2555-30-8

Basic information

• Product Name: 7-HYDROXY-4-PHENYLCOUMARIN 97
• Synonyms: 7-HYDROXY-4-PHENYLCOUMARIN 97;7-Hydroxy-4-phenyl-2H-chromen-2-one;7-Hydroxy-4-phenylcoumarin;7-Hydroxy-4-phenylcoumarin 97%
• CAS NO: 2555-30-8
• Molecular Formula: C₁₅H₁₀O₃
• Molecular Weight: 238.24
• Product Categories: Coumarin;Building Blocks;Coumarins;Heterocyclic Building Blocks
• Mol File: 2555-30-8.mol

Chemical Properties

• Melting Point: 248-252 °C(lit.)
• Boiling Point: 458.3 °C at 760 mmHg
• Flash Point: 203.3 °C
• Appearance: /
• Density: 1.34g/cm³
• Vapor Pressure: 5.11E-09mmHg at 25°C
• Refractive Index: 1.666
• CAS DataBase Reference: 7-HYDROXY-4-PHENYLCOUMARIN 97(CAS DataBase Reference)
• NIST Chemistry Reference: 7-HYDROXY-4-PHENYLCOUMARIN 97(2555-30-8)
• EPA Substance Registry System: 7-HYDROXY-4-PHENYLCOUMARIN 97(2555-30-8)

Safety Data

• Hazard Codes: C,Xi
• Statements: 34-36/37/38
• Safety Statements: 26-27-36/37/39-37/39-45
• WGK Germany: 3
• Hazardous Substances Data: 2555-30-8(Hazardous Substances Data)

Usage

Uses

Used in Scientific Research:
7-HYDROXY-4-PHENYLCOUMARIN 97 is used as a fluorescent dye in biochemical assays for its strong fluorescence when excited by ultraviolet light. This property makes it useful in various fluorescence-based applications, such as detecting enzyme activity, monitoring molecular interactions, and studying cellular processes.
Used in Pharmaceutical Industry:
7-HYDROXY-4-PHENYLCOUMARIN 97 is used as a potential therapeutic agent for its antioxidant, anti-inflammatory, and anti-cancer activities. Its ability to modulate various biological pathways and exhibit synergistic effects with conventional chemotherapeutic drugs makes it a promising candidate for the development of novel pharmaceuticals.
Used in Drug Delivery Systems:
7-HYDROXY-4-PHENYLCOUMARIN 97 can be incorporated into drug delivery systems to enhance its bioavailability and therapeutic outcomes. Various organic and metallic nanoparticles can be employed as carriers for 7-HYDROXY-4-PHENYLCOUMARIN 97, aiming to improve its delivery and efficacy in targeted applications.
Used in Diagnostics:
7-HYDROXY-4-PHENYLCOUMARIN 97 can be used in diagnostic assays to detect specific biomolecules or cellular processes. Its strong fluorescence allows for sensitive and specific detection, making it a valuable tool in the development of diagnostic tests and assays.
Used in Bioimaging:
7-HYDROXY-4-PHENYLCOUMARIN 97 can be used as a fluorescent probe in bioimaging techniques to visualize cellular structures, molecular interactions, and biological processes in living cells and tissues. Its fluorescence properties enable high-resolution imaging and tracking of biological events in real-time.
Used in Environmental Monitoring:
7-HYDROXY-4-PHENYLCOUMARIN 97 can be employed as a fluorescent sensor for detecting environmental pollutants or monitoring changes in environmental conditions. Its sensitivity to specific analytes or environmental factors allows for the development of novel sensors and monitoring systems.

InChI:InChI=1/C15H10O3/c16-11-6-7-12-13(10-4-2-1-3-5-10)9-15(17)18-14(12)8-11/h1-9,16H

