10387-49-2

Basic information

• Product Name: 7-ACETOXYCOUMARIN
• Synonyms: HYDROXYCOUMARIN ACETATE;AKOS 236-62;7-ACETOXYCOUMARIN;ACETYLUMBELLIFERONE;7-Acetoxy-2H-1-benzopyran-2-one;Acetic acid 2-oxo-2H-1-benzopyran-7-yl ester
• CAS NO: 10387-49-2
• Molecular Formula: C₁₁H₈O₄
• Molecular Weight: 204.18
• Mol File: 10387-49-2.mol
• Article Data: 44

Chemical Properties

• Melting Point: 142 °C
• Boiling Point: 366.7°C at 760 mmHg
• Flash Point: 191.5°C
• Appearance: /
• Density: 1.319g/cm³
• Vapor Pressure: 1.44E-05mmHg at 25°C
• Refractive Index: 1.574
• CAS DataBase Reference: 7-ACETOXYCOUMARIN(CAS DataBase Reference)
• NIST Chemistry Reference: 7-ACETOXYCOUMARIN(10387-49-2)
• EPA Substance Registry System: 7-ACETOXYCOUMARIN(10387-49-2)

Safety Data

• Hazardous Substances Data: 10387-49-2(Hazardous Substances Data)

Usage

InChI:InChI=1/C11H8O4/c1-7(12)14-9-4-2-8-3-5-11(13)15-10(8)6-9/h2-6H,1H3

Upstream product

• 127-09-3 sodium acetate 
• 108-24-7 acetic anhydride 
• 95-01-2 2,4-Dihydroxybenzaldehyde 
• 93-35-6 7-hydroxy-2H-chromen-2-one 
• 507-09-5 tiolacetic acid 
• 64-19-7 acetic acid 
• 52924-53-5 acetic acid 4-formyl-3-hydroxyphenyl ester 
• 122-59-8 2-phenoxyacetic acid 
• 102-29-4 Resorcinol monoacetate 
• 471-25-0 Propiolic acid 
• 878-00-2 4-formylphenyl acetate 
• 27542-85-4 4-acetoxycinnamic acid 
• 108-46-3 recorcinol 
• 37783-17-8 Acetic acid 10-acetoxy-6,7-dioxo-6,6a,6b,7,12b,12c-hexahydro-5,8-dioxa-dibenzo[a,i]biphenylen-3-yl ester 

Downstream Products

• 93-35-6 7-hydroxy-2H-chromen-2-one 
• 6748-68-1 8-acetyl-7-hydroxycoumarin 
• 2555-29-5 8-acetyl-7-hydroxy-4-methyl-2H-chromen-2-one 
• 1155848-94-4 C₁₈H₁₄N₂O₄ 
• 1155848-96-6 7-hydroxy-8-{1-[(2-hydroxybenzoyl)hydrazono]ethyl}-2H-1-benzopyran-2-one 
• 146900-52-9 3-bromo-7-hydroxy-2H-1-benzopyran-2-one 
• 1562426-82-7 7-acetyloxy-3-(trifluoromethyl)-2H-1-benzopyran-2-one 
• 6724-42-1 7-methoxy-2-oxo-2H-chromene-8-carbaldehyde 
• 19492-03-6 8-hydroxy-7-methoxy-2H-chromen-2-one 
• 64-19-7 acetic acid 
• 77819-97-7 3-benzoyl-2-oxo-2H-chromen-7-yl acetate 
• 531-59-9 7-methoxycoumarin 

Relevant articles and documents

A fluorescent probe for a lewisite simulant

Herein, we report for the first time a highly sensitive fluorescent probe for the detection of an organoarsenic blister agent simulant, arsenic trichloride (AsCl3). This probe showed high selectivity to AsCl3, in the presence of other metal ions, even at low concentrations. Moreover, quantitative determination of AsCl3 in soil was achieved with a detection limit of 61.2 μmol kg-1 that is sufficiently lower than the reported LD50 of lewisite.

Total Synthesis of the Major Metabolite of Methoxsalen

The total synthesis of the 6-coumarinylacetic acid (15), the major metabolic isolate of methoxsalen (1), starting from umbelliferone (5) is described.Several derivatives of a second metabolite, 4, were also prepared from the common intermediate aldehyde 13.This preparation involves a novel rearrangement of the bromoacetate 20 to the acetoxyphenol 21.A mechanism for the displacement reactions of the metabolite 4 and its derivative 21 implicating the transient enone 24 is presented.

Optimisation of two-photon induced cleavage of molecular linker systems for drug delivery

Photoreactive linker systems for drug delivery in modern ophthalmology are crucial for the efficiency of such applications. We compare 5 different linker molecule candidates (truxillic acid and 4 dimers of coumarin derivates) in solution regarding their chemical stability and two-photon induced cleavage efficiency, and shed light into the role of molecular structure in the cleavage reaction. Dimers of the coumarin family showed much higher two-photon induced cleavage efficiency, achieving the highest reaction cross-section when tert-Butyldimethylsilyl (TBS) was used as a substituent, being almost 5-times higher than the unsubstituted coumarin dimer. Coumarin-based linker systems react promptly with nucleophilic solvents, in particular with short chain alcohols. The polarity of such solvents which do not cause a lactone ring opening seems not to influence the cleavage of the cyclobutane ring in coumarin dimers.

