino}-3-iodo-benzoic acid 
• 62830-32-4 2-Ethyl-3-hydroxy-4-[(2-iodo-4-methyl-phenyl)-hydrazono]-4H-naphthalen-1-one 
• 62830-28-8 2-Ethyl-3-hydroxy-4-[(4-iodo-phenyl)-hydrazono]-4H-naphthalen-1-one 
• 483-55-6 phthiocol 

Relevant articles and documents

Synthesis and structure elucidation of oxidative coupling products of 2-hydroxy-1,4-naphthoquinones

2,3-Dihydro-3-O-(1,4-naphthoquinon-2-yl)-2-oxo-1,4-naphthoquinones are the products of oxidative coupling of substituted 2-hydroxy-1,4-naphthoquinones (regardless of the presence of peri-hydroxy groups in their structures) under the action of lead dioxide

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.

Tuning the redox potential of Vitamin K3 derivatives by oxidative functionalization using a Ag(i)/GO catalyst

We propose herein initial results to develop optimum redox mediators by the combination of computational simulation and catalytic functionalization of the core structure of vitamin K3. We aim to correlate the calculated energy value of the LUMO

Towards targeting anticancer drugs: Ruthenium(II)-arene complexes with biologically active naphthoquinone-derived ligand systems

Anticancer active metal complexes with biologically active ligands have the potential to interact with more than one biological target, which could help to overcome acquired and/or intrinsic resistance of tumors to small molecule drugs. In this paper we present the preparation of 2-hydroxy-[1,4]-naphthoquinone-derived ligands and their coordination to a RuII(η6-p-cymene)Cl moiety. The synthesis of oxime derivatives resulted in the surprising formation of nitroso-naphthalene complexes, as confirmed by X-ray diffraction analysis. The compounds were shown to be stable in aqueous solution but reacted with glutathione and ascorbic acid rather than undergoing reduction. One-electron reduction with pulse radiolysis revealed different behavior for the naphthoquinone and nitroso-naphthalene complexes, which was also observed in in vitro anticancer assays.