549-99-5

Basic information

• Product Name: 10-hydroxyanthrone
• Synonyms: 10-hydroxyanthrone;oxanthrone;10-Hydroxy-9,10-dihydroanthracene-9-one
• CAS NO: 549-99-5
• Molecular Formula: C₁₄H₁₀O₂
• Molecular Weight: 210.228
• Mol File: 549-99-5.mol
• Article Data: 10

Chemical Properties

• Boiling Point: 390.8°Cat760mmHg
• Flash Point: 166.9°C
• Appearance: /
• Density: 1.317g/cm³
• Vapor Pressure: 8.3E-07mmHg at 25°C
• Refractive Index: 1.677
• CAS DataBase Reference: 10-hydroxyanthrone(CAS DataBase Reference)
• NIST Chemistry Reference: 10-hydroxyanthrone(549-99-5)
• EPA Substance Registry System: 10-hydroxyanthrone(549-99-5)

Safety Data

• Hazardous Substances Data: 549-99-5(Hazardous Substances Data)

Usage

General Description

10-Hydroxyanthrone is a chemical compound with the molecular formula C14H8O2. It is a derivative of anthrone, and is primarily used in dyes and pigments. 10-Hydroxyanthrone can be produced synthetically or isolated from natural sources such as plants or fungi. It has been studied for its potential therapeutic properties, including as an antiviral and anti-inflammatory agent. Additionally, 10-hydroxyanthrone has been found to have antioxidant properties, making it potentially useful in the development of pharmaceuticals and cosmetics. Overall, 10-hydroxyanthrone has a variety of potential industrial and medicinal applications, and ongoing research continues to explore its properties and potential uses.

InChI:InChI=1/C14H10O2/c15-13-9-5-1-2-6-10(9)14(16)12-8-4-3-7-11(12)13/h1-8,13,15H

Upstream product

• 120-12-7 anthracene 
• 7732-18-5 water 
• 7782-50-5 chlorine 
• 5471-63-6 1,3-diphenylisobenzofuran 
• 602-60-8 9-nitroanthracene 
• 4741-24-6 9,10-epidioxy-9,10-dihydroanthracene 
• 100-42-5 styrene 

Downstream Products

• 4981-66-2 9,10-Dihydroxyanthracene 
• 90-44-8 anthracen-9(10H)-one 
• 84-65-1 9,10-phenanthrenequinone 
• 7732-18-5 water 
• 89162-47-0 10-acetoxy-10-(4-acetoxy-3-methoxyphenylmethyl)-9(10H)anthracenone 
• 18792-80-8 1-phenylbenzanthrone 
• 1560-32-3 10-bromo-10H-anthracen-9-one 
• 79769-67-8 10-hydroxy-10-(4-hydroxy-3-methoxyphenylmethyl)-9(10H)anthracenone 

Relevant articles and documents

The development of 1,3-diphenylisobenzofuran as a highly selective probe for the detection and quantitative determination of hydrogen peroxide

1,3-Diphenylisobenzofuran (DPBF) has been developed as a selective probe for the detection and quantitative determination of hydrogen peroxide in samples containing different reactive nitrogen and oxygen species (RNOS). DPBF is a fluorescent probe which, for almost 20 years, was believed to react in a highly specific manner toward some reactive oxygen species (ROS) such as singlet oxygen and hydroxy, alkyloxy or alkylperoxy radicals. Under the action of these individuals DPBF has been rapidly transformed to 1,2-dibenzoylbenzene (DBB). In order to check if DPBF can act as a unique indicator of the total amount of different RNOS, as well as oxidative stress caused by an overproduction of these individuals, a series of experiments was carried out, in which DPBF reacted with peroxynitrite anion, superoxide anion, hydrogen peroxide, hypochlorite anion, and anions commonly present under biological conditions, namely nitrite and nitrate. In all cases, except for hydrogen peroxide, the product of the reaction is DBB. Only under the action of H2O2 9-hydroxyanthracen-10(9H)-one (oxanthrone) is formed. This product has been identified with the use of fluorescence spectroscopy, NMR spectroscopy, high performance liquid chromatography coupled with mass spectrometry, infrared spectroscopy, elemental analysis, and cyclic voltammetry (CV). A linear relationship was found between a decrease in the fluorescence intensity of DPBF and the concentration of hydrogen peroxide in the range of concentrations of 0.196–3.941 mM. DPBF responds to hydrogen peroxide in a very specific way with the limits of detection and quantitation of 88 and 122.8 μM, respectively. The kinetics of the reaction between DBBF and H2O2 was also studied.

Meso-disubstituted anthracenes with fluorine-containing groups: Synthesis, light-emitting characteristics, and photostability

(Chemical Equation Presented) Synthesis, photophysical properties, and photostability of 9,10-disubstituted anthracenes with fluorine-containing groups (FCG) are described. The values of Φf and λem greatly go up by the meso-substitution with FCG, and a nice corelationship between Φf and Aπ (magnitude of π conjugation length in the excited single state) is observed. The C6F5 group at the meso positions exhibits an excellent ability in the photostability as well as in the emission efficiency.

Photocatalytic oxygenation of anthracenes and olefins with dioxygen via selective radical coupling using 9-mesityl-10-methylacridinium ion as an effective electron-transfer photocatalyst

Visible light irradiation of the absorption band of 9-mesityl-10- methylacridinium ion (Acr+-Mes) in an O2-saturated acetonitrile (MeCN) solution containing 9,10-dimethylanthracene results in formation of oxygenation product, i.e., dimethylepidioxyanthracene (Me 2An-O2). Anthracene and 9-methylanthracene also undergo photocatalytic oxygenation with Acr+-Mes to afford the corresponding epidioxyanthracenes under the photoirradiation. In the case of anthracene, the further photoirradiation results in formation of anthraquinone as the final six-electron oxidation product, via 10-hydroxyanthrone, accompanied by generation of H2O2. When anthracene is replaced by olefins (tetraphenylethylene and tetramethylethylene), the photocatalytic oxygenation of olefins affords the corresponding dioxetane, in which the O-O bond is cleaved to yield the corresponding ketones. The photocatalytic oxygenation of anthracenes and olefins is initiated by photoexcitation of Acr+-Mes, which results in formation of the electron-transfer state: Acr?- Mes?+, followed by electron transfer from anthracenes and olefins to the Mes?+ moiety together with electron transfer from the Acr? moiety to O2. The resulting anthracene and olefin radical cations undergo the radical coupling reactions with O 2?- to produce the epidioxyanthracene (An-O 2) and dioxetane, respectively.