Upstream product

• 562835-40-9 7-hydroxy-4-phenyl-chromen-2-one-imine 
• 16299-27-7 2-oxo-4-phenyl-2H-chromen-7-yl acetate 
• 853926-01-9 7-hydroxy-2-oxo-4-phenyl-2H-chromene-3-carboxylic acid 
• 94028-56-5 7-hydroxy-2-oxo-4-phenyl-2H-chromene-6-carboxylic acid 
• 94-02-0 ethyl 3-oxo-3-phenylpropionate 
• 108-46-3 recorcinol 
• 1823-99-0 3-amino-3-phenylacrylonitrile 
• 569-37-9 ethyl 3-oxo-2-benzoylbutanoate 
• 131-56-6 2.4-dihydroxybenzophenone 
• 4071-85-6 trimetylsilylketene 
• 94739-93-2 2-oxo-4-phenyl-2H-chromen-7-ylbenzoate 
• 87468-02-8 7-furoyloxy-4-methylcoumarin 
• 94739-95-4 7-(β,β-dimethylacryloxy)-4-phenylcoumarin 
• 94739-94-3 7-hexanoyloxy-4-phenylcoumarin 

Downstream Products

• 108979-94-8 7-ethoxy-4-phenyl-2H-chromen-2-one 
• 110876-08-9 7-(benzyloxy)-4-phenyl-2H-chromen-2-one 
• 94739-93-2 2-oxo-4-phenyl-2H-chromen-7-ylbenzoate 
• 6275-80-5 (±)-7-hydroxy-4-phenyl-3,4-dihydrocoumarin 
• 175603-19-7 3-bromo-7-hydroxy-4-phenylcoumarin 
• 482-82-6 nordalbergin 
• 94739-96-5 7-furoyloxy-4-phenylcoumarin 
• 139286-96-7 3-Hydroxy-2-[(7-hydroxy-2-oxo-4-phenyl-2H-chromen-8-ylmethyl)-amino]-propionic acid 
• 139286-95-6 2-[(7-Hydroxy-2-oxo-4-phenyl-2H-chromen-8-ylmethyl)-amino]-3-phenyl-propionic acid 
• 94739-95-4 7-(β,β-dimethylacryloxy)-4-phenylcoumarin 
• 94739-94-3 7-hexanoyloxy-4-phenylcoumarin 
• 139286-94-5 2-[(7-Hydroxy-2-oxo-4-phenyl-2H-chromen-8-ylmethyl)-amino]-3-methyl-butyric acid 
• 80494-06-0 8-diethanolaminomethyl-7-hydroxy-4-phenyl coumarin 
• 139286-92-3 N-(7-hydroxy-4-phenyl-8-coumarinyl)glycine 

Relevant articles and documents

Implementation of a spraying-assisted fine droplet formation-based simultaneous liquid-phase microextraction method for the determination of copper in clove extract samples

A simultaneous liquid-phase microextraction method was investigated as an alternative to the traditional dispersive liquid–liquid microextraction for the determination of copper. The potential of this approach is based on the simultaneous complexation and

Nano-BFn/cellulose: a bio-based nano-catalyst for synthesis of bio-active 7-hydroxycoumarins

Nano-BFn/cellulose as a modified bio-based nano-catalyst has been synthesized from nanocellulose and boron triflouride via very simple steps. This novel nano-catalyst exhibited many advantages in the synthesis of 7-hydroxycoumarins such as good

2-Aminobenzoxazole-appended coumarins as potent and selective inhibitors of tumour-associated carbonic anhydrases

We have carried out the design, synthesis, and evaluation of a small library of 2-aminobenzoxazole-appended coumarins as novel inhibitors of tumour-related CAs IX and XII. Substituents on C-3 and/or C-4 positions of the coumarin scaffold, and on the benzoxazole moiety, together with the length of the linker connecting both units were modified to obtain useful structure-activity relationships. CA inhibition studies revealed a good selectivity towards tumour-associated CAs IX and XII (K i within the mid-nanomolar range in most of the cases) in comparison with CAs I, II, IV, and VII (K i > 10 μM); CA IX was found to be slightly more sensitive towards structural changes. Docking calculations suggested that the coumarin scaffold might act as a prodrug, binding to the CAs in its hydrolysed form, which is in turn obtained due to the esterase activity of CAs. An increase of the tether length and of the substituents steric hindrance was found to be detrimental to in?vitro antiproliferative activities. Incorporation of a chlorine atom on C-3 of the coumarin moiety achieved the strongest antiproliferative agent, with activities within the low micromolar range for the panel of tumour cell lines tested.

