101736-47-4

Usage

Uses

Used in Analytical Chemistry:
1-ANTHRACEN-9-YL-BUTANE-1,3-DIONE serves as a reagent for the determination of carbohydrates. It is used as an analytical tool for identifying and quantifying the presence of certain carbohydrates in a sample. The reaction between anthrone and specific carbohydrates results in a blue-green color, which can be measured quantitatively to ascertain the concentration of the carbohydrates.
Used in Pharmaceutical and Biomedical Applications:
Anthrone has been studied for its potential anti-inflammatory and antioxidant properties. In the pharmaceutical industry, it is considered for its capacity to mitigate inflammation and combat oxidative stress, which are important factors in various diseases and conditions. The exploration of anthrone's therapeutic potential is ongoing, with the aim of developing new treatments and interventions based on its beneficial effects.
Used in Research and Development:
Due to its unique chemical structure and properties, 1-ANTHRACEN-9-YL-BUTANE-1,3-DIONE is also utilized in research and development settings. Scientists and researchers employ anthrone in experiments to better understand its interactions with biological systems and to explore its potential applications in new areas of chemistry and medicine. This includes investigating its use in the synthesis of other compounds and its role in various chemical reactions.

InChI:InChI=1/C18H14O2/c1-12(19)10-17(20)18-15-8-4-2-6-13(15)11-14-7-3-5-9-16(14)18/h2-9,11H,10H2,1H3

Upstream product

• 784-04-3 9-acetylanthracene 
• 141-78-6 ethyl acetate 
• 120-12-7 anthracene 

Downstream Products

• 1548842-67-6 3-(2-hydroxyphenylimino)-9-anthrylbutan-1-one 

Relevant academic research and scientific papers

9-Anthroylacetone and its photodimer

9-Anthroylacetone undergoes a head-to-tail [4π+4π] photo-dimerisation reaction that leads to the formation of 5,11-bis(1,3-diketobutyl)-5,6,11,12- tetrahydro-5,12,6,11-di-o-benzeno-dibenzo[a,e]cyclooctene both in solution and in the solid state when irradiated with different sources (sunlight, tungsten lamp, xenon lamp, UV laser beam 351-364 nm), the reaction being accompanied by a colour variation from bright yellow to colourless. Quantum yields >0.023 mol/Einstein are evaluated for the solid state reaction. Interestingly, the dimer dissociates to give 9-anthroylacetone, both thermally (T>130°C) and photochemically, by short UV wavelength irradiation. The single-crystal X-ray structure of 9-anthroylacetone and its dimer are reported. 9-Anthroylacetone undergoes a head-to-tail [4π+4π] photo-dimerisation reaction both in solution and in the solid state when irradiated with different sources; the dimer reversibly dissociates into 9-anthroylacetone, both thermally and photochemically.

Carbohydrate-appended tumor targeting iron(III) complexes showing photocytotoxicity in red light

Glucose-appended photocytotoxic iron(III) complexes of a tridentate Schiff base phenolate ligand [Fe(bpyag)(L)](NO3) (1-3), where bpyag is N,N-bis(2-pyridylmethyl)-2-aminoethyl-β-d-glucopyranoside and H 2L is 3-(2-hydroxyphenylimino)-1-phenylbutan-1-one (H 2phap) in 1, 3-(2-hydroxyphenylimino)-9-anthrylbutan-1-one (H 2anap) in 2, and 3-(2-hydroxyphenylimino)-1-pyrenylbutan-1-one (H2pyap) in 3, were synthesized and characterized. The complex [Fe(dpma)(anap)](NO3) (4), having bis-(2-pyridylmethyl)benzylamine (dpma), in which the glucose moiety of bpyag is substituted by a phenyl group, was used as a control, and the complex [Fe(dpma)(anap)](PF6) (4a) was structurally characterized by X-ray crystallography. The structure shows a FeN4O2 core in a distorted octahedral geometry. The high-spin iron(III) complexes with magnetic moment value of ～5.9 μB showed a low-energy phenolate-to-Fe(III) charge-transfer (CT) absorption band as a shoulder near 500 nm with a tail extending to 700 nm and an irreversible Fe(III)-Fe(II) redox couple near -0.6 V versus saturated calomel electrode. The complexes are avid binders to calf thymus DNA and showed photocleavage of supercoiled pUC19 DNA in red (647 nm) and green (532 nm) light. Complexes 2 and 3 displayed significant photocytotoxicity in red light, with an IC50 value of ～20 μM in HeLa and HaCaT cells, and no significant toxicity in dark. The cell death is via an apoptotic pathway, by generation of reactive oxygen species. Preferential internalization of the carbohydrate-appended complexes 2 and 3 was evidenced in HeLa cells as compared to the control complex 4. A 5-fold increase in the cellular uptake was observed for the active complexes in HeLa cells. The photophysical properties of the complexes are rationalized from the density functional theory calculations.

Propargyl bromide as an excellent α-bromoacetone equivalent: Convenient and new route to α-aroylacetones

A variety of α-aroylacetones 4a-g have been prepared in excellent yields following a new protocol wherein α-aminonitriles 1a-g as the aryl acyl anion equivalents readily react with propargyl bromide as the α-bromoacetone equivalent. The alkylated product undergoes one-pot unmasking of the keto functionality along with Markovnikov's hydration of the terminal alkyne with CuSO4·5H2O in aqueous methanol at 60 °C to furnish the desired target in excellent isolated yields.