Rational design of a highly selective fluorescent sensor for l-histidine detection in aqueous solution

Computational studies in combination with experimental research were used to design a new rapid, selective and sensitive "turn-on" fluorescent sensor (H3) for l-histidine, which can be first quenched by Ni2+ and then recovered upon addition of His.

Facile total synthesis of xanthotoxol

Xanthotoxol, a biologically active linear furocoumarin, has been efficiently synthesized from 7-hydroxycoumarin in six steps. The key steps included two efficient rearrangements - Fries rearrangement and Claisen rearrangement - and a Baeyer-Villiger oxidation process. The overall yield of xanthotoxol was 29%. This approach also provided a new strategy to furnish easily furocoumarins with a hydroxyl group in the framework. Copyright Taylor & Francis Group, LLC.

-

-

Synthesis and anticancer activity of some 8-substituted-7-methoxy-2H-chromen-2-one derivatives toward hepatocellular carcinoma HepG2 cells

Based on the reported anticancer activity of coumarin and pyrazoline derivatives, the present investigation dealt with the design and synthesis of coumarin derivatives bearing diversely substituted pyrazoline moieties 7-10. The non-cyclic isosteres 11a-e

7-Acetoxycoumarin inhibits LPS-induced inflammatory cytokine synthesis by IκBα degradation and MAPK activation in macrophage cells

Acetylation involves the chemical introduction of an acetyl group in place of an active hydrogen group into a compound. In this study, we synthesized 7-acetoxycoumarin (7AC) from acetylation of umbelliferone (UMB). We examined the anti-inflammatory properties of 7AC in lipopolysaccharide (LPS)-treated RAW 264.7 macrophage cells. The anti-inflammatory activity of 7AC on viability of treated cells was assessed by measuring the level of expression of NO, PGE2 and pro-inflammatory cytokines, namely interleukin-1β(IL-1β), interleukin-6 (IL-6) and tumor necrosis factor-α(TNF-α) in 7AC-treated RAW 264.7 macrophages. The 7AC was nontoxic to cells and inhibited the production of cytokines in a concentration-dependent manner. In addition, its treatment suppressed the production of pro-inflammatory cytokines in a dose-dependent manner and concomitantly decreased the protein andmRNAexpressions of inducibleNOsynthase (iNOS) and cyclooxygenase-2 (COX-2). Moreover, the levels of the phosphorylation of mitogen-activated protein kinase (MAPK) family proteins such as extracellular signal-regulated kinase (ERK), c-Jun N-terminal kinase (JNK), p38 and nuclear factor kappa B (NF-κB) were reduced by 7AC. In conclusion, we generated an anti-inflammatory compound through acetylation and demonstrated its efficacy in cell-based in vitro assays.

Visible-Light-Induced Direct Csp2-H Radical Trifluoroethylation of Coumarins with 1,1,1-Trifluoro-2-iodoethane (CF3CH2I)

Herein, we developed the first visible-light-induced direct Csp2-H radical 2,2,2-trifluoroethylation of coumarins with commercially available and cheap reagent CF3CH2I at room temperature. This transformation proceeded smoothly under mild conditions and showed excellent functional group compatibility. The synthetic value of the protocol was also demonstrated by the successful functionalization of several pharmaceuticals.

Mitochondria-targeted pH-viscosity dual-channel detection fluorescent probe as well as preparation method and application thereof

The invention discloses a mitochondria-targeted pH-viscosity dual-channel detection fluorescent probe and a preparation method and application thereof, wherein mitochondria-targeted pH-viscosity dual-channel detection fluorescent probe is as follows. The mitochondria-targeted pH-viscosity dual-channel detection fluorescent probe can generate non-interference double-color fluorescence response to pH and viscosity in vitro. The cytotoxicity test shows that the fluorescence probe has good biocompatibility, and the confocal fluorescence microscopic imaging experiment shows that the fluorescence probe is good in HeLa cell light stability, can effectively position mitochondria (a positioning coefficient of 0.92) in cells, and is suitable for confocal fluorescence imaging and double-channel detection in cells.

Flexible RuII Schiff Base Complexes: G-Quadruplex DNA Binding and Photo-Induced Cancer Cell Death

A series of new RuII Schiff base complexes built on the salphen moiety has been prepared. This includes four flexible monometallic RuII compounds and six rigid bimetallic analogues that contain NiII, PdII or PtII cations into the salphen complexation site. Steady state luminescence titrations illustrated the capacity of the compounds to photoprobe G-quadruplex (G4) DNA. Moreover, the vast array of the Schiff base structural changes allowed to extensively assess the influence of the ligand surface, flexibility and charge on the interaction of the compounds with G4 DNA. This was achieved thanks to circular dichroism melting assays and bio-layer interferometry studies that pointed up high affinities along with good selectivities of RuII Schiff base complexes for G4 DNA. In cellulo studies were carried out with the most promising compounds. Cellular uptake with location of the compounds in the nucleus as well as in the nucleolus was observed. Cell viability experiments were performed with U2OS osteosarcoma cells in the dark and under light irradiation which allowed the measurements of IC50 values and photoindexes. They showed the substantial role played by light irradiation in the activity of the drugs in addition to the low cytotoxicity of the molecules in the dark. Altogether, the reported results emphasize the promising properties of RuII Schiff base complexes as a new class of candidates for developing potential G4 DNA targeting diagnostic or therapeutic compounds.