B(C6F5)3-catalyzed synthesis of coumarins via Pechmann condensation under solvent-free conditions

Tris(pentafluorophenyl)borane [B(C6F5)3] catalyzed simple, efficient and environmentally benign protocol has been developed for the Pechmann condensation using variety of phenols and β-ketoesters under solvent-free conditions to afford coumarin derivatives. The present protocol displayed significant advantages such as low catalyst loading, short reaction time, mild reaction conditions, low toxicity, easy work-up, high yields, and compatibility with other functional groups. In addition, it is a convenient, clean, and fast alternative approach for synthesizing variety of coumarin derivatives. Moreover, the applicability of this method towards large-scale synthesis demonstrated its suitability for the industrial application. Graphic abstract: [Figure not available: see fulltext.]

Synthesis of C4-substituted coumarins via Pechmann condensation catalyzed by sulfamic acid. Insights into the reaction mechanism by HRMS analysis

A series of functionalized C4-substituted coumarins were synthesized by exploring the reaction of activated and non-activated phenols and β-ketoesters under solvent-free conditions in the presence of sulfamic acid as a Br?nsted acid catalyst. Fifteen exam

MnSb2O6-chitosan nanocomposite: An efficient catalyst for the synthesis of coumarins via Pechmann reaction

In this work, MnSb2O6-chitosan nanocomposites were synthesized and have been employed in Pechmann condensation for the synthesis of coumarin derivatives. MnSb2O6-chitosan nanocomposites were characterized by Fou

Promising new inhibitors of tyrosyl-DNA phosphodiesterase I (Tdp 1) combining 4- arylcoumarin and monoterpenoid moieties as components of complex antitumor therapy

Tyrosyl-DNA phosphodiesterase 1 (Tdp1) is an important DNA repair enzyme in humans, and a current and promising inhibition target for the development of new chemosensitizing agents due to its ability to remove DNA damage caused by topoisomerase 1 (Top1) poisons such as topotecan and irinotecan. Herein, we report our work on the synthesis and characterization of new Tdp1 inhibitors that combine the arylcoumarin (neoflavonoid) and monoterpenoid moieties. Our results showed that they are potent Tdp1 inhibitors with IC50 values in the submicromolar range. In vivo experiments with mice revealed that compound 3ba (IC50 0.62 μM) induced a significant increase in the antitumor effect of topotecan on the Krebs-2 ascites tumor model. Our results further strengthen the argument that Tdp1 is a druggable target with the potential to be developed into a clinically-potent adjunct therapy in conjunction with Top1 poisons.

New nanodrug design for cancer therapy: Its synthesis, formulation, in vitro and in silico evaluations

The aim of this study was to develop a novel nanosize drug candidate for cancer therapy. For this purpose, (S)-methyl 2-[(7-hydroxy-2-oxo-4-phenyl-2H-chromen-8-yl)methyleneamino]-3-(1H-indol-3-yl)propanoate (ND3) was synthesized by the condensation reacti

Synthesis, computational studies and assessment of in vitro inhibitory activity of umbelliferon-based compounds against tumour-associated carbonic anhydrase isoforms IX and XII

Coumarins are widely diffused secondary metabolites possessing a plethora of biological activities. It has been established that coumarins represent a peculiar class of human carbonic anhydrase (hCA) inhibitors having a distinct mechanism of action involv

Synthesis of Novel Anti-inflammatory Psoralen Derivatives?-?Structures?with?Distinct?Anti-Inflammatory?Activities

As a continuum to our work with coumarins, 12 psoralens were synthesized and evaluated for their anti-inflammatory activity. Psoralens were prepared in three steps; at first, 7-hydroxycoumarins were synthesized by von Pechmann condensation and then converted to 7-(2-oxopropoxy)coumarins. In the final step, a fused furan ring was introduced in an intramolecular ring-formation reaction. Based on a SciFinder search, two out of the 12 synthesized psoralen derivatives (compounds 9 and 12) were found to be novel. The derivatives displayed anti-inflammatory activity by suppressing iNOS and IL-6 expression, but their mechanism of action seemed to be dependent on the substitution. Compound 6 with propyl side chain inhibited NF-κB mediated transcription, while compound 10 with a phenyl substituent down-regulated iNOS expression in a posttranscriptional manner. The results introduce psoralen derivatives as promising anti-inflammatory compounds with potential for treatment of conditions involving iNOS and/or IL-6-mediated adverse responses.